Nathan Barry is a designer and author who has recently become fascinated with building and launching products. In the show he discusses marketing, self-publishing, and any other topic related to building a profitable online business and living a great life!
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© Copyright Nathan Barry 2020
The Nathan Barry Show
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Reviews
Chaim K.
5 out of 5 stars
Fun show
Good insights
MetaBLUF
5 out of 5 stars
My new favorite Podcast
Just jumping into the newsletter space seemed so daunting because of the gurus and spammy ads out there. This podcast helped so much! Actually getting to listen to people in the space have real conversations about their journey and their business. Not getting some up sell every 30 seconds. This podcast is a game changer and can’t wait to hear more!
Chuck Frey
5 out of 5 stars
A cornucopia of priceless advice
I have never been a fan of podcasts. The majority don’t deliver enough value in return for the time invested. Nathan Barry’s The Art of Newsletters is a notable exception. Each episode is filled with practical insights, inspiring ideas and engaging conversations with really smart creators. This podcast actually inspired me to launch a new newsletter on how to thrive and differentiate yourself in today’s post-COVID workplace called NEXT/EDGE. I love The Art of Newsletters!
malfoxley
5 out of 5 stars
Great show!
Nathan, host of the podcast, highlights all aspects of marketing and more in this can’t miss podcast! The host and expert guests offer insightful advice and information that is helpful to anyone that listens!
Brian215
5 out of 5 stars
In the sea of entrepreneur podcast, Nathan’s rises to the top
Have come across Nathan and his work in other podcasts and online venues but have only recently started “following” him. His podcasts seem a step above and to ring a little truer than some of his contemporaries, even those with the same guests. Look forward to future episodes.
Dhayne4
5 out of 5 stars
Excited for this Show
Just subscribed at around episode 10 and listened to a few extremely valuable episodes. Nathan shares some great information that I'm am immediately able to apply to my marketing and business efforts. If this is just the beginning, I'm really excited to see where this show grows and I know it will be even more valuable as Nathan continues to show up. Highly recommend!
linjava
4 out of 5 stars
11 insights was his best yet
I'd say this is a four star trending upwards. The recent (at time of me writing this) 11 insights episode was his most "useful" episode to date and he also seemed to have prepared and presented the best on this one. That said, also like his interviews (especially if/when it stays focused).
Harris_Bryan
5 out of 5 stars
Light Bulb Moment
I've loosely followed Nathan for the past 16 months. Then in January I read his book Authority. It was a lightbulb moment for me. Since then my blog has taken off, email list grown past 10k and revenue is up 500% in the past 10 months. Did Nathan shake some magic potion on me? Nah. But his teaching style, personal example and incredible audience has been a huge contributing factor. Keep up the good work!
RyanBattles
5 out of 5 stars
Honest, Open Discussion on the Business of Design, Online Marketing, and Self-Publishing
One of the things I love about Nathan is his transparency and desire to share what does or doesn’t work for him. Like his blog, I look forward to what he puts out on his podcast to continue to learn about what others in the trenches are going through.
TMarcS
5 out of 5 stars
Thank you.
Great show with a lot of information. Looking for that sales strategy podcast. Keep up the good work.
Heath | ArtsyNow.com
5 out of 5 stars
PURE GOLD
Nathan is a master at teaching valuable insight directly, trimming the fat and saving the listener time. I love his approach and leadership and am looking forward to many more episodes...and books... And pizza parties
Javipas
5 out of 5 stars
You can do it, too
Nathan is a great speaker, and he is repetitive with his messages and his lessons, but this is precisely what makes them valuable. They convince you to move forward, to take that step and try new things. And of course, he shows you how to take those steps and demonstrates that you can do it too by showing how others have been able to do that with great success...
Caleb Wojcik
5 out of 5 stars
Knowing Nathan Barry has led to tens of thousands of dollars of revenue for me.
I’ve know Nathan for a couple years now and we’ve talked almost every week. His help, advice, and friendship led me to a five-figure digital product launch earlier this year. Listen to his podcast and learn how he has earned a great living for his family through blogging, teaching, and self-publishing. You won’t regret it.
shsunnyday
5 out of 5 stars
Great Podcast
I discovered Nathan's blog and work a while back and am so excited about his new podcasts. Nathan does a wonderful job with his podcasts. They are so inspiring and motivational.
Matt Kremer
5 out of 5 stars
Makes my commute meaningful
Since taking a now job and having my commute go from 20 minutes to an hour, I’ve been looking for new useful ways to spend that time instead of listening to Spotify. Nathan Barry runs a great show that is well worth your time if you’re into entrepreneurship, email marketing or writing. Make your commute mean something!
Brandon Hilkert
5 out of 5 stars
Nathan Barry consistently delivers on topics like product launches, email marketing and design
Nathan has continually released reliable and valuable information on the topic of product launches, email marketing, and design. His book Authority should be required reading for anyone looking to launch a product online. The podcast is just as good! You won’t be disappointed.
MDCKC
5 out of 5 stars
Worth the time for those who value their time.
I have only subscribed to three podcasts (Tim Ferris, Dave Ramsey's EntreLeadership, and Passive Income) and I have never written a podcast review. Nathan's podcast is my fourth subscription because he knows how to run a business on the web and he understands how to share his failures and successes so that others can avoid them as they build their online operations. I am happy to write my first review recommending Nathan's podcast and I look forward to the many great episodes that will be worth my time because Nathan knows how to teach success in business.
Travis Hellstrom
5 out of 5 stars
Integrity + Genius
I'm a big fan of Nathan's and how generous he is with what he knows. He brings wisdom from great people and gladly shares his own wisdom with his readers and listeners. You won't regret giving him a listen.
Dion Lynk
5 out of 5 stars
Nathan is Knowledgable for Sure!
Nathan has a refreshing take on product creation and internet entrepreneurism. He speaks directly to concerns and errors that we all face when we go at it alone. I’ve learned the ‘right way’ to work on the internet from his teachings.
LitSuppGuru
4 out of 5 stars
Motivational
I recently listened to Nathan's book, Authority, and watched all of the video interviews. Listening to the case studies Nathan brings to us is very motivational. I'm looking forward to getting more of those via this podcast.
Joshua GK
5 out of 5 stars
Engaging and Informative
If you want to grow a meaningful online business, learn from Nathan Barry. He will teach you how to make money by developing a valuable skill, teaching that skill, growing an email list, and launching a product, service, or SAAS. He has done it and surrounds himself with others who are doing it. Only practical, no hype, helpful information here!
eileenbfang
5 out of 5 stars
Nathan is a great teacher
I have bought his book and follow him across various media.
GBaldwin
5 out of 5 stars
Awesomeness
Nathan Barry is a small biz wizard. He's built a solid business and is regularly trying new things to grow and expand. Do yourself a favor and subscribe to this one.
Bentley Davis
5 out of 5 stars
Love the book and the podcast
I just got done listening to the updated audio book for Authority and learned alot. I look forward to continuing learning with you through this podcast.
Omar Zenhom
5 out of 5 stars
Nathan Barry Knows What He’s Talking About
I’ve gotten to know Nathan and his work over the last couple of years and learn a ton from him. When I heard he launch a podcast, I didn’t hesitate to subscribe- I knew it would be incredibly useful. A straight forward show that gives you the info and insights you need. If you create products or are thinking of creating products, subscribe NOW! Thank me later. Omar Zenhom, 100mba.net
Madrobby
5 out of 5 stars
If you sell stuff on the internet, listen to this
Nathan not only knows about building email lists, marketing and selling products; he’s also an excellent designer and knows how to present things in the right way. Highly recommended!
Podcast information
- Amount of episodes
- 73
- Subscribers
- 1
- Verified
- No
- Website
- Explicit content
- No
- Episode type
- episodic
- Podcast link
- https://podvine.com/link/..
- Last upload date
- January 9, 2023
- Last fetch date
- March 19, 2023 12:52 PM
- Upload range
- MONTHLY
- Author
- Nathan Barry: Author, Designer, Marketer
- Copyright
- © Copyright Nathan Barry 2020
susbcribers
- 073: Thomas Frank - How I Make Six Figures per Month as a CreatorToday I’m talking with Thomas Frank. Thomas built a YouTube channel called College Info Geek to over a million subscribers. Since then, he’s rebranded and grown the channel to nearly 3 million subscribers. He’s also built a massive business around courses and Notion templates. In this episode we talk about making a pivot as a creator. Thomas has an interesting and understated approach that’s worked quite well. We also talk about the Notion templates he’s selling, the YouTube productivity channel he started strictly about Notion, and how it’s driving hundreds of thousands of dollars in sales per month. Thomas also explains why it’s easier getting started on YouTube today than it was 10 years ago, and I get Thomas’ candid thoughts on how Gumroad’s new pricing has affected his business and creators in general. In this episode, you’ll learn: Why now is a great time to get started on YouTube How to pull off a successful rebrand of your creator business Why your subscriber count isn’t as important as you think Was Gumroad’s price increase a mistake? Thomas’ Links (H5) Thomas’ website Follow Thomas on Twitter Subscribe to Thomas’ YouTube channel Download Thomas’ Notion templates Check out Thomas’ Notion YouTube channel Thomas’ Nebula.tv content Follow College Info Geek on Twitter Thomas’ Skillshare page0 comments0
- 072: Brian Feroldi - How to Skyrocket Your Twitter GrowthIn this episode I talk to Brian Feroldi. Brian is an incredible creator in the investing space. He Tweets about money, investing, and self-improvement. He also has a free newsletter with over 40,000 subscribers. Today Brian talks about his recent experience migrating his newsletter to ConvertKit. He’s also a member of the ConvertKit Sponsor Network. I haven’t said much about the Sponsor Network, so Brian shares how he’s using it to book sponsors. The bulk of our conversation, however, is about Twitter and how he’s grown his account to over 400,000 followers. Brian has an interesting idea using your Twitter profile as a sales page, and he explains why conversion rates are important. We also pull up my Twitter profile and Brian gives it a tear down live on the show. In this episode, you’ll learn: How to get more followers on Twitter Twitter profile strategies that increase your conversion rate Why your Tweets aren’t getting more impressions How to write Twitter threads that people will share Links & Resources (H5) ConvertKit Sponsor Network Sahil Bloom James Clear Tim Urban Blake Burge Austin Lieberman Brian’s Links (H5) Brian’s newsletter Follow Brian on Twitter Connect with Brian on Facebook Brian is on Instagram Check out Brian on YouTube Brian’s LinkedIn page0 comments0
- The Nathan Barry Show Sep 5 · 53m 071: Turner Novak - Easy Ways to Ignite Your Audience GrowthThe podcast is back! Today I’m talking with Turner Novak. Turner is someone I’ve followed for a long time. He has an amazing Twitter account where he drops hilarious memes, talks about life as an investor, and makes fun of venture capitalists and founders. He also posts deep dives on companies like Snapchat about how their earnings work, what’s going on in TikTok ads, and a lot more. It’s an interesting balance, and he does all this while investing in early-stage companies as a venture capitalist. In today’s episode Turner and I talk about how he creates content. We get into how he uses his funnel to raise capital, and how to generate the highest return on investment (ROI) for your audience. We also talk about how he grew to 130,000 followers on Twitter, why he failed to get a job in venture capital and had to start his own firm, and how to create a successful newsletter. In this episode, you’ll learn: Easy ways to grow your newsletter audience How Turner varies his content to get more engagement Why getting to know your audience is so important How Turner used writing to expand his venture capital network Turner’s Links & Resources (H5) Subscribe to Turner’s newsletter, The Split Follow Turner on Twitter Banana Capital’s website Follow Banana Capital on Twitter0 comments0
- 070: Katelyn Bourgoin - Stop Selling Courses & Start Selling TheseIn this episode I talk to Katelyn Bourgoin. Katelyn is a creator and entrepreneur. She’s built several successful companies and agencies, and built a consultant company that she later sold. We dive into why customers buy, and how to market and sell to them through the Jobs-to-be-Done framework. Katelyn has a wealth of marketing knowledge she shares with us today. We talk about different business models. We get into why you should focus on selling checklists, cheat sheets, and outcomes rather than the traditional video courses. We also talk about how she grew her newsletter to 10,000 subscribers, and got to over 50,000 followers on Twitter. In this episode, you’ll learn: Tips and strategies for acquiring more users A subtle mindset shift to make your marketing more effective What content should be free, and what should be paid for Why Katelyn transitioned away from launches and courses Links & Resources Episode 061: Rachel Rodgers – Simple & Consistent: How To Build an 8-Figure Business April Dunford Nathan Barry: Authority Katelyn Bourgoin’s Links Customer Camp Follow Customer Camp on Twitter The Why We Buy newsletter Jobs-to-be-Done The Trigger Technique Twitter thread about The Trigger Technique Follow Katelyn on Twitter0 comments0
- 069: Laura Roeder - Building the Best Brand in Your NicheIn this episode I talk to Laura Roeder. Laura and I have been friends for a long time. I’ve learned so much from her, and it’s great to have her on the podcast. Laura started an online community and a course called Creating Fame. She’s done a bunch of stuff in the internet space. She’s one of the people who’s been doing it since the early days. She got into software with a company called MeetEdgar, which is a social media scheduling service, and grew it into a successful company before selling it. She recently started another company called Paperbell. Paperbell is the all-in-one software that solves all the problems of running a coaching and consulting business. There’s so much to learn from Laura. I love her direct, blunt style. She’s given me great advice over the years, and you get to tune in as we jump on a call, hit record, and start catching up. In this episode, you’ll learn: Benefits of choosing a narrow niche for your business Common branding mistakes to avoid when starting out Laura’s advice for writing great copy Tradeoffs between hiring freelancers and employees Links & Resources Mama Gena MeetEdgar Laura Roeder’s Links Laura’s website Follow Laura on Twitter Laura is on Instagram Paperbell Follow Paperbell on Twitter Paperbell is on Instagram Follow Paperbell on Facebook Check out Paperbell on Pinterest0 comments0
- 068: Justin Moore - Game-Changing Newsletter Sponsorship StrategiesIn this episode I talk to Justin Moore. Justin is a Sponsorship Coach & the founder of Creator Wizard, a school & community that teaches you how to find & negotiate your dream brand deals. In today’s episode Justin reveals how narrowing in on sponsorship coaching was a huge boost for his business. We talk about him growing multiple audiences between different YouTube channels (he and his wife, April, have well over a million combined followers on YouTube). My favorite part of the episode is when we dive into From Boise, my side project newsletter. Justin breaks down what we’re doing wrong with sponsorships, how we should be selling them, and how there’s quite a bit more to be earned. We also dive into the way he runs his newsletter and how he’s grown it. In this episode, you’ll learn: The differences and similarities between sponsorships and newsletters Justin’s tips for starting your newsletter and getting traction How a simple change in Justin’s Twitter headline led to amazing growth for his brand Why you need to charge your sponsors different amounts Links & Resources Deepak Malhotra: Negotiation Genius: How to Overcome Obstacles and Achieve Brilliant Results at the Bargaining Table and Beyond Justin Moore’s Links Justin’s website Justin's newsletter Follow Justin on Twitter Join Justin’s group on Facebook Justin’s TikTok Justin is on Instagram Check out Creator Wizard on YouTube Trending Family AprilJustinTV on YouTube0 comments0
- 067: Kaya Yurieff - Finding Your Niche in the Creator EconomyIn this episode I’m joined by Kaya Yurieff. She is the Creator Economy Newsletter writer for The Information. It’s the publication I read when I want to know what’s going on in startups and funding, learn about Spotify’s latest launch, find out what’s going on with Instagram, and things like that. Kaya has a great approach. I love her writing. I love the way she profiles both individual creators and the moves happening from big businesses in the creator space. We talk about her writing process and her system for publishing four days a week. We talk about how they’ve grown the newsletter and what they pay attention to for monetization. We also talk about what it means to be a creator through crises like the pandemic, the social justice issues of the last few years, and now the war in Ukraine. In this episode, you’ll learn: Tips for finding your niche in a crowded field How to get more paid subscribers Benefits of adding visual content to your newsletter How to balance free content and paid content Links & Resources Embedded Kate Lindsay’s post on Embedded: You don't need to post through a crisis Kaya Yurieff’s Links The Information’s Creator Economy Newsletter Follow Kaya on Twitter0 comments0
- 066: Wes Kao - Creating High-Dollar Online Courses That SellIn this episode I talk to Wes Kao, co-founder of altMBA. Her latest startup is called Maven, and it's all about cohort-based courses. Wes is fantastic at course design. Before Maven, she did a bunch of amazing things working with a lot of different creators. We talk about the State Change Method, which is something I use to make my presentations much more interesting. We talk about building an audience on Twitter. We also talk about course design, cohort-based courses, and a lot of other fun things. In this episode, you’ll learn: Tips for writing short-form content that boosts engagement A big advantage Twitter gives you over other platforms How to know if your content is ready to publish Why cohort-based courses are so lucrative Links & Resources (H5) Seth Godin altMBA Gagan Biyani Wes Kao’s Links (H5) Maven Wes’ website Follow Wes on Twitter Wes’ blog post: Course Mechanics Canvas: 12 Levers to Achieve Course-Market Fit Wes’ blog post: The State Change Method: How to deliver engaging live lectures on Zoom0 comments0
- The Nathan Barry Show Mar 21 · 1h 2m 065: Brennan Dunn - Leveraging Automation To Get More Engagement and SalesOn today’s show I’m talking with Brennan Dunn. Brennan is a longtime friend. He's been around since the very early days of ConvertKit. He helped me review pull requests from our very first developers. These days Brennan is an expert in all things email marketing and automation. He’s fantastic at segmenting lists, personalizing content, using Liquid, and other advanced techniques to create a custom experience for subscribers. We talk about some of the ways you can gradually get into automation. We go over some examples of the advanced things Brennan does with Liquid and snippets to create custom experiences for subscribers. We also talk about how you can earn more money from email with these systems, and much more. In this episode, you’ll learn: Strategies for tailoring your website to boost engagement & sales How to free up more time so you can focus on growing your audience Brennan’s tips for creating and sharing the right content for your audience How to make your repurposed content feel fresh & relevant Links & Resources ConvertKit Shopify’s Liquid RightMessage Brennan Dunn’s Links Create & Sell Creator Email Template Pack Double Your Freelancing Brennan’s book: Double Your Freelancing Rate Mastering ConvertKit Follow Brennan on Twitter0 comments0
- 064: Sahil Bloom - How To Unlock Growth as a CreatorIn this episode I talk to Sahil Bloom. This is Sahil’s second time on the show. He’s doubled his audience from an already large number since then, and he’s now a full-time creator. Sahil is someone I’d love to have on the show every six months or every year. He’s putting out incredible content. I’ve probably learned more from Sahil in the last few months than I have from any other person. We talk about Twitter growth, monetization, growing a podcast, and newsletters. I also try to sell him on switching to ConvertKit. You can be the judge of how well I did to convince him. In this episode, you’ll learn: Two game-changing habits that can lead to big results How Sahil categorizes his content for more engagement Sahil’s strategies for growing a new podcast How Sahil monetizes his newsletter Links & Resources (H5) James Clear Shane Parrish The Generalist (Mario Gabriele) Greg Isenberg The Tim Ferriss Show, episode 362: Talent Is the Best Asset Class — Graham Duncan Sahil Bloom’s Links (H5) Follow Sahil on Twitter Listen to Sahil’s podcast, Where It Happens Visit Sahil’s website0 comments0
- 063: Isa Adney - Free Up Creative Time Using Systems and ProcessesOn today’s show I talk to Isa Adney, a resident storyteller at ConvertKit. Isa came to ConvertKit as our webinar producer. You get to hear the arc of what she was doing before, how she joined the team, and how it morphed into her current role. Isa is very good at systems. She shares how she uses systems to free up time for creative activities. We also talk about reusing content, and how to create systems and flywheels to make one piece of content work across many platforms. In this episode, you’ll learn: How to connect with popular creators you admire The best medium for building a relationship with your audience Isa’s advice for hosting workshops and webinars How Isa utilizes systems to create content across multiple mediums Links & Resources (H5) ConvertKit ConvertKit podcasts Don Hahn: Brain Storm: Unleashing Your Creative Self Kimberly Brooks The Nathan Barry Show 053: Kimberly Brooks – Taking Intentional Breaks To Reignite Creativity Harlem's Fashion Row (HFR) The Nathan Barry Show 026: Khe Hy – How You Can Do $10,000/Hr Work ConvertKit Creator Stories Isa Adney’s Links (H5) Follow Isa on Twitter Isa is on Instagram Follow Isa on TikTok0 comments0
- 062: Ellen Hyslop - Turn Your Pain Points Into a 400K Subscriber NewsletterIn this episode, I talk to Ellen Hyslop, Co-Founder of The Gist. The Gist is a newsletter all about sports, written entirely by women. Ellen and her co-founders have scaled a massive team to 20 people. They’ve grown The Gist to almost 400,000 subscribers, and they’re earning fantastic revenue from it. Ellen talks about how they grew The Gist in the early days. She also talks about their process of testing, how they launched with a launch party, and a bunch of other things. In this episode, you’ll learn: How to get subscribers when you’re first starting out Why you need to create a style guide for writing your newsletter Tips for growing your newsletter to 400K subscribers When niching down can lead to more revenue Links & Resources The Gist Co-Founder Jacie deHoop The Gist Co-Founder Roslyn McLarty Ellen Hyslop’s Links The Gist website The Gist newsletter The Gist of It podcast Follow Ellen on Instagram0 comments0
- 061: Rachel Rodgers - Simple & Consistent: How To Build an 8-Figure BusinessIn this episode I talk to Rachel Rodgers. Rachel is an attorney turned business coach. She’s someone I’ve admired and respected for a long time. She helps small business owners understand contracts and the legal side of running a business, and helps them scale their business. Rachel is a lot of fun, and she’s brilliant at business. She’s my hero because of the way that she approaches scaling a massive and successful business, and how she thinks about brand and everything else. On today’s show we talk about why business partnerships are a bad idea. Rachel shares her keys to building a successful membership community, and the benefits of publishing a book. We also talk about why you should take expensive vacations, how to build a great team, and much more. In this episode, you’ll learn: Why offering more products can hurt you in the long run Rachel’s clever method for scaling a business The relationship between current events and a successful creator business How Rachel builds an effective team Links & Resources (H5) Nathan Barry: Authority Denise Duffield-Thomas ConvertKit Rachel Rodgers’ Links (H5) Hello Seven The Hello Seven podcast We Should All Be Millionaires: The Club We Should All Be Millionaires: A Woman’s Guide To Earning More, Building Wealth, and Gaining Economic Power Small Business Bodyguard Follow Rachel on Twitter Rachel is on Instagram0 comments0
- 060: Reid DeRamus - Marketing Tips From HBO Max’s Former VP of GrowthIn this episode I talk to Reid DeRamus. He comes from the video streaming world of Hulu, HBO Max, and Crunchy Roll. His background in data analysis helped these companies grow their streaming services. Now he’s taking what he learned into the creator space to help people with their paid newsletters and courses, bringing these growth habits and growth techniques into their solo or small team creator businesses. We spend this episode riffing on business models, and the analytics that you should pay attention to as an individual creator. We also discuss branding, positioning, and local meetups. It’s a fun episode that I think you'll enjoy. In this episode, you’ll learn: Tips for developing your brand and community Reid’s process for curating content How to get your work in front of an audience The path to over 500K subscribers Links & Resources Patreon Wait But Why Crash Course on YouTube minutephysics on YouTube MinuteEarth on YouTube Reid DeRamus’s Links Follow Reid on Twitter Yem0 comments0
- The Nathan Barry Show Feb 7 · 1h 3m 059: Samir Chaudry - Using YouTube To Launch Your Creator EnterpriseIn this episode, I talked to Samir Chaudry. Samir is the co-host of the popular YouTube channel, Colin and Samir. He and his business partner, Colin Rosenblum, have built a really interesting enterprise. It’s been fun getting to know them. We talk about how they built and structure their entire business, and what drives revenue. Then we get into storytelling, and at the end we even talk about designing the perfect day, what’s driving growth on YouTube, and much more. They’ve got a show, they’ve got a newsletter, a bunch of different stuff. It’s a fun story of two people who were shining in a specific niche, took what they learned from that experience, and are serving the broader community with their knowledge and wisdom. In this episode, you’ll learn: How to avoid being overwhelmed as a creator How Samir & Colin developed a culture around their content Tips for curating your content The journey to over 500K subscribers on YouTube Links & Resources ConvertKit Samir Chaudry’s Links Follow Samir on Twitter Colin and Samir on YouTube The Colin and Samir Show on Apple Podcasts The Colin and Samir Show on Spotify The Publish Press newsletter Colin and Samir on Instagram0 comments0
- 058: Andrew Gazdecki - How To Supercharge Your Audience GrowthAndrew Gazdecki is the founder and CEO of MicroAcquire, the world’s most founder-friendly startup acquisition marketplace. MicroAcquire helps entrepreneurs buy and sell startups. After founding and later selling two successful startups, Andrew decided there needed to be a better way to connect buyers and sellers in the startup marketplace. He founded MicroAcquire to fill this void in the startup acquisition arena. In this episode, Andrew shares how he grew his Twitter audience from 30,000 to 70,000 followers in a few short months. He uses his connections with others, his partnerships, his brand, and savvy marketing techniques to boost engagement and attract followers. It’s a fun and entertaining episode, and I think you’re going to enjoy it. In this episode, you’ll learn: The one thing you should spend at least half of your startup’s budget on Proven strategies and tactics to grow your Twitter account How to bootstrap your business and retain your autonomy Links & Resources TechCrunch Cameo Effie Empire Flippers Flippa Bizness Apps Sam Parr Stripe Baremetrics ChartMogul Bumble Brandarrow Bootstrappers.com Y Combinator Salesforce Nick Huber David Cancel Josh Pigford Clearco AngelList Avaloq Naval Ravikant Dharmesh Shah The Ladders of Wealth Creation blog post Andrew Gazdecki’s Links Follow Andrew on Twitter Follow MicroAcquire on Twitter Episode Transcript 00:00:00 Andrew: I’m a big fan of stair-stepping and entrepreneurship. One of my favorite tweets that I’ve ever written is, “Start with an agency, get to cashflow positive, and then bootstrap an asset—whether that’s a SaaS company or your e-commerce business—sell that asset, become financially secure, and then do whatever you want.” Along the way, you prepare yourself for the next stage of business. 00:00:35 Nathan: In this episode, I talked to Andrew Gazdecki, from MicroAcquire. Andrew started a couple other businesses and sold two of them. In that process, he decided there needed to be a better way to buy and sell businesses. So, that’s where MicroAcquire came from. Their marketplace originally focused specifically on SaaS businesses, but they broadened to all of software. The reason I want to talk to him—he doesn’t write a traditional newsletter or something like that—but he uses audience really well to grow MicroAcquire. He uses his personal brand connections with others, partnerships, a bunch of fun things. We get into how he grew his Twitter audience from 30,000 followers just a couple months ago, to over 70,000. His approach to Twitter, some of the arguments or beefs that he started with TechCrunch and others, and where he thinks those lines are. We also get into how he uses Cameo; he has these great ads announcing partnerships and others from Russ Hanneman on Silicon valley talking about this, and they’re really entertaining. So, there’s a lot of fun things in this episode, and I think you’re going to like it. I’ll get out of the way, and we’ll dive in. Andrew, welcome to the show. 00:01:41 Andrew: Thanks for having me, Nathan. Always a pleasure to be chatting with you. 00:01:44 Nathan: There are a lot of companies in the brokerage/help-me-sell-my-business space. I think of Effie International, Empire Flippers, Flippa, all of these. So, one, you’re going into a really crowded market with MicroAcquire, and then, two, you’re coming at it like you’re a force of nature. Sam Parr and I we’re actually talking about this, of how some people start a project and it’s like, “Oh, I’m going to do this thing.” And then other people do effectively the same thing. I mean, it’s different in a lot of ways, right? But the same category, and come in and just completely dominate, and grow so fast, and it feels like a fundamentally different thing. What’s your take on that, of coming into a crowded space, and then the amount of momentum that you’ve come in with? 00:02:34 Andrew: Yeah. I have a lot of respect for all those companies that you mentioned, and appreciate the compliment. The market that is specifically acquisitions hasn’t seen a lot of innovation in a decade. Two of the businesses you mentioned are service businesses, Flippa being a marketplace. I looked at that, and I just thought, there’s an angle here where sellers could benefit more than the buyers, and I felt buyers were benefiting. So, I took a left while everyone was going right. Then coming in from an entrepreneur’s view instead of a buyer’s view, or an investment bankers view, or an MNA advisor view, this was me saying, okay, I’m gone through two acquisitions, I think I have a few unique insights into what it would take to make me comfortable putting my business, generating millions of dollars, on a new marketplace. Then, what information and educational pieces would I need to feel comfortable to facilitate an acquisition. So, I just built what I felt acquisition should be. We still have a long way to go. We’ve done a really good job of connecting buyers and sellers, and all the acquisitions are facilitated off platform. We’ve been working on a lot of tooling to really add value to the acquisition, if that makes sense. So we’re looking to innovate on things like due diligence or even simple items like writing a letter of intent or streamlining escrow, because everyone complains about escrow.com. so yeah, I mean, sometimes it just happens in markets. Like a new entrant comes in with a different angle towards the problem And different viewpoint. and I think my unique, insight there was just, I had been on. The side of the table that maybe the other, companies had not. but it’s also, a giant market. So I, think, arising boat lifts all tides. So, you know, we’re here to my require. I just made my group or to help entrepreneurs get acquired and, and, succeed. And so, I think also as, you know, Mike require pick steam and helps everyone else in the market as well. So, but, yeah, I don’t have a good answer to that. I don’t know. I think if I, if I, this, this will sound cheesy, but you know, I, I I’d like to say I built my group hire would love, like I launched it in the middle of the pandemic. I didn’t have a business model. I had no idea how I was going to make money. I just knew I wanted to work with entrepreneurs and startups. And the rest is kind of history, you know, along the way, talking to customers, getting feedback from them, pretty much everything we do is basically feedback from customers. I’m not Steve jobs or anything like that. So I can’t read people’s minds. So I ask what, what ideas do you have? but yeah, it’s been, it’s been a fun journey so far. my group is about to turn two, which is pretty wild. 00:05:56 Nathan: That first version, that you launched, what did that look like? What, what was the very early stages of it? 00:06:02 Andrew: The first version was, it was just a simple marketplace with a couple of. Changes that I haven’t seen in the market. One was privacy and anonymousy and then no fees or commissions for founders. So it was the first marketplace where you could meet buyers and sell your business without paying a 15% commission like you typically would with a broker or something like that. So I think that was kind of a change. And our business model today is we charge buyers for access to the platform to connect with sellers and, you know, having negotiations that lead towards negotiations. But yeah, the first version, required a lot of vetting of the buyers. Every buyer needed like a LinkedIn profile. Some people have complained about that, but I personally would never sell my business as someone, without a LinkedIn profile. I need to know where you worked, like you know, do you have anyone that’s bad for you? not just like John 9, 9, 2, 4 5. You know, I need to know, who you are. and we’re going to add other ways of verification, but I think that was a big one. and then also real-time metrics integration. So when we launched, you could connect like Stripe and chart, mobile and probable and bare metrics to get like a real, like a nice, pretty graph, like the revenue to help with due diligence. and then also founders and everything was private. So you didn’t know what the business was. And as a founder, you had complete control over the process. So when you were with a broker, sometimes it could be kind of showing your business to a lot of people And you may not know who those people are. they could even be competitive to your business. And so I think what Mike required did that kind of, and I’m just guessing here because I haven’t really liked. Taking a step back and then like, what did we do? Right. you know, I’m usually thinking about what can we be doing better? we really put the founder in control. You know, they were the ones able to choose which buyers to speak to. they were the ones able to share which information they wanted to and which information they did not want to share. And again, it was completely free. So it was very low friction to get onto the platform. And then I think just the, the high, the caliber of buyers and the caliber of listing. So we vet every listing. We vet every buyer. Now that registers as a micro require premium buyer, that’s where you can contact sellers. so I think it was just kind of like, you know, going from let’s just call it like a car dealership to like a Ferrari shop that makes sense where all the cars are, That it, and if you want to know who the owner is, you have to pay for that access, but it was a very specific towards startups, specifically SaaS. So I think that’s another thing that I’m thinking of now is we, we went very narrow at the beginning, very narrow. So we were very specific on, specifically, bootstraps, SaaS companies. 00:08:59 Nathan: Yeah. I think the approach in different marketplaces is always interesting when, you know, a marketplace is how businesses has like is a generic category, but then the twist on it, of, the seller not paying anything. And it being the buyer who pays, you know, a subscription for access. Why I think that that makes for an interesting twist, because then you’re going to have this much higher pipeline of, you know, high quality businesses to look at. And so if a seller is paying for that, that makes sense. It reminds me of like, Bumble as a dating app being like, yep. So within the category of dating apps, but, women have to send the first message, you know, and, and like, that little bit of a twist makes it the marketplace feel, very different and changes the dynamics of. 00:09:40 Andrew: Yeah. I was going to say something, someone called micro fire shark tank, like if shark tank and dinner had a kid, I thought that was kind of an interesting analogy. but yeah, I’d say the, the key. The unique insights I had was again, like, from my perspective, if I’m going to list a business, I need to know who’s seeing my information. I want to be in control of, you know, what information is being disclosed or being displayed publicly. and I don’t want to commit until I really know, the quality of the buyers. And so that I think was very appealing to just being an entrepreneur. I think I. You know, understood the needs of other entrepreneurs and just kind of got it. Right. But I’m not gonna lie. When I, when I first launched it, I have this, I keep a journal that I update every month. It’s not like a weird, you know, Hey dear diary thing. It’s I do like, what’s going really well. What are some things I’m worried about? and then things I’m grateful for, just to, you know, kind of keep it story log of my life. And before I launched my group wire, I actually, cause this idea had been attempted before, like a real startup acquisition marketplace. I think some of the other market places are more, geared towards, you know, content sites and domains and 00:11:07 Nathan: Yeah, 00:11:08 Andrew: Affiliate websites, but not real. Startups like SaaS companies, e-commerce companies, crypto companies, we’ve moved into a number of different categories. But, I wrote in my journal, I was like, I don’t know if this is going to work, but at least it looks good. cause I, I just thought it needed to exist so bad for entrepreneurs that, we put a lot of thought into user experience and design. So it felt modern. You know, when you’re working with startup founders, you kinda, you know, you want to really build trust, like yeah, if you’re going to sell your business with us, your startup, you know, we also, we know how to build startups as well, and design them well and make them feel like something like this, this feels legitimate. And I think that’s a, what I would call, you know, closing the credibility gap, you know, really, that first impression is so important. So we really kinda overdid the initial MVP. 00:12:06 Nathan: Yeah. I think that design is one of those things where you can go a long ways. And it’s probably the first thing that people cut when it comes to the MPP. And that’s just, I’m like, Nope, that’s not an MVP. You have to cut features. You can’t cut like the quality of, of the design. And if I have a limited budget, I’m for sure. Spending half of it, if not more on design. So I think you made the right move there. 00:12:29 Andrew: Yeah, I think, I think today, I don’t know if we’re going to go off topic here, but I think a lot of startups today can legitimately have user experience in design as their competitive advantage. Just saving people, a Couple of clicks, making things easier to use, having a product where you don’t have 50 tutorial videos, you’ve got to watch, or course you have to take. that’s a huge advantage. and there’s a lot of products that are very clunky and kind of feel like a car with, you know, like a jet ski engine added in. And I just kind of like a Jenga thing, you know, there’s just so much technical debt to the product. I think though there’s some products out there that I think could be rethought in terms of like the experience and the design they’re delivering to the customers. But that’s, that’s probably a whole nother topic. 00:13:22 Nathan: Yeah. Yeah. But we agree. And anyone who’s listening to this show knows that I care deeply about design. one thing that I want to ask about and spend a lot of time on is content strategy. if I go to your website and go to the about page, it just lists your title or like your, your job description and your role as marketing. and so I’m imagining that’s where you spent the majority of your time in, from the outside. It looks like content marketing is, either a very large or the largest portion of where you spend your time and how you’re looking to grow MicroAcquire. Can you talk about how you think about content marketing and the growth of the business? 00:13:59 Andrew: Yeah, I think that was twofold. So number one, the first thing that happened to me when business apps was acquired, I had like five founder friends reach out and they said, how did you sell your business side is, is, were what, you know, so as entrepreneurs, we’re not trained to sell businesses, we’re not educated on what is due diligence, what are the legal steps of an acquisition? So I felt it was a twofold, the problem with the benefit. And when I say two folded, not right. Prom, but well point number one. Yeah. It’s a phenomenal growth channel for us. we think heavily in terms of, you know, what is the content that, entrepreneurs will need when they’re going through an acquisition, because the more we can educate them on acquisitions, the more we’ll be able to facilitate. And I think that’s been crucial, but then two there’s just no content in the market that like there’s books on fundraising, there’s books on marketing there’s books, on design there’s books on there’s a couple of books on, exits, but there just is such a disproportional amount of content available for everything, but a startup being acquired, that we felt, you know, there’s an opportunity here to kind of be almost a, I don’t want to say thought leader. 00:15:20 Nathan: Yeah. 00:15:21 Andrew: Kind of write the book, if you will, on, you know, this is, but also important to note is we write content for the seller, not for the buyer. we kinda think, you know, the buyers are set, you know, the buyers that we work with are, you know, private equity firms, corporate dev teams, other startups, people that, generally are sophisticated with, and also a lot of first-time buyers, but so the condoms still applies, but it gets you in the head of the entrepreneur, but we wanted to really empower the founder. So you’ll notice every piece of content is angled towards the seller, not the buyer, if that makes sense. And I felt that was critical and just something cool to do for other founders, not like, Hey, this is an article on how to get like the cheapest SaaS acquisition possible. so we read articles on how to maximize your startups exit as. 00:16:14 Nathan: Yeah. I mean, that, that perspective is in your, like your founding story for the company, But then it’s interesting, like, all right, it makes sense that it carries through all of your content marketing as well, because in the same way that you have know who your customer is, which in the marketplace, you have a lot of different customers or you’re, you know, you have both sides of it, but, 00:16:32 Andrew: That’s that’s something. Yeah, you’re onto something. So that’s something that, we determined, very, very early. So when we raised our, our seed round, I hired my former VP of product, VP of engineering. My former CFO, and my former head of marketing who’s now gone. Cause he went, he was, he was, he was like one foot in he’s started this, agency called brand arrow. so if anyone needs help with, Facebook ads or just any sort of SaaS marketing shadow, Tim brown now I told him like, Hey, you got to, I’m a big fan. I need like a micro mafia at one point. So I, I told him to dive in on that, but, we did an offsite and we, defined our culture, you know, our values, but really specifically, like you said, who was our customer? Cause it could be so many people, it could be okay, buyers, but there’s so many different types of buyers. You know, which ones are we going to cater towards? And then there’s sellers, you know, there’s so many different types of sellers. There’s people looking to sell comments. Again, domains, Amazon FBA businesses, SaaS founders. And so we really narrowed in, got super specific with our buyer And that really guides a lot of the decisions that we make all the way from the content to the product. I think that’s really crucial in the early days, because you can always expand outwards. There’s a theory. I don’t know if you’ve heard of this, but the bowling ball theory, you’ve probably gone through this with your business where, you know, you start with one sorta audience and then I one customer segment, and there’s just like these natural sort of like, you know, other segments that target for us, it was like e-commerce. And then we’ve been seeing a lot of just miscellaneous. You know, profitable software companies. So now we’re a little bit more broad. So when I described my required of people, I say, it’s a marketplace. So profitable software businesses, not just SaaS anymore, but yeah, we started really specific with SaaS founders being, our initial customer, 00:18:37 Nathan: Yeah. Like narrowing it on. That is always a good thing. Okay. So content strategy, I’m seeing you do a lot of different things. one at let’s just take Twitter, as a starting point. So I was looking back in August, you had 30,000 followers on Twitter. You have 73,000 followers today. You’re tweeting five to 10 times a day. Often. Like you got a lot of, a lot of posts going out. It seems like they’re resonating, obviously from the growth and all of that. you have a lot of these single posts are like single sentence. You know, here’s an idea latch onto it, like positioning type things. So like one, one example is, instead of thinking of a hundred plus startup ideas, pick a customer you’d love to serve and solve their problems. That gets a thousand likes, 150 retweets or more. I want to know, two things, one, tell me about your Twitter strategy of how it fits into the broader business and what you’re trying to do there. And then two, we’ll just get into what’s working. What’s not working. 00:19:33 Andrew: Yeah, definitely. So Twitter strategy, there is absolutely none, aside from having fun. And I’m a firm believer of this, I think when people try to have a social media strategy where their goal is to grow followers. And so you start doing stuff like looking at other people’s tweets, and then you take a tweet and this how I see this all the time with some content I put out like, oh, that looks very familiar, but I don’t, I don’t, you know, I don’t care. but they’re trying to grow their audience and they’re not being authentic to who they are. And they’re trying to be, you know, they’re trying to, I guess what I’m trying to say is, Find a way to utilize, you know, social platforms in a way that you enjoy. So, one thing notice if you look at all my tweets, they’re all from my iPhone. Like they’re not from my web app. They’re not from a scheduled Twitter thing. I just like that tweet. I remember writing that tweet. I was like, in my kitchen, I was just like, did it, you’ll also see a tweet right before this podcast. That’s just me. I was waiting for you to come on this podcast. I was like, so I think my point being, and I think this goes even broader is just, you know, if you want to be great at anything, and I’m not saying in any way, shape or form, I’ve created Twitter, but you just have to enjoy it. And then if you enjoy it, you’re consistent at it. And then, I do have a few rules though. I don’t usually comment on people’s cause like you know, once you start getting to a certain point on Twitter, people, you can just post like Entrepreneurship is awesome. And then people have like a hundred questions and I just don’t have the bandwidth to answer all those questions. So I usually will, I’m watching those questions and I’ll usually, if some, if something’s interesting, I’ll, use that as a new tweet. and then you get tweeted out a lot, like, Hey, follow me. Like, Hey, we’d be on my podcast. So I kind of have a rule of like stay in my lane, if that makes sense. I’ve done a little bit of like beef marketing and stuff like that, you know, I’m sure you saw me like call out like tech, Raj, or maybe like throw a couple of shots at like, just joking, like VC sort of like, you know, shit posting type stuff. And that works. It definitely works. And there’s some strategy behind that. That’s probably one part of my social media strategy that was, strategic, it’s effective, but it’s not for the faint of heart. cause you do you make people pick sides, so you’re going to upset some people and you’re going to make some people really cheer you on. And so, I’m kind of done with that phase. that was fun. 00:22:20 Nathan: So if someone is in that phase or they’re thinking about it, right. They, have a specific audience for their business or like a specific focus. They’ve chosen a niche and they have some strong opinions and they’re not that kind of person who’s like, you know, like let’s not cause any conflict. They’re like, no, I’m actually, I’d be, I’d be willing to get into a little bit of conflict. what would you say what’s, what’s your advice on going down that path of like, if you’re thinking of oh, there’s a TechCrunch in your space or someone else that you might want to pick a fight with? 00:22:49 Andrew: Did you just gotta really believe it? like, and I think it has to be factual, like what I said about, TechCrunch, as an example, just go on their website right now and see it. And tell me if you can find an article about a bootstrap startup. like, that’s all I said is like, you guys are a publication that writes about just venture backed businesses. and you know, what kind of really struck a chord with me with that was my prior company business apps. You know, we were in TechCrunch, all the time. Like they loved writing about, you know, real business building storage partnerships, you know, version 2.0 launches, you know, international exp like, you know, stories that inspire entrepreneurs. And they moved towards, you know, this really venture backed sorta, you know, you’re, you’re either in it, or you’re not in it. And I just blindly called them out on time and then some people. were like, yeah. And then I was like, huh, maybe there’s something here. And then I just, and this is how I always think of or how I validate ideas as well as, so I have a publication now called, bootstrappers.com, which is just kind of like my. Like what I wanted, like just, you know, I want inspiring stories, like back in like 2010, you would read articles on TechCrunch about like, two people. They just launched a product, no funding. I remember some of the writers I used to work with, are they all left? They’re all gone. It’s like a new, it’s a new company. It’s, it’s been acquired by four different companies. And you know, some of the older writers you’re out, but, the older crew, would kind of joke and say, Hey, BC’s like, I hope you banked me one day for writing about all the companies that I discovered. and then you find it later. now the opposite is entirely true. And so I, I wanted to bring that style. You know, journalism back where it’s stories about companies making like 200,000 a year or 500,000 or 2 million. because you know what, I read an article about a company raising 200 million and then 500 million, like the next week. it doesn’t really inspire me too much. And I think that celebrated so much today and, you know, the startup community that I think it’s a little dangerous, I think, as a young entrepreneur, like if you think the path to being a successful founder is. Get into Y Combinator, raise a bunch of funding, get featured in, you know, these magazines, because that’s what happens when you get fun. That’s like the only way to get covered sometimes, is funding announcements. and even then it’s hard cause there’s so many. so I think that creates an environment where a lot of entrepreneurs are focused on raising capital rather than raising or generating revenue from customers. And that was just something that I lived through. I had a really good mentor. We’re told, are we going off topic too far? 00:26:04 Nathan: Well, I do want to take you back to, like the idea of like picking a fight. But finish the thought with a mentor. Who’s everyone, everyone listening knows that ConvertKit is bootstrapped. I’m a huge fan of that and the same things, the same reason that you’re picking a fight with TechCrunch or that you did, I would do the same because we experienced that, you know, we could have more revenue, more customers, all of that than, anyone else, but they’re only going to write about the VC funded version. So, 00:26:28 Andrew: Yeah. So so long story, short business apps, my company prior, boot shove that business, and I just had a really good mentor Christian free Freeland. And he was always challenging me to think against the difficult soak on early pap. And we were based in San Francisco for five years, eventually moved to San Diego and that’s where we exited the business. but, yeah, now that like I’m on my third, I took a little hiatus and went into crypto land for a little bit. So it got away from like SaaS and stuff like that, but now I’m back home. and yeah, just saw that and said, okay, and then actually TechCrunch did write a little bit about bootstrapping and then I’ve also seen a lot of other people start saying the same thing, like agreeing, which I think has been cool. It, which isn’t like it’s not a bad thing that TechCrunch or any publication, I don’t want to just hone in on, on TechCrunch. because th they’re, they’ve done so much for so many founders. but yeah, other people, I feel like the first shot was fired. Like, Hey, You know, we miss the old version of, you know, maybe mix it up a little bit. And they’ve taken some of that feedback and I’ve actually written about some bootstrap companies and then other people have kind of said the same thing. Like, you know, the startup ecosystem is really turning into this, you know, fundraise craze news cycle. And, you know, there’s 99% of other startups that aren’t going down that path. So that creates kind of like a movement. So that was like the benefit of, of beef marketing sometimes is you, again, make people pick sides. Some people agree with it, some people don’t. yeah. So advice for anyone in terms of beef marketing, I, I, again, I, going back to my original point, it how you have to believe it, you have to believe what you’re saying. It can’t just be like, you know, one foot in, from my perspective, Most of the major tech publication should write about, you know, businesses that are profitable and sustainable and ones that are raising a bunch of capital and going public like a good mix would be amazing because then that gives you a true picture of, you know, all the different styles of entrepreneurship, you know, the ones that are at the top of the top and the ones that are taking a more sustainable practical approach, just giving a more realistic view into the world of entrepreneurship instead of just kind of, you know, putting this one style on a pedestal. Yeah, I mean, just get ready for, I mean, nothing bad happened. so I would just say also with beef marketing, it doesn’t have to be just, an individual Oregon or, or an organization. Like good examples. So I’ve always had a, like, kind of an, a branding, an enemy, and all my businesses for business apps. It was a large businesses. Like our main sales pitch was, you know, Starbucks down the street, paid 2 million for their, mobile app, blah, blah, blah. You know, would you like to create that same customer experience for your customers and, you know, like David versus Goliath type story, you know, Mike group, we’re kind of fighting for the founders. Then all the other stuff that I just talked about, but Salesforce had, their, their enemy was on-premise software. They essentially invented SaaS, you know, the company. Say a little chat thing. Yeah. They had a big campaign of just no forums. Like no one wants to download an ebook anymore, like forms go away, please. and I thought that was very clever, box.com had some beef with Microsoft, which was definitely fun to watch. I’ve I’ve been around long enough where I remember seeing in San Francisco, like, the billboard of like box, just basically saying Microsoft sucks. you know, Uber and Lyft were throne, had a food fight for awhile. That one probably went over over the line maybe. but yeah, my point is, is there’s other examples it could be, for your business, it could be expensive. To like, I don’t know, like it could be, it doesn’t have to necessarily be like a organization or it definitely shouldn’t be a person either. Like don’t ever like just straight up call. That’s just, that’s not cool. Like if you have a problem with a person, call them and tell them your problems, like, that’s it now. Like that’s not, I don’t, I don’t support that at all. I think that’s ticky-tacky and just a sign of just weak character, if you’re just literally, you know, trying to tear someone down for your business’s benefit, 00:31:28 Nathan: One thing that’s interesting, I think is you probably watch some, maybe beefs between individuals is just how many of them, maybe are planned or facilitated in some way. that is interesting. Like someone, messaged me today because, sort of like Nick Huber who’s, has a popular Twitter profile under sway startup. Hopefully we’ll have him on the show soon. He was, he posted something like controversial, which I know is one of his top of funnel tweets, right. To try to get as much attention. And so I purposely like aggressively disagreed with it, you know And then we’re just separately texting, like, Oh, thanks for the engagement, you know Right. Because we know that by deceit, like if he strongly takes one stance and I strongly take the other stance, then like one, no one will think we’re actually mad at each other, but then too, like, it’ll get a lot more attention engagement. So a lot of people are doing. Some version of that. or if you see a happening usually between two individuals often, they’re probably on really good terms behind the scenes. 00:32:26 Andrew: Yeah, I did not know that that’s, that’s me staying in my lane. I, I, I missed it. but yeah. I, mean that’s business entertainment, you know, there’s, there’s nothing wrong with that, but I, think there’s a line to be drawn, you know, like, If you do engage and stuff like that. number one, I think it’s always great when, like, if it’s real and then they like, like, Hey, we’re cool now. Like, you know, we did this in pub and now like, okay, we’re on 00:32:59 Nathan: Close that loop. 00:33:00 Andrew: Yeah. I think, I think that’s really cool to see. but yeah, public food fights, not my thing. don’t have appetite for that or any advice, but I will say, I will say Nick is coming hard on some, some of the stuff I’ve said, like, 00:33:16 Nathan: Whole angle. 00:33:17 Andrew: Yeah. The, the one thing I’ll say about that though, that style like shit posting, you know, I was like some view of like VC funds just based on like shit posting and stuff like that. what I’ve noticed, ‘cause this, this actually, this is probably a good tidbit for, you know, if you’re considering, beef marketing and what happens is you draw in a type of crowd that likes that negativity and it, and that can drain on you. And so if you should ship posts all the time, like a large amount of your followers are just going to be shipped posters, and they’re going to be, then all your comments are like, use a blah, blah, blah. I mean, if you go on Nick’s feed, you can just kind of look, just look at his comments. He has like a million people. Unfortunately insult, I kind of feel bad for him sometimes because I’ve also seen him comment how it affects him personally. I, I don’t know him, so maybe it doesn’t give a shit, but, that’s why, again, I say, stay in my lane. Just keep it positive. Aye. Aye. Microfibers entire marketing strategy is literally just inspire or support encourage entrepreneurs. It did. not, I mean, not getting beefs with people and stuff like that. 00:34:33 Nathan: Have you. like, there’s the side that you’re, you’re taking of, using your personal brand for marketing, you know, growing a Twitter audience, all of that. You’re very off the cuff of like, you know, just firing off, tweets or things that you, you think about. But at the same time, like you’re a professional marketer and you tend to, from my new at you and other places, like you’re very methodical, you tend to attract things really well. Do you track efforts that go into Twitter and Like how that translates into, you know, deals on MicroAcquire or new buyers or sellers, you know, like listing listing companies or any of that. 00:35:10 Andrew: So I’m a big believer in, so David can sell from drift said this really well where, I think I might’ve mentioned this to you the last time we talked, but, he, he broke it down into like three phases where, we’ve gone through three phases of SaaS. Like the first phase was invention murder. The first person to kind of build a tool one, the market. And then the second phase was the first company to really figure out the best, go to market strategy, like LTV to CAC, you know, AEs STR ratio who could, who could land grab the market fast enough. And then right now he says, he calls what we’re in today, the Procter and gamble phase, which is your brand. So it’s most defensible part about, your business is your brand. Your technology can be copied. it’s easier than ever to raise capital to build a team to do that. There’s also other things like your culture and your team’s talent and just, you know, again, your unique insights into the market. People can copy chapter one, but not chapters two and three and four that you have planned. so I think a lot about that, a lot in terms of just brand and market reputation. But So, no, we don’t, I don’t measure it. when a tweet goes viral, like the one you just mentioned, I don’t look at the comments because when a tweak gets like a thousand likes 00:36:33 Nathan: Yeah, 00:36:34 Andrew: Is gosh, like the questions and the people like disagree with you and just, you know, you start to enter, it’s like, you’re in a stadium of, you know, 200,000 people are reading this and then like 200 people have comments, not everyone’s going to be like, yeah. Like half of them are going to be like negative stuff. So, yeah. So I, I push, I push away all negative energy. So if, if it’s not positive, I’m over it. 00:37:05 Nathan: W what you’re describing is interesting of the city of idea of, if you think about it, like maybe your immediate group of friends, you post something, the people who reply right away, you interacted with them a bunch, like that’s who’s on the field or whatever. And then the next group is like the coaches, the diehard fans, like the re the support staff, everyone else, like those are your Followers. And then you can tell every time that this tweet goes beyond that, because you start to get, like, I had one on company culture that, was like a thousand retweets and went really far. and you could just immediately tell when it had gone to like two levels beyond the people who follow me, cause it just, it went totally off the rails. And you’re right. That the only thing you can do is like mute your own thread and move on. 00:37:50 Andrew: Yeah, I just, and you could tell, cause I usually will like everyone’s tweets just cause I respect everyone’s opinions, like bringing, Nick back up. He, I remember I had a tweet, just something about how entrepreneurs that have maybe struggled in their childhood, have an advantage. He came in with like a strong disagreement and kinda, but I respected it. But then I, we, we kind of close the loop with like, Hey Mike, I think you’re taking this out of context. so I’ll respect everyone’s opinion, but once it goes, you know, I’ll like all of, them. And then once it goes viral, that’s when it’s like all, everything is just nuts. Like, you know, I can’t, I would never want, I can’t keep up with it. And then too, I’ve probably already moved on to like three or four other tweets that, you know, I’m thinking of or something like that, but I think, I think that’s another important side of, just social media in general is just understanding like everyone has a right to their opinions. So even if people do strongly like disagree, that’s awesome. You know, everyone is entitled to their opinion. Everyone has, You know, unique view of life And how things work. and I respect all those opinions, but I think one. thing about social media that can get kind of crazy is when you’re taken out of context, I’ve had that happen a couple of times. Like the one time with Nick, maybe, he took it as I think like, people with really great families, you know, like divorced dads make less than married men. and I, was like Nick, no, this isn’t about diverse families. It’s just about like entrepreneurs struggling with when they grew up. Like I were Joe, and then I had another one. This one was, this is a crazy one. I had one, I tweeted out. Hire people you’d be friends with. And that was, literally someone literally took that as far as saying, nice job describing why tech is sexist and racist in five words. And I, and I was like, what? And I was hanging out with my sons. I didn’t have like enough, I didn’t catch it in time. And so I come back, to my phone and I had to delete the tweet. And then I actually, you know, put more con like, Hey, I meant that as like, you know, hire people, you’d be friends with and you’d care for them personally and professionally, not just hire a bunch of white people or something like that. Like what? So sometimes you gotta be careful, when that kind of stuff goes down. And it’s also just fascinating how people can, again, their, their perspectives, like their perspectives and their viewpoints. you know, you can say one thing and it means one thing to you and something completely different to someone 00:40:47 Nathan: Right. Yeah. I remember a time that Josh Pigford, for bare metrics, had a tweet about concerns in your, in a resume when someone, you know, has had 10 roles in 10 years or kind of thing, or like jumped between roles every 12 months. And that, I I’m not even fully sure why, but, but that one, like he got jumped on in a very similar way of people taking out of context and saying like, this is what’s wrong with technology and 00:41:14 Andrew: Let’s talk about that for a second. So when you’re, when you’re taken out of context, Just admit it, just say, Hey, that, that this is not what I meant. And then I recommend is deleted tweet, and just clarifying, just like, Hey, I wrote a tweet, this, this is what I actually did. I deleted the tweet. And then I said, Hey, I had a tweet taken out of context and it’s obviously a little embarrassing, you know, but it’s the right thing to do is like, Hey, like that’s not what I meant. So also admitting, you know, that’s not what you meant, but clarifying when people like, that’s not that that was not my intention of those five words in any way, shape or form, even like, that, that, that experience was so far off. I still kind of scratch my head on it. But my point being is, you know, it, you know, take one back, like, Hey, listen, I, I said something, it was taken out of context. I apologize. this is what I really meant for further clarification. And it’ll just make your life a lot easier instead of trying, to defend, because I know the thing is if Mrs. Also I don’t really comment too much on social media. Number one, it’s just exhausting because you can have so many, then you’re like a, full-time like customers support person on Twitter. again, you know, once You kind of engage with someone who vehemently disagrees with what you’re saying, or has taken you out of context, it’s really hard to change their opinion, if not impossible. So even trying, once you, if you just try you lose. You just start throwing food and stuff like that. So that’s just kinda some of the crazy stuff I’ve seen happen on, on Twitter as, you know, gone a little bit more active. cause I, I wasn’t active on Twitter, so all this is like new to me too. I’m still learning like, oh shit posers. I didn’t, I didn’t know those existed or like, oh wow. You can get really taken out of context and it can go viral and people can say some mean things. So yeah, my, again, going back to just saying I stay in my lane and just talk about stuff that I liked it. Talk about. 00:43:35 Nathan: I like it. something else that you’ve done that I hadn’t seen other people to do before, but I get it as a strategy. so separate from like just sort of specific, but it’s using cameo and using spokespeople on cameo. for your business specifically, you got Chris, demon topless from Silicon valley and all of that to do announcement videos for partnerships and one they’re amazing. but like w where did that come from? And, how’d that turn into something that like, And, now if someone says like tres commas, like in relation to micro choir, everyone’s like, oh yeah, that makes sense. 00:44:15 Andrew: So for the longest time, it was just me running Mike requir. I was a solo founder. and on the team page, we just like, as I was working on the design with, I initially use an agency to help with, the development. And, there was a team page and I was like, ah, just put Richard Hendrix, Gavin Belson, and Jen yang from Silicon valley. And it just kinda was, I just thought it was cool. And some people like, you know, called it out and was like, are these really your team members? And I’m like, yeah, they were super harder recruit. So I’m, I’m a huge fan of the show because it is shockingly accurate and just hilarious. and then, yeah, so I actually, you know, before, like right when I launched my crew choir, I. When on cameo saw Russ Hanneman Chris. I can’t pronounce his last name off the top of my head, but, you know, he was available and he was like my favorite character. And I was like, yeah. W do you want to talk about my group choir? And since then we built, you know, a pretty good relationship in terms of, you know, just working with them. And he’s a really great guy. Like he’s a really, really, really nice person. but my point here is I’m always thinking about what’s, I’m always learning and I’m always trying to think of what is changing in marketing today? For example, the marketing playbooks that worked five years ago don’t work as effectively today because everyone adopts them and starts using them. And then it starts to, feel like marketing and the best marketing doesn’t feel like marketing it’s entertaining, or it, captures your attention in a way where you go, whoa, I haven’t seen that before. So I’m always trying to think of unique ways to, capture or actually I should say, earn audience attention rather than buy it, or, you know, writes an ebook and engaged it and get your email and then send you 30 trip emails, which worked fantastically a decade ago, which killed a decade ago. But So that’s kind of where the thought process and then candidly. I would say, I might laugh the hardest out of those videos. So it’s like my like guilty, like pleasure. cause you know, they’re not free. So like, you know, I, I probably am lapping the hardest, like when those go out. 00:46:46 Nathan: I’ve I’ve laughed pretty hard at a lot of them, especially as like, they end up in a series where they like build on each other. The, he uses jokes that he first coined and, you know, first video. And, 00:46:58 Andrew: Yeah. a little background on that too is, I didn’t tell him to make up anything like he’s made of like gas Decky style, micro Gaz, micro, and like, I don’t tell, I just basically, cause you’re only able to write in like two sentences and he he’s just a hilarious person. So any startup looking to, you know, announce something, I highly recommend checking it. 00:47:21 Nathan: I guess how has the business side of it work? Right? Cause if you go on, on his page in particular, it says $349 for personal use or 909 plus for business use, which makes sense that there would be a split there because you’ve obviously gotten a lot of earned, earned, attention from those. how does it work actually on the payment side? 00:47:41 Andrew: In terms of like using Kamya. 00:47:44 Nathan: Yeah. Using cameo, maybe using Russ specifically. Well, Chris, not Russ. But using him specifically or, you know what you’ve done, you’ve done with, other people on cameo. 00:47:56 Andrew: Yeah. So he’s kind of the only we did a partnership with Clearco and I had like the game, the rapper, duke came here just because I kind of went on like a cameo binge, like I’ve been a fan of you forever. 00:48:12 Nathan: Cards on file. You know, you’re just like 00:48:15 Andrew: Yeah. I was like, I’d love for you to just say micro choir. Like this is awesome. who else did we get? I can’t remember off the top of my head, but, what’s been interesting to see what Chris is. when I first booked him, he was $200. Now he’s 5,000. So he, has definitely, you know, made some waves in the startup community. And So it’s, it’s cool to see him like, you know, making people laugh and helping startups get exposure and then raising his prices too, which is, I think something that, you know, most startups should do. So he’s done a very good job of that. It, it went from like one K to two K to three K. Now it’s at like, 5k, so he’s expensive. 00:49:00 Nathan: So that’s like when we see something like that, right. If the nine and nine plus, in the buying process, then later, does it tell you like, oh, here’s like once you fill out, the initial form, it’ll tell you what, what the price is or how’s that work? 00:49:13 Andrew: So there’s, there’s a personal use. So you can use his personal, I don’t know his like personal cost, but let’s say it’s like 500 bucks and that would be for like a birthday wish or something like that, which can be a great way to motivate like your team, like, Hey team, great. You know, Q1 or Q4 that’s ending, here’s our goals for next year, you know, made, they want to me to give you all shout out, that’d be 500 bucks, but then a business use where you posted, externally, so on Twitter or social media, or, within some sort of piece of marketing content. The price for that is usually 10 X, you know, internal use. 00:49:55 Nathan: Did any of the other ones that you tried? Did you feel like they got attention or that kind of thing make you want to do it again? Or was it more just the ones with Chris that really resonated. 00:50:04 Andrew: I think probably you’ll see less cameos, out of me, I think, you know? there, there, there gets to a point and we could, we could probably have another podcast about this, about like things with diminishing returns. And I think I’ve kind of, you know, used them so many times that, I mean, for the really big like, announcements that we have coming up, like maybe twice next year or something like, that but I think there’s sort of a diminishing return, especially with the cost, you know? I think building in public kind of falls into that category a little bit. audience exhaustion in terms of like paid ad campaigns. you know, so I’m always thinking of that stuff too. I like, are we overdoing it? cause then it just kinda starts to get corny is when you’re doing it over and over and over and over. and it’s not really like, whoa, he’s here. Like I didn’t expect this. And when it starts to become expected, I think if there was just kind of a little bit of luster. 00:51:05 Nathan: Yeah. That makes a lot of sense. something else that you do a ton of is partnerships, whether it’s with PYP or angel list or whoever, it feels like micro choirs coming out with a partnership. Every, I don’t know what the actual cadences, I feel like it’s every two weeks to a month. what’s the, what’s the strategy there. And is that like a very deliberate, marketing strategy or is it just like, look, this is a natural fit. And so we’re just going to do a better job. It made sense to do the partnership and we’re just going to do a better job promoting it than most people do. And when they come out with a partnership, 00:51:35 Andrew: Yeah. I mean, so the pipe Clearco Angeles partnerships all made total sense. They help startups get acquired, which is, you know, the purpose of our business. And, you know, our, our main metric of success is helping startups get acquired. So helping them get financed, increases the buyer pool, which then can lead to more acquisitions. So there’s, those made a ton of sense. and then we also want to expand internationally. So we partnered with, essentially like the angel list of, Africa that serves 40 countries in Africa. And so I thought that was a really fun partnership in terms of, you know, helping, really underserved. areas of the world, or support underserved areas of the world with my group who are in terms of, you know, just our message and just our encouragement and we’re going to continue those. So we’re looking, actively speaking with, individuals that are, you know, accelerators or like, start a boot camps and like Turkey or Europe or the UK or Australia. I have a number of conversations, but we’ll probably go a little lighter on those because I also feel like the partnership thing is it’s like, okay, another part is another partnership might require really. but that’s, I think partnerships are, what I would call a non-linear growth strategy. So it’s basically, you know, what you’re doing is you’re leveraging, you know, number one, Another company’s brand So you’re, you’re borrowing some of their brand equity saying like, Hey, we’re partnering. So their capabilities are now part of our capabilities and vice versa. so there’s benefits on both sides. And then you know, with products that, you know, pipe clear co and Angeles offers specifically, it adds value to our product. So it’s like a win, win, win. It’s a, it’s a good marketing play, good brand play. And then it’s good. Just, you know, product play without, a lot of, you know, engineering needed. 00:53:41 Nathan: Is there, like, do you have engineers internally just devoted to, you know, these integrations or, or did they tend to be more on the marketing? you know, our business ops side rather than on the product side, because then they can be expensive on the product side. 00:53:55 Andrew: Yeah, they definitely can. I would say they’re more. On the marketing side then on, like for example, the angel is partnership is just a landing page that so Avaloq, the CEO of Angeles is an investor in might require and then evolve in an investor in my rewire. And so I just asked, I pointed out this other company that was making an SPV product for private equity firms. And I just said, can you make me a landing page? I’ll promote it. And so inside my group where there’s like a drop down that says raise bonds, and then it takes you to a landing page. So minimal product integration there, but it’s just kind of like us saying, Hey, if you, if you’re looking to raise funds, this is where we recommend you doing it. We’ve done that with mercury bank as well, which is just, again, you know, you acquire a company, you probably want to transfer those assets and do a new entity. That new entity is going to need a bank account. So we’re just kind of getting all the re they’re almost like perks. If you will. 00:54:54 Nathan: Yeah. That makes sense. And then it’s not this big integration that you’re having to maintain for years to come or. 00:55:01 Andrew: Yeah, no, it’s not like a, like a Facebook, like a, you know, SSO log-in or something like that. you know, it’s a, it’s a lot simpler. It’s usually just like a lane kicking over to a landing page, you know, driving traffic to them and then we get some sort of kickback for whatever business we drive to them. 00:55:20 Nathan: Is there anything in particular that’s worked well on, like the partnerships that have been a, a, huge boost, right? Where either you’ve gotten a bunch more attention for Mike require built the brand. Like, are there things that you see in common on those ones where you’re like, yes, that was a home run versus the ones where you’re like, I think that was worth the time to put together. Maybe 00:55:40 Andrew: Yeah. I mean, I’d say, I’d say all of them, I’d say my favorite are definitely the Clearco and pipe partnerships. like. Hers is he, oh, he bought me this to kick off our partnership. It’s assigned Mike Tyson glove and we’ve done a number of acquisitions together. I think their company’s fantastic. I love working with our team. Clearco same thing. So pipe, I was finance all of our SaaS deals exclusively, and then Clearco all of our e-commerce deals exclusively and they’re just great teams and it’s a clear need. You know, some people want to finance these with, these companies and we make it extremely seamless to connect to those companies. And we even do like pre-financing. So if you’re a founder looking to sell on Mike required and you want to give a line of, you know, potential financing in advance to a buyer, we can, pre-approve a seller. So it just makes kind of the, you know, when you’re going to buy a home, it’s like it’s pre finance or something. I don’t know if that’s a good analogy, but, those are, those are partnerships that really add, like they were on the product roadmap and they just, you know, we just went to the best ones in the market with the most credibility, with the largest capital pools. but also with the engineering resources. So, you know, anytime a company is, you know, financed through pipe, we get a notification within slack. It says like, Hey, add preapproval number to this company. So we just, we, instead of working with like a ton of different financing partners, we just pick the best ones and then then integrated deeply with them. 00:57:23 Nathan: That makes sense. One of the things that I wanted to ask about before we wrap up is, on the sort of the investor influencer side, you have a lot of people, like know, you mentioned Deval and, and others who, have invested in MicroAcquire. And is that, helping of like helping you you know, amplify some of these things on Twitter amplify, these partnerships, open doors in some way. Do you think you get something similar with like a influencer program or has the investor side really been a good, good angle for that? 00:57:54 Andrew: Yeah, that’s a good question. So yes, there’s definitely the group of investors that my career has is like all my, like idols, like, you know, founders of companies that, you know, I like, you know, Dharmesh from HubSpot, Neval like, From Angeles, like those are some of my favorite companies and I get to, interact with them on a, on a very limited basis. I don’t reach out to them for advice, very often. So I think that also adds to just, you know, brand equity of just, being a marketplace, you know, and us wanting to build this with the startup community. That was kind of more of the thought process behind it. But now, I mean, you could even look at my likes. I, I ha I, was, has evolved over, liked something of, mine now has Dharmesh maybe once, like, so now I don’t rely on them for like social media support or anything like that. but it, it is, a good way in terms of, you know, when you raise your entreprenuers, you get kind of, again, unique insights because most of them have been through MNA. so, so typical VCs, but, I, I really liked that, style of, of fundraising is when, obviously I’m a bigger advocate of bootstrapping because that’s kind of, you know, where I’ve spent, or had the most success. But if you’re gonna raise capital, I, I recommend entrepreneurs for us because they have experienced building a business. And then typically with, you know, acquisitions specifically in my case, which is you know, extremely helpful. 00:59:33 Nathan: Yeah, you and I are both known for bootstrapping. And we’re also, I think, pretty well known for not being that dogmatic about it, of being like, here’s what we did. Here’s why it works well. Here’s why the other path can be fine too. you know, rather than being super dogmatic in one camp or the 00:59:49 Andrew: Yeah. That’s one thing I’ve noticed since being vocal about bootstrapping that I think is a little toxic; if you’re funded, it’s like, I hate you. Then, if your bootstrapped, venture capital’s just a tool. If you know how to use the tool correctly, it can be a great accelerant to your business. Everything comes with a cost. So, when you bootstrap, you have to kind of eat glass for much longer. I’ve lived that life, but at the end, the rewards can be epic. So, if your goal is to make money, you should probably bootstrap, because you can sell the business whenever You want. You have no approvals. You own the whole thing. Nathan, if you wanted to sell your business, you don’t have any investment or approvals, or anyone saying, “No, you need to hit that billion dollar mark.” If you want to really disrupt the market, or change a market or, go a little bit bigger, faster, venture capital is just a tool to accelerate that. It all comes with a cost. The cost of bootstrapping is, sometimes you have to do customer support for longer. You have to do some of these roles where you can’t bring in talent earlier. The cost of venture capital is, you give it back equity and control within your business. There’s usually controls. You need approval to raise capital. You need approval to sell your business. So, everything comes with a cost, and it has pros and cons. I think bootstrapping makes sense for 99% of entrepreneurs, because the bar today is building a billion dollar business, and that’s not easy to do. So, for many first-time founders, I’m a big fan of stair-stepping and entrepreneurship. One of my favorite tweets that I’ve ever written is, “Start with an agency, get to cashflow positive, and then bootstrap an asset—whether that’s a SaaS company or your e-commerce business—sell that asset, become financially secure, and then do whatever you want.” Swing for the fences, go on a beach, whatever. Along the way, you prepare yourself for the next stage of business. 01:02:24 Nathan: Yeah, I completely agree with that. I have an article titled “The Ladders of Wealth Creation” that touches on the similar idea of using the skills from one ladder to move up to the next, and go from there. Well this has been fun. I always enjoy watching the partnerships, what you’re doing on Twitter, and everywhere else. I think that MicroAcquire is a great example of what you can build with an audience. Thanks for coming on and hanging out with me and, and we’ll have to talk soon. 01:02:52 Andrew: Yeah, Nathan, thanks for having me, man. I enjoyed the chat. 01:02:55 Nathan: Alright. Catch you later. 01:02:56 Andrew: See you, man.0 comments0
- 057: Sherrell Dorsey - Getting Your Newsletter Open Rate Near 50%Sherrell Dorsey is the founder and CEO of The Plug, a publication and community for news, insights and analysis on trends in Black innovation. The Plug features stories that show the substantive ways Black people engage with the innovation economy, including analyses of modern technologies. On today’s show, Sherrell shares about building an audience and growing The Plug. We talk about sponsorships, The Plug’s revenue model, and her background in journalism and how she brings that into her current work. We also talk about choosing a niche, staying consistent, and much more. Sherrell has worked in marketing and consulting for companies such as Uber, Tresata, MarketSource, and Build The Good. Sherrell has also worked as a correspondent for Fast Company, Essence, Next City, and Black Enterprise. She earned her master’s degree in data journalism from Columbia University. In this episode, you’ll learn: How to grow your subscribers when first starting out Different strategies for monetizing your newsletter The right way to include advertising in your newsletter Tradeoffs between having a team and working as a solopreneur Links & Resources Clay Hebert Monica Melton Farnam Street Shane Parrish Ryan Holiday Daily Stoic James clear Uber Google Fiber Microsoft Fast Company The Root Black Enterprise GoDaddy theSkimm Signal Bloomberg Terminal Business Insider The Moguldom Nation Sherrell Dorsey’s Links Follow Sherrell on Twitter The Plug The Plug newsletter HBCU newsletter TPinsights.com Episode Transcript 00:00:00 Sherrell: I think that we’ve gotten into this very fast pace, and this idea of constant information and voices in your head. I don’t know that more information is making us a better society. I think that this idea of community and grappling with ideas, calling things out or bringing things to attention, but having something meaningful to say really outweighs just being visible all of the time. 00:00:31 Nathan: My guest today is Sherrell Dorsey. Sherrell is the founder of The Plug, which is a newsletter, and really a publication at this point, about the black tech ecosystems and all the interesting things that black and brown founders are doing in technology and business. She started in 2016, and she’s built it up to have a full-time team of five people now. I’m so impressed with what she’s built. We get into talking about sponsorships, the revenue model, how she built the audience, her background in journalism, and how she brings that into what she’s doing now. I actually grew up in tech and some of the ecosystems that she was a part of that inspired her. We talk about choosing a niche and staying focussed there. We talk about consistency. There’s really a lot of things in this episode. I love what she’s doing and how she’s built this niche business into something that now employs full-time journalists. At a time when a lot of other publications are dwindling, she’s growing. So, let’s dive into the episode. Sherrell, welcome to the show. 00:01:35 Sherrell: Thank you so much for having me. 00:01:37 Nathan: I actually want to start talking about experimentation. We’re going to jump around a little bit. You like to run a lot of experiments, and you’ve taken an approach on experimentation where you’re doing it at a stage in the business where you have a lot going on. A lot is working. This is a point where I see a lot of content creators freak out and stop experimenting because they’re like, “This is what my audience likes. I have to show up in exactly this way.” So, they don’t experiment. Even at this level of success, you’re like, “No, experimentation is a core part of what we’re doing.” Could you talk about that, and some of the experiments that you run, and then your mindset around it? 00:02:12 Sherrell: We’re constantly challenging ourselves as a team, and trying not to get bored. Part of our experimentation may have more to do with the attention deficit issues that we have as a team, as a collective. Maybe not as much as our audience, but we also assume that they also have attention issues. Let’s be honest, there’s so much competing for our audience’s attention, right? I mean, outside of the inbox, theres social media, there’s the day-to-day of all the crazy, all the push notifications. So, for us, experimentation really is at the core of challenging ourselves to face something new and interesting, and really tapping into what. The sort of timeliness of news, and really finding a way to put it into our voice and share some of our opinions as well. Even with running The Plug’s weekly briefing experimentation is really even just how I got started. The Plug for me was an experiment. I was getting up at 5:00 AM, pulling together a newsletter, wanting to cover diverse voices in tech. Doing it just as this labor of love, and also nerdiness and curiosity, and it started to grow. Then I said, well, maybe I can do this every single day. Then I did it every day. Then at some point we realized, hmm, are people having inbox fatigue? What if we slow things down and really make people cherish every single sentence that we’re writing in our newsletters, and giving them a long and deep side of slow conversations on Monday mornings as they’re starting their day. We’ve seen those questions that we’re asking kind of manifest in this idea of experimenting with just our curiosity. We’ve seen that well, I mean, honestly, Nathan, we’re getting 45% to 48% open rates on every single newsletter, and it has been pretty consistent. When we were in the daily phase, we were starting to see those open rates go down. People just didn’t even have enough time to read. So, again, we start with the question, “Well, what if, or how do we personally sort of engage with our news and with our information, and how do we create a moment of almost intimacy with our audience and our subscribers?” Where instead of just having the breadth, we can actually have the depth. 00:04:40 Nathan: Yeah. I want to talk about the consistency and the schedule later in the episode, but let’s go there right now because I think a lot of people, when they’re writing their newsletter, they struggle with how often to send. And, you know, if you look at someone like Seth Godin who publishes every day and has done it for, I don’t know, decades at this point, it’s like, oh, I should be like Seth Goden and publish every single day or send out, you know, a newsletter five days a week. But one that’s incredibly hard to maintain. And then two, I think you’ll see exactly what you’re talking about. The engagement and interest drops off, too much of a good thing is still too much. What do you think about that? 00:05:18 Sherrell: I think that we’ve gotten into this very fast paced. I mean, I, you know, Twitter became a thing when I was like exiting undergrad and this idea of just constant information and voices in your head. Was kind of standard and status quo. And I feel as though now we really wanted to hyper focus on how do we get people to sit with ideas and thoughts before we kind of bombard them with just more information. And I don’t know that more information is making us a better society. I think that this idea of community and grappling with ideas, you know, calling things out or bringing things to attention, but having something meaningful to say really outweighs, just being visible all of the time. I think especially with the newsletter, with the newsletter, you’re telling stories, you are bringing ideas to the forefront, you’re surfacing news and information for people to kind of ruminate on. And then we can kind of hit people later on in the week, which we do with here’s opportunities to engage further. Or did you check out this data set that we’ve pulled together that will allow you to look at. How HBCs are graduating, like the top black engineers in the country. And so for us, it’s about what is the value that we’re providing to our audience? Why, why would they want to continue to open the email instead of just, let’s be there for the sake of being there, you know? And it’s like, it’s like small talk at networking events where like people are pushing their business card on you. And you’re like, I don’t ever want to 00:06:50 Nathan: Okay 00:06:50 Sherrell: You ever again in life. And we definitely did not want to be that like pushy networker. We just wanted people to be able to sit with us, have a cup of coffee, have a tea, and just, you know, Really, really, connect with us and our work. And so, thus far, you know, like I said, we really saw our open rates increased drastically going from the daily into that weekly and it being meaningful. And our managing editor, Monica Melton, who was our first employee at The Plug has really, really ramped up subject lines and experimenting, in AB testing that has been so beneficial in terms of how the newsletter is being received. 00:07:36 Nathan: Well, that’s something that you just can’t do when you’re on a daily deadline. I’m trying to rush out on that scale, or you have to have a much larger staff to be able to bring that level of thoughtfulness and testing to each piece of content. 00:07:50 Sherrell: So true. So very true. I mean, you know, we’ve always sort of operated and I think most startups, you kind of have to do more with less. And I think from the standpoint of delivering higher value really wanted our team to be able to think through, well, what should that Monday newsletter say? What are the opportunities that we can really present to our audience that are thoughtful? Even during our editor, our weekly editorial call, like we, we, we really deep dive into what are some of the top issues? What do we think about it? We really get to massage it out and be thoughtful. And I don’t know, even if we had a larger team, maybe we would do more, maybe, maybe less. General newsletter, maybe more profiles would be really nice. And we’ve recently launched a new newsletter as well. it’s kind of the niche of the niche. our incredible HBCU innovation reporter recently launched an executive newsletter for those who are recruiters, HR professionals who are really trying to understand how do historically black colleges and universities play a role in the future of work and just breaking down stats, breaking down the kinds of patents that are being developed, breaking down the kind of research coming out of these institutions ways in which to engage with faculty, new entrepreneurship centers, all of these like really incredible stats that you don’t really hear on a daily basis. So that now that is a subset where now we have increased the cadence of our newsletters, but we’ve created that for a very specific niche within the niche of audience that we serve. 00:09:26 Nathan: You said something about it’s almost the environment that your newsletter is received into of your app. Like telling someone slow down, this is be thoughtful. This is a thoughtful part of your morning. Like have your cup of coffee, have your tea. And I’m realizing that as a newsletter creator myself, I often don’t think about like, I’m not asking. The reader to get in a state of mind to engage with my content or get in a physical space. And so this is it’s interesting, I haven’t thought about before and it would change the approach to the content and it would for sure change the approach to the writing because instead of going okay, punchy headlines quick, this is for the busy professional, reading it on the subway, you know, like that’s one style and it sounds like you’re hitting in a completely different style, I guess. Tell me more about that. And then the other aspect of it is what are the ways that you reinforce that message to your readers? Cause it’s one thing, if you think in your editorial room and conversations, but that you have to actually translate that to the reader so that they feel it as well. 00:10:31 Sherrell: Yeah, we just didn’t want to be forced to speed up. honestlyit was who I always liked this idea of, of slower journalism. I grew up such a reader like my mom and I get up on Saturday mornings and go to Barnes and noble when like bonds. And like when we actually went into bookstores, right. She would like leave me in the kids’ section. And I would just like, get a mountain of books and just sit and read. And I always think about that opportunity of like just saying. And reading and in sitting and like digesting ideas and information. And when I think about some of my favorite newsletters, I think about, the, the Farnam street blog and, and Shane Parrish, Paul Jarvis used to write an incredible newsletter. There’s just so many incredible writers and thinkers that create these kinds of long form pieces. I think, right in holiday and the daily, it does a really interesting sort of long form, you know, he does, he definitely does like the, the Daily of course, cause it’s the daily. but these kinds of newsletters that really made you think about the world around us and sort of the new ideas that are emerging and. I felt as though, as we were starting to deep dive into this Nisha space, of course we cover black and brown innovators, future of work, future of business, inclusive business ideas that are highly data-driven. You have to really sit and think about what this data means when it means within your work. And it’s not just like a flash in the pan, series or subsets of ideas. It really is how do I take this and apply it to my work and everyday capacity. So we didn’t want to just give like bullet points of actions. It was more of, you have to apply this in your world in your way. And so I wanted to kind of recreate that to an extent. and as I mentioned before, you know, experimenting with. Subject lines and titles and flow. And I mean, even just organization of information, you know, there’s always sort of the backend analytics that you can take a look at. What are people actually clicking on? What kind of things do they care about? serving our audience, a great deal to understand what they want to hear more about. I know that there are a lot of investors who subscribed to us who are always looking at our startups to watch section, and just the fact that people are able to kind of read this very long email and find a section that resonates with them and decide to take an action from that. That for us really demonstrates kind of a metric that we did not even anticipate going into this. And that really has to do with listening to our audience, quite frankly. 00:13:11 Nathan: Yeah, that’s good. I have more people will take that approach. cause I think. Now you say that and noticing that trend in a lot of these newsletters, like Shane Parrish, or like James clear, some of these others that have been going for a long time and built these substantial audiences is there’s a level of intentionality that really makes it unique in that way. Let’s go back. And, now that we’ve gotten into some of the tactics and the high-level things, let’s talk about, you know, actually starting The Plug. So you started in 2016, is that 00:13:39 Sherrell: I did. I started at 2016 as a labor of love. I had been writing freelance. I was working in tech, so I am an alum of Uber, as well as Google fiber, Microsoft and high school. I like worked, as an intern and like tech was always just such a big part of my life. And I grew up in Seattle. So it’s like, go figure of course, like the girl that like grew up in Seattle is like a tech person. So, so it was always a huge part of my life. And what was really cool about my experience in Seattle is that I was trained in coding and network administration and all these really cool programming language and languages from a woman who was a retired software engineer from Microsoft, who like converted a storefront. And she was like, I want to teach inner city kids like about technology because. I’m female, I’m brown, I’m gay. Like there’s not many folks like me in this space. And like, I want to create back in this space. And so my experience was just so unique. And when I got into the workforce and the conversations that were happening in media did not include voices from folks like myself or from Trish who started the center that I went to. And the folks who kind of raised me while I was at Microsoft, who were from all kinds of backgrounds and all kinds of experiences and like would burn me like, remember back in the day when you were burning, This amazing mentor who like she was like, burn me, like all of the Mo like the brand new heavies, most Def like all of these, like really amazing like albums. And, you know, at the same time, like teach me about like walking through this space of tech in a very male dominated field. And so when it come to the workforce and the media was kind of always a grandizing like all of these men and their ideas about the future, I was like, well, I’ve met some really like dope, you know, women engineers, or really dope, like black software developers and test engineers. And, I shared, you know, office spaces with, you know, incredible like female engineers from India. And I just did not see that like thought leadership component coming from these different facets of society. And I was like, well, you know, I want to start covering communities outside of these kinds of normal technical. Right. And I also was just walking through the world in living in places like New York city, living in Charlotte, North Carolina, even Bridgeport, Connecticut random. And just really finding these genius ideas and people in business leaders who were kind of unsung to a degree, but were working on really hard challenges and finding some success. So I had been kind of freelancing and, and writing for fast company, the route black enterprise and sharing these things. And I started to kind of become known as like, oh, like she’s like the black girl Tector list. Who’s like trying to cover everyone. and so at some point, you know, I got to a point where like, I really want my own column. I really want my own column. And you know, I think editors thought like, okay, your writing is okay, but it’s not like, great. And like, this space is kind of cool, but like, that’s just not what we do. And so, you know, I was like, okay, I’m going to spend my $10. I go daddy and buy my domain name. And I’m, you know, people were already calling me like The Plug, like, you know, where everything is, whoever went is, you know, what’s happening, what’s going around. And so I just started like this newsletter, I just went for broke and it was like, I’m going to create this daily newsletter. I’m going to get up at 5:00 AM every day and let’s see what happens. It wasn’t a business yet. Nathan. It was just an idea. Like, let’s see if I can kind of create an environment where we are covering, you know, innovation from the perspective of communities of color, startup leaders, VCs, and grappling with like really interesting ideas and trends. And then also sourcing storylines from around the web. So that went on for about a year and a half. but about six months in is when I got like, we got our first corporate deal and I was like, oh, you want to give me money for this? Hm. I wonder what I can do with this. and, and that really enabled me to really get started and bring on some freelancers to help support the production of the every day. And at some point we decided, you know, following grad school, like let’s, let’s go for the school throttle and see if we can really build a substantive business here. 00:18:15 Nathan: So, what did it look like that first year to grow subscribers? Right? Because going from maybe let’s just talk the first three months going from buying a domain on GoDaddy to the first hundred, the first 500 subscribers. Like what was that process? 00:18:31 Sherrell: Yeah. Well, first I like spammed, my friends and family was like, you better subscribe. so that was, 00:18:36 Nathan: Which I highly endorsed as a strategy, like legitimately, because going from zero to a hundred is so hard. If you’re like, no, I will only do it. people who come in through major publication or like, I dunno, what 00:18:48 Sherrell: Yeah 00:18:50 Nathan: Your friends. 00:18:50 Sherrell: You’ve got to like break The rules and you just have to like go literally go for broke, you know? And so that first hundred, you know, it was really looking at the audience. I had sort of built through my reputation of covering this beat. Over the last few years, like a few years prior. And so, you know, those were people who were immediately bought in, friends and family. I asked people to push up a newsletter very frequently. I was like, shamelessly plugging The Plug and like, Hey, you know, if you like this, like share it with your friends, share it with your colleagues. it definitely was not easy. It was a, it was a kind of one by one getting people bought in. And of course I had the power of social media, you know, on my side. Whereas had I started this like years prior, like in, in, in college before Twitter became a thing or Instagram or Facebook, perhaps I wouldn’t have had as much visibility. some things that also helped to supercharge quite honestly, was like sharing across LinkedIn, just from a professional capacity standpoint. I was still freelance writing as well. So it allowed me to share, you know, Sherrell is like the creator of The Plug and you can sign up here at the bottom. 00:20:02 Nathan: It changes your byline. 00:20:04 Sherrell: I was able to, yeah. I was able to really leverage my, my byline. but it was a lot of pushing. It was a lot of, it was a lot of like asking people to share and to subscribe all the time. 00:20:15 Nathan: Yeah. I was talking to someone, a friend who has a book coming out right now. And I asked him like, how’s it going? He was like, oh, it’s a lot of work. I’m doing a lot of begging right now. You know? And I was like, yep. That’s Write of like, Hey, will you share this? Will you, do you know anyone who could subscribe? Will you subscribe? and a lot of the people who end up like getting traction and making something are the people that are willing to do that. And then the people who are like, you know, I tried this new venture, I put it out in the world and it just didn’t resonate. And so I shut it down and moved on after three months or whatever. It’s like, you dig into their stories and they’re the ones who weren’t willing to, you know, as long text all their friends. And so it just takes that level. 00:20:55 Sherrell: Absolutely. I mean, three months is hardly enough time. I mean, you almost need like a solid two to three years to really, really like solidify yourself. The right conversation, get in the right rooms, build it, that level of credibility. I know some people who are able to do it very quickly. I think you’re, you know, you’re leveraging relationships, you’re leveraging interviews and it’s nonstop. You’re nonstop promoting yourself. And you know, I’ll be honest, Nathan, there’s a bit of discomfort, in promoting yourself constantly. I think also like as a woman, I had to get very, very comfortable. I think that’s something I had to learn in tech of, you know, watching like my male counterparts, like constantly talk about how great they were. And like, I was always so uncomfortable the exact same demeanor. but I had to find my own way to talk about the work that I was doing and what I found interesting. And the more that I did that, I found that again, you know, folks were just subscribing because I asked they actually cared about what I was doing. And even to this day, We are full fledged, you know, running media company. And we have people who were literally those early subscribers who have been with us since the jump. So when we have typos or when we’ve had titles in the past, or we’ve had a glitch or an email accidentally without, I mean, these folks didn’t berate us or like drag us online, they were just like, Hey, just want you to know this link doesn’t work. And I hope you’re well, like I’ve been following you for years. Like I get those emails like every single week. And it is so incredible to really know that like, people have been rocking with you from your early days when you were less sophisticated, less refined, you know, and, but still they, they understand the intent. And they’ve seen that throughout the process of you growing your, your business, that you have been intentional. And I think that that’s the value that they find. 00:23:00 Nathan: Yeah, that makes a lot of sense. what about, well, was there a point in there either three months in or two years in or something where you were wondering, is this working like, should I keep going on it or was it just steady progress without any self doubt? 00:23:17 Sherrell: Wish that I was the most confident person ever. I mean, fine. Find me someone who was just like, yes. I mean, you know, maybe Elon Musk, talking that he knows that everything he does is going to turn to gold. I definitely am not one of those, those individuals. I definitely, would have moments of discouragement, you know, you know, we talked about open rates, right. And I think, you know, sort of like as you’re ramping. Your open rates look really good because your list is, is smaller. And then as your list grows, your open rates change and fluctuate. And, and if you’re not familiar with, with that, it’s really rough. You know, especially when you’re still just learning the tools, you’re still learning the techniques of AB testing or you’re learning the tools of how to really create a captivating subject line or a captivating headline overall. And so, you know, when, as we continue to grow or you see the unsubscribes, right, like unsubscribes are still deflating. Even now years later, Maven is like, oh my gosh, like, why would you leave me? You know, it’s like a breakup, you know, you’re like, why would you ever leave me? And honestly, most people just get overwhelmed. And we, what we saw was transitioning to that. Weekly versus the daily. We’ve seen significant drops in unsubscribes. You know, folks, folks have time to actually read us. They don’t feel overwhelmed with seeing our name in their inbox every single day. but there are, there are challenges for sure. You know, I think that, you know, I think that when you start to kind of compare yourself against sort of others emails or their newsletters or seeing their growth and the tactics that they’re using, and also knowing sometimes you don’t have the resources, you know, we didn’t put money into Facebook ads or any other kind of platform. Everything for us had to be organic and it had to be intentional. And without having a huge marketing budget to try to get across certain milestones. And sometimes that can be discouraging if you’re like, oh wait, like they’re lists maybe twice the size of mine and they’ve not been doing this as long. And they’ve been able to put in the resources to kind of move the needle, or, you know, even in wanting to kind of stay intentional and practice this idea of slow journalism and slow information. When you see others who are like quick flash in the pan and, and they’ve grown exponentially, but it’s also like, okay, we have some of the most engaged readers ever. You know, again, people who will show up will continue to show up to our events when we do something in person, or kind of contribute and show up to our virtual launches and things like that. And so I had to always kind of refocus on who my audience is and who has really stayed and stuck with us and the value that we deliver because the outside comparison will definitely. Kill any kind of confidence that you may have and, I think overall we had to get out of the game of becoming like the wonder kid company that sells to some major entity 12 months in, I think there was just this huge rush, especially with media newsletters of like, oh, you build this up, you work, work really hard. And then, you know, the New York times comes and purchases you, right? And like it’s kind of far and few between. And if we’re playing that race, you know, if we’re playing that kind of game, it’s, you know, it’s, it’s, it’s not necessarily the right north star and being rushed into this idea of what success looks like. We have to really redefine for ourselves and what, like our core values have been. And we have to revisit that time and time again, and really just focus on delivering the best value that we can deliver. 00:27:04 Nathan: Yeah, it sounds like you have a long time horizon, which I think is really, really important because so many people are. They’re focused on like, okay, this has to work in the next month, the next three months, the next two years. And you just, you burn yourself out. Like I I’ve been working, in six weeks. It will be the new year. And I will have been working on convert kit for nine years and like, realizing that I was like, oh, this takes a long time. And you get those best compound results over. It’s just a lot of time. 00:27:33 Sherrell: It takes a while. Good things. Take time. And it’s really hard. you know, I’m a millennial and everything where we want it to have everything like yesterdayandwant it tolike Right. I mean, yes, of course, absolutely. Like, that’s why I don’t cook. Right. Like Uber eats me please. So, it humbles you to really understand. I always, I always say, you know, like we’re understanding our own minds right now. we had to kind of go through our mature, our maturation phase of who are we? What is our content and our work stand for who is our audience? You know, having to kind of make those shifts and adjustments as we grew, the newsletter that we started is not the newsletter that we have today. We. We are going to have this highly kind of consumer driven newsletter. And as we started to look back at emails and names and titles, we kind of quickly realized, yes, our folks are kind of on the, on the periphery of like being consumer based. But these are people who hold really interesting titles at top tech companies, or they are, you know, coming from vaping companies. And so it really allowed us to see and understand, well, our content is helping to inform and give intelligence to these people who are going into work everyday, making decisions. It’s not just information for information sake. We have to fundamentally cater to a very different audience than, than how we started. And I’m honestly very proud of that evolution. And I’m also proud of the time that it’s taken, even for me to evolve as a. I mean, I went from me and my laptop and wifi to now having four full-time employees and 10 contractors that help us to build this thing, like every single day. And so that’s fundamentally over this time, horizon has been a transition and an evolution across the board, and I’m sure who you were and where you started nine years ago is fundamentally different than what you have built as a company today. But you need each of those steps, right? It’s that kind of crawl to walk, to run, to fly sort of phase. And I think we’re just working on practicing more intentionality. And now I have more brains. I have more, more hands, more ideas in this that makes it better every single day. And I, and I just try my best to like, honor that. 00:30:03 Nathan: I love that. Yeah. It’s exactly what I think of it as what’s a journey that I can go on that will make me a different person. By the time I get there, like what’s the, not the easy path, but what’s the thing that I can undertake where it’s like, I, the only way to accomplish that is by becoming like leveling up and becoming a different person. And, and it sounds like you’re on a similar journey. 00:30:27 Sherrell: Absolutely. I mean, I don’t know how you do this and you, and you don’t change or transition. And I mean sure. Would it have been nice to get that early win, whatever that looks like, and then kind of had the clout to say, oh yeah, I sold my first company and blah, blah, blah, blah, blah. And it’s like, yeah, sure, man. But that would have come with its own, you know, challenges. I mean, I, you know, went to grad school during the process and, you know, had to hire a managing editor to help the flow. So it was like getting up super, super early to go to class and like run the newsletter and deal with clients like in between class transitions and homework. And, you know, deliverables was not an easy feat, but I needed that time to help me become the leader that I am today and the journalist than I am today. And also to build the kind of network and relationships that would help us continue to grow into thrive. And I think more so now, and I, and I’m not sure if this is true for you as well, Nathan, you know, it’s less about just general execution and more about. What room. So I need to be in where I can learn and kind of see my business differently and see the opportunities in a way that are effective. I mean, we’ve always run a remote company and I’ve always wanted to run a remote company. And now that we’re remote and I have. Folks across time zones, you know, it is how do we continue to produce at an excellent level, but then also like be, you know, be sensitive to different time zones. And when we move an all hands meeting, how that kind of affects the workflow for the week, or, you know, some of my team members are juggling full families. And, told you earlier, you know, that we are our two-year-old director of mayhem with like, he has like three teeth. He’s like, you know, one of our favorite employees, sometimes like, you know, he calls it like 7:00 AM and just wants to chat and you have to be available for those conversations. And so, you know, again, you know, I think, I think this whole entire process is a growth journey and sometimes your north star does change. You know, I think that when I first started out, it was like, yeah, like we want to be just as great as this. You know, we want to be just as great as kind of these superstars that, you know, had access to a great deal of funding. Well, here was the thing they think when I was in grad school, I went to school for computational journalism. I went to journalism school at a time that there was a 40% reduction in staff of actual journalists. Like the industry itself was like, we’re dying, come on a Janice. Right. And watching these major publications that were like dominant leaders, completely lose their valuations and have to sell for pennies on the dollar compared to what they raised in venture capital. And so the other component to Nathan was that I realized I can’t compete on resources cause I hadn’t raised any money. Then we were doing strictly revenue. Advertising and sponsorship checks, and then eventually reintroduced subscriptions and subscriptions giving access to more premium content and developing an entire sort of newsletter experience and product experience that would cater to the subset of folks who wanted more and shared with us that they wanted more. And so I think the slowing down also enabled us to listen a lot more to our audience about who they were, what they were looking for, what they wanted. And it put us into a great place, even though it kind of felt like, okay, folks where they knew about us, but, you know, once the pandemic kind of shot off and our work was just out there and everyone’s online, they’re like, oh wait, like The Plug like has been doing this work for a very long time. Like their stuff is really dope, like that really catapulted us. And so I’m lab that we had built up such a body of work and reputation. So that once we started to kind of get this influx of subscribers and this influx of folks paying for the premium membership, we were ready. We already had things that they could tap into that were of excellence. And so, it is, it’s definitely a journey all the way. 00:34:46 Nathan: So on that journey, well, so you have tens of thousands of subscribers now for The Plug. What were some of the inflection points in growing that audience? Was it perfectly linear or were there some things, you know, certain stories that took off where you added hundreds of thousands of subscribers in one go. 00:35:03 Sherrell: Yeah. I mean, doing our work in public has been such a great benefit to us. I think before we were kind of in this closed community space, we just want to talk to our audience in there. well, we had to create greater opportunities and we learned this through a survey to our, to our subscribers. And they said, listen, like we love this work. And folks would email me or email our managing editor and have conversation, but they’re like, we want more conversation like amongst each other. we want to know who else is subscribed here. And so we had to do a lot more of our work in public, really engaging people across social media, because that really is just where people are, you know, whether it’s frequently or infrequent. That was kind of where audience, also wanted to engage either with myself or with our team members. And so pushing out our articles, creating, very engaging data visualizations to really show the prowess of our work and our reporting. a lot of our work has gone viral. A lot of our data, our data sets and visualizations have gone viral. It gives, it’s given us an opportunity to, again, like teach and allow people to grapple with information and sort of how that information plays a role in sort of some of the challenges people of color in tech have faced and also the opportunities and trends, that are on the horizon as there’s more distribution of access to capital and access to. And so doing that work in public and having clear stances and, continuing to host conversations, bold conversations, courageous conversations in public have really drawn more attention back to our original work back to our original newsletter. And so, and so again, experimentation, right? I mean, I would love to say we have this grand strategy. Most of it was listen, we’re doing really dope things. We need everyone to see what we’re doing. And so we’ve just, we’ve just refined it. you know, a lot more, we’ve ensured that our team has access to the tools to build out charts and graphs and things like that. 00:37:09 Nathan: Yeah, that’s good. So a lot of content creators, you know, come into it from some other path, like I’m a designer turned blogger, right. but you really came to it from, I mean, you’re a journalist, you went to school for journalism and you have this tech and data background. And so I’m curious as you work, you know, these really data-driven stories and you bring like true journalism. Each of the stories, what’s something, well, I want to go two different directions, which always makes for a terrible question. one is, I, I’m curious for more of your process, like, you know, are you finding the data and then uncovering the story within it? or does it, you know, you hear a great story and that leads you into the data or does it, is it both directions? 00:37:53 Sherrell: It’s definitely both directions. I mean, sometimes just being out and about whatever that looks like these days, you come across really interesting stories. we’re always engaging on social media and listening in to conversations and sometimes like that sparks, like. But mostly we are driven by a question and just the curiosity of, Hey, I wonder what’s going on with this, or I saw this opportunity, but what does this actually mean? And then it kind of finding the dataset and end, or having to build out our own datasets and then being able to tell a story from that. And the cool thing is that, you know, numbers can tell one side of a story, or, or they can tell multiple stories. And so the great thing is that it’s a constant feedback loop that’s going on in the way in which we identify, find or even presented. A lot of our readers are really, really great at even just sharing like, Hey, you know, I live in Oakland and like, this is what’s happening here with this particular company or organization, or, you know, I stumbled across this thread and just wanted to get your thoughts. And then we’re like, oh, Hey, you know, maybe we should, maybe we should kind of think through this and, and what data exists, where can we kind of go and find more insights? And then also, you know, on the weekends, I like long walks on the beach and reading a lot of research papers. And so,so like sometimesit helps to spark ideas and I’m sure that, you know, as someone like yourself, who’s also a creator and, you know, someone who loves to read really great work, having a multifaceted array of content around you all the time, whether you’re listening to it, reading it, watching it, it also helps to spark new ideas on how to, as we say, as journalists, like how to enter a story from like the back door, right. Not everything on its surface is what it is, but when you have an eclectic mix of content and, like I subscribe, you know, to, to things that are kind of way outside of my purview from tacking day, And that helps me to kind of think about other spaces and industries. I had a great conversation with a founder a few weeks ago, who was talking about these like warehouses. She has a data software company that like maps, supply chain and food and food ingredients as well. And she was just talking about how, like, there’s so many entrepreneurs, like in the state of Georgia who owned these like warehouses and manufacturing facilities and how like, you know, no one’s talking about these hundred million dollar plus companies that employ a hundred plus people. And they’re doing really well because everyone kind of wants to be on social media, like selling their product. And they’re the ones that like, ensure that products actually get made. And I just thought like, that is so fascinating. Like I wonder, you know, regionally, like where are the manufacturing plants in a, in a country that has shipped so much of its, you know, manufacturing overseas. And so just the curiosity of it. All right. It’s just the curiosity of, interesting conversations that we try to bring to the forefront. 00:40:58 Nathan: That makes sense. Is there a story that you’ve worked on that. Or that you’ve worked on a published, broken in some way that has changed the conversation. Like one of these that’s gone viral. and I’m sure there’s plenty, but a favorite that you’d want to share. 00:41:11 Sherrell: Yeah, I actually, this was a surprise, piece that went viral. this was, following the murder of George Floyd, last year. And I happen to be, on Twitter as I started to see a lot of tech CEOs, speak out and really address this issue on police brutality, and justice. And, you know, I had mentioned, you know, I’d been working in tech for a few years and you know, it’s not like this was an anomaly, right? We we’ve seen this happen in play out, unfortunately, in so many different ways, but I had never really seen corporate leadership or, even just tech leadership really speak out. And so I started documenting the public statements that were coming across my timeline and really scraping Twitter to kind of see which brands which companies were making these states. And also kind of comparing that across the board of what their diversity equity inclusion results were saying about their commitments to, black and brown workers who was actually in leadership roles, who was actually on the board and really getting a sense of our companies kind of here for the moment. Or are they actually kind of living what it is they say their, their actual core values are. And again, this was kind of a, project that I just want it to be able to have ready and to have something to say for the following week and decided with my team, well, we’re going to need some additional help so that we don’t miss out on any conversations that. May have happened. And so I allowed the database to kind of be open for people to contribute to. And I started creating a visualization, really creating a timestamp of when companies were speaking out against, sort of against just the general timeline as like the country sort of erupted in protests on a national level. It went viral immediately. and again, without intent, I was really trying to do some research and also just kind of share, like, here are some of the companies that have made statements and here’s the timelines. it went viral and it was overwhelming. I started getting messages across the board from CEOs, from recruiters. I even had. Folks who I’d worked with in previous years, reach out to me like they were like in Amsterdam, they’re like, you know, your, database your visualization, like we’re, it’s at our all hands. And like we’re talking through, 00:43:44 Nathan: Sorry 00:43:44 Sherrell: Our statement will be. I started getting signal messages and for those who are unfamiliar signal is like the private messaging app and encrypted and all of that. And I mean, people are sending me company emails and I mean, it was a great time be a journalist in that moment. And to really like, experience the wave of like what journalism should be in terms of, public service. It was also a very hard time, as you can imagine. as, as it was the middle of a pandemic, I’m at home by myself, with my plants in my wifi feeling somewhat powerless and just feeling like this is how I can contribute to the conversation into the movement and what really spurred out of that. And this idea of transparency as well as accountability. And, a year later we were able to work in partnership. The Plug was able to work in partnership with fast company to do an evaluation out of all of the commitments that had been made and all of the sort of, public statements and kind of PR moments where have companies now come when it relates to inclusion and diversity justice. And so it appears now. And so there’s much more, practice around evaluating those commitments, and asking companies to be much more transparent. And I think some policy as well, that is, that is kind of getting started in DC around how reporting on equity and inclusion should be commonplace for all employers And so, so that I feel very proud of, from our work, in terms of helping to spark that movement. And there were other folks who started building very similar databases in their specific industries. So from beauty to music to gaming, just across the board. and again, that was unexpected. I felt like there are stories that I like thought were going to go viral. Cause they, I thought they were really dope to me and people enjoy them, but this one definitely took off. And, I’m very proud of, of the work that we did. And I’m proud of the, the interns that we also had to, who, who stayed up with me for 36 hours to kind of get as thorough who could, 00:46:00 Nathan: Yeah. 00:46:00 Sherrell: As well. 00:46:02 Nathan: Yeah. When you’re leading with data, that way the data has to be correct. It has to be accurate. that often is hard to do on a tight time on like that. Let’s talk about the business model for The Plugin. so you mentioned, you know, paid memberships as well as sponsorships. if you’re sharing it, what’s kind of the split maybe percentage wise between, you know, revenue from sponsorships or memberships and then any other 00:46:24 Sherrell: Yeah, I guess so. So memberships or subscriptions really make up about 25% of our total revenue. That’s something that we’re looking to actually increase. Our biggest goal was not to be wholly dependent on advertising response. 00:46:37 Nathan: Yeah. 00:46:38 Sherrell: But advertising sponsorships still does very well for us. And the great thing is that because we have a very specific audience, we are really able to capture advertisers and sponsors that are, you know, providing products, tools, and solutions to that audience in a meaningful way. And so those relationships have been really, really strong for us. and then we also have, licensing. So, we do original reporting, you know, as, as, as mentioned. And, we syndicate on the Bloomberg terminal, and that parts came about in April. and so all of the Bloomberg terminal subscribers folks across financial industry also receive our work and, you know, Bloomberg pays us annually, you know, for that particular access. We’ve also had prior relationships with folks. Business insider and mobile dumb. that’s a very small percentage of our total revenue, maybe about 10%, you know, advertising and sponsorships really make up the core. and then also, I mean, this isn’t necessarily like earned revenue, but, grants have been really, really critical to part of our growth is. I think, especially we haven’t taken on a lot of venture capital. you know, we’ve, we’ve raised a pre-seed round last year, which allowed us to bring on some employees. And so we’ve wanted to be very intentional with the way in which we took on capital, in order to grow. And, fortunately we’ve been able to participate in really great, journalism based accelerators, which have provided really cool grants and have allowed us to do things like spend on advertising, do website redesigned and audits and bring in, you know, a chief marketing officer. And so, so I’m, I’m still very proud of that because even though grants aren’t necessarily considered revenue, like there’s still work involved to apply to. 00:48:36 Nathan: Yes. 00:48:37 Sherrell: So the ROI is really strong. and it also means that I give up less of the equity in my business, and we’re able to use those dollars, effectively. So that’s the breakdown. 00:48:47 Nathan: Yeah. like working with sponsors, what’s something. You know that, you know, and understand now that like you wish you knew two or three years ago where you’re like, 00:48:56 Sherrell: My God. 00:48:57 Nathan: Pull aside server out to use it it’s three years ago and be like, let me give you a little advice. What would you say? 00:49:02 Sherrell: It’s just so many things. My gosh, I just wish we had like a full day, day, maybe like a nice hearty drink. you know, honestly, just did not know what I was doing in the beginning. kind of took whatever. I think because we never tried to compete on numbers, we tried to compete on value, demonstrating that. And, and being able to articulate that to sponsors, is always kind of an ongoing challenge. you know, and, and knowing the leads the lead times as well. We’re very fortunate in that. So much of our revenue from advertising is typically inbound. So we haven’t had to do a lot of like chasing. and, and as you know, like just pitching, it just takes a while. And if you don’t have the team, the staff to kind of manage that process, it can get a little crazy. but one thing I will say is really identifying, the assets early on and sort of being clear about the metrics that you can deliver. I think a lot of times, you know, we’re kind of only measuring, like click through rates or things like that. We did a lot of like virtual events before that became commonplace in the world. we really should have, created full packages that helped us to both expand our brand, and also really highlight, the core product of our partner. But I think we could have been a bit more judicious in terms of who we partnered with and why, and sort of how that was going to be a best fit. And then also, the retention as well, selling not just for that time, but really looking across the spectrum of opportunities to continue that relationship and continue that inflow of cash, every quarter or, you know, every year. Again, we, I think we got some really good lucky breaks, but I think overall we’ve had to be a bit smarter about overall inventory, and ensuring that, that, you know, we’re, we’re keeping more than we’re having to go out and pay. 00:51:05 Nathan: Yeah. So when you’re talking about packages, is that like saying, Hey, you’re sponsored the newsletter for three months and these events that we’re doing, and like, you’ll be a title sponsor across all of this, rather than saying, you know, we chart our CPM on the newsletters, this, and so a single slot 00:51:21 Sherrell: Yeah, absolutely. I think that, we’ve had to measure against like, what is the actual work involved in integrating a particular advertiser into our emails? you know, a, a CPM kind of works well when you have a significant subscriber list. Right? And so I think that that kind of delivers tremendous value, but for us, because our newsletter, you know, isn’t the tens of thousands versus hundreds of thousands. You know, we’ve had to really charge based on value and engage with. And sort of caliber of our audience, and really also tie that into how do we reinforce messages so that your ad or your promotion or your call to action is not lost in the sauce? right. So whether it be through like dedicated emails, a, an IgG live or a LinkedIn live conversation, the biggest thing for us is really being able to deliver value to our audience at the end of the day. And not just like, oh, like here’s like a random sort of like product, we should buy it more. So, you know, how do you, like we, we’ve had some financial institutions that have, advertised with us and their goal has been to recruit. More companies into their accelerator programs or things like that. So there’s really a strong use case that you can easily sell to advertisers at this level where they’re really looking for much more than just like the banner ad. they’re also looking for engagement. so how do we create engagement opportunities that fit our brand and also give, an opportunity for that engagement piece amongst our readers, who also want to kind of get to know each other. And so creating those kinds of moments, we’re able to sell those as packages versus kind of that one-off like here’s a banner ad go a God, give us a report later. so, so, so a little bit more 00:53:21 Nathan: Yes. 00:53:21 Sherrell: But you, you kind of build for longevity. 00:53:24 Nathan: Yeah, that makes sense. Okay. I want to talk about the, the team side of things. Cause a lot of people start, you know, it’s relatively easy to start a newsletter these days and it’s just them for a period of time. And then it gets to the point where you realize, okay, I’ve built something bigger than myself. And sometimes people scale up really fast and then they find that that’s really challenging and really unsustainable, you know, if you have a down couple months with, sponsorships or whatever your revenue stream is. so it’s just hard. So when did you really think about bringing on your first team member and how did you go about like methodically scaling up the team, to what happen. 00:54:02 Sherrell: I could say like the first nervous breakdown. 00:54:08 Nathan: I should, I should lead with that question going forward. When was your first nervous breakdown? As a creative, 00:54:14 Sherrell: Right? 00:54:15 Nathan: Will have a story. 00:54:16 Sherrell: Absolutely. No. It really, I really looked at, where I was feeling too exhausted to do the kind of work that I wanted to do, because I was kind of in the weeds of the newsletter also feeling like, okay, what’s going to make people stay subscribed. What’s going to make them feel like The Plug continues to be interesting on the nose and giving me something that no one else is going to give me. And that’s hard to do consistently when you’re by yourself, because you have great days. You have not so great days. You have, sometimes you get sick. Sometimes you need to fly to back home for a friend’s wedding. And it’s like, your level of concentration has to really, really scale through other people who are talented, if not more talented, to really bring you to the next level of your work. And so. Once we sort of were able to take on a little bit of capital from an angel investor. I brought on our managing editor, to really take over that process of the newsletter and to really help ideate with me where the newsletter was, where it should go. we really benefited from being in different sorts of, journalism accelerators, as I mentioned earlier, because we also got to learn from other news teams and newsrooms about the anatomy of a strong newsletter and sort of thinking through the entire process from start to finish of how we build out our newsletter. And then of course getting feedback and doing more surveys and collecting the data from our audience on what they were looking for. So again, constant experimentation, but also being open to, to realizing like, okay, this is good, but how do we go from good. And just even now, as we’ve had one of our reporters launch the HBCU newsletter, you know, we kind of talk through the shifts of that as well. And sort of know this is a completely different newsletter compared to our weekly briefing. and so it takes on a different tone. It takes on a different feel. It has a different kind of, objectivity that we kind of want to ensure, continues to serve in, in feed our audiences. So, everyone on our team is in some way connected to building the newsletter. We have a section in our slack, called editorial and everyone just tosses, really interesting articles they bred or tweets, or just Abe. I found really interesting into that and it helps us to really like brainstorm like what the newsletter should be. And the cool thing is that it really has. Gives you an insight into the minds of your team members to see like, well, what are they reading, right? What are they subscribed to? it that they find interesting? So we’re all contributors, you know, at the end of the day, and it’s helped so much because it’s not just all on you as a leader, right? Like we have to continue to grow the business. We have to hire more people, make sure that money comes in so that everyone can like, you know, get paid and by crispy cream or whatever it is, they buy with their money and, and continue to, to find ways, to grow even just the subscriber list, which has its own kind of marketing needs. But yeah, it really came from that breakdown of like, I’m getting sick of this and I want this to be great, but I’ve reached my capacity on the day-to-day basis and I need other people to help chime in to make this great. 00:57:43 Nathan: Yeah. I like that. Working with the team. It’s just remarkable and wonderful. I know a lot of people who like their whole dream is to be a solo entrepreneur and they set up, you know, they’re publishing and everything they do so they can run it just themselves. And it’s a highly profitable business and I have a ton of respect for them, and that’s just not at all what I want. Cause I want a team exactly what you’re talking about to produce a newsletter and to put all of this content together. And you can just do so much more with the team. So anyway, I’m preaching to the choir here. 00:58:13 Sherrell: Well, I get it. Like, I was such a huge fan of like Paul Jarvis has company of one. And I think initially that’s kind of the direction I was going in. but I realized like I didn’t want to just do this. I wanted to produce really strong visualization. I wanted to produce really strong, original content and also do, you know, live conversations and host events and, and, and just really like create. Opportunities for touch points and the ways in which people learn and engage, which isn’t always like through reading. Right? Some, some of it is audio. Some of it is, is visual. So, totally hear you. I mean, I think that we all would like some kind of like automated system that works like kind of perfectly. But I find that I also learned so much from having a team and people who think vastly different than I do. And, and, and people who are bringing new ideas every week, it keeps, it keeps the work exciting. 00:59:10 Nathan: Yeah. And I think that, what I love about Paul’s work is that he’s pulled together all these examples to say, Hey, if you want it, this is something that’s available to you. You can, you know, and then people could look at it. So yes, that’s what I want. Or they can, you know, like so many people, you know, in your early career where that mentor for you or something else. We can have those examples, as well. I want to wrap up with that, related to goals for the next year. My friend Clay Hebert likes to ask this question of, “If we were to meet a year from now with a bottle of champagne, what would we be celebrating?” What’s the thing that you’re working towards that you hope to accomplish in the next year, that we’d sit down and celebrate? 00:59:54 Sherrell: That’s such a great question. I really love champagne, so I want to get this right, so that this happens. I think for us, it is launching at least two additional newsletter verticals. One hyper-focused on climate and green tech, led by innovators of color. Secondly, sort of a more essay exposé from thought leaders in this space, that becomes a regular cadence for us. That’s kind of one of my major goals. I think also, secondarily, that we really have a full fledged functioning team, growing by maybe four additional team members, which would include researchers as well as additional journalists. Again, we’re fully remote, but we are producing great work at a very, very high level. We’re also seeing that reflected in the kind of partnerships and advertising that we have. That, for me, as a leader I have effectively curated an incredible team, and we’re doing the work that we said we wanted to do, and it’s having impact and it’s setting a standard, and we’re in all the rooms that we want to be in. Those were lots of things, Nathan. So, a year from now I expect champagne. 01:01:15 Nathan: Sounds good. We’ll make it happen. Well, where should people go to subscribe to The Plug and follow everything that you’re doing? 01:01:21 Sherrell: Absolutely. Head over to TPinsights.com. We’re also TPinsights across the web, and you can always come hang out with me as well on Twitter, because that is where my life starts and ends every day. 01:01:37 Nathan: Sounds good. Well, thanks for coming on, and we’ll have to make a plan for that bottle of champagne. 01:01:42 Sherrell: Absolutely. Thanks so much for having me, Nathan.0 comments0
- 056: Matthew Kepnes - Making Your Competition Irrelevant as an InfluencerMatthew Kepnes runs the popular travel blog, Nomadic Matt, and also writes a successful newsletter. In fact, Matt’s newsletter is one of the biggest I’ve had on the show. His book, How to Travel the World on $50, is a New York Times Best Seller. After a 2005 trip to Thailand, Matt decided to leave his job, finish his MBA, and travel the world. Since then, he’s been to nearly 100 countries, and hasn’t looked back. Besides being a New York Times best-selling author, Matt’s writings have been featured in countless publications. He’s a regular speaker at travel trade shows, and is the founder of FLYTE, a non-profit organization that sends students overseas to bring their classroom experience to life. I talk with Matt about his unique approach to running his business. While others are building online courses, Matt has shifted to doing more in-person meetups and events. We talk about his newsletter, and we also talk about growing your Instagram follower count, scaling a business as a solopreneur, and much more. In this episode, you’ll learn: When & why you need to start outsourcing day-to-day tasks Matt’s email opt-in strategies and tips to get more subscribers The most important metric about your email list How to quickly get more followers on Instagram Links & Resources Blue Ocean Strategy Matador Lonely Planet Blue Ocean Strategy book Pat Flynn Women In Travel Summit Traverse Cheryl Strayed ConvertKit TravelCon FinCon Podcast Movement World Domination Summit Hootsuite Tim Ferriss Seth Godin OptinMonster Seth Godin: This is Marketing Rick Steves Nathan Barry Show on Spotify Nathan Barry Show on Apple Podcasts Matthew Kepnes’ Links Matt’s website Follow Matt on Twitter Matt’s Instagram The Nomadic Network Nomadic Matt Plus Episode Transcript [00:00:00] Matthew: When I started these courses back in 2013, there wasn’t a lot of folks. Now you have so many people with courses, so many Instagrammers and TikTokers selling their stuff. It’s sort of like, is this worth the time to really invest in it when my heart really isn’t in it? How can I maintain 400K in revenue a year? Is that the best use of our resources? The answer is, not really. [00:00:33] Nathan: In this episode, I talk to my long time friend, Matt Kepnes, from Nomadic Matt. Matt’s got a travel blog that’s wildly popular, and he gets into that—shares all the numbers. He’s probably one of the biggest newsletters that I’ve had on the show, so far. What I love about him, in particular, is how thoughtful he is about his business model. Most people are just adding more courses and figuring out how to grow revenue; honestly, what’s now fairly traditional ways, and it’s quite effective. Matt takes another approach. He gets into in-person events and meetups. We get to talk about why in a busy, crowded online world, he’s actually going offline. I think that Blue Ocean Strategy he references, the popular book by the same title, I think it’s interesting, and it’s something worth considering when some of the online strategies don’t work. We also get into a bunch of other things like growing his newsletter. Like I said, it’s quite large. Then, also growing an Instagram following. Instagram is not something that I’m going to actively pursue, but it’s interesting hearing his approach of what you do if you’re at 5,000 followers on Instagram, and want to grow to 50,000 or more. So, anyway, enjoy the episode. If you could do me a favor and go subscribe on Spotify or iTunes, or wherever you listen if you aren’t subscribed already, and then write a review. I check out all the reviews. Really appreciate it. It helps in the rankings, and I’m just looking to grow the show. So, anyway, thanks for tuning in today. Let’s go talk to Matt. Matt, welcome to the show. [00:02:06] Matthew: Thanks for having me, Nathan. I’ve been trying to get on this podcast for ages. [00:02:10] Nathan: Well, don’t say that, that’ll make people think they can get on just by asking. Really, you came to my house and stayed in my cottage on the farm, and then you’re like, “Yo, have me on the podcast!” And that’s when I was like, “Absolutely.” But if anyone just asked, that would not be a thing. [00:02:26] Matthew: No, I just mean I finally—I’m excited that I’m worthy enough in my blogging career to be on. [00:02:33] Nathan: Oh, yes. [00:02:35] Matthew: I’ve made it. [00:02:36] Nathan: Yeah. It’s only taken you, what, a decade and a half? [00:02:39] Matthew: 13 and a half years. Slow and steady wins the race. [00:02:43] Nathan: That’s right. I actually want to start talking about that side of it, because I’ve been in the blogging world for 11 years now. But even I feel like things changed so much in the first couple of years, even before I entered into the world. So, I’m curious, going back to the early days, what were the prompts for you to come into the blogging world and say, “Hey, I’m going to start publishing online”? [00:03:10] Matthew: Yeah. You know, it was a very haphazard, there was no grand plan. Like I had Zanger when people had Zeno’s, which is, you know, a personal blog, way back, you know, 2003, whatever. And so what, I went on my trip around the world in 2006, I just kept updating this Zynga. You know, it was called, Matt goes the world and it was just like, here I am friends here I am. And then, you know, everyone was really excited in the beginning. And then after a while I got sick in my update because the know their back of their office job. So I kinda just forgot about it until I came home and January, 2008 and I need money. And so I started a temp job, and I had a lot of free time and I really just hated being back in the, the office with the walls and everything. And so I was like, I need to earn money to keep traveling. And so I started the website really as with the goal of it being an online resume, you know, it was very bare bones. I used to share a travel news, have an update, like tips and stories from my trip. And then there was a section where we’re like, hire me and it had my features and, you know, the guest blogs I did, I used to write for Matador travel. So just as a way to sort of build up, a portfolio of like, Hey, Yeah, freelance writing because I’m wanting to read guidebooks, you know, I wanted to write for lonely planet. That was a dream, right. The guidebooks. And so just the blog was a way to hone my skills and just get in front of editors to be like, Hey look, I do right. You know, here’s where I’ve been, you know, and, and sort of build that base. And eventually that became a thing where I didn’t need to freelance. Right. [00:05:03] Nathan: Was it called nomadic Matt from the beginning. [00:05:06] Matthew: He was, yeah. I B two names, nomadic Matt. And that does the world. Right. Because I like the double entendre of it. Right. Even though, but just cause I have a weird sense of humor and all my friends were like, you can’t do that one. You gotta do nomadic Matt. It was really good because it’s much better brand name, you know, in the long run. But again, I wasn’t thinking about that. Right. I wasn’t thinking like, oh, I’m going to start this brand. You know, I gotta think of a clever name that people can remember. It was like, Oh a place where people can see my work. [00:05:39] Nathan: Right. Okay. So now 13 and a half years later, what’s the, what’s the, the blog and newsletter look like. and I want to dive into the business side of it because I think a lot of people build successful newsletters, audience-based businesses, but don’t make the leap to like something bigger than themselves. And so I want to dive into all those aspects of it. [00:06:01] Matthew: 13 years later, it’s seven people. We just hired a new events coordinator to help. my director of events, Erica, coordinate all these virtual in person events that we’re going to kick off again. I have a full-time tech guy, a full-time director of content. We changed his title, but like three research assistants, because. I picked a niche that like is always changing. Right. You know, you have a fitness website, how to do a pull up. It’s just, that’s it, [00:06:37] Nathan: You ranked for that keyword. You’re good to go. [00:06:40] Matthew: Yeah. Like how to do a pull up, doesn’t change what to do in Paris or the best hospitals in Paris, constantly changing, you know? so it takes three resources, distance. Plus my content guy, me that basically keep up the content and then I have a part-time, graphic designer and part-time social coordinator. [00:07:00] Nathan: Nice. And how many subscribers do you have in the list now? [00:07:03] Matthew: We just called it, so it’s a two 50 because we just, cause I haven’t shaved it off in like five years or so. So we basically everybody that hasn’t opened the email in one year where we’re like, you want to be on. And like 2% of them click that button. And then we just got rid of the other 90%. It was like 60,000 names. [00:07:30] Nathan: Yeah. So for everyone listening, two 50 in this case means 250,000. [00:07:35] Matthew: Yeah. [00:07:36] Nathan: Just to clarify, I 7% businesses off of 250 subscribers would be remarkable. That would be just as impressive, but that’s not what we’re talking about here. going into, so a lot of people, talk about or worry about, should I prune my list or that kind of thing? What were the things that went into that for you? That’s a big decision to, to prune 60,000 people off a list. [00:08:00] Matthew: I think it was probably more, maybe I want to say six 60 to 80 I somewhere around there. we were pushing up against our account before I went to the next billing step. So that’s always a good impetus to prune the list, but you know, I I’ve been thinking about it for a while because. You know, I I really want to see what my true open rate. Is You know, like, okay, I have all these people and we were sending it this, I have multiple lists, but the main weekly list was like, 310,000-315,000 but it’s been so long since we called and we have so many emails there and I just really wanted to get a true sense of like, what’s our active audience. And so between, between that and, pushing up against the next tier price tier. Yeah. it yeah. It’s cool to say like, oh, we have 300,000 300, you know, rather than 250,000 Right. But who cares? Right. I mean, at the end of the day, it’s just a vanity metric, right? Yeah. It sounds cool. I get a million emails. Right. But if you only have a 10% open rate, You really only have 100,000. [00:09:20] Nathan: Right. I think that the times that it matters is maybe when you’re selling a book to a publisher and that might be the only time that you like that dead weight and your email us actually helps you. [00:09:33] Matthew: Yeah. Like if you’re, or you have a course, you know, are you trying to promote your numbers, but people would probably lie about that stuff too. yeah, so like, it really doesn’t matter because all that matters is like, what’s your true audience? Like who Who are the people that are really opening your stuff? [00:09:50] Nathan: Yeah. So let’s dive into the, well, I guess really quick, I should say I am a hundred percent in the camp of, like delete subscribers, like do that once a year, that kind of thing. Clean up the list, go for the highest number of engaged subscribers, rather than the highest number of subscribers. It’s just [00:10:06] Matthew: Right. [00:10:07] Nathan: To track. [00:10:08] Matthew: And, and I think you would know better than me, but isn’t this a good. Like signal to Gmail. And you know, when you, you don’t have a lot of dead emails, just go into a blank account. It’s never getting opened or marked as spam or whatever. [00:10:24] Nathan: Yeah, for sure. Cause a lot of these times, there’s a couple of things that happen. One is emails get converted to spam traps. And so it’s like say someone’s signed up for your email list six years ago And, they haven’t logged into that email account for a long time. Google and others will take it and convert it to a spam trap and say, Hey, this email hasn’t been logged into in six years. And so anyone sending to it, it’s probably not doing legit things now you’re over here. Like, no that person signed up for my list, but they’re basically like you should have cleaned them off your list years ago. And then if that person were to ever come back and log into that Gmail account, do you remember like, oh, just kidding here, have the, have the email account back, but they’re basically using that. And so you can follow all the. Best practices as far as how people join your list. But if you’re not cleaning it, then you will still end up getting these like spam hits and, and other things. So you absolutely clean your list. Let’s talk the business side, on revenue, I don’t know what you want to share on the, on revenue numbers, but I’d love to hear any numbers you’re willing to share. And then the breakdown of where that comes from, whether it’s membership, courses, conferences, that sort of thing. [00:11:35] Matthew: Yeah. So there’s like the pre COVID world and the post COVID world. Right. You know, like, [00:11:40] Nathan: Yes. [00:11:41] Matthew: Cause I work in travel, so like, you know, pre COVID we did over a million and like I was probably gearing up to like in 2020, like one, five, I think I were going to get a little over one five. and again, you know, this is, I work in the budget travel side of things, right. So like it’s going to sell a lot of $10 eBooks to get up to seven figures. salary books are 10 bucks. and so. Postcode during COVID week, I think in 2020 made like half a million. and this year we’ll probably get up to three quarters, [00:12:23] Nathan: Okay. [00:12:24] Matthew: K. [00:12:25] Nathan: He was coming back, [00:12:26] Matthew: Yeah. Yeah. and I think next year we’ll, we’ll get back over seven and then basically like how to go from there. You know, so maybe 20, 23, I might get to that one, five that was going to get to in 2020. most of the revenue now comes from ads, and then affiliates. we did, we did do a lot on courses, but then I, one of the things that, you know, a big pandemic that stops your business, allows you to do is really look at the things you’re doing because every. Zero. So it’s like when we start back up, is this worth investing time in? And so the answer is no. So we dropped down from, I think, peak of doing like $400,000 a year and horses, and this year we’ll do maybe 40. and that’s mostly because we just leave it up as like, you can buy this, we update it every six months. If it needs, it’s basically like a high that blog course get all my numbers and tactics and strategies in there. but we don’t offer any support for it. Right. It’s just, you’re buying information. and so it’s very passive in that sense, but it’s not like a core business where we’re really moving and we were doing this pre COVID is moving into events and membership programs. So like we have pneumatic map plus, which gets you like all our guides, monthly calls and sort of like a Patriot on kind of thing, but like free. [00:14:03] Nathan: That cost. [00:14:04] Matthew: Five to 75 bucks a month, depending on what you want. So it’s 5 25, 75. Most people opt for the five, of course. And it’s really geared to like, get the five. But you know, that brings now, I think like three or four K a month. and then we have the events, which is donation based, but there’s just like another two K a month. And so this is like, since COVID right. So like, that’s say call it 50 K a year of, of revenue that we’ve added in. They didn’t exist before. And now I know you’re, you can compare that against the loss of the courses, but we had been phasing those out for years. and so that’s really where we want to grow is bringing in more, you know, monthly revenue for that. Right. You know, Once we started, it’s easy and we’re gonna start doing tours again and, you know, so more high value things that don’t take as much time. [00:15:08] Nathan: Right. So on the core side, I think a lot of people listening, maybe they have an email list of five, 10, 15,000 subscribers, and they’re like, Hey, the next thing is to launch a course. And they’re hearing that’s where a bunch of the revenue is. And so it’s interesting you moving away from that. So let’s dive in more. What, what made you look at the core side of your business and say, I don’t want to like restart that in a post COVID world. [00:15:33] Matthew: Yeah, there’s just, there’s a lot of competition, right? So like, I think it was like a blue ocean, red ocean strategy, you know, to think of that book of, you know, Blue Ocean Strategy. Right? One of the reasons we went into events is because a lot of our traffic comes from Google. And so it’s a constant battle of always trying to be one or, you know, in the first couple of spots. Right with every blogger in every company with SEO budget, but there’s not a lot of people doing in-person events or building sort of a community in the travel space. So I looked at that of being like, okay, there are a lot of people doing courses and they love doing courses and they’re great teachers, you know, they’re, you know, you get folks who know like path when, you know, low, like everyone, all these teachable folks, you know, they, they love that stuff. That’s not where my heart really was. And so thinking of like, this is a red ocean now, because you have, when I started this, these courses back in 2013, there wasn’t a lot of folks. Right. But now you have so many people with courses, so many Instagrammers and tic talkers selling their stuff. It’s sort of like, is this worth the time. To like really invest in it when my heart really isn’t right. Like how can I maintain your 400 K in revenue a year? [00:17:02] Nathan: Right. [00:17:03] Matthew: What’s it going to take, you know, is that the best use of our resources? And the answer is not really, you know, let other people do that. Who love it. I mean, you want to buy my information. It’s it’s solid stuff. Right. Everyone loves the advice, but to really create like a cohort, like your class, which is sort of like the new version of courses, you know, like, whether it’s a month or three months, it’s sort of like, you go with this like cohort, right. My heart really wasn’t into it because we can invest more in doing events and conferences and really in-person stuff. Especially now that everyone’s really excited to do stuff in person again, with a lot less competition. It’s easy. It’s easy to start a course, but there’s a lot of capital investment in doing events that we have the resource to do that, you know, somebody with a 10,000 email list might not. [00:18:03] Nathan: I think I see a lot of people going into courses in, particularly as you alluded to cohort based courses where they’re doing it, like, Hey, this is a whole class that you’re doing, you know, you’re doing the fall semester for the month of October or whatever it is, I’m doing it, doing it the first time and really enjoying it because it’s a new challenge they’re showing up for their audience. It’s just, it’s super fun on that, doing it for the second time and going, huh? Okay. That was way easier and way less. And then the third time they go, I don’t think I want to do this anymore. Like if the money is good and I just don’t enjoy showing up at a set time for a zoom call or whatever else. So it’s interesting of watching people jump on a bandwagon and some people it works for really well, and that is their strength and they love it. And then other people that I’m going to like, look, the money’s good. And this is this just, isn’t what I want to spend my time on. [00:19:02] Matthew: Yeah. You know, I’ve been doing it for, you know, seven, eight years now and I just sort of lost the passion for, you know, I think it’s, I like when people take the information, they succeed with it. But I think after a while you start to realize, you know, it’s sort of a 90 10 rule, right? You, 90% of your students, aren’t really going to do anything with it. And it’s not your fault. It’s just because they become unmotivated or, you know, so we tried to switch to the cohort based to be like, okay, this is the class weekly, weekly calls. You know, come on, come together and you still get this drop off rate. That’s, you know, sort, it gets this hard and you’re like, all right, I’ve been doing this for eight years, you know, like moving on. But I mean, if you have the love for like pat loves it, you know, like you’ve got a whole team about it, he’s got all these cohorts stuff that speaks to him where I think I’d rather do stuff in person that [00:20:01] Nathan: Right. Well, let’s talk about the in-person side. Cause you did something that most people think is really cool and almost no one realizes how hard it is. I think I know how hard it is because I’ve attempted the same thing and that starting at a conference where everyone’s like, you have this big online following, like what you just need to, you know, you have hundreds of thousands of people you just need, I don’t know, 500 or a thousand of them to show up in a suit, that’s gotta be easy. Right. And so they go and sort of conference, it’s wildly difficult. And so. [00:20:33] Matthew: Difficult. [00:20:34] Nathan: I’d love to hear what made you want to start the conference and then yeah, how’s it. How’s it gone so far? [00:20:40] Matthew: Made me want to start the conference was I really don’t think there’s a good conference in the chapel space. Yeah. And there are good conferences in the travel space that are very niche and narrow. you know, like there’s a woman in travel summit. That’s really great. There’s one in Europe culture verse, which I liked, but that’s like a couple of hundred people there. Wasn’t like a, something to scale, right. With wits, which is women to travel is like 300 people. There was, this is no thousand person, 2000 parts. And like mega travel conference for media that has done like, you know, the conferences we go to where it’s like high level, you know, people coming outside of your immediate niche to talk about business skills. You know, there’s, you know, In the conferences, there are, there’s always the same travel, like it’s me and like these other big names, travel bloggers over and over and over again. I want to take what I’ve seen and, you know, from social media world to, trafficking conversion, to mastermind talks, you know, to take all these things that I had gone to, we were like, let’s bring it together for travel. Let’s create a high level, not a cheap, like hundred dollar events, like, you know, with major keynotes who get paid to speak, because you know, in a lot of travel conferences, you don’t get paid to speak, right? So you’re high. You’re going to get, you know, Cheryl strayed that come to your event for free. That’s not waking up to do that. You know, I, you know, and while I can get nice deals from my friends, you still got to pay people right. For their time. And, and so that allows us to have a larger pool of people to create the event that I want to do. Because we will also get into the point where why should somebody who’s been blogging for five or six years, go to travel blogging conference app when nobody is at a more advanced stage of blogging than you are, you know, nobody understands SEO better than you do, right? So like after a while you get into this, just drop off of people being like, do I want to fly around the world and hang out with my friends? So I wanted to also create an event where that I could go to and learn something is that I knew that would attract some of the other OJI, travel bloggers. [00:23:06] Nathan: Yeah. So how the, how the first one go, like what was easier than you expected and what was much harder than you. [00:23:14] Matthew: The first one went really well. We had 650 people, and you know, the next one we had 800. But now we’re closed because of Kobe, but we’re going to do one in 20, 22. And hopefully we get 800 again, things that shocked me, people buy tickets and don’t show up. Right. That’s weird. Right. Cause I was like, okay, we have 700, you know, I expected maybe like a 5% attrition rate, you know? So like I sold my 750 tickets, but then like six 50, those 600 showed up because the other 50 of those speakers, right. I was like, wow, that’s a lot of no-shows for not achieving conference, you know? And so we plan, you know, a 10% attrition rate now. [00:24:04] Nathan: And you just mean someone who doesn’t even pick up their badge? Not even, they didn’t come to share us rates keynote, but just like they didn’t show up to anything at the conference. [00:24:13] Matthew: Yeah, they just did not show up to the conference at all, you know? And. So that was a shock me. I mean, I know I work in travel and, you know, people get last minute of press trips or they, you know, they buy their ticket and they can’t come cause, or they got stuck in the Seychelles or whatever, but I did not expect such a high level of no-shows. Because the food here’s another thing, food costs a lot of money. Right. You know, I, I fully understand why the airlines took one olive out of your salad. Right. Because it’s one olive, but times a million people every day it’s actually adds up. Right. So like you think, oh, well it drinks five bucks. That’s cool. We’ll do a happy hour. Okay. Now times that by a thousand drinks Write, you know, times two, because everyone’s drinking two or three, at least two. Right. So then you’re like, okay, that’s a $15,000 bill that you ended up with. you know, when everyone is all set up. Tax and tip hotel. It’s crazy. It’s like, okay, these fees, you’re like, oh, I got to spend this like, yeah. Okay. Here is your lunch bill 50 grand. But then there’s this fee that fee, this fee, this fee like Jake had like 65. You’re like, all right. I guess I got a budget for that too. So that was, that was really weird. Like high is the lunch cost, $40,000, you know, and actually hotels, overcharge, and they add a bunch of fees and yeah, you can get them pretty quick. [00:25:46] Nathan: So if you were, if I was starting to conference. They have 50,000 people on a email list or a hundred thousand. And I’m like, Matt, I heard you started a conference. I’m going to do it too. What advice do you have for me? Like what are the first things that you’d call out? [00:26:03] Matthew: It’s going to cost like three times more than you think. pricing. Where I went wrong in the second year. Right. So like we’ve lost money the first two years doing it, but I expected to lose money. It wasn’t because I was investing in this long-term thing. Right. But we’re at where I lost more money on the second year is that I really factor in flights as well as I did, like I kind of low balled it. And so I always think he should. Oh. And I also invited, I kept inviting people without really seeing, like, where was I? on my like speaker fees. Right. So like really creating a budget and then sticking to it. And even if that means not getting some of your dream folks, to a later year, but working up the food and beverage costs first, because you know, you go to the hotel and they’re going to say your F and B, you know, is $90,000. And if they never going to hit that, no, you’re going to go way. You’re going to blow cause you got to get them to say, what are all the fees? You know, like, okay. You know, if I have a 300 person conference and I want to do two lunches, what does that look like? Plus all the taxes and fees, [00:27:23] Nathan: Okay, well, you, the launch price and you’ll, you’ll pencil that into your spreadsheet and they’ll fail to mention that there’s mandatory gratuity on top of that and taxes and whatever [00:27:33] Matthew: Yeah, And whatever, you know, plate fee there is. Right. So you gotta factor all that in and then look at what you got left. [00:27:40] Nathan: It’s like when you’re buying a car and you have to talk in terms of the out the door price in [00:27:45] Matthew: Yeah. [00:27:46] Nathan: The sticker price, [00:27:47] Matthew: Yeah. I made that mistake when I bought my car last year, I was like, oh 17. And I was like, wait, how did 17 go from 17,000 to 22? And like, well, [00:27:56] Nathan: Right. [00:27:57] Matthew: Thing that I was like, ah, okay, [00:28:00] Nathan: Yeah. Do you think w what are some of the opportunities that have come out from running the conference and has it had the effects of your community that you’ve hoped? It would, [00:28:10] Matthew: You know, this is a very, blogger faced event, you know, more than just travel consumers. but it’s definitely allowed me to, you know, meet folks like Cheryl Austrade, you know, great way to meet your heroes. Is there pay them to come speak at a conference? so, you know, I, I know Cheryl, like, that’s cool. The becoming more ingrained in sort of the, the PR side and with the demos and the brands, because, you know, on the website, I destination marketing organization. [00:28:44] Nathan: Okay. [00:28:45] Matthew: So they’re like, you know, visit, you know, Boise visit Idaho, we call them a DMO. And so like since I don’t really do press trips on the website, I don’t know a lot of them really well. And so this has been a way to be, become more ingrained on that sort of industry side of events and not live in my own. and that’s helpful because now I know all these folks, when we want to have meetups that might be sponsored when I do a consumer event, which is next up. So get these folks to come for that. So it’s just really been good, just professionally to meet a lot of people that I would normally just not meet simply because I go to events and they were like, Hey, come to our destination, we’ll give you a free trip. And like, you have a policy. And so I don’t get invited to as many things as you would think. [00:29:37] Nathan: Yeah. Why, why do you have that policy? What do you like? What’s behind it. And why is that different from other travel bloggers? [00:29:45] Matthew: Hi, it mostly stems from my hatred of reciprocity. You know, like if you, if I go on a free trip and it sucks, like I then create, it’s awkward. If I have to go like hot, like, Hey, you suck. And I have to write this online. Then it creates a lot of bad blood that gets talked about, you know, it’s a very small industry. People move around a lot, so you get less opportunities or I can just go, Hey, I’m not going to write that. And then they feel bad. Cause like, you know, like you’re a nice person just doing their job, you know, like it’s not your fault. I had a bad time. you know, I did this once with a friend and she gave me a couple of places to stay, at a hotel in San Jose, Costa Rica and chill out and sort of tell was really far out of town. And th the amount it took me to take a taxi back and forth. Like, I could’ve just got a place right. In the center of San Jose, you know? And so I was like, I really, I just don’t think it’s a good fit for my Anya. And she was very unhappy about it. I was like, I mean, I could write in, but I have to say that. Right. Yeah. And so I just never wanted to put myself in those situations again. I also think that taking a lot of free travel, like I do budget travel. So you given me a resort like that. Doesn’t how does that help my audience? So if I start living this awesome life and getting free stuff, that’s great for me, but it’s not good for my audience. And so I don’t mind taking free tours. Like, let’s say I’m going to go to Scotland. Right? I did. This actually was real life example. I wanted to access cause I wanted to write about scotch. So I was like, Hey, I don’t want to do like the public tour. you know, that 20 bucks, you know, it’s like 10 minutes and you get the, I like, I want to talk to people because I want quotes for articles. I’m going to do like history stuff. So I contacted the Scottish tourism board and they got, got me visited. I that’s where I went to. I just love P scotch. and so they got me like private tours. So I can like take notes in such. and they gave me a free accommodation that I was like, I want to be really clear about this. I’m not mentioning this place. And they’re like, just, just take it. And so, and I didn’t mention it and I didn’t mention that, you know, I got access to these, you know, distillers to ask some questions, but it was more about building this article as a journalist than, Hey, I want like free tours, you know, like, I mean, I saved 20 bucks. Right. But the point was, I wanted to learn about the process to write about this story beam. And then they offered me free flights and stuff. It was like, now I just, I just want the tourist, please. Thanks. [00:32:44] Nathan: Yeah, it’s interesting of the, what a lot of people would view as the perks to get into travel blogging. Right. I want to get into it because then I’d have these free chips or I can have these offs or whatever else, I guess the right apps you get, no matter what, but, You know that that’s the other side of like, everything comes with a cost. And I think it’s important to realize what you’re doing because you want to versus what you’re doing, because now you feel obligated because someone gave you something for free. [00:33:12] Matthew: Yeah. The most thing is I tend to accept our city tourism part, which gets you like free access to museums and stuff. I was like, okay, that’s cool. But beyond that, I just, you know, I don’t want to get into, like, you want to give me a museum pass. I’m going to see these museums anyway. Sure. I’ll save some money and I’ll, I’ll make a wheel note, but I’m going to no obligation to write about which museum, because I write about the ones I like anyway. So, [00:33:39] Nathan: Right. [00:33:40] Matthew: You know, that’s not to me like free travel. That’s not what people think of Like the perks of. the job are. [00:33:46] Nathan: I, that was funny. When I learned about the, like the welcome packet that cities will, will give, like the first time I saw it in action was. I went to Chris, Guillebeau’s like end of the world party in Norway. and I was hanging out with Benny Lewis there who runs, you know, fluent in three months, a mutual friend of both of ours. You’ve known him longer than I have, but like, we’re both at our check into the hotel and he’s got like this whole thing of all these museum passes he’s got, and he’s just like, yeah, I just emailed the tourism board and said, I was going to say, and they’re like, oh, blogger. And they gave him like, you know, access to everything and you only ended up using half of it because we weren’t there for that long, but, [00:34:28] Matthew: Yeah. That’s great. You should always get these discount cards, like the comparison museum pass or the New York mic go card that will save you a lot of money if you’re doing lots of heavy sites in. [00:34:39] Nathan: Yeah. Yeah, for sure. okay. So how does actually let’s dive into the COVID side, right? Cause COVID took a hit huge hit on the entire traveling. we saw that just in the like running ConvertKit where, you know, having bloggers in so many different areas, we had a lot of growth because lots of people were stuck at home and start like, I’m going to start a new blog. I’m going to have time to, to work on this or whatever. And it was a lot of cancellations, mostly from the travel industry. If people like, look now that what this 50,000 person list, that was a huge asset is now just a giant liability. because no one’s planning trips. How did you navigate that time? And what, like, what’s the journey been? You know, the last 18 months, two years, [00:35:28] Matthew: Well first I would say that’s really shortsighted of someone canceling their 50,000 person list like [00:35:34] Nathan: I think they were like exporting sitting on it and they’re going to come back. But, but I agree. It was very shortsighted. [00:35:39] Matthew: Yeah. Like just like throw it away. 50,000 emails, right. I mean, it was tough in the beginning. You know, we went from like January and February were like best months ever, you know? And like, I mean, even, and then all of a sudden like, like March 13th is like that Friday, you know, it’s like everything crashes, like again, like we were on our way to have a banner year, like, like, like hand over fist money, you know? And, and then to being like, how am I going to pay the bills? You know? and so, cause you know, we, haven’t sort of the, the overhang from Java con, right. You know, like we didn’t make money on the first two years. And year three was the, the breakeven year and travel con was in, Right in the world ended in March. Right. And so I had laid out all, like, you’re so close to the event, that’s you? That’s when you start paying your bills. Right. And the world hits and all the sponsors who, you know, have their money, you know, in the accounting department are like, oh, we’re not paying this now. And so you’re like, well, I’ve just paid $80,000 in deposits and all that money that was going to offset. It has gone. and then you have people canceling. A lot of people were really mean about it. They’re like, oh, I’m, I’m back now. And we’re going to do charge backs, that, you know, you have that overhang and just, you know, fall in revenue it’s it was really tough. thank God for government loans, to be quite honest, like I, I went to native through if it wasn’t for, all that, because a lot of my. My money was tied up in non-liquid assets. So it wasn’t like I could just like sell some socks though, you know, pay the bills. but things have come back a lot. I mean, there’s a lot of paint up the man, for travel, I view it like this way, right? You got kids, right. You know, they get in trouble, you take away their toy and then you give them back. Right. Where do they want to do now? They just want to play with that toy even more because it’s like, no, it’s mine. No one else can have it. And like where you want to do this other toy. No. And so now that the toy of travel is being given back to people like people are like, never again, am I going to miss out on this opportunity to travel on my dream trips? Let’s make it happen. So we had a really good summer. I spoke to mediocre fall and winter just as the kids are back in school, people are traveling less, you know, but as more in the world, that? will be good. but again, as I said, at the beginning of this, it’s going to take awhile for us to get, to get back to where we were, but there’s definitely demand there, [00:38:36] Nathan: When’s the next conference when the travel con happening again. [00:38:39] Matthew: April 29th, [00:38:41] Nathan: Okay. [00:38:41] Matthew: 22, [00:38:42] Nathan: So what’s the how of ticket sales benefit for that? Is there like that pent-up demand showing up and people booking conference tickets or are they kind of like, wait and see, you know, you’re not going to cancel this one too kind of thing. [00:38:55] Matthew: Yeah, I mean, we’re definitely not canceling it. I mean, the world would have to really end for it. We just launched, this week. So, early October, we just announced our first round of speakers. and we sold like 10 or 15 tickets. I don’t expect a lot of people, to buy until the new year I saw this. And the old event, right? Because in the old event we were had in May, 2019. Right. And we announced in the fall, but it wasn’t until like, you know, a few months prior that people started buy their ticket. Right. Because they don’t know where they’re going to be. You know, where are they flying from? What were the COVID rules going to be like, the demand is there. But I, I know people are probably just waiting and seats for their own schedule too, you know? So, but you were against so 800 tickets and honestly, from what I’ve heard from other events, you know, people are selling out, you know, because there was such demand, like it’s not a problem of selling the tickets, so I’m not sure. [00:40:01] Nathan: Yeah, one thing, this is just a question that I’m curious for myself. since I also run a conference, what do you think about conferences that rotate cities or like Mo you know, move from city to city, which we’ve been to a lot of them that do it. You know, the fin con podcast movement are Two longer running ones that you and I have both been to. obviously that’s what you’re doing. The travel column. well, domination summit, which we’ve both been to a lot, you know, it was like very much it’s Portland. It’s always Portland. We’ll never be anywhere anywhere else. What do you think, why did you chose? Why did you choose the approach that you did in what you think the pros and cons are? [00:40:39] Matthew: Yeah, for, for me it was, you know, we’re in travel. I wanted to travel. Right. And plus, you know, I mean, you get up, we get a host, right? So like Memphis is our sponsor. Right. It’s in Memphis. Yeah, it was supposed to be in new Orleans. New Orleans was our host sponsor. Right. So moving it from city to city allows us to get, you know, a new host sponsor every year is going to pony up a bunch of money. Right. I don’t know how Podcast move into it, but I think if I wasn’t in travel and it was more something like traffic and conversion, or maybe we’ll domination summit, I would probably do it in the same place over and over again because you get better consistency. you know, one of the things I hate about events is that they move dates and move locations. Right. And, and so it’s a little hard to in travel cause you know, COVID really screwed us. Right. But we’re moving to being, you know, in the same timeframe, right. We’re always going to be in early May. That’s where I want to fall into like early may travel car, change the city, but you got the same two-week window, because it’s hard to plan, right? So like if you’re changing dates in cities, you’re, you’re just off of a year. So I wanted some consistency, make it easier for people to know, like in their calendar, Java con early Mac, Java con, early Mac, you [00:42:17] Nathan: Yep. [00:42:18] Matthew: It doesn’t really work out cause of COVID, but post COVID we’re we’re moving to that, that, early may [00:42:24] Nathan: Yeah. Okay. So let’s talk more about sort of scaling different between different levels of the business. So there’s a lot of people who say, all right, 10, 20, 50,000 subscribers, somewhere in there. And it’s very much the solopreneur of like, this is, I’m a writer. I just do this myself. Or maybe they, you know, contract out graphic design or a little bit more than that. What were some of the hardest things for you and why and what worked and what didn’t when you made the switch from it being nomadic, Matt being just Matt to Matt plus a team. [00:43:00] Matthew: Yeah, it It’s definitely hard to give up that control, right. Because you always think no one can do your business better than you can. And I mean, even to this day, I still have issues doing, you know, giving up control. Right. [00:43:14] Nathan: What’s something that you don’t want to, that you’re like still holding onto that, you know, you need to let go of [00:43:19] Matthew: Probably just little things like checking in on people and, you know, Content probably like Content. I’m very specific about my voice, the voice we have. So. But I should let my content, people make the content that I know is fine. but I definitely, probably overly check on my teams to be like, what’d you do today? You know, you know, that kind of stuff. but I did take a vacation recently and I went offline for a week and they didn’t run the thing down. So I was like, oh right. That was my like, okay, I can, I can let go. And it’s going to be okay. But, so getting comfortable with that much earlier on, I would probably save you a lot of stress and anxiety. I definitely think you should move to at least having somebody, you know, a part-time VA, if you’re making over six figures, hire somebody because you know, how are you are not going to go from a 100k to 500k really by yourself? Unless, you know, you just have some crazy funnel that you do, but even the people I know who are solopreneurs, they still have two or three people helping them a little bit part, even if it’s just part-time because the more money you make, the more time you have to spend keeping that income up. And so your goal as the creator in the owner should be, how can I grow? How can I make more money? It should not be setting up your WordPress blog. You know, It should not be answering joke emails It should not be, you know, scheduling your social media on Hootsuite, that kind of low level stuff can be done by, you know, a part-time VA And maybe that part-time VA becomes a full-time VA as you scale up more. But you know, if you, you have to free up your time and you’re never going to free up your time, if you’re spending a lot of that time, scheduling. So you mean that the people I know who have half a million dollar businesses, selling courses, you know, and they’re really just a solopreneur. They have somebody do that grunt work, right. Plus if you’re making that much money, is that the best use of your time now? Really? Right. So getting somebody to do sort of the admin front work, as soon as you can, even if it’s on a part-time basis will allow you to focus on growth marketing, and monetization, which is where you should be like Podcast. This week. I have like four or five podcasts I’m doing, right. You know, that is a good chunk of my week. If I have to spend that time scheduling on social media, you know, or setting up blog posts, like I can do that. And this is where the growth in the audience comes in. [00:46:12] Nathan: Okay. So since we’re talking about growth, what are the things that you can tie to the effort that you put in that drives growth? Are there direct things or is it a very indirect unattributable [00:46:27] Matthew: Yeah, I think there’s some direct things like, you know, before, you know, asking 10 years ago, I would say guest posting on websites. Right. You write a guest post on like Confederacy’s site and boom, tons of traffic. Right. that doesn’t exist anymore. I mean, yeah. You can get a lot of traffic, but it’s not like the huge windfall it used to be, but it’s still good for brand awareness. SEO. Great for links. Right. I would say things today that I can tie directly to stuff Podcast and, Instagram. So doing, like, doing a joint Instagram live with another creator. Right. You know, like me and, you know, it’s I know pat. because someone with a big following there, we do, we do a talk, you know, 30 minutes, you know, I can see in my analytics, like a huge spike in my following right after that. And so that’s a great way to sort of grow your audience is to do Instagram collabs in just like 30 minutes tops and [00:47:32] Nathan: Podcasts [00:47:33] Matthew: I get a lot of people will be like, I saw you on this podcast. I was like, wow, cool. [00:47:37] Nathan: I always struggle with that of like, of all the activities that you can do. Cause you get to a point where there’s just so many opportunities open to you and it’s like, which are the best use of time. What should you say yes to, what should you say no to, and I don’t know. Do you have a filter along those or do you just, is it just kind of gut-feel [00:47:53] Matthew: I will say yes to any text-based interview, normally it is the same questions over and over again. So I sort of have a lot of canned responses that I can just kind of paste. and tweak But those are links, so I’m like, sure. Yeah. Send your questions over. Cut paste, tweak, you know, you know, [00:48:12] Nathan: Customize [00:48:13] Matthew: Customize a little bit, but you know, how many times do I need to rewrite from scratch? How’d you get into blogging, you know, what’s your favorite country, Podcasts I definitely have a bigger filter on like you, I don’t do new podcasts. [00:48:27] Nathan: Okay. [00:48:27] Matthew: I know that’s like bad. because you know, this new podcast could become the next big thing, but come back to me when you have some following. [00:48:36] Nathan: I like Seth, Godin’s rule I’m not on south Dakotan’s level by any means, but he says like, come back to me. When you have 100 episodes, I will happily be your 100th interview on your podcast or something [00:48:47] Matthew: Yeah. [00:48:48] Nathan: And he’s just like, look, Put in your time and then we’ll talk. [00:48:51] Matthew: Yeah, so I like, I don’t look for just following, but like again, you know, knowing that people give up on blogs, people give up Podcast too. So. You know, you have to have been doing it for like six months a year, like week a weekly, you know? So I know like this something you care about. and I like to listen because you know, you get a lot of new people and they’re not really great. You know, they asked us like a lot of canned questions and you’re like, listen, you’re taking, you know, an hour, hour and a half of my time. You gotta make it interesting for me. Well, yeah, Podcast. And then for Instagram stories you gotta have, or Instagram lives, either a brand new audience, or if you’re in travel, at least 75,000. Cause I have like a one 30, so I want to keep it in the same in a level. [00:49:43] Nathan: Yeah. I know nothing about Instagram and promotions on Instagram and all of that is there. If someone were to, like, in my case, if I came to you and say, Hey, I want to grow my Instagram following. I’ve got 3000 people or 5,000 people or something like that. And I want to be have 50,000 a year from now. Where would you point me? [00:50:05] Matthew: I would say, do you join Instagram lives with people like once a week, you know, and just, or maybe once a week for you and then go to somebody else on their side once a week. So, and just kind of work your way up, like find people in your, your sort of follower count level, you know? So in this case, I’d probably do, you know, you know, 1000 to 5,000, I would look for in your niche and like get online for 30 minutes and talk about whatever it is you want to talk about and and then go to someone else’s channel and do that, and then keep doing that because you’ll just see giant spikes and then you can move up the the ladder. Then you have 10,000 followers and someone with 25,000 followers might give you the time of day. And then you talk about that, you know, and you just sort of build awareness because you’re always there. You’re always around. [00:51:03] Nathan: It’s a really good point about the figuring out what those rough bands are and reaching out within those. Because I think a lot of people are like, I’m going to go pitch whoever on doing Instagram live together. And it’s like, you have 5,000 and they have 150,000. And like the content might be a perfect fit, but they’re most likely going to say no, because you’re not [00:51:24] Matthew: Yeah. [00:51:24] Nathan: Driving that much value for, or that many subscribers for their audience. [00:51:29] Matthew: Yeah. You know, and so you, maybe I would, you know, someone was like a finance blogger, and they had like 40,000, 30, 40,000. I’d probably. We do it because people who like to say money, like say money on travel. So it’d be like, there’s probably a good fit. And you know, 30,000 people, they might not know me or they have like, like you said, 3000, come back to me, you know, when there’s another zero, [00:51:57] Nathan: Right. Well, and then the other thing that’s going to be true is if I’m bringing you to, to my audience to share and teach something, if you’re using this strategy, like go do another 20 of these or 50 of these, and your pitch will be better. And the way that you teach finance to travel bloggers or whatever else it is, is going to get so much better. [00:52:17] Matthew: Yeah, [00:52:18] Nathan: It’s like, I kind of don’t want to be your Guinea pig. You know, I don’t want my audience to be your Guinea [00:52:23] Matthew: Yeah, [00:52:24] Nathan: Pig for your content. And so just get more experienced and come back. [00:52:28] Matthew: Yeah. And you know, you also gotta think about, you know, people are so time-starved right. You know, when I started blogging, I could. There was no Instagram. There was no Snapchat. There was no Tech-Talk, you know, Twitter was barely a thing. So I didn’t have to split my focus on so many different platforms and channels. Right. I can just, alright, I can be on this one blog, but now when people are like, whoa, sorry, I have to like manage all these different social channels and all of these comments in the blog and everything. They not don’t have like an hour to give, you know, to just anybody way do you could have before, [00:53:12] Nathan: Yeah. Yeah. That’s so true. Okay. So on the email side, specifically, if someone came to you with say 1,000 newsletter subscribers today, and they’re like, I want to grow, I mean, you’re looking to grow to 5,000. This might be so far removed from where you’re at that you’re like, I don’t even know if that was, you know, a decade ago that I was in that position, but what are you seeing that’s working? Where would you point them? [00:53:33] Matthew: What works for us right now? one having email forms everywhere on your site, sidebar, footer, we have one below the content below the content forms, and popups, popups, the work they’re really great. we find for really long posts, having a form in the middle of the post converts better than, at the end of the post, because know a A lot of people don’t read to the end, but when they get to in the middle you’re still there. You know, if you look at heat maps are really long websites, right? You just see that drop-off right. So if all your forms are at the bottom of the page, they’re just not getting the visibility, that you need. so middle of the page, [00:54:19] Nathan: Do you play with a lot of different incentives of like, you know, Opt-in for this fee guide, you know, or are you customizing it to something for a particular country or there, the content that they’re reading [00:54:30] Matthew: Yeah, so we use OptinMonster for that. and so we have, like, if If you go to our pages that are tagged Europe, you get a whole different set of options. than if you go to Australia, like, and like the incentives are like, you know, best hostels in Europe, you know, best hostels in Australia, right? Like little checklist guides. And I tweak what the copy for that, you know, just to see what wording, will lift up a better conversion rate. But yeah, we definitely, because, you know, we cover so many geographic areas. The needs of someone going to Europe are a little different than somebody going to New Zealand. So we, we definitely customize that kind of messaging. And I think that helps a lot, you know, and definitely customizing messaging as much as possible. Um know, but in terms of just, you know, we can talk about, you know, the market, like how do you word things, but middle pop-ups and mil of blog posts definitely converts the best. And so like that’s where we see a lot of growth, as well as, just on Instagram telling people to sign up for my newsletter or Twitter or Facebook, but don’t let the algorithm, you know, keep you from your travel tips, sign up now and people do. [00:55:58] Nathan: Okay. And is that like swipe up on stories that you’re doing [00:56:02] Matthew: Yeah. [00:56:03] Nathan: You know, on an Instagram live or all the above? [00:56:06] Matthew: All the above. [00:56:07] Nathan: Yeah. [00:56:07] Matthew: You just constantly reminding people to sign up for the list, you know, and. One of the failings of so many important for influencers today is, you know, They always regret everyone as everyone does. They always regret not starting to list, you know? And so, you know, you just got to hammer into people, sign up for the list, sign up for the list, sign up for the list. Yeah. And a lot of the copy is, do you see all my updates? No. Would you like to sign up for this newsletter? [00:56:39] Nathan: Yeah, because everyone knows. I mean, I come across people all the time. It’s like, I used to follow them on Instagram. I haven’t seen, oh no, I do still follow them on Instagram. Instagram just decided that I apparently didn’t engage with their content enough or something. [00:56:53] Matthew: Yeah, [00:56:54] Nathan: So now I no longer see their posts, [00:56:56] Matthew: Yeah. You like, I go, I always go to my like 50 least interacted profiles. Right. And, you know, there are some people that aren’t there. I interact with this guy all the time. How is this the least attractive? But that that’s Instagram and saying, here are the people we don’t show you in your feet. [00:57:13] Nathan: W where do you see that? Is that [00:57:16] Matthew: If you go to your, who you’re following, it’s it should be up on the top. [00:57:20] Nathan: Hmm. All right. I’ll have to look at that. [00:57:22] Matthew: Yeah. I’ll send you a screenshot. and so like, that’s the algorithm be like, here are the people who you interact with the least, but it’s like, no, I, I love their stuff. why why do it take them from me? So, [00:57:36] Nathan: Zuckerberg is like, do you really love their stuff? I just not feeling it. [00:57:40] Matthew: Yeah, yeah, yeah. And so, yeah, it’s just, you know, the algorithms are terrible and what I hate and I learned this last year, and this was sort of a unsurprising, but surprising thing is that stories, which used to be like the latest first. [00:57:59] Nathan: Yeah. [00:57:59] Matthew: That is, they have an algorithm for that now, too. And I was like, I, I shouldn’t be surprised, but I am surprised. And I’m annoyed by that because like, I liked it when it was just the newest first, but Nope, now that is based on, you know, sort of like Tik TOK thing of like, oh, this story is getting really a lot of interactions. We’ll bring it up the front of people’s queue or, you know, so it’s not just like your first, because you had one, one second ago, you know, like it could, it’s based on an algorithm [00:58:35] Nathan: Yeah. And that’s how it’s all going to go. Facebook did that a lot, you know, with Facebook fan pages back in the day where it used to be fantastic for engagement. And then they were like, yeah, it’s fantastic. If you pay us [00:58:46] Matthew: Yeah. And even then it’s like, I would pay to boost posts. I was like, great. You saw, I lectured five people. What? I just gave you a hundred bucks and that was. And there was some guy you remember him commenting last year. He was like, whatever happened to this page? I was like, I’m still here. He’s like, no, no, no, no. And this isn’t a common thread in Facebook. He’s like your pages to get a lot more engagement. What happened? I was like, oh, Facebook algorithm. I was like, people just don’t see it. Let me tell you where all my analytics side it’s like this page. So I have 2000 people. You’re like great. 1%, woo [00:59:23] Nathan: Do you do paid advertising? I’d like to get email subscribers. [00:59:28] Matthew: We used to, but, the CPMs went up so much that it wasn’t worth the effort. You know, like paying a dollar 52 bucks for an email subscriber, is just a lot of money for, for, for things. We don’t mind ties directly. Like we’re not taking people through finals buy a course, right? Like just to get rot email, I’m not paying two bucks for. Yeah. And, and so I just, we stopped paying, like during the pandemic, like, June, June of last year, we were like, oh, we’re going to take a break. And then we paid somebody to help us for it to make kind of reset it up. But I just had to spend down so much. I was like, you know what, I’m going to turn off for a bit. And yeah, that’s been like, [01:00:17] Nathan: Didn’t really miss it. [01:00:18] Matthew: Yeah, I looked at the numbers recently cause I was thinking, should we do it? And it’s not that big of a difference of just doing it organically on like Instagram stories or just on the page. Right. And I also don’t really like giving money to the Zuckerberg empire of VO. I just not a fan of that business. And so like, I know my ad spend is low, but I can’t say just. On a rod number. Like it wasn’t that big of a deal. Like, you know, like, cause the CPMs were so high, we were having to pay a lot of money. So like we put in like two grand a month and we weren’t getting thousands. We getting hundreds of people, you know, I want four for two grand. I want thousands of people. [01:01:06] Nathan: Yeah. For my local newsletter, we’re doing paid advertising on Facebook and Instagram and averaging about $2 per subscriber. And that I think now that’s considered pretty good. You’d like a lot of, with a broader audience, you’d be at $3 or more per subscriber and it gets expensive pretty fast. [01:01:23] Matthew: Yeah. I mean, but I think at some point you’ll just see such diminishing returns that, you know, I mean, how many people are in Boise, can you hit, you know, over and over again? Right. [01:01:35] Nathan: Yep. [01:01:36] Matthew: I, I was just reading Seth Godin’s book. This is Marketing. And he said, you know, they talked about ads. You turned off ads when the Content says turn ‘em off. And my Content, I was like, you know, they’re not really paying for themselves. [01:01:50] Nathan: Yeah. Let’s see. Yeah. You turn that off. Looking forward, maybe like two or three years is that I think your business has fascinating of the approach that you have of taking an online audience, building a real team around it, and then building it into the in-person community. what do you think the business is going to look like in two, three years? Where, where is revenue coming from? What’s your vision for the events and meetups and what are the things that like over that time period, they get really excited. [01:02:19] Matthew: Yeah. Two, three years. So we’re talking, you know, 20 by 20, 23, most of our revenue coming from stuff in person, you know, having chapters around the world, people pay to go to them. So, you know, it it’s like 10 bucks and you can bring your friends for free, right. So it’s like five bucks versus. Just for the cost of like hosting events. Right. doing lots of that, doing tours, we’re bringing back. and they won’t be just with me cause they’re community events. Right. So we’ll have guides, right. So it’s not just, you’re coming to travel with me, sort of what Rick, Steve does. Right. You go on and Rick Steves tour, it’s his itinerary, but he’s not on the tour. Right. He shows up to a couple of them throughout the season when it’s not like you don’t expect him to be your guide at the time. So moving to that, having a consumer event for like, like a, like a world domination summit, you know, a weekend somewhere just for travel consumers, having an app for both having an app for that company. then online just being a lot of and affiliates and you know, even me. Just even taking away just having this like passive income course, just because, you know, one less thing to worry about. Right. And then travel con, so being around, but actually making money this time. [01:03:47] Nathan: Do you think travel con is going to turn into, I mean, obviously it’s a significant amount of revenue, but the expenses are so high. Do you think it will turn into a profitable business [01:03:56] Matthew: Oh yeah. Yeah. Like, I mean, a lot of the unprofitability is just comes from the fact that I had no idea where that was doing. [01:04:02] Nathan: Yeah, I know that firsthand from my own conference, so yeah. [01:04:07] Matthew: It was, I didn’t realize how quickly expenses gets that. Right. You know, being like, oh, okay. Like my food and beverage budget is 120,000 writing that in there. And then getting $145,000 bill because, oh yeah, it’s 120,000 food, but then there’s tax fees, which we, you know, all this stuff and like, Okay, well, that’s $25,000 off the profit. Right. and so with a better handle of expenses, like we were definitely like this year, we were gonna like reg even, you know, at the very minimum, we’ll pre COVID and this year we’ll also break break event. Um it’s and just keeping a handle on, you know, like, well, how will I don’t invite a hundred speakers, you know? And, and be like, oh, I had planned to only budget, you know, 50,000 speaker fees, but now I’m at 80. Okay. Like, handling the cost better. We’re good. Now I have a professional events team that kind of slaps me around and it’s like, can’t spend that money. [01:05:06] Nathan: I know how it is, where I’m like, Hey, what if, and then just like, now [01:05:10] Matthew: Yeah, [01:05:10] Nathan: Love it, but no, [01:05:12] Matthew: Yeah, [01:05:12] Nathan: Don’t like, you don’t have the budget for it. [01:05:15] Matthew: Yeah. But no, I mean, you know, we used to have a party. And we’re getting rid of the second night party because people don’t want to go. Like we didn’t have a lot of people show up cause like they’re out and about on town. So it’s like, wow, I just spent, you know, $40,000 for like a third of the conference to come, you know, why not take that money and use it to something that’s more valuable for everybody that has more like impact for dollar spent and still not like go over budget. You know, same thing with lunches. We got, we were getting rid of, we’re doing one lunch now. You know, cause people don’t really care that much, you know, about in [01:06:01] Nathan: Yeah, it’s super interesting. Well, I love the vision of where the conference is going, and particularly just the way that the whole community interplays. I think it’s been fun watching you figure out what you want your business model to be, because obviously, with a large audience, your business model can be any one of a hundred different variations. I like that you keep iterating on it, and figuring out the community. [01:06:26] Matthew: Yeah, we’re definitely going in-person. We’re definitely going to expand to colleges. So, taking the meetup and doing a presentation to a local student union. Because you got to keep people in the grind, right? Keep feeding the grind. So, college students love saving money. We are experts at that. They love to travel. So, just giving a presentation to college campuses around the world as a way to expose them to our brand, and get them to our local event. Like, “Hey college students in Boston, do you like this event? Well, we have a local chapter here. Come join us.” [01:07:08] Nathan: Right. Yeah. [01:07:10] Matthew: They sign up for that, and they get my email. [01:07:13] Nathan: I like it. Well, if anyone wants to sign up and follow along, and all of that, where should they go to see the Instagrams, and subscribe to the newsletter, and everything else? [01:07:22] Matthew: Yeah. You can find me at NomadicMatt.com. The community website is, TheNomadicNetwork.com, and @NomadicMatt on every social media platform. [01:07:32] Nathan: That’s the good thing about finding something somewhat unique, and doing it nice and early. [01:07:37] Matthew: Yeah. [01:07:38] Nathan: You can claim it, rather than being “The” whatever, at underscore something. [01:07:43] Matthew: Yeah. I mean, it also helps having an established brand and the trademark, because if someone took my name on TikTok, and I was just like, “Nope, TikTok.” And they’re like, “Okay, it’s now yours.” [01:07:54] Nathan: There you go. Yep. That’s a good way to go. Well, man, thanks for hanging out today, and I’ll catch you later. [01:07:58] Matthew: Yeah. Thanks for having me.0 comments0
- 055: Andrew Warner - Turning Your Podcast Into a Successful BusinessAndrew Warner has been part of the internet startup scene since 1997. Andrew and his brother built a $30 million per year online business, which they later sold. After taking an extended vacation and doing some traveling, Andrew started Mixergy. Mixergy helps ambitious upstarts learn from some of the most successful people in business. Andrew and I talk about his new book, Stop Asking Questions. It’s a great read on leading dynamic interviews, and learning anything from anyone. We also talk about longevity and burnout as an entrepreneur. Andrew gives me feedback about my interviewing style, the direction I should take the podcast, and much more. In this episode, you’ll learn: Why you need to understand and communicate your mission How to get your guest excited about being interviewed What to do instead of asking questions How to hook your audience and keep them engaged Links & Resources ConvertKit Gregg Spiridellis JibJab Ali Abdaal The Web App Challenge: From Zero to $5,000/month In 6 Months Groove Zendesk Help Scout Jordan Harbinger Noah Kagan Bob Hiler Seth Godin Morning Brew Alex Lieberman Keap (formerly Infusionsoft) Notion Sahil Bloom Ryan Holiday Brent Underwood Ghost Town Living Trust Me, I'm Lying: Confessions of a Media Manipulator Damn Gravity Paul Graham Y Combinator Nathan Barry: Authority Ira Glass NPR This American Life Barbara Walters Richard Nixon interview Oprah interview with Lance Armstrong Matt Mullenweg Chris Pearson Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue Peter Thiel Gawker Nick Denton The Wall Street Journal Rohit Sharma SanDisk Jason Calacanis Dickie Bush Sean McCabe Daily Content Machine Jordan Peterson Tribes Warren Buffet Sam Walton Ted Turner GothamChess LinkedIn Learning (formerly Lynda.com) Inc.com: Selling Your Company When You're Running on Fumes Chess.com Mark Cuban James Altucher Rod Drury Andrew Warner’s Links Andrew Warner Stop Asking Questions Mixergy Episode Transcript [00:00:00] Andrew: The top 10 interviews of all time are news-based interviews. We, as podcasters, keep thinking, “How do I get enough in the can, so if I die tomorrow, there’s enough interviews to last for a month, so I can be consistent, and the audience loves me.” That’s great, but I think we should also be open to what’s going on in the world today. Let’s go talk to that person today. If there’s an artist who’s suddenly done something, we should go ask to do an interview with them. [00:00:32] Nathan: In this episode, I talk to my friend, Andrew Warner, who I’ve known for a long time. He actually played a really crucial role in the ConvertKit story in the early days, and provided some great encouragement along the way to help me continue the company, and get through some tough spots. We actually don’t get into that in this episode, but it takes an interesting turn because we just dive right in. Andrew’s got a book on interviewing. He runs Mixergy. He’s been, running Mixergy for a long time. We talk about longevity and burnout, and a bunch of other things. He dives in and challenges me, and gives me feedback on my interviewing style. Where I should take the Podcast, and a bunch of other stuff. It’s more of a casual conversation than the back-and-forth interview of how he grew his business. But I think you’ll like it. It’s a lot of what I’m going for on the show. So anyway, enjoy the episode. Andrew, welcome to the show. [00:01:25] Andrew: Thanks for having me on. [00:01:26] Nathan: There’s all kinds of things we can talk about today, but I want to start with the new book that you got coming out. This is actually slightly intimidating; I am interviewing someone who has a book coming out about how to be good at interviewing. Where do we even go from here? You were saying that you have thoughts? [00:01:47] Andrew: I have feedback for you. I have a thoughts on your program. [00:01:51] Nathan: I’m now even more nervous. [00:01:52] Andrew: I’ve been listening, and I’ve been following, and I’ve been looking for questioning styles. Is there feedback I could give him? I mean, I’ve wrote a whole book on it. I should have tons of ideas on that. I don’t. Here’s the thing that stood out for me watching you. There’s an ease and a comfort with these guests, but I’m trying to figure out what you’re trying to do with the Podcast. What is connecting them? Are you trying to bring me, the listener, in and teach me how to become a better creator who’s going to grow an audience and make a career out of it? Or are you trying to learn for yourself what to do? How to become closer to what Ali Abdaal doing, for example, or Sahil Bloom? Are you trying to do what they did, and grow your audience? Or is it a combination of the two? I think the lack of that focus makes me feel a little untethered, and I know that being untethered and going raw, and letting it go anywhere is fine, but I think it would be helpful if you gave me a mission. What’s the mission that Nathan Barry’s on with the Podcast. Why is he doing these interviews? [00:02:56] Nathan: Oh, that’s interesting. Because it’s probably different: my mission, versus the audience members’ mission. [00:03:05] Andrew: I think you should have a boat together and, but go ahead. [00:03:08] Nathan: I was going to say mine is to meet interesting people. Like that’s the thing I found that, podcasts are the pressure from two sides, one as a creator, as an individual online, like I’m not going to set aside the time to be like, you know what, I’m going to meet one interesting person a week and we’re just going to have a conversation riff on something like that. Doesn’t happen the times that, you know, the years that I didn’t do this show, I didn’t set aside like deliberate time to do that. And then the other thing is if I were to set aside that time and send out that email, I think a lot of people would be like, I kind of had to have a busy week. I don’t know that I’ve, you know, like yeah, sure. Nathan, whoever you are. I did a Google search. You seem moderately interesting. I’m not sure that I want to get on that. Like a, get to know [00:03:58] Andrew: They wouldn’t and it would be awkward. And you’re right. The Podcast gives you an excuse. I think you should go higher level with it though. I think you should go deep to the point where you feel vulnerable. I think what you should do is say something like this, isn’t it. You have to go into your own into your own mission and say, this is what it is. And just, so let me set the context for why this matters. I think it helps the audience know, but it also helps you get better guests to give better of themselves. I talk in the book about how I was interviewing Greg spirit, Dallas, the guy who created jib, jab, you know, those old viral video, it was a fire video factory that also created apps that allowed you to turn your yourself into like a viral meme that you could then send to your friends. Anyway, he didn’t know me. He was incredibly successful. He was, I think, person of the year, a company of the year named by time. He was on the tonight show because he created these videos that had gone viral. And yes. He said yes, because a friend of a friend invited him, but I could see that he was just kind of slouching. He was wearing a baseball cap. It wasn’t a good position. And then he said, why are we doing this? And I said, I want to do a story. That’s so important. That tells the story of how you built your business. Yes. For my audience. So they see how new businesses are being built online, but let’s make it so clear about what you did, that your great grandkids can listen to this. And then they will know how to great grandfather do this and put us in this situation. And that’s what I wanted. I wanted for him to create that. And he told me that afterwards, if he had known that that was a mission, he wouldn’t have put his hat on. He said that after that, he started thinking about the business in a more in depth way, visualizing his great grandchild. And then later on, he asked me for that recording so that he could have it in his family collection. So the reason I say that is I want us to have a mission. That’s that important that yes. You could get somebody to sit in front of the camera because you’re telling me you’re doing a podcast, frankly. Right. You’re with ConvertKit they’re going to say yes, but how do you bring the best out of them? And that’s it. And so that’s why I’m doing this. And so one suggestion for you is to say something like. I’m Nathan, I’ve been a creator my whole life, but I’m starting from scratch right now with YouTube. I’ve got 435 people watching YouTube. It’s not terrible, but it’s clearly not where I want to end up. And so what I’ve decided to do is instead of saying, I’ve created the book authority, I wrote it. I’m the one who created software that all these creators are using a ConvertKit. Instead of, instead of allowing myself to have the comfort of all my past successes, I’m going to have the discomfort of saying, I don’t know what it’s like. And so I’m going to bring on all these people who, because maybe I’ve got credibility from ConvertKit are going to do interviews with me. And they’re going to teach me like Alia doll and others are going to teach me how they became better creators, better business people. I’m going to use it to inform my, my, growth on YouTube. And by the way, You’ll all get to follow along. And if you want to follow along and build along with me, this is going to come from an earnest place. Now I’ve obviously gone. Long-winded cause I’m kind of riffing here, but that’s a mission. And now we’re watching as you go from four to 500, now we care about your growth. Now there’s someone giving you feedback and more importantly, there’s someone who then can go back years later and see the breadcrumbs. Even if the whole thing fails and say, you know what? Nathan made it in virtual reality videos. And he’s amazing. But look at what he did when YouTube was there. He clearly didn’t do it, but he aspired right. I could aspire to, if I don’t do it, I’ll do it in the next level. That’s that’s what I’m going for with it. I talk too much sometimes and give people too much, too much feedback. How does that sit with you? [00:07:14] Nathan: I like the idea. I particularly love anytime a creator’s going on a journey and inviting people along for it, right. When you’re sitting there and giving advice or whatever else, it’s just not that compelling to follow it unless there’s a destination in mind. So I did that with ConvertKit in the early days of, I said, like I called it the web app challenge said, I’m trying to grow it from zero to 5,000 a month in recurring revenue. Within six months, I’m going to like live blog, the whole thing. people love that another example would be also in the SAS space, but, the company grew, they did a customer support software and they, I think. They were going from 25,000 a month to 500,000 a month was their goal. and they even have like, in their opt-in form, as they blogged and shared all the lessons, it had like a progress bar. You’d see, like MRR was at 40,000, [00:08:08] Andrew: Every time you read a blog post, you see the MRR and the reason that you don’t remember what the number was is I believe that they changed it, you know, as they achieve the goal, they, they changed it to show the next goal on their list. And yeah, and you’ve got to follow along now. Why do I care? The groove, HQ or groove is, is growing a competitor to Zendesk and help scout. But now that I’m following along, I’m kind of invested now that I see how they’re writing about their progress. I really do care. And by the way, what is this groove and why is it better than help scout and the others? Yeah. I agree with you. I think that makes a lot of sense. I think in conversations also, it makes a lot of sense. I think a lot of people will come to me and say, Andrew, can I just ask you for some feedback? I’m a student. Can I ask you for support? It’s helpful for them to ask, but if they could ground me in the purpose, if you could say to somebody I’m coming to you with these questions, because this is where I’m trying to go, it changes the way that they react. It makes them also feel more on onboard with the mission. I have a sense that there is one, I’m just saying nail it, you know, who does it really good? who does a great job with it is a Jordan harbinger. He starts out his each episode is almost if you’re a fan of his, it’s almost like enough already. I get that. You’re going to do an opt-in in the beginning of the Podcast. I get that. What you’re trying to do is show us how to whatever network now and become better people. But it’s fine. I’d much rather people say, I know too much about what this mission is. Then I don’t. [00:09:26] Nathan: Do you who’s afraid anyone else tuning in? What, what is Jordan’s mission? What would he say is the mission that [00:09:32] Andrew: It’s about, see, that’s the other thing I can’t actually, even though I’ve heard it a billion times, he’s adjusted it. It’s about, self-improvement making me a better person better, man. And so the earnestness of that makes me accept when he brings somebody on who’s a little bit too academic who’s, Jordan’s interested in it or a little bit too practical to the point where it feels like I’m just getting too many tips on how to network and I don’t need it, but I’ve got his sensibility. He’s trying to make me a better person. And so I think with interviews, if you, if you give people the, the mission, they’ll forgive more, they’ll accommodate the largest and it does allow you to have a broader, a broader set of topics. [00:10:14] Nathan: Yeah. I’m thinking about the mission side of it. Like all of that resonates. and I love when an interview is questions are Like are the questions that they specifically want to know? It’s not like I went through my list and this seems like a good question to ask instead. It’s like, no, no, no, Andrew specifically, I want to know what should I do about, this? And I’ll even call that out in a show and be like, look, I don’t even care if there’s an audience right now. Like this is my list, you know? [00:10:41] Andrew: Yes. [00:10:41] Nathan: But the, like if we dive into the mission, the one that you outlined doesn’t quite resonate. And I think the reason. I think about, creators who have already made it in some way. And it starts to lose that earnestness. Like, honestly, I’m not that interested in, in growing a YouTube [00:11:00] Andrew: I don’t think that that’s I don’t think that that’s it for you. It’s true. That’s a little bit too. I don’t know. It’s it’s a little, it’s a little too early in the career. There is something there. I don’t know what it is and it can’t be enough. It can’t be enough to say I need to meet interesting people because that’s very youth centric and I’m not on a mission to watch you, unless you’re really going to go for like the super right. And we’re constantly aspiring, inspiring. the other thing it could be as you’re running a company, you’re trying to understand what’s going on. No Kagan did that really well. I actually have the reason that I know this stuff is in order to write the book. I said, I have all my transcripts. I can study all the ways that I’ve questioned, but I also want to see what other people have done. And so Noah Kagan did this interview with an NPR producer. I had that transcribed to understand what he did and what he learned. One of the things that he did in that, that made that such a compelling interview is. He was a podcaster who wanted to improve his podcasting. And he, I think he even paid the producer to do an interview with him on his podcast so that he could learn from him. Right. And in the process, he’s asking serious questions that he’s really wondering. He’s trying to figure out how to make a show more interesting for himself. Now. Clearly someone like me, who wants to make my Podcast more interesting. I’m like mentally scribbling notes as I’m running, listening to the podcasting. Oh yeah. The rule of three, like what are the three things you’re going to show me? Well, yeah, at the end he did summarize it and he did edit. I don’t like the edits at all because the edits take away some of the rawness of it and the discomfort which I personally enjoy, but I see now how he’s editing it out. And it’s, it’s interesting to watch that progress. [00:12:32] Nathan: Yeah, I’m thinking through. The different angles that I could take with this. cause I like it and I feel like there’s a, a thread that’s not quite there. And I felt that on the show. Right. Cause people ask, oh, why are you having this guest on versus that guest? and it is that like, I, I find them interesting. There’s also another angle of like probably half the guests maybe are on ConvertKit already. And so I want to highlight that. And then the other half of the guests aren’t and I want them on ConvertKit and so that’s an, you know, an incredibly easy, I can send you a cold email and be like, Andrew switched to ConvertKit. Right. Or I could be like, Hey, you know, have you on the show, we could talk. and we’ve gotten great people like in the music space and other areas from just having them on the show and then [00:13:18] Andrew: Can I give you, by the way, I know it’s a sidetrack and I give you a great story of someone who did that. Okay. it’s not someone that, you know, it’s a guy who for years had helped me out. His name is Bob Highler every week he would get on a call with me and give me advice on how to improve the business. And then at one point he said, you know what? I need new clients. I want to start going after people who are, I want to start going after lawyers, helping them with their online ads, because lawyers aren’t, aren’t doing well enough. He started doing all these marketing campaigns because he’s a marketer. And so one of the things he did was he got these cards printed up. He said, they look just like wedding invitations, beautiful. He, he mailed them out to lawyers. He got one, two responses. Like nobody would pay attention to a stranger, even if they were earnest and sending those out. And he goes, you know, and then he gets on a call. He doesn’t even know what to say to people. If he just cold calling goes, I’m going to try to do that. And Andrew, I’m going to do an interview show for lawyers. He picked bankruptcy lawyers. He started asking them for interviews. They were all flattered because they also want another good Google hit. Right. And so they said yes to him and he asked them questions. Then I started learning the language. I forget all the different terms that he learned about how, about how they operate. But he said, inevitably at the end, they’ll go after it was done. And say, by the way, what are you. And then he’d have a chance to tell them. And because he’s built up this rapport and they trust him, they were much more likely to sign them. He signed up his customers, just like that, just like that. It’s a, I think it’s an, it’s an unexplored way of doing it, of, of growing a business, taking an interest in someone, shining a light on them, helping them get that Google hit and helping them tell their story. And then by the way, will you pay attention to the fact that I’ve got a thing that if you like me, you might like also, [00:14:50] Nathan: So a few years ago, I was in New York and Seth Goden had come out to speak at our conference and he’d ever said, Hey, if you’re in New York and want to make the pilgrimage up to Hastings on Hudson, you know, of outside the city, like come up and visit. And so I did that and it’s so funny, cause it is like this pilgrimage to you, you like take the train up along the river. You know, I don’t know what it is an hour and a half outside of the city. and I was asking Seth advice at his office, about like how to reach more authors. I think that was the question I asked him specifically and he just, he was like, well, what do authors want? And I was like, ah, I, some more books I guess. And he’s like, yeah know. And so like we went through a series of questions, but he’s basically what he came to was, find a way to get them attention so that they can grow their audience to sell more books. And he was suggesting a podcast is the way to do that. What’s interesting is that’s the side, like that’s the other half of it, right. I want to meet interesting people. I want to, Like get more of those people that I find really interesting on ConvertKit pushed the limits of like, our customer base in, in those areas. And then the third thing is I want to do it in a way that’s high leverage in my time. Write of, I want to do it. That creates something, for people watching and listening along so they can follow the journey. But I still don’t see, I would say two thirds of that is about me, right? [00:16:18] Andrew: It’s not only that, but all these things are byproducts more than they are the clear goal. You’re going to get that. No matter what, if you just talk all day about what? No, not talk all day. If you do, what was it? I’m the founder of morning brew does nothing, but like a 15 minute, if that sometimes five minutes. [00:16:37] Nathan: Alex Lieberman. [00:16:38] Andrew: Yeah, just what, what goes on in his life now it’s changed over the years or so that he’s done it, but it’s just, here’s what we were thinking about today. Here’s how I’m deciding to hire somebody BA done. He’s just doing that. That’s enough to get attention enough to also broaden his audience enough to bring us in and then so on. So I think if you just did nothing, but get on camera and talk for a bit, you’ll get that. But I think a higher leverage thing is to tap into that personal mission and let all the others come through along the way and all the other benefits, meaning that you will get to meet people and change the way you think you will get to get people to switch to convert kit. And so on, by the way, that’s such a, like an impressive thing for you to admit, to say, I want to have these guests on because I want to assign them up. I think a lot of people would have those ulterior motives and [00:17:23] Nathan: Oh, no, you got to just talk about, I mean, that’s something you and I, for as long as we’ve known each other have been very, very transparent in both of our separate businesses and our conversations and it’s just, everyone wants that. Right? Cause they’re like, I think I know why Nathan is doing this, but he wants. And that would be weird, but if we go to the mission side of it, there’s mission of like this, I’m going to improve the world side of mission, which definitely exists that can protect you. And I got my little plaque behind me. It says we exist to help creators are living. And so we can take that angle of it, thinking of like the, the goal journey side of things, since we’re just riffing on ideas. One way that might be interesting is to make like a top 100 list of the top 100 creators we want on ConvertKit. And the whole podcast is about interviewing those people and reaching them. And, and so it could be like, this is what I’m trying to accomplish. And you’re going to learn a whole bunch along the way as a listener, but you, you know, we check in on that. And then another angle that we could take that would be different is the, like we’re going together. We’re going to help the creator make the best version of their business. And so you make it more of a. We’re both peers diving in on your business, riffing on it, you know, how would we improve it? that kind of thing. [00:18:43] Andrew: I think helping creators create a business, seems like something others have done, but not quite your approach, your style, the way that you will go and carve something is this is the thing that’s over your head that says create. Is that something you carved in your wood shop? Then I saw on Instagram. Yeah, right. The sensibility of I’ve got to create it my way. Instead of that’s a pain in the ass, I got a business to run who like, right. You’re not going to see, for example, infusion soft, go, we need a plaque. Let’s go to the wood shop. No, you’re not. It’s just not their sensibility. Right. Coming from a sensibility of someone who cares about the details, who every button matters in the software, everything behind your shoulder matters to you for yourself, even the stuff I imagine. If you look forward would have a meaning there, it wouldn’t be random chaos. Is it random chaos in front of, on the [00:19:32] Nathan: The desk is random chaos, but there’s a sign that says the future belongs to creators up there. And [00:19:38] Andrew: Okay. I think I might’ve even seen that online somewhere. So I think that coming, coming from the business point of view, With a sense of creator’s taste, I think is something that would appeal to a lot of people. For whom seeing, for example, my take on business would be completely abhorring. All I care about is where the numbers are and what it’s like. Right. Well, even allium doll’s take on, it would not be, would not be right, because he’s much more about every movement needs to matter. He can’t just have a checkbox in notion it Ellis has to fire off five different other things that notion because otherwise you’re wasting time. Why type five things when you could type one, right. It’s a different sensibility. And I think you’ve always done really well drawing in that audience. I remember talking to a competitor of yours who started around the same time, also done really well about why you were, you were really growing tremendously faster. and they said he nailed it. He nailed who his audience is. It’s the bloggers. It’s these early creators who, who didn’t have. Who didn’t have anyone speaking for them. And you did that. And I think maybe that’s an approach to saying, look, we are creators. And the business of creation is, or the business of being a creator is evolving and we want to learn about every part of it. And then it’s interesting to hear how somebody growing their audience in an interesting way. How is somebody thinking about writing? I love that you asked Sahil bloom about how long it took him to write. I know he talks about it a bunch, but it’s, it’s interesting to hear him go with you about how it is like a five hour, seven hour writing job for him, right. To write fricking tweets. He’s writing tweets, right? You’ve got people just firing off the tweet. He’s spending five, seven hours on it. And, and he’s also not a guy who’s just like, right. It would be something if he was still in school playing baseball, and this is his intellectual, whatever. No, he’s now running in investments. He’s making decisions. He’s helping promote his, his portfolio companies and he’s spending five hours writing and he’s doing it like one a week instead of one an hour. Right. It’s all very interesting. And that approach, I think, ties completely well with ConvertKit. [00:21:41] Nathan: Okay. So where does that take us on like the mission or the hook for the show? Cause we’re. [00:21:48] Andrew: Okay. Here’s what I would do. I would, I would just keep riffing go. My name is Nathan Barry. You probably know me from convert kit. I’m doing this podcast because I like to meet interesting people. And here’s the thing I’m trying to do or I’m I I’m doing it because I’m compelled to talk to these people who I admire. And I also want to learn from them about how they create and just riff on it. Like every week, even have every interview have a different one, until you feel like, oh, that’s the one that feels just right. But if we just here, I want to have this person on, because I’m trying to learn this thing. I want to have this on because secretly I’m trying to see if I can get him to be at, see if I can get Ryan holiday to actually be on convert kit. Right. Boom. Now, now we’re kind of following along as you’re figuring it out. And that’s also [00:22:29] Nathan: Yeah. [00:22:29] Andrew: The way, is Ryan holiday going to be on here or what? [00:22:31] Nathan: On the show, [00:22:33] Andrew: Yeah. [00:22:34] Nathan: Probably we were just talking the other day. We have a shared investment in a ghost town, So we, we often talk about that, [00:22:40] Andrew: Oh yeah. I’ve [00:22:42] Nathan: Other thing [00:22:43] Andrew: That ghost town. Oh, that’s a whole other thing I’ve been watching that [00:22:45] Nathan: I need to have speaking of the ghost town, I didn’t have Brent Underwood on because that Is an insane story of everything going on with town, but it’s just been building this massive audience. [00:22:58] Andrew: Who’s doing YouTube videos from there? He [00:23:00] Nathan: Yeah. And he’s now got 1.2 [00:23:01] Andrew: Yeah, [00:23:02] Nathan: Subscribers on YouTube, like 2 million on [00:23:04] Andrew: I had no idea. I watched him in the early days of the pandemic go into this place by himself. Almost get trapped, driving his car to get there. Right. I go, this is fun content. And usually when you watch someone like that and good morning, America go, and I’m going to jump out of this thing. And I’ve never jumped before, maybe whatever. I don’t know. Yo, the producer’s not going to let you die. It’s fine. Here you go, dude. Who’s just trying to get attention for this thing. Cause he has some investors who he wants to make sure get what they want. Yeah, you could die. What the hell is you doing? What? Like I’m going to, I’m going to go down this hole and see if there’s anything over you yet. Dude, you could [00:23:41] Nathan: Yeah. It’s, it’s pretty wild. I actually, some of the weeks that he don’t, he, that he didn’t post the videos. I’d like, texted him, be like, Brett, you’re still alive because you know, the video was the way that we knew every Friday, like, okay, Good Brent. Still alive, everything. Everything’s good. Anyway, I got to have him [00:23:58] Andrew: All right. If you do talk to, if you talk to Ryan holiday, I feel like you totally nailed his writing style, where you, you said in one of your past episodes that he can take a whole historical story, sum it up in two sentences to help clarify the moment that he’s writing about. And it’s like a toss away thing, right? Just toss it away and then move on and go, dude. That’s a whole freaking book. In fact, just turning the whole thing into just two sentences to fit in there would take silo, bloom five hours. You put it in a book with other, like there a bunch of other sentences. So that’s good. But here’s what I think you should talk to him about. Or here’s my, my one suggestion. He has not talked about Marketing since he created, trust me. I’m a lot. Trust me. I’m lying, which was a phenomenal book that then I feel like he distanced himself from when he became more stoic and more intellectual. Fine. He is still a great, great marketer along your style, your tasty. And in fact, he’s becoming the people who I can think of that are very, ConvertKit like philosophy in their creation plus promotion. He nails it, right? Art that takes so much pain that you’ve mentioned, and we’ve all seen it. He has boxes of index cards to create these sentences that most people would just throw away, not pay attention to, but are super meaningful. And at the same time, he knows how to promote. He knows how to get his ideas out there. He knows how to sell a coin that says you’re going to die in Latin, that people put in their pockets that are more than just selling a coin. It’s selling this transferable viral, real life thing. Right. So anyway. And is he should be on a ConvertKit too. [00:25:29] Nathan: He is, he is [00:25:30] Andrew: Okay. Good. [00:25:31] Nathan: Half of his list started in Berkeley. The other half are in the process of switching over. So, you know, [00:25:36] Andrew: Okay. Yeah, that’s the hard part, dude. I I’m with infusion soft. I can’t stand them. If you understand how much I do not like them. I do I ever talk negatively about anyone. No. Bring up politics, Joe Biden, Donald Trump. I got no strong opinion about anything you talked to me about, about infusions. Ah, but the problem is it’s so hard to wean yourself off of these things because once you’re in a system, that’s it [00:25:56] Nathan: Well we’ll make it happen. W w we’ll figure out a way, but the new book landing page for it, I went on there and inspected element. It’s definitely a ConvertKit for them. I was pretty happy about it. [00:26:06] Andrew: Oh yeah, yeah, yeah, yeah. So truthfully it was, I said, I’m not going to school around here. It would have probably been easier for me to go with, with infusion soft because then we all we’d have to do with tag people who were interested. And then I could, I don’t want that. I don’t want that nonsense because it comes with overhead. That becomes an obstacle to me, communicating with my audience by, by overhead. I mean, they’ve got historic legacy. Requirement’s that mean I can’t do anything right. You I’m on my iPad. I could just go in and send a message out. Or actually I haven’t sent a message out. Someone else has sent a message out. Our publisher sent a message then from damn, ah, damn gravity. But I, but if someone says there’s a problem, I can go in and see it. [00:26:44] Nathan: Right. [00:26:44] Andrew: And make adjustments. The whole thing just fricking works. Right? [00:26:47] Nathan: So I want to talk about the book more. Let’s talk [00:26:49] Andrew: Sure. [00:26:50] Nathan: And now I have you here. [00:26:52] Andrew: Ben needs, us to talk about the book. He’s the publisher. [00:26:54] Nathan: We’ll get to that, then don’t worry. Ben, we’ve got it covered. so you were giving unsolicited feedback, which by the way is my favorite kind of feedback. Okay. So as you’ve been listening to the show, what are some other things that maybe you recommended the book, maybe like as you set people up for interview questions, any of that advice that you would give beyond? We started with the men. [00:27:15] Andrew: I’m going to suggest that people who listen to you do pay attention to this. One thing that they should, I I’m interrupting you in a roadway now there’s some good interruption that I write about in the book and I can tell you how to do it. Right. And I also have to say that there’s some new Yorker that’s built in, even though I’ve left New York a long time ago, that I, I always interrupt when we need to get into the bottom line. Okay. Here’s one thing that I think people should pay attention with you. You don’t just ask questions. You will, at times interject your own story, your own, take your own experience. And I find that a lot of times people either do it in a heavy handed way. It’s like, look at me, I’m equal to you. I deserve to be in this conversation too. And that doesn’t just happen on Mike. It happens at dinner parties or it’s more like I have to be reverential. So I’m asking questions and it’s me asking about them. And one of the things that I learned over the years, Getting to know someone interviewing someone, whether it’s like you and I are doing in our podcasts and shows or doing it, in a, in a dinner conversation, it’s not asking questions. It’s not about saying here’s my next thing. Here’s my next question. It’s overwhelming and draining to do that. You do need to say, well, here’s me. You do need to sometimes just guide the person to say, now tell me how you wrote the book. Now tell me how long it takes to, to write a tweet, right? Whatever it is, you need to sometimes direct the person. And so I call the book, stop asking questions because that counter intuitive piece of knowledge is something that took me a fricking interview coach to help me accept that. It’s true, but it helps. And you do it really well. And here’s why you do it. Well, you interject something personal. Somehow you do it succinctly. You don’t get rambling off. Maybe you edit that. No, no, because the videos are there. Yeah. It’s, it’s not edited. It’s just you saying here’s, here’s my experience with this. And then when you come back and you ask something. It informs the guest about where you are and what they could contribute to that. It lets them also feel like this is a dialogue instead of them being pounded with demands of, in the forms of question. [00:29:15] Nathan: Yeah. Yeah. I think that for anyone listening and thinking about starting a podcast, it’s really like, what’s the kind of thing that you want to listen to. And I like it where the host is like a character in the, in the Podcast, in the episode where they’re contributing content and it’s not just like, oh, if I listened to Andrew on these 10 shows, I’m just going to get Andrew. Like, I want it where it’s like, no, I’m getting the blend between these two people. And the unique things that come from that intersection rather than, you know, I’ve heard this [00:29:46] Andrew: Yes. [00:29:47] Nathan: I’ve heard about it. [00:29:48] Andrew: I think also it took me a long time years of, so I started doing this in 2007, give or take a year and I think. No one needs to talk about, I don’t need to talk about myself. They don’t care about me. They care about, you know, Paul Graham, who I’m interviewing about how he found a Y Combinator, someone. And I would get tons of emails from people saying, tell us who you are. Tell us a little bit about yourself. And I would argue with them and say, no, but I understand now on the outside, when I listen, I don’t know who you are. And it feels very awkward to hear it. It feels very much like, I don’t know why, where you’re coming from. And so I don’t know why I should listen. It’s kinda, it’s it’s counterintuitive. [00:30:29] Nathan: Yeah. I think it just comes with comfort over time. Like, I, I don’t know this for sure. If I bet if I listen back to my first podcast episodes, the ones that I did in like 2015. I have a different style because I bet I’m less comfortable or more worried about like, make sure that I shut up quickly so that the guests can talk more because people came here for the guest and then over time you just get more comfortable. [00:30:53] Andrew: So you wrote authority and I remember you, I remember buying it and I remember you bundled it with a bunch of stuff, right. And oh, by the way, it’s so cool. I was listening to it on a run and I heard you mention my name in the, in the book I go, this is great and I’m running. but I remember you did interviews there. I don’t remember whether the style matches up to today or what, but you did interviews in it. Right. [00:31:15] Nathan: I did. [00:31:16] Andrew: And what you had there that I think is always important to have with all, all interviews is you had a sense of like, well, the sense of mission, I knew what you were going for, because you were trying to say, here is this book that I’ve written on this topic. I’m want to bring these people in to bring their, their take on it. We were all kind of working together. And I feel like, when I look at my earlier interviews, I listened to them. The Mike sucks so badly. I was too ponderous. Cause I wanted to be like, IRA glass from, from NPR, from this American life. And you could hear the same rhythm, the same cadence, like I’m copying him. Like I’m his little brother trying to learn how to be like a real boy. but I had this real need. I was trying to figure out how these people were building companies that work to understand what holes I had in my understanding to see what was working for them that I didn’t know before. And you could see that and it, it helps. It helped me continue. Even when I was nervous with the guest, it helped the guests know where to go. Even when I wasn’t doing good job, guiding them and help the audience keep listening in, even when the audio stopped, because there’s this thing that Andrew is trying to understand. And you almost feel like you’re the sense of vulnerability. If it doesn’t scare you away, then it makes you want to root. [00:32:40] Nathan: Yeah. And I personally love that style because I want to follow someone going on a journey and, and trying to accomplish something specific. But let’s talk about the not just the book, but asking questions or in this case, stopping it, stop asking questions. What are the things that not even just specific to this job, what are the things that you listened to interview shows? And you’re like, okay, here are the three things that I want to change or that I want to coach you on in the same way that I was coached on. [00:33:10] Andrew: Okay. So what I started to do is I go through my own transcripts. I mean, I had years of transcripts to see what worked and what didn’t I already done that. So I said, I need to now add to it. And so I went back and looked at historical interviews, like when Barbara Walters interviewed Richard Nixon and got him so frustrated that he didn’t want to ever talk to her again. Or when Oprah finally got to sit with Lance Armstrong, how did she do that? I think. You know, you know, let me pause on, on Oprah and Lance Armstrong. She got to interview him after he, he was basically caught cheating and he was about to come out and do it. Great. Get, I think the fact that she interviewed him, there’s a lesson there for, for all of us who are interviewing, interviewing the top 10 interviews, I think of all time. And you go back to Wikipedia and look it up. You see art or interview podcast or interview, sorry, our news-based interviews. We as podcasters, keep thinking, how do I get enough in the can so that if I die tomorrow, there’s enough interviews to last for a month or whatever, so that I can be consistent in the audience loved me. That’s great. But I think we should also be open to what’s going on in the world today. Let’s go talk to that person today. If there’s an artist who suddenly done something, we should go and ask to do an interview with them. If there’s a creator, if there’s someone. So for me, one of the top interviews that people still it’s been years, people still come back and talk to me about is when Matt Mullenweg decided that he was gonna pull out Chris [00:34:35] Nathan: Pearson. [00:34:35] Andrew: Per Pearson. Pearson’s, themes from WordPress. And I got to talk to both of them at the same time and I published it and it went all over the internet with all over the WordPress internet. So hundreds of different blog posts about it, eventually all the people in the WordPress world write a lot of blogs, but also it became news. And so we don’t do enough of that. [00:34:57] Nathan: I remember that interview because I was in the WordPress community at that time. And I remember you saying like, wait, I’m in Skype and I have both of you in two different things and you pull it together and not to pull Ryan holiday into this too much, but that’s where he ended up writing the book. Was it, he realized he was one of the only people who was talking to like both Peter teal and, who’s the Gawker guy. Yeah. Anyway, people know, but, but being in the intersection of that, so you’re saying find something that’s relevant on the news [00:35:33] Andrew: Yeah. Nick Denton was the founder of Gawker. Yes. Find the things that are relevant right now. And when people are hot right now, and they know you and you have credibility in this space, they trust you more than they trust. Say the wall street journal, even right, where they don’t know where’s this going. I think that’s, that’s one thing. The other thing is I think we don’t have enough of a story within interviews. If we’re doing S if we’re doing at Mixergy, my podcast and interview where we’re telling someone’s story, we want them to be somewhere where the audience is at the beginning and then to have done something or had something happen to them that sets them on their own little journey. And then we make this whole interview into this. Into this a hero’s journey approach. So I think better when I have an actual company in mind, so, or a person in mind. So last week I was interviewing this guy, Rohit Rowan was a person who was working at SanDisk, had everything going right for him. His boss comes to him and says it, you’re now a director, continue your work. But now more responsibilities he’s elated. He goes back, home, comes back into the office. Things are good, does work. And then a couple of days later he’s told, you know, we mean temporarily, right? And he goes, what do you mean? I thought I got, I got a promotion. No, this is temporary. While our director’s out you’re director of this department. And then you go back, he says, the very next day, he couldn’t go back into the office. He sat in his car, just, he couldn’t do it anymore. And so he decided at that point, he’d heard enough about entrepreneurship heard enough ideas. He had to go off on and do it himself. And so we did. And then through the successes and failures, we now have a story about someone who’s doing something that we can relate to, that we aspire to be more. [00:37:13] Nathan: So, how do you, you, your researchers, how do you find that moment before you have someone on? Because so many people will be like, yes, let me tell you about my business today. And oh, you want to know about that? How’d, you know, you know, like, as you, [00:37:27] Andrew: Yeah, [00:37:28] Nathan: That hook in that moment? That actually is a catalyst in their own dream. [00:37:33] Andrew: It’s tough. It’s it takes hours of talking to the guest of, of looking online of hunting for that moment. And it takes a lot of acceptance when it doesn’t happen. One of my interview coaches said, Andrew, be careful of not looking for the Batman moment. And I said, what do you mean? He goes, you’re always looking for the one moment that changed everything in people’s lives. Like when Batman’s parents got shot. And from there, he went from being a regular boy to being a superhero. Who’s going to cry, fight crime everywhere. His life doesn’t really work that way. There aren’t these one moments, usually the change, everything. So I try not to. Put too much pressure on any one moment, but there are these little moments that indicate a bigger thing that happened to us. And I look for those and I allow people to tell that without having it be the one and only thing that happened. So if Pharaoh, it, it wasn’t that moment. It could’ve just been, you know what, every day I go into the office and things are boring. And I think I have to stop. What I look for is give me an example of a boring. Now he can tell me about a day, a day, where he’s sitting at his desk and all he’s doing is looking at his watch, looking at his watch and he has to take his watch, put it in his drawer so that he doesn’t get too distracted by looking at his watch all day. Cause he hates it. Now was that the one moment that changed everything? It was one of many moments. It might’ve happened a year before he quit, but it’s an indication. So when we’re telling stories, we don’t have to shove too much pressure into one moment, but I do think it helps to find that one moment that encapsulates their, why, why did they go on this journey? Why does someone who’s in SanDisk decide he’s going to be an entrepreneur? Why did someone who was a baseball player decide that he had to go and write a blog post? Why is it? What’s the thing that then sends them off on this journey? It helps. And I would even say, if you can get that moment, it just helps to get the thing that they were doing before that we can relate to. So what’s the thing that they did before. So anyway, we have two different types of interviews. One is the story-based interview where we tell a story of how someone achieved something great. And so that hero’s journey is and approach. The other one is someone just wants to teach them. All you want to do is just pound into them for an hour. Give me another tip another tip another tip of how to do this. Like pound, pound, pound, pound pound. If you want the audience to listen. I think for there, it helps to have what I call the cult hook because I said, how do I, how do cults get people to listen to, to these people who are clearly whack jobs sometimes. And so studying one called I saw that what they did was they’d have a person up on stage who talked about how, you know, I used to really be a Boozer. If you came into my house, you would see that there’d be these empty six packs. I was so proud of leaving the empty six packs everywhere to show myself how much alcohol I can drink. My wife left me. And when she left me, she just told me that I hadn’t amounted to anything in my life. And I was going nowhere. And I just said, get I here. Instead of appreciating that this was just like terrible. And I ran out of toilet paper and don’t even get me started with what, what I did for that. And so you see someone who’s worry worse off than you are on this path of life. And then something has. They discover whoever it is. That’s the cult leader. And they say, now I’ve got this real estate firm I encouraged by, oh, by the way, all of you to come over and take a look at that at this, I couldn’t believe it. My whole life. I wanted to buy a Tesla. I now have the Tesla S it’s amazing. It’s just so great. And I did it all because I changed the way I thought once I came in and I found this one book and the book told me, I mean, anyways, so what we try to do is we say, if you’re going to have somebody come on to teach how they became a better blogger, let’s not have them start over elevated where everything they do is so great that we can’t relate, have them start off either relatable or worse. I couldn’t write here’s my grammar, mistakes. My teacher told. Right. And now what’s the thing that they did. They pick them from where they were to where they are today. it’s this real set of realizations. Now I want to go into that. Let’s pound into them and see how many of those tips we can get. Let’s learn that I want to go from where he was to where he is. [00:41:28] Nathan: Yeah, I liked that a lot. Cause my inclination would be like, okay, we’re we’re doing the, educational, tactical conversation. I’m going to facilitate it. Let’s dive right in and let’s get to the actionable stuff right away. So I like what you’re saying of like, no, no, no. We need to, even though this is going to be 90% packed, full of actionable material, we need to dive in and set the stage first with the story and making it relatable. And I like it. [00:41:55] Andrew: Yeah, [00:41:55] Nathan: Oh, yeah. I was just, just in my own head for a second. Cause I say, ah, that makes sense a lot, so much so that I’ve had three different guests or listeners email me and say like, just don’t say that makes sense as much would, now that I’m saying it on the show, I’ll probably get more emails every time that I say it. Cause that’s like my processing, like, oh, oh, that makes sense. As I’m thinking of the next question and all that, so [00:42:22] Andrew: I do something like that too. For me. It’s IC, [00:42:25] Nathan: Everyone has to have something. [00:42:26] Andrew: I can’t get rid of that and yeah. [00:42:28] Nathan: So what systems have you put in place on the research side so that you’re getting this, are you doing pre-interviews forever? Yes. Are you having your [00:42:38] Andrew: Almost every single one, some of the best people in some of the best entrepreneurs on the planet, I’m surprised that they will spend an hour or do a pre-interview. And sometimes I’m too sheepish to say, I need an hour of your time and I need you to do a pre-interview. So instead of saying, I need you to do a pre-interview. I say, here’s why people have done it. And I’ve paid for somebody to help make my guests better storytellers of their own stories. And truthfully people will go through that. Pre-interview even if they don’t want to do an interview, they just need to get better at telling their story for their teams, their employees, their everyone. Right. and so I say that, and then they will take me up on the pre-interview and say, yes, I do want to do the pre-interview. and so what I try to do is I try to outline the story. Ahead of time in a set of questions. And then what we do is we scramble them up a little bit based on what we think people will tell us first and what will make them feel a little more comfortable. And then throughout the interview, I’ll adjust it. So for example, no, one’s going to care about the guest unless they have a challenge. No guest wants to come on and say, I’m going to tell you about what’s what I really suck at or where I’ve really been challenged. If they do, they’re going to give you a fake made up thing that they’ve told a million times to make themselves seem humble. So we don’t ask that in the beginning. We don’t even ask it in the middle. We save it till the very end. Now they’ve gotten some time with us. They’ve gotten some rapport, they trust us. Then we go into tell me about the challenges, what hasn’t worked out for you. And we really let them know why tell people the higher purpose you want the audience to relate. You want them to believe you. You want them to see themselves in you, and to learn from you. We need. They tell us, and then I have it in my notes as the last section, but I use it throughout the interview. I sprinkle it. So the goal is to get the pieces that we want and in whatever order makes the most sense and then reshape it for the interview Day. [00:44:33] Nathan: So on the interview itself, you would, you would flip that and you know, okay, this is what I want to start with and, and dive in right [00:44:41] Andrew: Yup. Yup. [00:44:43] Nathan: Lose. They already told you about that. And so now, you [00:44:46] Andrew: Right, [00:44:46] Nathan: In and start with. [00:44:47] Andrew: Right. That helps. Now, if there’s something I want to ask someone about that they’re not comfortable with. One thing that I do is I, I tip them off. So Jason Calacanis invited me to go do, interviews with, with investors at one of his conferences. It was just a bunch of, investors. And I looked at this one guy, Jonathan tryst, and he looked really great. But he, what am I supposed to do? Ask him about what startups should do to run their businesses. He’s never run a startup. His, he hadn’t at that time had a successful exit. As far as I knew, like mega successful exit. He’s just a really nice guy. You can tell he was going places, but that’s it. And the money that he was investing came from his parents. So what is this rich parents giving their kids some money. Now he’s going to tell everyone in the VC, in the startup and VC audience, how to live their lives. So I said, I’m either not going to address it, which I think most people are, or I have to find a way to address it where I’m not going to piss them off and have them just clam up on me and then go to Jason and go. This guy just is a terrible interviewer, which is not true. So what I decided to do was tip him off. I said, look, Jonathan, before we do this, before we start talking to the audience, I have to tell you, I saw it, that you don’t have much of a track record as an investor. Your money came from your parents and you’re not like a tech startup, like people here. If we don’t talk about it, people who know it are going to think, oh, this guy, Jonathan, look, who’s trying to pass him soft self off. I don’t have to force it in here, but if you allow me to, I’d like to bring it up and let’s talk about, and it goes, yeah, absolutely. If it’s out there, I want to make sure that we address it and sure enough, we talked about it and he had a great answer. He said, no, this came from my parents. It’s not my own money. I don’t have as much experience as other people, but I took my parents’ money. I invested it, fat parents and family and so on. We’ve had a good track record with it. And now have raised the second Fallon fund from outsiders who saw what I was able to do with the first one. And by the way, I may not have this mega exit as a startup investor, as a startup entrepreneur. But I did have this company that did okay. Not great. Here’s what it did Here’s what I learned And that’s all informing me. And that’s where I come from now. You’ve got someone talking about the, the, the thing that matters without pissing them off so much that they don’t say anything else. And you feel like you feel superior as an interviewer. I got them. But in reality, you got nothing [00:46:57] Nathan: Right. [00:46:57] Andrew: Cares. [00:46:58] Nathan: I think that’s a really hard line of talking about the things that are difficult and like the actual, maybe things that someone did wrong or lessons that they learned without just like barely dipping into it for a second. And I liked the format of tipping them off in like full transparency. So on this show, I had someone on who I really, really respect his name’s Dickie Bush. He’s one of the earlier episodes in this series and in it, he, okay. Yeah. So in that interview, one thing that I knew is that his, the first version of his course plagiarized text from another friend, Sean McCabe, actually Shaun’s company edits is Podcast and all that. And I’ve known both of them for, for quite a while. I’ve known Sean for like, I dunno, six, seven years or something. And I was like, struggling with how to bring that up. And I wanted from the like founder, transparent journey, that sort of thing I wanted it brought up because I, I actually like, I’m happy to talk about like some pretty major things that I’ve screwed up and what I’ve learned from it. And I just think it makes a better conversation. And then from the interview side, I don’t feel good, like doing an interview and not touching on that, but I didn’t tip Dickey off to it. And I, that was one of the things that I’ve regretted that he gave a great answer. He talked about the lessons that he learned from it. It was really, really good, but I felt bad that I didn’t set him up for the most success in like in setting up. And part of that, part of it is because even at the start of the interview, I was still wrestling with now, I’m not going to bring that up that, ah, maybe I should, it wouldn’t be an authentic interview if I didn’t like wrestling with that, I hadn’t figured out my own, like made my own decision until we were in the middle of it. And so I didn’t, I didn’t set anybody up for success. And so it’s an interesting line. [00:48:52] Andrew: It happens. And it seems like I’m now in the point of your transcript, where you, where you ask him, it’s a 31 minutes into the interview. I think his response is great. He came in and he took responsibility for it. He says, yeah, that, that, that was a dramatic mistake, or a drastic mistake on my side and caught up in it. He wasn’t the most articulate here and he’d repeated words. Like I, I, a couple of times, so I could see that he probably was uncomfortable with it. but I think his answer was great. I think, I believe that we all are broadcasting out, whether we know it or not, our intentions and where we’re coming from, as some people are really good at faking it. And so I’m not going to talk about the outliers and some people are so uncomfortable that they’re messing up the transmission, but for the most part almost. broadcasting our intentions. If you walk into that, Nathan, with the, I got to get him because he, he got one of my friends and I need him to finally get his comeuppance. He’s going to pick up on that. And truthfully, it’s such a small thing for a person like you who’s, who’s already a likable person. You have a lot to offer people, right? As far as like promotion and everything else, it will be forgiven, but it’ll be picked up on, it’s also something that people could pick up on, which is Nathan really want to know this thing. It’s been bothering him for a while. And if you could, just, before you asked the question, say, where am I coming from with this? And know that the audience will mostly pick up on it. And obviously people are gonna like read in whatever they feel like, but trust that the vast majority of us understand, I think it’ll work [00:50:21] Nathan: Yeah, [00:50:22] Andrew: You don’t have to even tip. You don’t have to tip off, but it does help. It, it definitely helps. [00:50:26] Nathan: It’s interesting. I was watching an interview with, Jordan Peterson who wrote 12 rules for life. He’s like a very controversial figure. And I was just often these controversies pass by, on Twitter and other places. And I realized like, oh, I don’t understand them. And rather than jumping on one side or the other, at least try to like dive in a little bit and understand it. So watching this interview, and I can’t remember, I think it was some major Canadian TV show or something, and that you would tell the interview was just trying to nail him it every possible chance, like whatever he said, just like dive in. And, so I think you’re right, that you see the intention, like in that case, you would see the, the interview, his intention was specifically to try to trip him up in his words. And then in other cases where it’s like, This is something that, you know, if you take the other approach, this is something that’s been bothering me, or I want to talk about it. Like I genuinely want, you know, to ask or learn from this. It’s a very different thing. [00:51:20] Andrew: I think people pick up on it. I remember you, you mentioned Seth Godin. I remember interviewing him when he wrote the book tribes back before people had online communities. And I didn’t just say, okay. All our heroes, all the best entrepreneurs just run their businesses. Then don’t run a tribe. I brought out books. I said, here’s a book about Warren buffet. Here’s the book by Sam Walton. The Walmart here’s a book by Ted Turner became a multi-billionaire to creating all these, these media empires didn’t have communities. They don’t have tribes. And now you’re telling me that in addition to my job, I also have to go and build out a tribe. It feels like, you know, an extra job. That just seems right for the social first. This just sounds right on social media and you could actually see. He’s watching me as I’m saying it, and he’s smiling, he’s watching it because he’s trying to read me, is this like what I get wrapped up? Is this going to be some kind of thing where some guy’s going to try to be in the next Gawker media? Or is, is this a safe place? We’re all doing that constantly. And then he also saw, okay, this is someone who really wants to understand this. And he’s challenging me. I like a challenge. And you could see him smile with like, this is what I’m here for. And so I think when you come at it from a good point of view, people can see it and then you can go there and you can go there and you can go there and it will be shocking to you and them and the audience, how far you go. But when you’re coming from that genuine place, they get, they get it. They want it. [00:52:44] Nathan: Yeah, that’s good. I want to talk about longevity in like the online world. I think that so many people that I started following in say 2007, 2008, nine, and then I didn’t start creating myself until 2011. most of them aren’t around anymore. Like a lot of the big blogs, Yeah, just so many that I can think of. They’re not around anymore. They’re not doing this. You’re at a point where like you started messaging in some form in what? 20, sorry, 2004 to somewhere in there and then interviews. [00:53:17] Andrew: Yeah, I keep saying 16. It’s like, yeah. 2004 is when I started the interview started 2007 ish somewhere there. Give or take a year. yeah, long. I, I will say that there are parts of my work that I am burned out on right now. This year has been that, but I’m not on the interview. And the reason I’m not is because I do enjoy conversations. I hated them for a long time in my life because I just didn’t know how to have them, how to have it make sense. I also didn’t give myself permission to take the conversation where I wanted it to go. And it helps now to say, I can talk to anyone about anything. That’s an opportunity that, that feels fun because I know how to do it. It’s an opportunity to, it feels like, like, you know how everyone’s so happy. You can go to YouTube and you could get the answer to anything. Well, I could go to anybody and I could get the answer to anything and talk about how they didn’t have a customized to me, YouTube, not customized thing to me, I’m watching Gotham chess on YouTube. He’s teaching me how to play chess, but he will not customize to the fact that every time I get into a car con defense, all the pieces like bunched over to my side. But if he and I did an interview, or if I do an interview with an tomorrow’s entrepreneur, it’s going to be about, here’s the thing I’m trying to deal with. How did you get past that? Talk to me about what you’re up to there. [00:54:31] Nathan: Yeah, that’s definitely energizing. Okay. But what are the things that you’re burnt out on? Because I think a lot of people are seeing that burnout. And so I guess first, what are you burned out on? And then second, we can go from there into like, what are you changing and how are you managing. [00:54:46] Andrew: I’m burned out on parts of the business behind, behind Mixergy I’m burned out on. I was aspiring to like unbelievable greatness with the, with the course part of it, with the courses, it didn’t get there and I’m tired of trying to make it into this thing. That’s going to be super big. I’m tired of that. [00:55:10] Nathan: His greatness there, like linda.com? Like what, what was that? [00:55:15] Andrew: Yeah, yeah, yeah. Yes. Yeah. She was one of my first interviewees and, and so yeah, I saw the model there and I am frustrated that I didn’t get to that and I, I don’t have a beat myself up type a personality, despite some of the questions that I ask. Maybe it seems that way. I’m pretty good with it, but, but I’m tired of being, trying to get it there and not getting it they’re trying and not, and trying another way. And so to answer your question of what am I doing, I’m going to give myself space to not, to not try to do that, to not try to, to go for greatness for a little bit, and instead give myself room to do the interviews that I care about and play more chess and then experiment with random things that I don’t know what will come up, you know? I don’t know. At one point I, I think I, so I get together with some friends for monthly calls and, and one of the calls I said, I’m looking at land and what if I get some land near San Francisco, right? It’s super cheap in San Francisco. You can buy a tiny house for two, 200, excuse me, for $2 million. But if I just go 45 minutes down south a little bit further down than Silicon valley. For $400,000, I get acres. And then I could put some tents on there. Maybe get an Airstream, let people stay on it and see what that goes. Anyway. That’s such a random thing that I think that they were a little worried about me, but I’m even open to random ideas like that. And then who knows, maybe come back after a year of taking that space. [00:56:53] Nathan: Yeah, that makes sense to me, of, of taking space and time, you know, like first you know, years ago it was the great recession. Now everyone’s talking about the great resignation where like the, I don’t know the exact statistics, but a crazy number of people across the industry, but especially like knowledge workers and people in tech are either switching jobs or just like putting their notice and like saying, I don’t know what I’m going to do next. But like, I, I, I’m fully confident that when I’m ready to come back, there will be a job, you know, some kind of Write of like, I’ll find another programming job. That’ll be fine. And so I think it’s a good thing to talk about because so many people are feeling. And most people just leave it at, like I’m burned out, so whatever. Right. You know, so I pushed through or I’m burned out. So I left, you know, and so actually talking about those things that that either drove the burnout or, you know, specific things that you’re doing about it. [00:57:52] Andrew: So are you asking me what drove my book? Me to my burnout. [00:57:56] Nathan: Yeah. I’m, I’m curious for more of that. [00:57:58] Andrew: Sure. I think I have this all or nothing. Personality I’m all in or nothing. So, it, it’s not like I’m going to do a nice two mile run. I have to do a marathon and then I have to do another and another and another, [00:58:17] Nathan: In a year. [00:58:18] Andrew: Right. Yeah, exactly. And that fits me. I want to be the person who I love scotch. I’ve been in Austin for a little bit and they don’t sell them everywhere. You have to go to special liquor stores. I haven’t had any here. Right. So I’m down to zero. That’s also, excuse me, fine. But if I’m drinking scotch with people, I’ll finish a third of the bottle, half the bottle, no problem. And then I’ll wake up the next morning and be the person who is so proud that he’s like Up before everyone else and running into work. I think that that type of thing suits me, but I think that the downside of that is that then I do just burn out and I can say that that’s happened now twice before. So I think that that’s what’s happening now. The first was in college. I took college really seriously because I thought this is going to show you. I thought it was gonna shape my future. it really didn’t, but I wanted to really do well in all those classes. Especially since I finally got business classes after years of wishing I could study business or something practical, but instead being given things that like the Pythagorean theorem, that didn’t matter, I had it. So I took it seriously. But I remember at the end I graduated, burned out where I remember my boss offered me a job and I said, I really just can’t think, I think what the offer you’re making me make sense. I just don’t know. And I took time off. I drove my parents crazy is I finished school and didn’t want to work anywhere. And then again, after my greeting card company, I worked on that endlessly. I would take a keyboard with my phone into bed so that I can type out long emails in response to people. and then I burned out and decided I would just go ride my bike on the Pacific coast highway for a year, whatever for years. [00:59:56] Nathan: Is there anything that you’re taking into this period of, of like space. That you’ve learned from the, from the past months or your added level of intentionality, [01:00:07] Andrew: No, I don’t, I’m not there yet. I’m really excited about this book. And so I’m talking about it. I’m really excited about the process of interviewing. I feel like I underestimated the importance of it until I wrote this book. So COVID just had me locked up inside for a bit. And I said, all right, I’m how do I use this? And I ended up writing the book and then as I examined it, I realized I really do love the craft of conversations, the, the, the structure of them, of how we end up with, how, how do I end up in a great conversation with people? My kids this morning, one of them is seven. The other’s five to seven year old, said we are not shy on like other kids. We go in with adults and we have conversations with them all the time, because you always get us in, you talk to everybody. And I thought, what a gift that they could we’re in Austin, that they could go to somebody’s house and feel as comfortable in their houses as any one of their friends does, even though. You know, the first time that they’re, that they’re in the house and they don’t even know if there’s anything for kids to do. I love that. And that doesn’t just come from happenstance or gift from God. It just is spend time. I spend time thinking about it And working on it And I’m proud of it. So I’m continuing to do that. And then who knows what will come after burnout, maybe after burnout will just be sitting on the couch with chess.com all day. Just try to master that CARICOM defense. [01:01:21] Nathan: Yeah, that’s a good, good use of time. I think I say that genuinely. I, I am not on, [01:01:30] Andrew: Thanks. [01:01:31] Nathan: Of, of chess, but I thoroughly enjoy it. And I, you know, I play chess against a ten-year-old and a seven year old for the most part. And getting to the point where they can. [01:01:38] Andrew: The good actually seriously, if you take a look younger kids for some reason, if they’re good, they’re amazing. They’ve got to, I don’t even know how they can [01:01:46] Nathan: Yeah. And, but it’s, it’s also amazing to see. I mean, my kids aren’t, aren’t phenomenal by any means. I can still beat them, but they’re like, you see the, the rate of improvement over time, especially if you explain, like, don’t do this, where do I see why this is a bad idea? Like they will not make that mistake again, you know? at least in chess, I haven’t figured out the parenting side of that. If you have, let me know. I’m curious on the, on the other side, like going to the interviews, is there anyone that you have on your list that you’re like, oh, I really want to interview this person, or maybe this person tied to this a point in time as well, [01:02:24] Andrew: You know what it is? It’s sometimes something will make it into, into the news. Someone will have done something amazing. We’ll all start talking about them and I’ll want that person. And one of the gifts of this, of this experience of having been out there for so long as I could, I could say, there’s, there’s this person, who’s this, this guy, Andrew, I can’t remember his name. White. He just talked about. This is so small. You’re probably thinking about who’s it like a major mark Cuban. I’m not interested in mark Cuban. I’ve heard everything has to say here’s my excite, my excitement, this dude, Andrew he’s finally revealed how much money he made from. I think it was, he must have hit a million dollars. My memory is not great on this, but here’s what I do. He wanted to have his own software company. He had a wife and kid, he couldn’t find a way to squeeze it in. He knew he needed to learn to program. He decided that on the way into work on the train, he would sit there with a laptop. You ever see people on the train with the laptop? I feel so sad for them, right? This is no way to work. It’s not comfortable. And plus I feel like I, cause that maybe it’s because I had lived in New York and San Francisco, I feel like someone’s going to snatch it out of their hands, poor souls. And they’re going to lose the laptop too. But he’s one of those poor souls sitting there working. And he ends up creating this company that does charts because he realizes for developers hard to make nice looking charts. And so he says, I’ll create a way. Developers can just plug into my stuff and they’ll have nice looking charts. And suddenly people who are racing cars who need charts to see how the cars are doing and different parts of the cars are performing midway through the race. They’re using his charts to show that like it’s making great money and his life has changed. And I did that guy a lot and I love that. I have the freedom to say, people are talking about him right now. I am curious about him right now. I’m going to go and ask him right now. Can we do this interview? That’s helpful. And then one more thing I think for doing interviews and you’re, you’ve seen this in your own life in different ways. There’s also like a follow-up effect where the people who you’ve done interviews with you may never see them again. But some you have access to for the rest of both of your lives. I mean, literally for the rest of both of your lives. So one, one example is I started writing the book. I couldn’t keep on writing it. I’m sitting down here at my iPad, typing away. I couldn’t do it. I can’t, I can’t believe how many words a day I keep in my head. Someone asked you on Twitter while I was writing this. Do you still do a whatever number of words a day? And you gave the number of word I want to punch my screen. I go, how the hell is this guy doing it? I can’t do it. Hey, I said, I’m going to hire a ghost writer. And I started emailing Ryan holiday to go. This is terrible. I’m literally giving up other, every other part of my work in life, except for like, after, with my kids, after they’re done with school, I’m done except for writing this book. How do I continue this? How do I hire a ghost writer? And his response was the most in sympathetic response ever, but it was great because that’s what got me to like stop looking to hire a ghost writer. And I’m the type of person who I would just hire someone, give them a direction and be done. And so don’t think if I were just a random dude, messaging people all day, that they would respond like that. I don’t think I was a random dude, not knowing how to master the Cara con that James Altucher was a phenomenal chess, chess player, right. And a great writer I’m reaching out. He goes, let’s get on a Skype call or zoom call. We get on a zoom call. We only met during the interview. The dude is so good. He’s analyzing my game. He’s giving me homework assignments. I did one of his homework assignments this morning, and suddenly my game has improved because of it. There’s this extra benefit, and it reminds me of something that Ali Abdaal said in your interview. He said, if you stick with this (and for him, it was YouTube), if you stick with this for month after month after month, I guarantee you it’ll change your life. I’m not going to make promises on what you’ll have financially, but I guarantee you it’ll change your life. I wish he would have said change your life for the better, because I’m a little worried about the people sitting there creating YouTube videos, and their lives getting destroyed from all the hours. But, I think if you sit there and you do interviews, guaranteed it changes your life for the better. [01:06:17] Nathan: Yeah. I mean that consistent way of showing up makes a huge difference, and access to people is incredible, and the relationships, and everything else. [01:06:25] Andrew: Yup. [01:06:26] Nathan: Where should people go to check out the book? [01:06:28] Andrew: I got this great landing page from a company called ConvertKit. Alright, here’s all they have to do: [01:06:33] Nathan: I love it. [01:06:34] Andrew: All they have to do is go to: StopAskingQuestions.co, and here’s all I have to do. If I have to send out a message, I don’t have to figure out crazy charts, and all these systems and rules. I just log in—I could do it on an iPad—and then I send out my message. What I’ve been doing, Nathan, is when I hear that people have a problem with conversation, I find a chapter from the book and I email it out. Then I say, what do you think? Is this working? I send that out to the whole list, and it’s so helpful to have people email me back, asking for direction or saying how they’ve used it. One person had this terrible story about some bad thing that I did with the founder of Zero, the accounting software. I was hoping that people wouldn’t ridicule me for that, or judge me negatively for it. Nobody did. So, that made me feel good, and I left it in the book. But someone did say you actually misspelled his name. So, I went back and changed it in the book. Not just that, but the publisher made sure every single one of these names was double-checked. So, it helps. Thank you. [01:07:31] Nathan: An audience is so helpful for that. Well, everyone should go sign up for the book. When does it come out? [01:07:36] Andrew: StopAskingQuestions.co, mid-October. [01:07:40] Nathan: Mid-October. Okay, cool. Right about the same time that this episode will drop. So, it’ll be perfect. Alright, Andrew. Thanks so much for coming on. [01:07:47] Andrew: Thanks Nathan.0 comments0
- 054: Nick deWilde - Growing Your Audience While Working Full-TimeNick deWilde is a Product Marketing Principal at Guild Education. Guild is a fast-growing startup that partners with Fortune 500 employers. Guild unlocks opportunities for America’s workforce via education and upskilling. Nick also runs his newsletter, The Jungle Gym. The Jungle Gym helps readers build a more fulfilling career that integrates work and life. Before working at Guild, Nick earned his MBA from Stanford Business School, and was a Managing Partner at Tradecraft. Nick and I talk about his relationship with Twitter, and how social media can both serve you, and be a challenge. We talk about individual brands and growing a platform. Nick also shares his thoughts about marketing yourself as an individual, and we discuss how growing an audience plays into your career. In this episode, you’ll learn: Building an audience while working full-time Three reasons people start newsletters What to do when your follower count hits a plateau Links & Resources Morning Brew Fastly Joseph Henrich, The Secret of Our Success Julian Shapiro Sahil Bloom Dickie Bush Medium Tiago Forte Building a Second Brain David Perell Write of Passage Tradecraft Guild Hacker news John Lee Dumas Packy McCormick Mario Gabriele Seth Godin Rachel Carlson On Deck Gong Matt Ragland Charli Prangley The Nathan Barry Show, featuring Kimberly Brooks Harry Stebbings The Twenty Minute VC Isa Adney Liz Fosslien, No Hard Feelings: The Secret Power of Embracing Emotions at Work Discord Reddit Pallet Craft + Commerce ConvertKit Enough Ryan Holiday James Clear Marie Forleo Ramit Sethi Nick deWilde’s Links Follow Nick on Twitter Nick’s newsletter, The Jungle Gym To tweet, or not to tweet Episode Transcript [00:00:00] Nick: I’ve tried to do things in my writing where my employer benefits from them. I talk about work a lot, and whenever I talk about hiring, I mention Gild is hiring. There are things I do to just try to make sure that it still feels worth the company’s while. [00:00:25] Nathan: In this episode, I talk to Nick deWilde, who writes a popular newsletter called The Jungle Gym. He’s got a background in product and growth, and all these things from the startup world. I just love the approach that he’s taken to writing these days. We talk about growing as newsletter. We talk about his interesting relationship with Twitter and social media. How it can really serve you and be this great thing, and then it can also be challenging. Maybe you’re spending too much time on it, or time on it in a way that’s not actually serving you or benefiting you. We talk about the rise of individual brands being used to grow a platform. It’s something I’ve been thinking a lot about, watching Morning Brew and Fastly, and some of these other companies do it. It’s just interesting whether you’re marketing as a company or an individual. It’s just a good conversation. We also talk about audience, and just how that plays into your career. He recently made the switch from a full-time role, to doing more audience-based business stuff. He was just in the middle of that journey. So, it’s a fun place and time to catch up in the conversation. Nick, welcome to the show. [00:01:33] Nick: Hey, thanks for having me, Nathan. [00:01:35] Nathan: I want to start on this article you have, that I like a lot, called, “To tweet, or not to tweet,” That got you ahead. I also happened to go to the Shakespeare festival recently, and watched them do “The Complete Works of Shakespeare, Abridged.” So, you know, I could probably pull off a good, to [00:01:50] Nick: Nice. [00:01:51] Nathan: Be or not to be speech right now. It’s in my head because I think about all the wonderful things that Twitter and an audience beyond that does for me. Then also the negative sides of it. So maybe we dive into that, but I’d also love to hear what sparked you diving in and building an audience. [00:02:11] Nick: Yeah, I’m so conflicted on Twitter, and audience building in general. Like anything, I imagine there’s a fair number of people who you talked to, who are in the writing community, who feel that way. On the one hand, Twitter does so many things for me. Especially over the past couple of years. As we’ve been in lockdown, lives have moved online. I have met and made friends with so many amazing people through Twitter that I wouldn’t have met otherwise. Same with the newsletter, but Twitter is a little bit easier to build those relationships. Twitter has definitely helped grow my bank account. So, there are clearly things that being online and participating in the online world really does for you that are valuable. I think, building an audience is super valuable. When I think about the future of work, and what will be automated and what won’t be, I really think that human beings, our greatest strength that is the hardest to copy is our ability to influence other people. This really comes from some of the thinking of author Joseph Heinrich, who looked at what is the secret of human success. It’s cultural learning. It’s our ability to essentially watch what other people do, and mimic them. We’re really good at detecting what is a real human and what’s not, and who’s someone prestigious that we should learn from, and who isn’t. I think that audience building is super valuable. So, even though I don’t love the activity of building an audience, I have gotten a lot of value out of it, and I see the value in it. So, I very much come from a conflicted spot in this. I’m very impressed by people like Julian, and Sahil, and Dickie Bush, who have grown amazing audiences. Some days I aspire to 10X my audience, and some days I’m just like, please let me be a monk and live in seclusion. [00:04:20] Nathan: Well? Okay. So I had a Twitter thread last week that I did It was on company culture for remote teams, and I’ve had some that like take off and do well before, but this was like 1300 retweets, like almost a million impressions, a level of taking off. And on one hand I was like, this is amazing. And the other, I like checked the notifications and the replies so many times, and it was fascinating watching it go from like my circle to the next circle, out to the next circle out. And like, we’re still in like positive replies, happy. Oh, build on it, refine it. And then like the one circle past that, which it took about, let’s say 12 to 18 hours to get to [00:05:06] Nick: Yeah [00:05:06] Nathan: And that was the. This guy’s an idiot. I’d never want to work at that company. you know, like all like the, the haters and the non from there, and then it like dies out and this is weird arc of his, we should graph it, but it just made me think of, is this something that I want to do and want, had I added thousands of Twitter followers? I think I could recreate it. Like maybe one in five attempts would like hit that big. Who knows. but I wrestle with the exact question of like, do I want this? [00:05:36] Nick: You and you’re, you’re just, you’re like jacked up on dopamine. You’re like, you’re, you’re sort of you’re you, you, you start just imagining all the good things that will come from this. I should be doing this all the time. Like, you know, I, I mean, I think it’s, it’s sort of pre progressive problems, right? Like, like there’s, there’s the problem of like having a smaller audience and like putting something out into the ether and then, this, this kind of, getting no response, right. That, that, that’s the first thing that, that actually like most people kind of deal with. Right. And, and, and that’s, that’s a weird thing because it’s like, it’s like, you’re, you’re then judging the quality of your ideas based on the ability of, based on basically your, your audience’s response and, and realizing like, you’re not actually talking to your audience, you’re talking to. Subsection that Twitter has decided that you can talk to at that specific point in time. And so, and then you’re basically judging your own ideas based off that. And if, if your idea is like, I think, I think when you hit a certain bar of audience, like you can, you can share ideas that are, pretty complex and nuanced and like you’ll, you’ll find some, some sort of interest for it and it has a potential to take off, but like there there’s stuff where if it’s kind of interesting and nuanced there, isn’t really kind of a built in audience for it. And people don’t really have the time to like always dig in and kind of engage and try to like, find what’s at the kernel of, it’s why I like newsletters a lot more than I like tweeting. But, but, but, but I think, I think what you’re, you know, then there’s, there’s, there’s the problem where once you get big enough, like you’re now being your ideas are being put in front of a bunch of people who like you didn’t intend them for. And those people for some reason have decided to invite into their lives, like conflict with strangers on the internet, because [00:07:19] Nathan: That’s like a primary goal, [00:07:21] Nick: Right, right. It’s like, it’s it. It’s what gives them a great day. Right. And, and, and so, so yeah, it’s, it’s such a weird thing. And so I, like, I mean, I, I think about this with like, I equate Twitter, often to, to kind of, like refined sugar, right. With refined sugar, right. It’s it’s, it’s what we call supernormal stimuli. Right. It, it, it, or super, super normal stimulus. and, and what that is, is basically something that like replaces some natural, like evolutionary desire you have with something kind of artificial that just sends your brain on like overdrive seeking that thing, seeking that thing over and over. And, and that is. That’s what Twitter is. It’s, it’s, it’s refined status instead of refined sugar. And that refined status is like, it just, it takes this thing that you normally do, which is like seek, prestige from your, your tribal group, which was a really good thing to do to make sure that you, you know, ate a good meal. And it, and it puts that into, into this crazy overdrive and it like, it centers your brain around it, and it’s, it’s such a, it’s a really powerful thing. And so I, you know, again, right, it’s like, there’s all these great gifts that come from Twitter and then there’s, then there are all these drawbacks and it’s, it’s almost like perfect equilibrium of, should you do it or should you not? And I don’t begrudge anyone either way for their decision. [00:08:46] Nathan: What I always wonder is if I could only have the benefits, like, is there a way let’s say that you don’t doom scroll Twitter with the latest news and whatever’s going wrong, or whatever, latest Twitter fight there is. Maybe you do in a separate app publish these like smart tweets or brilliant threads that are going to get all this attention. And you do one of those every day, but then like you jump in an hour later and respond to a bunch of comments and then like the next day you do it again for 30 minutes and then like, that’s it. And you just bat, like, there is this world where you could own Twitter rather than Twitter owning you, but like, are you capable of it? Do you have the self-discipline to pull that off? [00:09:33] Nick: Totally. And, and I, and I think, I think like, you know, I I’ve talked, I think Julian about this and I think he uses like tweet deck for it. And I think, I think there are ways you can do it. Right. I like for awhile, I was good at like, I would tweet in the morning and then I would like uninstalled the app off my phone. So I wouldn’t look at it. and like, there are things that you can do. it’s just, it’s just really hard because I think to some degree what Twitter, rewards, especially when, when you’re on the audience building path. Right. I think when you’re like, tens of thousand or hundreds of thousands of followers, you, you actually have a lot more leeway to do what you want. Because, because like, you’re just, it’s likely that your tweets will work, but like when you’re building your ions, there’s, there’s something that like, it’s sort of like, there’s a Turing test that’s happening, right. People are sort of looking, are you an engaged human being? Cause I I’ve I’ve I knew some people who sort of, they, they schedule and preplan all their tweets and like, and to some degree they, they just, they don’t hit, they don’t work because it doesn’t feel real time. They’re responding in real time. So like [00:10:35] Nathan: Out of pace. You’re out of touch with what’s happening with. [00:10:38] Nick: Exactly And so, and so it’s, it’s sort of, Twitter’s kind of like looking for these weird signs of life. So I think it’s, I think it’s doable. There, there must be some way to do this, but, it’s tough. I think the, the other, the other thing that Twitter did to me, that I, disliked is, it makes me feel like my relationships are very transactional because you have these likes retweets, and like these, these, Very clear, like signals of engagement. You, you start to like, or I start to like, to like keep score. Right. And, and I, and I don’t, I like, I don’t do that anywhere else in life. I think a good, like obviously good relationships tend to start out transactional and then like, they, you kind of forget what the transactions are and like that, that’s what creates a close friendship where like, look like you may have paid from the last time I paid for you this time. It doesn’t really matter anymore because we transacted so many times, but, but Twitter, for some reason, the score always feels out there. And, and so that was, that’s really been like a little bit of a red flag to me. And I, I I try to keep a generous mindset and a generous spirit on Twitter, but I find it harder than in real life. [00:11:52] Nathan: That makes sense to me. So maybe taking a step back, and maybe we’ll wrestle with some of these, like to grow an audience or not to grow an audience questions [00:12:00] Nick: Sure [00:12:02] Nathan: What was the thing that, sparked for you? I’m like, I’m going to go start a sub stack. I’m going to actively work to build an audience. [00:12:10] Nick: Yeah, I, so I was writing on, on medium starting in like 2013, maybe. Um and and really got a lot out of it. I, I started my career out as a, as a screenwriter, so I was planning to go into the TV industry and like, and, and for, you know, for, for many reasons, found that to be, a path where like, you didn’t really control your destiny. I saw I met lots of, you know, mid thirties, you know, production assistants who were slightly bitter. And then, so I just kind of realized like, this, this wasn’t exactly a good path, for me. And so, but I, I wanted to kind of keep that like, that creativity, that like interaction with an audience, I think, you know, it, it was. And found that in writing. And so And so started publishing on medium. Um we was a great experience in terms of how quick it was to publish, but like the distribution of publishing a medium sucks, right? Like, you’re you you, you publish ones and then like you spam all your friends and like, you’re, you’re just, you’re working super hard to like push this thing and promote it. And I was like, there’s gotta be some way that’s a little bit easier. and so I actually ended up in, I think I took, I took Tiago Forte is building a second brain course that kind of like, magically grandfathered me in somehow to like David Pearl’s first um uh cohort or Write of Passage, which was awesome And like, I would say, like, I took a lot out of that, but like the biggest thing was, was like start a newsletter. and so basically I started out, I think I started out with a review even. but but anyway like started publishing. Opted in when I knew onto the email list, which I’m sure they, they may or may not appreciate it, but this is before there were tons of sales tax out. And so I felt like it wasn’t, it wasn’t that crazy. I probably wouldn’t have done that in like 20, 20, but, but w really wanted like a way to like, continually kind of interact with my audience without having to worry about like, you know, just, just kind of constantly doing the heavy promotion work. Um now that’s because I now you know posts just as a part of medium but but at least there’s those sort of a built in audience that kind of grows over time that you kind of keep with you. and, and so. doing that, it was kind of it’s kind of a mix of for work and for life. I, I was, at the time, the managing partner of a, of a, uh immersive education program called Tradecraft. And like we, we would help people make sort of complex career transitions into the startup world. And and so a lot of what I was writing was kind of about that. It was about careers. but it also tied in with, with kind of deep interests. It was sort of why I took the role in the first place. and, and what I found when I, when I moved from Tradecraft over to Guild was like that kind of nicely traveled with me. and, and I think there’s, there’s something, something really nice about a newsletter, being a kind of an appendage to your career, where, like it expands your professional identity to a certain degree. You, you can become a little bit more than just your job, especially working for, like, like a single individual company, especially if you’re, if, if the company is larger you, have to deal with a lot of like coordination challenges. there there’s a lot of bureaucracy that happens at a company And one of the nice things about having a newsletter is you are in charge of it. It’s like you’re the CEO of it. the product ships, when you choose to ship it and you have complete editorial say over it, and the distribution that you put into it is what you get out of it. And and there’s something really nice about that. It helped me kind of identify as a person who who, ships a lot, even when, sometimes, you know, you know, you you have to work on something at at work that takes a long time. [00:16:12] Nathan: Have you found a dress core even a strong correlation between the effort that you put in to your newsletter and your audience growth and the results that you get out, or does it feel like a more tenuous connection? [00:16:24] Nick: I think, I think there is a pretty good, like w w when I think a post is going to really hit it usually does and so I would say like, like when I put effort into, into writing something really good, I think usually it meets it meets or exceeds my expectations. And when, and when I feel like something is, I’m kind of honing in on, on a, on a post, like usually I get that too. So I think what, what can also happen. You know, sometimes you post something to hacker news and it turns out it’s somehow on the front page and like that your audience growth spikes, or like you get featured in someone else’s newsletter and your audience grows spikes. And like, there there’s a lot of activities that like, you know, I’m not doing directly to promote it, but but it just sort of, um you know, happens in a nice way. And so that’s happened, you know, more than a few times and like, that’s a pretty neat thing, but like, I think to some degree that comes from just trying a lot of different things and then like, there’s sort of like a, a second order effect of some of those things really, you know, hitting it off. [00:17:28] Nathan: Yeah, I think that’s that’s right. I knew in the early days of starting my newsletter, I felt a strong correlation between what I was working on and like the effort that I put in and the results that I got out, been been interested well at the time I do like a really epic blog post where I put of effort, you know, we’re kind of the, for, you know, off and on for weeks or months and like really a hundred and get friends to read it, all of that. Those pretty much always do really well. But what I’m surprised by is sometimes the throwaway posts really, throwing it. Like, it’s a simple idea that you flushed out into a post and you were. Hey, it’s Tuesday. I got to get something out. Like it’s sort of in that [00:18:09] Nick: Totally [00:18:09] Nathan: Sometimes those really hit. Sometimes they actually resonate. Have you had some of those that were like easy easy ones ones that hit? [00:18:18] Nick: So the, publishing cadence is I do, I do two, two posts a month and one a and it used to be, it used to be one post a month. And then I basically separated out into two. Cause I realized like it was too much to kind of condense into, into one post. And like, I wasn’t getting the. The, as many eyeballs on like the second half, so decide to pull them apart. One is kind of one big essay. And the second is a, is is of like a, a But I think of it as like, as like I do pretty deep them. So it’s actually of like a, here’s what this is about. And a little bit more like, here’s what this made me think about. And And, the, the essay is, I always spend a good amount of time on them. or at least this year I’ve spent a good amount time [00:19:05] Nathan: On all of them two hours, 20 hours, 200 hours? [00:19:11] Nick: 2020 is probably probably closest. a really slow writer. And so, and so, like, I, I do, I mean, I like like write and like re-edit the first paragraph, 20 onto the next And like I don’t either Yeah The the the the the, the, top of the like, it’s like a then like the last paragraph gets like one glance and I’m like, God, get this thing from Um don’t and I I that is the wrong thing to do, yet, somehow I do that anyway. but, but, so, so those, those posts, they tend to get, of. You know, time and care. and then what’ll happen is sometimes the, the ones that are like the link roundups, like will, will be very spiky. And I I’ll spend, you know, that’s, that’s a little bit more like a three hour thing, um or four hours or something like that. and yeah, so, and then, and then I had, I had a, a, something that I was doing when I was interviewing folks, I call it the key ring where it was like a pretty structured interview that I would do where I asked the same questions over and over again. That was, that was fun. It, it, it started taking a long time to like do the back and forth. And so I’m putting that on pause for the moment. I may pick it back up again. those are fun just cause you can, you can feature someone that, that you like and get a chance to just and hang out It’s kinda like [00:20:40] Nathan: Yeah. Those are always interesting to me. Cause I, I think about that on this podcast of asking the same questions, which I know New, I riff on the questions too or element But if you did, in theory, if you’re like, did you grow from a hundred subscribers to a thousand subscribers in your newsletter? And you asked that to every single person, then you could compile that over 40 episodes or 40 newsletters or whatever. like, Hey, here’s a guide on how to do it. And like, I pulled it from a whole bunch of sources. So that part of like standardized questions intrigues me. don’t love it the live, know, version of a or newsletter where it’s like, okay, it’s too formulaic. People have done super well with us formulaic, like, John Lee Dumas, who did the Podcast entrepreneur on fire. Like he went all out. He was like, this will be 20 minute episodes, we’re going to of release one a day, seven days a week and like works for him. I have no desire to do that, you [00:21:36] Nick: Totally [00:21:38] Nathan: Yeah, I don’t know. you think about the repurposing side of content like that, or is it more just about the, the upfront. [00:21:45] Nick: I’m at repurposing and, and I, it’s something that I, have like a psychological hangup about it. Like I always kind of feel like I need to be just like moving on to the next thing. The next thing, like I’ve, I’ve tried like going back and like, be like, oh, I should mind this thing for some, some tweets. And it always feels weird to do. And like, I want to write my Roundup, but I think, I think what I’ve just recognized as. Another reason why I write the newsletter is like, I want an excuse to have interesting new thoughts each month. I want essentially a performance, right. Where like, we’re like, there is a moment where like, if I, if I hadn’t been like reading and thinking each month, like, there is a moment that it will, that I will be embarrassed if I don’t do that. And like that, that’s the way I think about the newsletter. And so, and so repurposing content would be something it’s almost like an admission of defeat. which, which I don’t is is other people should think but that’s an area of my head. And so, and so I think it just like, I need to be onto doing the next thing. There’s a bunch of stuff where like, I would love to, I love ways to use the archives, my newsletter better. I think actually like stuff like this is a fun way to do it. Like through a articles and I was like, oh, there’s there’s stuff I can, I can reference from those. Um but it’s it’s, it’s tough. [00:23:05] Nathan: That makes sense. Okay. So let’s talk cadence for a second because this is one of the most popular, common, I don’t know, questions that I get from people starting newsletters. Is there, like it should be daily right now, weekly, monthly, twice a month. Can I just do quarterly? Can I grow an audience for the quarterly newsletter? You’ve settled on twice a month? What was the thought that went into that? And, and what’s your present cons on, on that particular. [00:23:33] Nick: I think. I mean, one of the weird things, which I’m like, I don’t think it’s just me, but like, like, it was like, when you, when you release a newsletter issue, like you naturally lose subscribers, but like, like, like people are reminded that like, they’re like, know you have yeah You have keys to their inbox and they’re like, like, why why did I let this And so and so like and so ideally like that, you know what I mean, then that’s gonna have a rude awakening for, I think, I think people who are like, oh, this, this thing just goes on autopilot. but, but you need something that like is going to generate more new subscribers than it will lose subscribers because I’m a slow writer, like my, my ability to write something that I think is going to generate new subscribers is like twice a month. And like, and, and, if, and if I was, you know, Paki and Mario there, I don’t know how fast they are, but like they are, they’re dedicated. They can crank out some ungodly number of words, you know, once a week, twice a week, which is super impressive. And I think if I was them, I would do that. And like, you know, I, I love still like Seth Godin writes, like, you know, I feel like he writes every day. And I think so I think if you’re, if you’re capable of doing that, like, and, and, and doesn’t lose subscribers, then like do it and set an appointment. And I think all those things are really nice, but for me, it’s like, how do I make sure that like, one it’s kinda, it’s kinda manageable with a, with like a full-time job, which is the way I’ve been doing it for a long time. Right. and need to, I think, um you know, there, there are, there are weirdnesses of having a newsletter, any full-time job at the same time. And one of those is like, You are publishing, like if your hobby was sea kayaking, right? Like, like you could do that with no one knowing that you were doing it. Right. And like, and, and there’s, there’s nothing weird about that. Or like running a marathon or something like that. like it’s clearly the thing you’re doing on the side, writing a newsletter is like, it’s it’s knowledge work that is like akin to, to, type of work that you might do in an office Right Coding [00:25:41] Nathan: Marketing copywriting, whatever your your day job [00:25:44] Nick: A hundred percent. And like, and like, if you’re putting that out on LinkedIn, like, you know, your managers managers are seeing it and like, and so there’s, there’s just like, like doing that every day would be, a weird would feel weird to me even if, even if no one else felt weird about and so, and so I feel like twice a month it feels, feels good to me. It’s also, it also just like keeps me excited to keep, to keep at it versus making feel like it’s like a daily or weekly chore. And I have like a day off, I have a week off in between so that I can like, you know, spend the weekend, not writing if I want to, which is nice. [00:26:23] Nathan: Yeah. I like the idea of timing it to your, like your cadence as a writer. What advice would you have to someone who’s in that position of, building audience on the side there, maybe they’re doing it secretly at first where they’re like awkward about it’s this may maybe self promotional, but, but at some point, if you get to any scale right. will either you’ll tell people at work about it or they’ll find out about it in some way, hopefully be supportive, but I don’t know. What advice do you give to someone who’s in that [00:26:54] Nick: First, acknowledge that there is weirdness to it. Like there, are, like there are inherent trade-offs to everything and like, and like there is there’s weirdness and if, and if you’re your, like the, the company I’ve been working for Guild, like they, like everyone has been more than supportive at it, but, of the, the work and like, but I still have a weird complex about it. You know, I think part of the reason I ended up getting the job was because of, because of the newsletter, some of the stuff I publish of like, you know, shaped our marketing strategy. So there were things where like, I’ve tried to do things in my writing where my employer benefits from them. Like, you know, whenever I talk about work a lot and whenever I talk about hiring, I mentioned Guild’s hiring, Like there, there are, there are things that I do to just try to like, make sure that it still feels worth the company’s Weill. And also, like, I think, I think I try to bring in ID. Like I try to have ideas that are useful to what I do at work. so I I wrote this, this piece on, platform branding, which was all about, companies that essentially used their employees to build audiences that, also benefit the company And like, you know, we, ended up using that strategy at Guild which, which was, which was cool. And like that ended up being the strategy doc to some degree, around it, which was cool. And so so so, there’s there, there’s like ways that you can. think um you bring that in that that are, that valuable. And so I try to sort of look for those things. I, but I think, you know, acknowledged right. That there’s, good writing is vulnerable and sometimes it’s weird to be vulnerable in front of your colleagues. and, and like it’s naturally an attention seeking activity. And if like, if like there’s someone at work feels weird about you, like, will be, you know, something that they can talk about, the proverbial water cooler about like, you know, why, why you’re not doing your job and you’re, you’re off writing these letters So so there’s there there’s weirdness, but like, I think if you can make, if you can allow your company to benefit from the audience you are growing, I think that tends to be a pretty good fit [00:29:12] Nathan: What that made me think of is basically it’s going to accelerate or, magnify, whatever someone already thinks of you. So for example, if someone already thinks, like, I don’t know, next kind of. he just doesn’t contribute that much. Like is he even working half the time then if they publishing once a week, then they’re like, see proof of what I already thought. if like the executive at the company is like, Nick is one of the best hires we’ve ever made. Oh. And look now he’s like publishing and rhinos. Like he’s a thought leader as well. Like whatever they think is just going to accelerate more. And so maybe it’s looking what reputation you already have. [00:29:51] Nick: A hundred percent and it’s like, it’s like, I mean, the way I see it, and this is kind of what I wrote about in the platform, branding thing is like, I actually think that, having a bunch of employees who are, in a creator type role, um it’s like underdeveloped marketing channel. Like you essentially, you have these people who have. Hey, like, I’m going to, going to take my scarcest asset my time give it to this company. and and and now I’m going to build relationships with, with all of these thousands of people who, who listen to these ideas and like, and like that sort of just gives positive energy to the company. So, so actually, like when you compare it, even to like a, a side project that you’re coding nights and weekends, I actually think, I think companies should be really supportive of, of, of kind of audience building on the side because it really can benefit them but, but people naturally have a, there’s there’s a weird feeling about it. And so, and so you have to like, especially as a company, You know, like our, our CEO is, is, is really good at building her own audience on LinkedIn. And I think that gives everyone else some permission to like, you know write vulnerable and things like that. So I think, but I think it, it is, it is a really important thing to be able to have this kind of a group of people who are increasing the company’s sort of surface area in Serendip. [00:31:23] Nathan: Yep. I like that. I’ve wondered about doing something like that for ConvertKit. We have a handful of people on the team who are very prolific creators, for the two myself and then, our creative director, Charlie, frankly, she has like followers on YouTube and a popular channel and all of that. There’s a handful of other people who have podcasts and are, are active on Twitter. Our product managers are quite active when you talk to them about things related to ConvertKit, you know, they’re like active with customers, but I haven’t, or we haven’t taken this approach like fast or on deck, or I’m trying to think who else does it, but, but these companies where they’re like, okay, there’s 15 of us and we’re all going to. Become Twitter famous, you know, or start our thing and we’ll all drive back. Is it a strategy that you think works well? [00:32:17] Nick: The, the best example of this actually think is, I think on-deck did it, did it really has done it really well on Twitter Um I think gong is actually probably my favorite example. Um especially from a B2B what they do is like is all of their salespeople are out there, like posting content on LinkedIn, but it’s not like how great gong is. Almost has nothing to do with gum. It’s like you know, an a I’m I’m I’m grinding today. Can’t wait to get off for the weekend. It’s like, it’s like, it, it, it sort of, embodying kind of this, this, like this, the sales lifestyle. Right. And, and, and the, the engagement they get is, is crazy. Right. And like, and that, the thing is, if, so, so there’s sort of like, there’s kind of like, you can build lifestyle influencers among your employees Right But you can also. Like this idea of building up someone who is, who is a, I know this is kind of a gross word, but thought leader in the, in the, space you’re, you’re excited about. People kind of come to them, they build affinity with them. And I think you, you can build individuals as marketing channels where like starts out where like someone’s reading your posts on LinkedIn. maybe that person hosts a, a kind of invite only webinar for, for the people who engage most of them on LinkedIn. So, so then you’re building sort of deeper affinity towards that person. And, and as, as you go down the sales funnel um like marketing and sales, you actually transfer that affinity over to the company as, as like they get into the sale process. from kind of a B2B side, but like, I think you can do it also from a B to C. [00:33:49] Nathan: Do you think that a company like gone. Hired people are good at that and encouraged it, or do you think they like had the people that they hired and said like, okay everyone, this is now what we’re doing. a playbook, here’s best practices. Here’s a slack channel where you can talk about what’s working. What’s not, but like we’re this now. Get on board. [00:34:11] Nick: This is, would be a hundred percent pure speculation. What is, is someone at gong started doing this one of their salespeople and started crushing it. And they’re, you know, director of marketing was smart enough to. Hey could be doing a lot like, and B, because it’s their salespeople who do it, right. A natural incentive to do it. And so, you know, I would imagine they probably brought on a copywriter and said, Hey, if you need help, you know, crafting these posts, like you can do that It’s just, it’s such a, it’s such a virtuous right? It’s like, it’s like, because of the affinity you build with these individuals it translates to the company. And like it just sends it a bat signal out to other people who are like that, who want to build audiences, that like the company will help you do that. And they will be supportive. And like, and again, if we imagine that like, they’re like audience is this long-term career mode, it’s just like, it’s such a great gift. You can give to your employees for them to leave with like you know, like you leave ConvertKit and you have, you know, a hundred thousand subscribers or 10,000 it’s like, or whatever. Right. It’s, it’s, it’s as much of a gift as like the salary you’re giving them. It’s just, we don’t think of it that way. Cause it’s, it’s a weird thing to think about getting. From your company [00:35:27] Nathan: Yeah. I mean, that’s how we’ve handled it in that we’re very in favor of side projects. We want everyone who wants to, like, we’re not gonna force it on. But to have a way to be a, a creator on the, on the side and to have some actual reason to use ConvertKit as a customer. Because it’s so different when you’re the product and like clicking through the happy path to test something and you’re like, Hey guys, it works. Then some customers like this is really frustrating. and so that, like, it’s a very different, different, I think that it’s just interesting. You’re absolutely right about people with that. Like, Matt Reglan, who’s been on this show before he was at ConvertKit for years. joined when we were like 20,000 a month in revenues like that. when he eventually moved on to his nets, next thing, you know, he built an, a YouTube audience to like 10,000 subscribers at that point. And that was a whole thing that he’d done a lot with skills he learned at ConvertKit a lot with, you know, our creative director, Charlie, like promoting him and just, all right. But like, it still happens even we’ve got 70 people on the team and we’re talking like six are active in this way. I just wonder how much to encourage it versus how much to just say like, Hey, this is an option if you want it, but like you don’t push it any more than that [00:36:51] Nick: I mean, I think one of the interesting things, when you think about like the creator economy is like, I think the creator economy can support a lot of people, but the the challenge is like when you’re deciding, should I follow this person? there aren’t very good moats in the creator economy. And so and so one of the. Few moats you can have is like companies that you’ve worked for giving you this brand halo. Right And so, and, and, brand from your company sort of, it says this person might be a little more worth following because someone chose them now, does that true You know, don’t think so, but like, it at least sends this signal. And so I think, one, like your brand can do that for, for, for your employees, but also like I think there’s a. I think just showing that the company will pour fuel on whatever fire you’re starting, I think is like, it’s, it’s one of the best like employee value props. I think a company can have, It’s like, it’s like, look the life you want to have. Like, we, want to get you there. like, and like, and I think the kind of people who would come work for ConvertKit it should be that they want to do something in the creator space, because you’re serving creators that makes a ton That makes a ton of of sense [00:38:10] Nathan: Yeah. And we’ve definitely had people that we’ve hired, who are already creators, and that’s grown. So it, an interesting world in all the things that you could do to grow. Like a company or growing audience. I’m not sure that that’s the one would pick, but you, you see Morning Brew and, and gong in so many of others doing it and it seems to work, know? So [00:38:33] Nick: Yeah Like, I think it works for like, like select companies in select Right. And like, and there’s, and there’s probably a channel that works under and like the. way you do it for, you know, for Guild where, like we, you know, we really target, um you know, companies with huge employee populations at the very level Like like we wouldn’t do that on, on Twitter. Right. Just doesn’t make any sense, but like, would we do it on LinkedIn where like, where, you know, C-suite spends an increasing amount of time and we can directly with those individuals and maybe influence that the five to 10 people that, that matter at those companies with like, you know, one post a week. Totally. so, so it just, it kind of depends on like, um I think companies can, can kind of do it at different levels. [00:39:21] Nathan: So that’s interesting of the LinkedIn approach, which I think a lot of creators are either all in, on LinkedIn and loving You know, people have built massive lists over there, or they’re like, what’s that like, I’ll hang out in the Instagram, YouTube, Twitters of the world, you know? but if you imagine that B2B world where let’s say I’m, I’m working in sales, either as an executive, trying to get big deals done, or, you know, or as a team member, I have a meeting, we have a great conversation. We connect on LinkedIn, you know, we’re now an official connection. And now, even though you’re not going to buy my thing now, you’re like seeing my content every. Week or every few weeks. And then it’s like, oh yeah, you’re going to buy that thing from Nathan, you know, whatever B2B tool, like starts to come up. And then when I reach out again and you’re like, it’s not like, oh yeah, it’s that one sales rep that I wasted 20 minutes off on with, you know, six months ago. It’s like, oh yeah. I feel like we’re friends there. I’ve learned so much, even though it’s just been one to many communication. [00:40:25] Nick: I mean, I think the really powerful thing it’s like obviously a sales rep is incentivized to promote the product at company they work for So it’s like it’s product whether it’s in a sales call or on LinkedIn like it will not it will not move the needle for any customer. Because it’s sort of priced in that That’s what they’re expecting. But showing that you are an intellectually interesting person who has deep thoughts about the world, who is, who’s a smart person. And then the customer making the connection, man, this smart person out of all the places where they could go work has chosen to work here. [00:41:04] Nathan: Right [00:41:05] Nick: Of something, right. There must be something kind of interesting and special there. And so they built of this affinity and comfort and excitement about you and like, and, and then getting on a sales call with you, you’re at this just like this nice advantage, right? You’re, you’re, you’re now slightly a celebrity to them. Right Like and, and there’s something, you know, like when your, your email or even your company’s email then pops up in their inbox, like it’s just that much more likely to open that much more interesting. And sometimes it’s, it’s those, it’s those little things on the margin that can make all the difference. And so I think, especially when you’re talking like a, like really big enterprise sales, I actually think it’s still, a kind of, underrated strategy. [00:41:48] Nathan: Yeah, sense. talk about a, more from the creator side. Cause that was, know, we went more on the platform company side of the which, you know, someone running a company, I am intrigued in that direction, but I’m curious on the, on the creative side, how do you think about that audience as being for your career and that thing that goes with you as you between roles and giving you a future opportunities and all. [00:42:14] Nick: I think it comes to like writing a newsletter. There’s basically three reasons. You’d write a personal newsletter and earliest the way I think about it. Like it’s either passion, like, you know, I love cooking and like, this is a way I can express that side of me It’s it’s profit. I want to actually just make some side income or make this into my full income Or it’s General advancement. And maybe the relationship building kind of tithing relationship building probably ties into that. but, but in general, like the, I sort of see one things being being like the reason, like for me, at least for a long time, it’s probably been advancement. but, certainly the other two are mixed. Like I’m, you know I’m curious about, you know, turning on the profit spigot out of it And like, it certainly like I wouldn’t keep doing it if it didn’t hit the passion bucket. and so, and so I think that, that, you have to sort of figure out which of those you’re doing. I think, I think like if, if what you want to do, I think most people actually are doing it because they do want new opportunities and relationships. I think actually advancement to me is it’s actually, the best reason to do it. Um uh over the other two. And, in that world, like, you kind of want to imagine like, okay, Who is, what kind of job do I want, who is the person that I want to be at some point down the road? Who’s the gatekeeper that stands in the way of that. Whether it’s like, maybe it’s I want to publish a book at some point, right. a publisher stands in the way of that. and so what, what gets this publisher excited? Well, either, maybe I’m writing a newsletter for book publishers and this is the industry standard, but like more likely it’s like, it’s like, Hey, I built this audience that is then really exciting to a publisher. So-so I or, you know, it’s, I want to become a senior engineering manager. and so what’s going to be exciting to the VP of engineering who is going to interview me. You know, it, it could be that I have an audience full of engineers, who who like are easy to hire, maybe it’s that I just like think in a really deep level about this really complicated problem that is really important to them, but it’s, it’s sort of like, I think having that, kind of magic gatekeeper mind as as not the person you’re necessarily writing for all the time, but the, thing you’re trying to build up to, that can be a good north star in that direction. If you’re doing this, advancement thing, I still don’t think you should pick something that doesn’t light you up because it’s really, you know, it’s really hard to keep doing this, week after week when you’re grinding it out for some future version of yourself that you know, may may change. I, I think that, that that tends to be a pretty good path. [00:45:10] Nathan: Yeah, that makes a lot of sense to me and like networking connection and advancement side of things, I think is one of the best reasons to do. A lot of that. I remember like the first conference that I went to after having a blog and it being such a night and day difference. I wasn’t even a speaker at this conference, any of that, but people were like wanting to come up and talk to me because of the articles that I’ve written you. Whereas like months earlier, you know, pre blog, you go to a conference and I was shy and introverted. Like I didn’t talk to anybody. And so I was like, wow, because I published words on the internet. People will now do all the work. Like interesting people will come meet me instead of me having to like put out all the work. This is the best leverage ever on the same way, like podcasts and everything else Write being able to, everyone says the Podcast in there for the audience. It is right. You know, thousands of people will listen to this episode. I am more doing it because I get to meet people like you and Kimberly, who we just had on last week. And right. It’s just about meeting people. that’s so [00:46:09] Nick: It’s like it’s like you know, like I think with Podcast, it’s crazy because you like appear in somebody’s ears. Right. You’re like, literally like you’re right next to their head, you know And like and it’s it’s, just like, it’s this, it’s this wild, like intimate relationship, usually, like I’m listening, you know, on, on two X. So everyone sounds smarter than you than they would were listening to them on one X like it’s, it’s, it’s I think publishing and creating content, especially in a world where like we just live more online where like more of our interactions are, are remote. I think it’s, it’s a, it’s a pretty, it’s still sort of an underrated hack, especially in, in your career, right? Like you can, you can do. You know, you, you become inter like instantly, someone who someone wants to take a meeting with and like it’s those little, like, sort of marginal decisions, right To like chart the course of your career, right? Like, like, did, did this person meet with you or not? Were they predisposed to like you, before you came in and like, you don’t actually know which article is going to hit to make them feel that way, or which Podcast is going to, you know, which Podcast you’re going to meet, the person who, you know, might be an ex customer or investor or something like that. But like, there’s just such a powerful, you know, with that [00:47:26] Nathan: I think one of my favorite examples a people using an interview show or, you know, interviews in general to break into an industry Harry Stebbings, who does 20 minute VC, because I don’t know how old he was when he started it, but like 17, maybe I’m not [00:47:42] Nick: Totally [00:47:43] Nathan: nd he’s like, I want to break into the world of venture capital and, you know, interviewing all the biggest names at first people were saying yes to him, probably because of his hustle, because he was young. They’re just like, sure. I’ll take a chance on this kid on, your 20 minute. And [00:47:59] Nick: Now love I love people who have like, a, a 10 step plan for their career. Maybe you just, you just wanted to create a podcast. It was sort of like, [00:48:11] Nathan: Right [00:48:12] Nick: Doing this for fun, but like, not a ton of people have, have a plan. Right. like, like most people are just sort of doing stuff, but like, if you like sit down and just kind of think about it for like, like 20 minutes and you’re like, who might, I want to be like, who does that person like, like what would make me credible in that person’s eyes? Like, like how could I, you know, do that thing now. So that in two or three years, like, like Harry’s, I’ve been such a good example. Like, I, I think there, there are so many people who, who like, if they, they sat and gave that like 10 minutes and turn Twitter off, like you can just, like, you can do a lot of, you know, good, good strategy there. [00:48:52] Nathan: Well, I think can do it as a method to break into any business. So if we were like, know if you and I were 18 years old and we’re like, wouldn’t be in the music business or even right. You wanted to go into screenwriting. you with what you know now, and you and I were brainstorming how to get 18 year old you into like screenwriting, we would probably suggest starting a podcast and you interview all the screenings. In some format and it wouldn’t result in work, but then you’d imagine we have this network and this work would come from the network and you’re like, no direct connection, but then there’s a ton of indirect connections that wouldn’t have happened without it. [00:49:31] Nick: You know, it’s kind of a similar thing. We talked we’ve dragged them at Twitter at the beginning. Right. Twitter does this service for people that gives them like a feeling of prestige. Right. And like, and, and what you’re basically doing is like, it’s like, you’re giving an audience to people who don’t have time to build one for themselves. And like, you know, most of the people who are listening to this podcast are people who are building audiences in, in some way shape or form, but like most people don’t do that. Right And and so, and so you can find all sorts of people who are who are just like all the time, who like, would love to sort of rent someone else’s audience to build themselves up. And so like, and so you can be then 18 and it’s a total hack to be able to sort of bring on this screenwriter, this music industry, executive, this, you know, a VC. Right. And it’s just, it’s [00:50:23] Nathan: Right It made me realize another person on the ConvertKit team who does this really well is ISA Adney. Who’s our storyteller. she used to teach all of our webinars and workshops and, and, is branched into working on like brand development sides as he writes a lot of and else, but her personal audience, let me take a step back. If you talk to her, she’s like, know this person, or whoever at Disney or that kind of thing who worked on, you know, and just like the amount of people that she knows in the world of storytelling and film and everything else, you’re like, how do you know all these people? like, oh, I interviewed them for my newsletter, you know? And you’re just like, wait, what? And it’s like, I was going to say cartoonists, but like illustrators from, from will like draw her a birthday card. can tell us just for her, you know? And you’re like, how, and, and it just comes from this exact thing of like, oh, I just interviewed them on my newsletter, which is a fantastic newsletter, but it’s not like they came on it because she’s wildly famous. It’s that [00:51:26] Nick: It’s incredible. And I like there, there’s a couple other people I’ve seen who have like, who, who sort of, they have their, their, their full-time job, but like, on the side, right? Like, Liz Bostonian, someone I’ve known for awhile and interviewed, and she, she wrote a book called no hard feelings about emotions at work. She’s about to publish her second one and like the way she’s just like, she’s known by, by all of these people at all these different companies that like her company would be the perfect company to sell in, to sell into. you know, it’s just, it’s just there. There’s. There’s so many good things that can come a bit. I think one thing I’d advise to like, w going back to like this, how do you balance a, like a, like a newsletter and a full-time career is like don’t work for any company that doesn’t value it because because like you know, clearly there are places like Guild, like ConvertKit like there there’s so many different companies where like you can go where like, they will appreciate what you’re doing. And if you can, if you can, like, ideally, like, let’s say you love to write about cooking, right. If you can find a company where like, that is like, like, especially like building an audience around cooking, like it’s, you know, a dishware company or whatever it is, like finding that right place for not just you, but your publication, a really underrated thing, because it just makes everything so much smoother to find that right. Manager find that. Right. you know, [00:52:52] Nathan: Yeah. That makes sense. If it’s an uphill battle, like find another, another place where that’s actually a asset. [00:52:59] Nick: Someone will like it. [00:53:00] Nathan: Yeah, exactly. So maybe before we wrap up, let’s talk about the growth side. Cause everyone’s thinking about, okay, I have my newsletter and it has 100 subscribers or 500. How do I grow it to that next tier So I’m curious, what are some of the things that have worked for you on, adding 100 or 500 or a thousand subscribers at a time? [00:53:19] Nick: Twitter Twitter. You, you, you can use Twitter. [00:53:22] Nathan: Yeah [00:53:22] Nick: It’s It’s frought in many ways you can also use LinkedIn. I actually think LinkedIn is, an underrated place to do it. Like it’s to me, it’s not as stressful to write a LinkedIn post as it is to write. A tweet, it’s a little stressful, cause it’s like, it’s like, definitely definitely to your company And it’s a place where you’re in professional domain, but especially if your newsletter is somewhat professional, then I think, I think LinkedIn can be a really good place for it. and a little bit less of a pressure-filled way to do it. I probably one of the underrated things now is like, you know, I look at how many discord servers I’m suddenly in, like in in you know, months and like, I think those are probably good places to like promote. I don’t think it’s, I don’t think you can in communities, it’s harder to just be promotional. You need to sort of have earned it by, by building relationships. And so, but I think like, you know, I’m, I’m in a writing group called foster, right? Where, where like where, you know that they help with editing and like, and like everyone’s sort of publishes their stuff in there, but like that’s a great place to like, to, to sort of build a following, especially sort of early on. Obviously you can do things like hit Reddit, hit hacker news, you know, Reddit, I think I’ve been banned from like, you know, 20 different subreddits for, you know a just posting a blog post, which seemed to me. But, um and then hacker news, right? You, you, you never know. And, and, you know, getting to the top means you’re going to get barraged with terrible comments, but, I think ultimately though you kind of want something you can build, right. And this is, this is the, this is the challenge with Twitter, right? It’s like, it’s like, there is a weirdness about Twitter, but. Building an audience on Twitter Like it’s a great top of funnel for a newsletter, and same way with LinkedIn. And so it’s hard to totally steer away from those things. I think one thing I’d to try and toy with once I figure out the monetization piece, of my newsletter is I’d like to try paid ads. And there’s this weird discomfort with it with it. if what you value is value is, having an audience and people to write to and you want to grow that audience, I actually think it doesn’t need to be that literally every person you painstakingly gathered with your blood, sweat, and tears, right. It’s it’s I think there’s, there’s other stuff that you can try, but you obviously don’t want to be throwing a lot of money down the drain on, building an audience [00:55:53] Nathan: Yeah I’ve, I’ve done paid ads with good results of four. I have a local newsletter called from Boise, is just for the Boise area. And in the last month we actually went to a thousand subscribers and we doubled to a little over 2000 subscribers, almost entirely with ads. So like no ads to a thousand and, ads worked well, you know, and it helps to have the hyper-local targeting. So I was in the same boat of like, hadn’t played with it before. And, you know, at, I think we paid between $2 and two 50 a subscriber, [00:56:25] Nick: Facebook. [00:56:26] Nathan: Yeah, Facebook and Instagram. So we’ll play with it more. What are you thinking maybe we’ll end on this question. What do you thinking for on the newsletter? What are you paid? Is it a A A book? What other things are coming up? [00:56:39] Nick: It took me a while to find something I was comfortable with on modernization paid, never, appealed that much to me. just because there, there are some people who I like I will pay for their ideas, but like, overwhelmed with Content. that like, usually when I’m paying for, for, for, for a newsletter, it’s because I really liked the person, like their, their, just their style of analysis. I can’t get anywhere else. but, but, but the competitive dynamics of newsletter sort of, to me, like they’ll, they’ll kind of always be someone who something close to what you do for free. And so, and so that, that always kinda, didn’t appeal to me as much. Like I think of it as like, This audience, that you’re kind of building affinity with over time and like, and can you, ideally sort of find, build something or find something that’s going to be really valuable to them. So I actually, literally just this morning, teamed up with this, this company called palette, to, I swear, this, this, this time it was not planned. It just, it just happened nicely, to a team at this company called pallet in pallets, been sort job boards with a bunch of and I actually worked with them on this, this kind of beta product that they’re working on, which is this idea of talent collectives. And so what we’re doing is like, it’s like basically job searching really sucks. Like you’re filling out tons of applications. You are, waiting for a long time to hear back from companies. If you are highly desirable, you’re getting a lot of recruiter spam and they’re just like barraging you. so we’re going to do, is, is put basically just an air table form where you can say, Hey, like, this is who I am. This is the kind of role I’m looking for. pallet has this, this, all these companies that they are so, so they’re going to basically, send people and you can be anonymous if you want to all sorts of stuff, but they’re to their partner companies and then and then they’ll send you sort of the intro request, like, Hey, you know, do you want to, do you want to chat with ConvertKit right. And, and, and if you do right, we’ll, we’ll make the intro, but like, you don’t have to worry about our recruiter reaching out to you because they’ve, they’ve said they won’t do that. so yeah, I think it’s cool. you know, if, if, if any of the folks listening to this are like, exploring new job opportunity. We’d love you to come check it out. I think it’ll be really neat. I think it’ll solve a challenge that a lot of people are facing. For me it felt really native. It felt like I didn’t want to do a job board because I don’t know these companies. I’m doing a newsletter about careers, and it felt really important that I’m sending people to the right place. I said, “Hey, if you sign up for this, and you take one call from a company, I’ll do a 30 minute career coaching session with you.” Even though, I’ll get paid some commission, if the person goes to one of these companies, I will really try to give them the best advice for them, because that’s what I promised to readers. When you’re thinking about monetization, it’s like find something that feels native, and not weird to your audience. I think sometimes that can be a pure paid subscription, but you can be creative in different stuff. [00:59:51] Nathan: Yeah, I think that’s good. Let’s leave it there. I’m super excited to see what comes on the monetization side. It’s probably the coolest thing about newsletters and audiences that you can monetize different ways. So, where should people go to follow you and follow your writing, and see more about what you’re up to? [01:00:07] Nick: You can follow where I have a conflicted relationship, where there are days I will post a tweet, tweet threads, and the next day I’ll feel very ashamed of it, but that’s @Nick_deWilde. Then the better place to get my thoughts, I would say, is JungleGym.Substack.com. At some point I should probably switch that to ConvertKit, but yeah, that’s another time. We’d love that, and thank you so much for having me. This has been so fun. [01:00:42] Nathan: Yeah, It’s been a great conversation and, thanks for coming on, and we’ll talk soon. [01:00:47] Nick: Awesome, Nathan.0 comments0
- The Nathan Barry Show Oct 25 · 1h 6m 053: Kimberly Brooks - Taking Intentional Breaks To Reignite CreativityKimberly Brooks is a contemporary American artist and author. Kimberly integrates landscape, figuration and abstraction to address subjects of history, memory and identity. Her work has been exhibited and featured internationality. Kimberly received her bachelor’s degree in literature from U.C. Berkeley, and was Valedictorian. She has taught art as a lecturer and adjunct faculty instructor, and was a featured speaker at TEDx Fullerton. In this episode, I talk with Kimberly about her work as an artist, author, and editor. We talk about how she uses ConvertKit to reach and grow her audience. We talk about what people can learn from fine art, and apply it to their newsletters. We also cover the path to becoming a successful creator, and much more. In this episode, you’ll learn: The secret to achieving your breakthrough moment A job most creators should charge for, but rarely do What you should be doing instead of blogging Should you be posting on Instagram? Links & Resources Huffington Post ConvertKit Craft and Commerce Steve Jobs John Baldessari Adobe Photoshop Adobe Leonard Shlain Milton Glaser Macworld Walt Disney’s Imagineering Warner Music Group Seth Godin Leonardo da Vinci Arianna Huffington Huffington Post: Fine Art Later Anderson Ranch Arts Center Otis College of Art and Design Kimberly Brooks’s Links Find Kimberly on Instagram Kimberly’s website Kimberly’s Ted Talk Huffington Post article, “The Gap Logo, New Coke and the Legendary Walter Landor” Kimberly’s book, The New Oil Painting Episode Transcript [00:00:00] Kimberly: The fundamental way to learn is, you imitate, assimilate, and then you can improvise with anything. You’re going to be thwarted in the beginning many times, and you can’t give up. You have to say, “Okay, well, I don’t care if it sucks. I don’t care if I’m going to fail. If I’m gonna fail, I’m gonna fail big. Let’s just go on.” [00:00:29] Nathan: In this episode I talk to Kimberly Brooks. She is a fine artist. So, painting, she has all of her art in galleries, that whole world, which is super fascinating to me. She also plays in the creative world. Newsletters, podcasts, and interviews. She built the whole art editorial section of the Huffington Post. She built that to millions of readers. She’s done all kinds of things in the design community from the early days. So, we riff on that; Mad Men-style ad agencies in the ‘80s and ‘90s. Some great stuff. Then she brings it all the way through to talking about what she does with ConvertKit. How she sets up her sequences, and everything else, and things that people can learn from fine art, and apply to their email newsletters and sequences. So, it’s a fun episode. We have to do a part two, because we filled up all the time we had, and I think I only got through half my questions. So, anyway, I’m going to get out of the way and dive in. So, here we go. Kimberly, welcome to the show. [00:01:37] Kimberly: Thank you for having me, Nathan. [00:01:39] Nathan: There’s so many things I to talk about, because you come to the creator world from a different perspective than I do, though we both share a love for Photoshop. [00:01:50] Kimberly: Oh, yeah. [00:01:51] Nathan: We’ll start with where we met. It was at Craft and Commerce, some number of years ago. I can’t even think. Three years ago? Four? [00:02:01] Kimberly: I think it was three years ago, and it was such a random whim. I don’t even know how I ended up finding it. I fell in rabbit hole. And then I came upon ConvertKit. I was actively looking for a better way to send art show announcements. Because I’m a painter, I’m an artist. I just felt after my previous experiences, I knew how important having a subscriber-based service was. I don’t want to get too nerdy, but I didn’t really like the competitor who shall remain unnamed. But, I found you guys, and I started getting the advertisement for the conference, and it was in Boise, Idaho. And so I thought, I’ll just go. It was like a Ted conference for really creative nerdy people like me, but it was exactly what I was wanting. It was about marketing, which is really such a weird word because it’s really about sharing, and I loved the title. I loved everything about it. I met some of the people that I’m really, really close with now. Then the next year it was canceled because of the pandemic, but it was amazing, and I met you, actually. [00:03:28] Nathan: And, and we had a really fun conversation. one thing that I want to talk about, for you is the intersection between fine art, right. And painting and that world. And then now you’re also in this world of being a writer and a creator in the sense, right. You you’ve been a writer and creative for a long time, but, but it’s, it’s like a different world of the selling things to your audience. And. Earning money directly in that way. And so I want, like, I want to hear that as you like weave in and out of these two worlds and then just your experience there. [00:04:02] Kimberly: Yeah, it’s interesting. I, when I was in elementary school, we had a really competitive game of tetherball constantly going on on the playground. And it was just sort of that pole with a ball attached to a rope we would, people would line up and we would get it, and it was, see how many times, and it was just sort of like, it was very intense and I always felt like being an artist. Being an art to me was it was the pole, you know? So like my pole is art is making art and everything about what I do. I write about it. I interview people about it. I interview other artists about their work. I make paintings 90% of the time in my studio. Like, it’s all about art, you know? So that’s like the beginning. So I do see myself sashaying between different worlds. And I think everybody kind of does that. And then as the bicycle of technology was being built to use kind of like a vague reference to like Steve jobs is, you know, what happens if you put a man on a bicycle and you know, like how fast can he, as the bicycle was kind of entering our world, I thought, what if you kind of mixed art with the bicycle? You know, what, what happens if you, you know, Make an artist’s website. So I was like one of the first people I knew that made an artist’s website. And I remember, it was, I had, was having lunch with my mentor. Who’s, the late John Baldessari. He was a great, great, great artist. And, he’s famous for, you know, he burned all this stuff and graduate school and then became a conceptual painter, you know, very, you know, Howard work in, you know, conceptual anyway. So I brought my laptop to this Mexican restaurant in Venice, and I said, I wanted to show you something. I made a website and our studios were really near each other. And he said, Oh, I, I don’t know if I would do that. If I were you, I was like, why not? He said, because you’re, you’ll piss off the dealers, the galleries, the galleries, you shouldn’t be selling directly. It’s going to take away from what their job is. You know, when you hang a show and you have art in the gallery, the gallery is selling the artist and it’s their job, you know, and artists are supposed to be kind of this, you know, semi mute, black turtleneck wearing, you know, mysterious, mystical ShawMan goddess. I call it goddess on the hill. Like you’re not supposed to really get in the way of what your artists about. And so I thought, oh gosh, you know, this is, and I had put the paintings for a show was about to have. And so I started making, so my postcard for that show had the name of the show and it had the name of the website, cause no galleries had website. Then this is in like the two thousands, you know, this is a long time ago. And I remember meeting people when I handed them a postcard. If like I felt comfortable with them, I would like secretly write a password so that they could see the website, [00:07:20] Nathan: Oh was you were, you had the website, but it was [00:07:24] Kimberly: Yeah. So I password protected it. I password protected it because John Baldessari told me that it’s probably not a good idea to have a website. This is again, no artists ad website. [00:07:35] Nathan: How did the galleries and the community [00:07:37] Kimberly: The galleries didn’t have websites either. And the galleries, I remember. They started it. Like some of them had websites, but it was super janky. It was like sometimes most of the time they did an, and it was just sort of this mysterious world that 99.9, nine, 9% of the public didn’t understand. Doesn’t understand it’s better now. And you’d have to be walking down the street or you’d have to know somebody who knows somebody, you know, it’s, it was just a different world then. [00:08:08] Nathan: But did any of those negative things come about? Like, did anyone look down on you on it for having a website and for [00:08:14] Kimberly: No, no, no. Eventually I just said, screw it. And I took the password off. And, interestingly, I don’t want to date myself, but I think I already have, but the at the time flash was very. sexy. And it was like, and so artists would have, if they did have website, firstly, they would be horribly designed and they would have like a flash animation of a curtain opening and a door. And it was very like CD rom mentality. Like, you know, it was pre-internet thinking, you know, anyway, like I said, the big nerd here. [00:08:48] Nathan: Flash was big until 2000, like the iPhone 2007. [00:08:52] Kimberly: Until Steve jobs killed it, just took a knife. He took a sword and he just, during a keynote, just, you know, [00:09:01] Nathan: Yeah. Oh, and the two biggest reasons were, that the bandwidth of the phones couldn’t handle it. And then also the battery life on the phones couldn’t handle it. [00:09:10] Kimberly: Wasn’t there another reason there was another technical reason that had to do with plays well with others. I can’t remember exactly what it was, [00:09:20] Nathan: Yeah. I mean, it was a restricted technology. Like it was owned Macromedia. And so probably that apple was trying to do to get to play. And Adobe was playing hardball and apple was probably like, okay, [00:09:31] Kimberly: Yeah, [00:09:32] Nathan: You know, we’ll play this [00:09:33] Kimberly: Yeah. It was, was, it was, it was just the evolution of, you know, of Photoshop and Adobe products. And so I grew up with Adobe. I learned I was an early adopter, always, you know, I just sort of like analogy. Yeah. [00:09:49] Nathan: I want to dive into all kinds of things. I want to talk about, more in the financial world and the business of that and everything else. But back and maybe start earlier in your career. [00:10:01] Kimberly: Than elementary school. [00:10:04] Nathan: I guess we didn’t go to elementary school a little bit after elementary school. What what did the early days of your career look like [00:10:12] Kimberly: I was a, you know, I’m a first, or I guess I’m a second generation American, so, and I’m Jewish. So of course I was supposed to be a doctor. So my, we used to get, you can be anything you want just as long as you’re a surgeon first. So I got the makings of a woman’s surgeon and, you know, it was just like, as a book that was a book that I received many times in my middle school years. And then, you know, it was like, that’s great, you’re so talented. But you know, you really, you know, after you get out of medical school, you can, it was just sort of what you did in my family. And, and my father he was a well-known surgeon and he became an, I don’t want to say artist. He became a writer, so he’s a well-known writer. And he started writing. So he kind of became an artist before my eyes, you know, so as I was getting out, as I was graduating college, he published his first bestselling. That was just, and I would like sit at the book, you know, when he gave a lecture at an art gallery, because it was called art and physics. His name is Leonard Shlain so I would like sell, watch him, sell the books, you know, like give a lecture and then I would check out and I would get, take people’s cash and then give them a book, you know, at the end of the lecture. And he used to tell me, he used to say, honey, you have to be shameless. You have to be willing to just talk in front of four people. It doesn’t matter. You just need to do it. If it’s just, it was just a big, it did. It made an imprint on me because I was watching him grow out of his own discomfort zone, which I still struggle with of talking to people like instead of through your paintings or, you know, talking to an audience saying being on video, it took me six months to figure out how to be on video, but I’m getting ahead of it. So you asked me like my CR about my career. So I was an English major. I went to an English, major architecture, minor at UC Berkeley. And at the time that I was graduating, painting was considered dead. And I know that that for artists today, they don’t quite appreciate that. But after abstract expressionism, there was sort of this mood in the art world that everything had been done and like, forget about figuration was the last thing people wanted to see, you know, and I wanted to paint people. So I just figured, okay, I’m going to just do that on my own, but I’m going to, I love reading. I love writing. So I became an English major and I was valedictorian of, of the UC Berkeley English department. And so my first job, I wanted to combine my love for art and literature. So my first job was. Design. So my, so I, was mentored by a gentleman named Walter Lander, who is the founder of landlord associates. And he was sort of the west coast, Milton Glaser, Milton Glaser from a design point of view, like he was, he just recently passed in the last five or so years, but he like did the, I love New York, you know, like he’s this famous, famous graphic designer because the field of graphic design is, is relatively new. It’s relatively, it’s like a century old, you know, like th the serious field of it. And Walter was a pioneer in it. And he did, you know, my first job was like working cause I, cause I minored in architecture was, helping design the shell oil, gas station, you know, So I was doing like architecture design, and then he asked me to write speeches. And so they had, their company was kind of designed like a brain. So they had like a language division and they had like the design division, like they did the loose soon milk and they were so famous then such leaders. They had 1800 people in offices all over the world and it was like a big deal. And they had an office on a ferry boat. So that was my first job out of college. I was a speech writer for Walter and I was in the, I was in the word department. Like I think I designed, I helped name, a cigarette, you know, like was just a weird, but it was fascinating, you know? And it was meeting fascinating people. The grateful dead would like come over on the boat after it was, it was, it was a wild time at, in San Francisco in the late eighties, early nineties. Totally wild. So, So I was like, so all the designers are starting to learn Photoshop. So there was this thing called Photoshop because they were doing everything by hand, you know? And then I was like, oh, so I got Photoshop 1.0, you know, and then I had th there was no layers. So you had to do everything in alpha channels. And it’s interesting just to be a big nerd. Cause you’re a designer too, right? I mean that’s yeah. Yeah. So if you can try to imagine there was Photoshop without layers, it meant that you had to do everything inside the masking tool that’s built in that nobody really uses or knows about now called alpha channels. So I had to create everything using masks, but it was very oddly more similar to what you did with your Exacto knife and ruler, know, I still think one of the biggest, the saddest things about Photoshop. I mean, I think everybody should know it, but it has some feature bloat, but I think it kind of buries the power of alpha channels. And I think that if people knew how to use it, it would like, it’s like a little thing to know that would hugely leap them out of the more artificial aspects of doing those filters on things. [00:16:00] Nathan: Right. [00:16:01] Kimberly: Anyway, like I you have to be careful with me because I can go into real. I can crawl real deep into these nerdy things. But anyway, [00:16:08] Nathan: Are there other things from those early days of, of the graphic design art agency, like that kind of world, that you still take with you today [00:16:19] Kimberly: Thousands of Gillian percent. One of them is the four DS that every project is discover, design develop, deploy. And I know I lost that. I also saw that, like, if you could name it, you could charge it. [00:16:32] Nathan: Is there a story behind that? If you could name it, you could charge for it. [00:16:35] Kimberly: You know, you’d see these hundreds of thousands of million dollar contracts going out to these major people. And I used to have to help write the proposals and I would see how they would divide they’d phase out, like a lot of designers. Again, I don’t, I hope we’re so not too off topic, but a lot of designers will not charge for discovery. You know what I mean? Because they haven’t named it. They didn’t name it They’d Just be like, oh, let me Research all about your company. And then you’re going to pay me to give you some designs, and then I’ll give you the designs and then hopefully they’re smarter. Anyway, like I said, big, big topic. [00:17:10] Nathan: Yeah. But think there are a lot of people listening who are in the either freelance or agency space and they, provide services to newsletters or creators or they’re growing their own on the side. And I think it’s a really important point that, if you’re if you’re structuring your proposals and all your interactions with clients around the deliverable, then you’re failing to talk about a substantial portion of the work And probably the part of the work that differentiates you from the other freelancers who are just like, oh, you need a logo. And they dive like right into Photoshop or whatever tool. Whereas if you’re good at what you do, you’re probably taking a step back and looking at the whole landscape and spending probably more than half of your time in that Research discovery and learning stage rather than the deliverable stage. [00:17:56] Kimberly: It’s actually the most important time intensive stage of any project. And so not just design. I mean, I think you saw my Ted talk, the creative process in eight stages. And I think I talked about how as an artist, I don’t want to give anybody whiplash, but like you, as an artist, you have, a period of time where it’s like a rest in music where you don’t, you’re not making work. It doesn’t look like you’re doing anything on the outside, but that’s the most important part. And it’s when. Gathering, but you’re doing it in a subconscious, like in many different ways when I’m, when I’m making a painting, I’m having to listen a lot, you know, you have to listen and look and just inhale before you can exhale. So anyway, that, but I mean, we could, I think, I think we could do a whole hour on Landour. Cause that was just a, such an interesting, you know? And, and I was actually, I was actually there, I dunno. Well, you’re, you probably weren’t born, but there was a, Coke released a new design and they, they, and Landour was the leader of this new design. And I was like in the boardroom, in my. In pantyhose. Cause that’s what we that’s what, like you had aware that it was very far, it was like mad men. It was like mad men where like everybody smoked and the women were gorgeous and the men would like have these glass offices on the side of the boat. And they would like go in and light up a cigarette and call London, you know, like they were like, or Japan and, and they had, it was just extreme, chic, crazy environment, very male dominated. And I was like, I’ll often the lone woman in a room, you know, but anyway, that’s a separate side conversation and they were introducing the new Coke and it was a flop. It was like, it was like, there was a backlash against the new design because it had like big fat. It was like, whereas the old Coke kind of has that Victorian, which they still use now that, that very Sarah fee or Nate almost like your create above your head, but more, you know, whereas. Where the new version they were doing was super kind of chunky. It was like new Coke, you know, anyway. But, it was a wild experience. I wrote an essay about it and I’ll, I’ll give it to you if you, if [00:20:35] Nathan: Yeah, we’ll put it the Shona [00:20:36] Kimberly: Yeah, [00:20:38] Nathan: On time on that. [00:20:39] Kimberly: Yeah, no, the whole, here’s the thing. I wanted to be an artist, and a lot of times I believe a lot of, and I believe there’s a lot of people who have an artist inside them and a lot of times they will, work in a field that brings them near art decisions to make themselves feel better. That they’re not being an actual artist. And I was one of those people. [00:21:08] Nathan: Okay. So how did that play out for you of your you’re close to the design and that sort of [00:21:14] Kimberly: I was like, yeah, it was, I couldn’t be closer. I was like, I was like in, I was behind the curtain of Oz doing the, with the, with the best people and everything. Again, this is so long ago, but, but I felt like technology at the time, again, Photoshop was just starting. There was no whatever. I was like, you know, I needed, I need a break. I need to like push the table over. So I quit. I moved to Paris to paint for a year. I played piano in bars at night. That was like a whole other wild. We could do a whole show on that, but, you know, then I was like, well, I can’t, I’m not going to be able to make a living doing this. Like I was painting, I was sitting at the sore bone and I was like, I had this little gig in this bar, but it was a couple of Franks and I wasn’t legal in Paris. And I just had this big because of my literature background I have does such a, you know, I love you. I was so somewhat of afraid. [00:22:11] Nathan: So how old were you when you [00:22:14] Kimberly: I was in my early twenties. [00:22:16] Nathan: Okay. When you, quit and said it’s time to do painting. [00:22:20] Kimberly: Yeah. I was like, it wasn’t a straight line. And that’s another thing. Like most artists don’t like some artists grow up and everybody goes, oh, you’re so talented. Which by the way, like hate that expression. I must like tell people, like don’t ever tell people they’re talented. Say you have great raw material, you know, just say, you know, just like great mom material, but like, you have to like do it for eight hours a day in order to like express something. Great. And then, then we’ll talk about talent, but in any case, so some people have parents that say, you’re honey, you’re so talented. I want to send you to art school. I want to spend a couple hundred grand and I’m going to send you to art school. Undergrad, let’s say a good, let’s say a typical artist, a college education is this amount. And then I want you to get an MFA from Yale or the best school and have that checked off. And then I want you to go get in galleries and be an artist there’s 0.01% of artists have that route. They have parents that say, we support this. This is good. This is a good plan. I would say that’s like a very rarefied small group. Cause you have to have, well, there’s so many things that need to happen in order to have that setup. Most people, most artists, even artists that I know, like one of my good friends Enrique he was a PA getting his PhD in physics read my dad’s book, art and physics and decided he wanted to be a painter [00:23:49] Nathan: Okay, [00:23:50] Kimberly: So like, there’s a whole bunch of artists that were doctors that were lawyer, you know, that, that, that they, they were catching the train of you know, the I’m a good student, I’m a diligent worker and they, they, you get routed onto a track and then you’re on that track. And then suddenly you wake up at at 30 or whatever, and you say, you know, I’m here and I’m super successful, but this isn’t necessarily really how I want to be spending my time. You know? I mean, th this is the conversation, right? You know, how do you, how do you decide and what you can want changes in your life? You know, but if you know what you’re pull, the tether poll is like, if you know what, your deep inner core desires. are And, you know, and you, you have, you’re remotely in touch with that and you, you need to go, you need to go towards that light. You need to go towards that center then everything will radiate out from you afterwards. [00:24:58] Nathan: Was there a catalyst that pushed you, you know, you were thinking about it, you’re feeling this, but what was the thing that made you go like, all right, I’m [00:25:06] Kimberly: Well, okay. Like I said, we don’t have enough time to get into all of this, but there were, I made three huge dramatic, you know what? I don’t know. Maybe it’s a Monty Python movie, I don’t know. But like when you push the table over and you throw all the plates and you break everything, like you just come, it’s not a reboot, it’s way more violent than that. Just kind of like you take the tablecloth out and you just say I’m out of here. You know, I think I did that three times before I got closer to. You know what it is. And one of them was moving to LA after moving to Paris, I moved to New York and then, then I moved to LA and I was like, okay, this time is going to be it I’m being artist. Like, and you know, it’s a couple of years later, it’s after Paris. Like, you know, cause you have to get, you have to, I had to make money. You know, I had to make a, I had to have a job. And so I had to kind of like do, do design work and stuff like that. So when I moved to LA, my first, I went to a Mac conference, like it was like 60 booths. It was so small, like Mac was seen a teeny little thing and, and Microsoft was the big thing windows and, [00:26:18] Nathan: Yeah. [00:26:19] Kimberly: And I made a business cards and I said, it said artist. And then when I, I walked, went to this conference and I was practically like often the only woman, you know, and I would say, yeah, I’m an artist. And I know. And so the first job I got was making the first CD rom for apple computer that they said distributed to every single apple. So they distributed over 2 million copies worldwide, and my name was on it. And that kind of, that was a huge breakthrough because suddenly I was being offered insane jobs. And next thing you know, I was anyway, like, I don’t want to dwell on this because we haven’t talked about newsletters yet. [00:27:01] Nathan: That is okay. that is okay. So you just made a leap from, I went to this conference to, [00:27:08] Kimberly: Yeah, by the way speaking, we started with going to a conference. Yeah. [00:27:12] Nathan: A big deal. We are we talking about that as well, but this leap from going to the conference to your work, being on the CD, [00:27:19] Kimberly: Well, so they were, it was like, again, I was on the bleeding edge. I could not explain to my father Who would come down and visit me. In the warehouse. I, it was, it was an artist and a coder who, but they had both met in art school and they brought me on to be the creative director. And it was like, it was almost no money at first. And then it became like a bigger thing and apple, the more that apple saw it, the more they were like, wow, this is really good. so then the next conference I went to was in San Francisco was Macworld and my art was everywhere, everywhere, and I got job offers from Imagineering. They wanted me to design why the Disney, they wanted to be the head. Of Warner music was doing a new interactive division and digital don’t digital. I can’t remember the names, but it was very, it was a very heady time. It was very, it was very fun. I felt like, wow, I found this place that has it’s the intersection of art design, narrative and technology. And it was exactly where I want it to be. And that was just, that was sort of, and I set up an easel in my office, I had a lot of people working for me and it was just, it got very, it got very fancy, you know, and I, and I took a lot of, I took a lot of like what I knew at Landour to attach in this before email this before the internet. [00:28:45] Nathan: You’re talking early nineties at this point, [00:28:48] Kimberly: Yeah. Like you no, like a mid yeah. Mid nineties, you know, 96, maybe. So, yeah. So I took a lot of my, knowledge that I gleaned from working at land or like the discover design develop, deploy to whip these engineers and designers into shape, you know? And anyway, I was still stalking what I really wanted to do, you know? [00:29:10] Nathan: Okay. So tell me more about the difference between what you wanted to do and what you were doing, because you just described your art being on everything. [00:29:17] Kimberly: No, no, no, actually, honestly, honestly like I would listen to like Liz fairs, exile in Guyville, as I drove downtown by the toy factory in downtown Los Angeles back and forth, like every day, like at these, I was a big album listener. And when I was designing, I would listen to full albums and I was just like, wow, this is it. I am so excited and energized and everything. then I started studying painting again. So I started so like I had taken a hiatus. And then I got into the, Otis, which is the art school here, You know, when you get professional, when you become a professional in anything, even being an artist, there’s a, single-minded rigor focus and clarity. one brings their whole self to what they’re doing, you know? And if you know that if If you’ve been successful in anything else or anything like that, you can, if you bring that to your art, there’s literally nothing that can stop. You. You become a wire cutter. It’s like, you’re going to munch through like, I, you know, really understanding, painting in the deepest way possible. Like I was thinking if I can understand alpha channels, I can figure out how to tone a canvas. You know, just like I just, because painting is a technology, honestly. I took everything in my being to it. And that was like a third moment. Like that was like another moment I skipped some moments, but there was like where I was knocking at the door, knocking at the door. And then I knew that in my art would become the, that I had when I started painting in full force. Like not just having it in my office, but saying this is what I’m going to do. And I’m going to do it as so ferociously, like stand back, everybody, nothing is going to get in my way. [00:31:13] Nathan: So you were painting, I mean, you had is this like painting a few hours a week, a few hours a day, and then you dove into doing that, just like. [00:31:22] Kimberly: This is like 40 hours. I mean, I basically gave myself an assignment and my assignment was I was going to paint a hundred new. Because that’s the hardest thing to do as a body. Cause you have to deal with the translucency of skin. And I could literally talk about painting all day, but you have to deal with light form and shadow and thinking in three dimensions and it creates it’s. I don’t want to knock marketing and technology and the stuff that you do, but painting is that most people do, but painting is a true, like you have to really, it’s a very intellectual as well as mindful and spiritual, but it’s a very, it’s a very deep, deep, deep way to approach the world. And when you become a painter or you actually like listen to the little voice inside you that says that they want to learn this. It’s a skill, it’s a skill. And when you do that, your brain expands and your world expands and you see things differently. So it’s a very transformative thing and it takes years. It takes years and years. So my assignment was I’m going to paint a hundred nudes and, and if I have like 10 good ones, I can have a show. [00:32:41] Nathan: So I want to tie that to maybe the experience that other creators listening would have, or anyone who’s on the fence about getting started. Right. It might not be painting that they’re trying to do, but they’ve had these fits and starts of like, I’m going to, learn to code, start a podcast, start a newsletter, any of these things, you know, learning to play an instrument, whatever it is. And then like start and it goes, maybe it goes well for a week or a month, or like what, what advice would you [00:33:11] Kimberly: Isn’t there, isn’t there like a guru isn’t there like a guru in the subject that calls it, the. Who’s that guy. Do you know what I’m talking about? Yeah. Somebody told me that, cause I was saying this to somebody and they were like, oh yeah, that’s somebody’s Seth, Godin’s the dip. But yes. You know, when I was younger and all through all through my, you know, middle school and high school and college, I played piano quite seriously. I was a classical pianist and whenever I would learn a difficult piece, I would play it over and over and over again. And I would have to, like, I would start to suck. I would get better, but then I would start to suck and I’d have to walk away and then come back at it the next day before I would be able to play it perfectly. Like, I mean, you know, [00:34:01] Nathan: Yeah. [00:34:04] Kimberly: Learning an instrument actually teaches you this better than anything, because if you make a painting at first and it sucks, you can be easily thwarted, like a, you know, a drawing or whatever. But, but in order to like worry the bone of like how to get that legato, right. And that Greek piano concerto or something like you got to just sort of do it again and again, and again and again, you know, like it’s, the fundamental way to learn is you, you imitate, assimilate, and then you can improvise. So you have to like, you play these pieces. And so with anything, you’re going to be thwarted in the beginning many times and you can’t give up, you have to say, okay, well, I don’t care if it even sucks. I don’t care if I’m going to fail. If I’m gonna fail, I’m gonna fail big. Like I’m [00:34:52] Nathan: Right [00:34:52] Kimberly: Go all out. Let’s just go on. [00:34:54] Nathan: But that specific assignment that you gave yourself of painting 100 nudes, do you think that an assignment like that is a good way to go as a creator of saying this is the commitment that I’m going to make, I’m going to get to a hundred podcast episodes or I’m going to, I don’t know, write a hundred blog posts, and then I can decide if this is something I actually want to pursue. [00:35:13] Kimberly: Absolutely. I think that when you make a commitment like that, to devote your energy into building a body of work of any kind in any media, you, your life will change everything. You are going to gain skills that involve every facet of that media. So like, if you’re a podcaster and let’s say you record in iMovie you’re going to learn iMovie or whatever they, whatever they edit podcasts. In And, and I think if, you know, if Leonardo DaVinci were alive today, trusts me. He would know Photoshop He would know he would be all over this stuff, you know, he would love, he would love it in this nether world space, because there’s, I’m, I’m going off topic a little bit because there’s a little bit of a prejudice in the art world where people were thinking they were resisting the newer technological versions of artwork. But back to process, what you were saying is that if you do something in a committed way and you basically measure it and say, I’m going to do it until I get to this point, I think a hundred might be excessive, but you’re going to get the hang of it. [00:36:28] Nathan: Yeah [00:36:28] Kimberly: I mean, I haven’t mixed feelings though, about blogging cause I started a blog again, when I was, really getting into. Consuming. I mean, consuming isn’t the right word. When I was throwing my entire body into the art world, one of the things that I did to expand my own knowledge was to write about other artists. And I think that’s also something that’s super unspoken, especially in the art world, because a lot of artists are just saying Me me me I want attention. I want to get people to focus on my show and my work, and I want a gallery and I want this and that. And I think one of the most important, aspects of breaking through to any next level of anything is generosity. Generosity of your attention to other people who are doing the same thing. And that for me, that general, I mean, I didn’t think of this. This is red, this is a in retrospect, but at the time when I look back on it, I was airlifting artists that nobody had heard of and writing about them along with other big art, you know? And so I had a successful weekly column where I was keeping a blog again, this was before social media and that’s how, and then the Huffington post came along and then I started publishing it, the, having a post. And that’s how I said, I was asked by Arianna Huffington to be the, to found an art section. And so I was like, I was perfectly positioned because I was, I was a big nerd. I had had these other experiences. I was a full-on painter. I was having shows galleries the whole thing. And then she was building this incredible Site to celebrate bloggers. And I was one of the bloggers So I had to build an audience from zero to 10 million people within two years. I didn’t have to that’s what happened. [00:38:26] Nathan: Right. I have so many things that I want to ask about in this, one thing that I want to highlight that you talked about is as you’re doing the painting, there’s the side of it, of, Research where you’re researching other painters, learning from them and all that. Most people keep that Research to themselves, right? That is not a public thing that happens. And I think a lot of the most successful creators that I see are the ones who do that recent. And, and share their notes and share that and work in public and do the interviews and all of that that you were doing. because it does a couple things. One people follow you, not only for your own work, but then also for your notes on other people. And then too, it’s incredible for meeting people. Like when you do a profile, either if they’re a, say an upcoming artist or someone who’s established either way, they’re going to be like, when you, you know, when you send them an email, they’ll like respond and be interested and engaged. And, you know, I mean, that’s a reason that I do this podcast is so that I can meet and hang out with people that I want to more about It’s amazing for network. [00:39:30] Kimberly: Yes. I think you’re exactly spot on. This is no different than what I did with artists, this, except for I wasn’t involving video, I was writing about it and interviewing them. You’re right. You’re absolutely right. I also think that you can get too carried away with that though. Like you have to be careful, you have to make sure that you’re, you know, I can become easily like Clydesdale the horse. I’m like, well, that’s another month and I have to do another, [00:39:57] Nathan: It becomes more important than the art, which was the [00:40:00] Kimberly: Well, yeah, [00:40:01] Nathan: It feels more time than [00:40:02] Kimberly: Yeah, yeah. Like, so eventually I had to leave, because it was just sort of eclipsing. It became so much bigger than everything else I was doing that I had to like go, okay, this isn’t, you know, I’ve got a show coming up. I can’t devote all this time and energy. And then of course, social media kind of made it all really different. [00:40:24] Nathan: Like in what way? [00:40:25] Kimberly: Well, because not only we could, you know, writing a really thoughtful piece about an artist and looking at their work and, you know, relating it with art history. And I also found that if I could relate it to like a contemporary event, like there was this one painter who painted battle scenes and we were just going to war with Iraq, I think, anyway, we were going to war somewhere. You know, it was a horrible time, but like, I would talk about going, you know, this contemporary news event. And I would link it with the artist who was painting these battle scenes. And then seeing that it went, go. [00:41:04] Nathan: Right. [00:41:04] Kimberly: Was another, that was another big learning lesson is like, if you put a number in a headline, like 10 things, you, you should tell, you know, 10 rules for your kids and screens, you know, then people would read that more. So I could see the analytics of what people clicked on. You know, that was like a interesting learning experience. But when social media happened, then suddenly you also had to tweet it. You had to post it on Facebook and then you had to tweet about it and then it just got to be social media. here’s my take, if I could just say one thing, because I want to get it out there. I think social media is great for first impressions so that when people see you for the first time they’re going to go that person’s like a real artist or they’re a real whatever, and they’re legit. And they don’t just have like three things that they’ve said about the subject. They’ve actually like, I trust that they’ve done some deep things. Like me painting a hundred nudes, you know, like this person knows how to paint. So I think social media, it’s just so easy to get carried away. I hope one day it goes away. Is that terrible to say? I think emails should be everything. It should just go away. [00:42:14] Nathan: I don’t think it’s terrible to say at all. You have something in your Ted talk. you talked about like the compulsion to paint being taken away by your smartphone and these distractions, And I’d love for you to talk about that because I think there’s so many things of like, if I’m on Twitter or checking my email, or even interacting with the ConvertKit team 2,700 times a day, you know, it makes it so much harder as a creator. And so I like, I just want to hear more of your experience there. [00:42:45] Kimberly: Well, I mean, in order to even get into my zone mentally to paint, I have to like have at least 90 minutes where I haven’t spoken with anybody. Like I just need to kind of like clear it. Like I need to, I mean, I can be in it and I’ve got all these, you know, because people everybody’s different. Some people like beginnings, some people like middles, other people’s like ends. So you have to get in touch with which person you are, you know? So I, I love middles and beginning. I actually like all of them, but like, I’m better at certain things. So whenever I go into the studio, I have to start in paintings that are in the middle, that many going on at once. so you have to get in touch with like what time of day you’re best at. And I always begin things at the end of the day when I’m already like nice and a well-oiled machine, well-oiled creating Machine. I never begin things in the morning. I always begin. at the end of the day, I never begin paintings in the morning. I was beginning, you know, I mean, I, I’m not, I know I’m not answering your question. Your question is, compartmentalizing your time to protect it away from social media. I teach a master class and I teach a Masterclass with artists who are building their first body of work, or they, they want to build a body of work in the masterclass. I make them take an oath an Instagram oath Instagram is it’s so draining psychologically, emotionally, mentally, and the effort that you put into it that you really have to like commit and, and, and artists feel pressure to post their progress and post once a day and stuff like that. And the truth is, that algorithm, the algorithm is so fraught right now because you really only see the last 20 people that you liked more often than not. And you’re not, it it’s just, it’s not healthy. It’s not healthy for a visual artist Because you’ll be on it. You check it like a diabetic checking their insulin level. It’s just like, oh, did it get enough? Likes all that. It’s like, Ugh. So I use, later to post once a week because I don’t really want to deal with it. So I’ll do like four months at a time. But if like I have a museum show opening up on Saturday, so I have to make a post this week. And so that that’s like in my brain, oh God, I got to make a post this week. And when my book was coming out, like that’s a whole other topic about promote, you know, how to tell people and that a book is coming out. yeah. So I just kind of look at it like, you know, kind of like a creative sinkhole, [00:45:15] Nathan: Yeah. And so it [00:45:15] Kimberly: So it [00:45:15] Nathan: Makes sense to avoid it. I think we hear that advice from a lot of talented creators and it’s easy to be like, yeah. Yeah. But I can, I’m the person who can sit down and write with a moment’s notice, you know? And then you you get totally stuck on writer’s block or whatever thing, because you’re like, you actually didn’t create that space. And, like you talked about in the Ted talk of that time to like daydream and to actually be there, present with yourself and your thoughts. [00:45:42] Kimberly: Yeah, it’s true. I mean, there’s this thing in neuroscience called empathetic mirroring. Do you know about [00:45:48] Nathan: I don’t know. [00:45:49] Kimberly: It’s this, it’s like when you see somebody, for example, write on a chalkboard, the neurons in your brain, I’m not going to say this. Right? So if a neuroscientist says I’m like slightly wrong, but like, it, it, it has this effect where you feel like you’re doing it, you know, like, and it’s, that’s why people love to watch people write things. That’s why a chalkboard is an excellent device for, I actually have a chalkboard in my office because I started to. Take videos of me make with my talking points of me writing it on a chalkboard, because even though it’s considered like, you know, yesteryear technology, it actually helps people receive the information better to see it written [00:46:34] Nathan: Rather than being next [00:46:36] Kimberly: Rather than just show a PowerPoint slide. Yeah. And so this, the act of seeing it rhythm, but so if, if you think about the power of empathetic mirroring, that’s going on in your brain, when you look at something happening, think about how much it can pollute your brain. If you’re watching a stream of all these things happening in your Instagram feed or your Facebook feed, it’s like dangerous. Like you have to be protective of what is going inside your mind. It’s that they say like garbage in, garbage out, you know, [00:47:04] Nathan: I want to hear about you getting into the world of, of like teaching classes and that side of it, and then you have a book as well. There’s a lot. [00:47:12] Kimberly: Oh yes. So I have this book, [00:47:15] Nathan: There [00:47:15] Kimberly: So, you know, around a decade into, you know, being a serious painter, I started to feel bad from the fumes because painting isn’t really taught the way other things are taught. Painting is sort of like, there’s, there’s been this somewhat mystical, you know, here’s a bunch of art supplies go to the art store and then let’s see what you come up with. And then the, the, the classes tend to be more about critiques, about what you’ve done versus about, [00:47:45] Nathan: How do something. [00:47:46] Kimberly: About the, the true, true granular house, you know, the, how, like the basics, like things that you should know. And, so I started to get sick and I happened to be the arts editor at the time of the Huffington post. And I reached out to, and blogging was a very interesting, it was around 2004 or five, I think. Maybe, maybe it was a little bit later, but it was an interesting time because other people were thinking what I was thinking and I could see it in search for it. Whereas I couldn’t, I couldn’t have done that a decade earlier. And so I would reach out to leaders in the field, scientists, whatnot, to write about this topic of safety, you know, like that. And, but then when I read and I had, by the way, been consuming, Disneyland books, everything about painting, and I just saw this huge gaping hole of knowledge of how. Communicated. So I started writing this book all about painting and the book that I ended up publishing with Chronicle books is just one small piece of it because it was kind of too big. It was like James Joyce’s Ulysses, you know, it was like a tone. It was like a Magnum Opus. and it’s one of the key things that people don’t realize is that you don’t need to use solvent’s P many people believe that you need to have like an open can of turpentine or some kind of solvent to dip your brush and defend the oil paint. So it’s like super basic and most people when they go to the art store, and this is just my short, my short, skinny on the book. As most people, when they go to the art store, it would be like only buying canned or prepackaged. They don’t know what’s in it, you know, they don’t know like that you don’t need all those things. Like, but if you were like learning how to cook, you would know the difference between a garlic and a shallot and when to use canola oil or olive oil extra-virgin, you know, so I wanted to create, to start a book called the Y that was like Strunk and White’s elements of style, but for oil paintings. So that’s like the famous book that most writers use and just sort of shows you. And it’s funny, actually, it’s like a great book. So I wrote that book and that’s called the new oil painting and it’s published by Chronicle and it came out in June and it’s like staying at the top, like five books of oil painting, which is great, you know? So I’m very excited about that. But in any way, in that journey of writing the book, the book, the book deal I got was two years ago. It was like a while ago. And so Susan. Did that I thought, you know, I would be a fool to not have a class that went with the book. So to the summer of 2019, I had, I had like four solo exhibitions in a row and I thought, okay, I’m going to devote six months and I’m going to record videos and I’m going to do that. You know? So I created this class that I wish that I had, and it was way bigger than the book. It was like everything I’ve ever thought about oil painting and that’s called oil painting, fluency and flow. And, so yeah, so I launched a class, so the classes are out there [00:50:52] Nathan: Are the classes something that, you know, you’re teaching in an online course? Are you there in person or through a partnership with. [00:50:58] Kimberly: So once I, once I learned about. That you can oil paint anywhere like you, Nathan tomorrow could decide, you know what? I w I’ve got an artist in me. I want to, I want to learn how to paint and you could set it up next year, you know, like in a little side table next to your computer, and there would be no fumes, no nothing. And it’s much better for the environment it’s not made out of plastic. It’s like, you know, you could do it. So I wanted to get the word out. And, so my first class is, and so I was started teaching at major institutions. So the Anderson ranch in Colorado and the Otis where I actually took lessons, I taught there. And then, I just thought to myself, you know, this is highly inefficient because I have to like schlep over there and go there for, you know, hours at a time. And I could reach so many more people if I recorded. Instruction. And so I made these recordings, that’s a hybrid of recordings and live sessions and critiques. And I have, you know, I have about 78 students right now. They’re from all over the world and it’s like the boast enriching wonderful, fabulous thing I’ve ever done [00:52:08] Nathan: Yeah. [00:52:09] Kimberly: To being an artist, you know, [00:52:11] Nathan: And so how does that interact with the newsletter that you have? [00:52:14] Kimberly: Well, I mean, so all of my experience, just as an artist has taught me that you, your value that you bring to any situation is the people that you can tell about what you do. It’s like a tree falls in the forest. Nobody knows you’re having a show. You know, you can’t just rely on your art dealer. And the The dynamic has changed where. People don’t have one, rarely do people have one gallery that represents them. And then they’ve got a bunch of satellite galleries. So you kind of have to be a little bit more entrepreneurial as an artist. And so you need to gather an email list. And so I stopped blogging and instead I have a newsletter because I want, you know, and I I have a narrative of stories that I tell about creativity about, about like I’ll crawl deeply inside the making of a single painting of mine, or maybe another one. And I, and each email I send out, I spend a lot of time on, and it’s like a work of art by itself because it’s, again, it may be a different thing. a newsletter may be slightly different than a blog, but it’s still words and image and it’s just how. It’s like another work of art, it’s another work of art. And I love, using ConvertKit. I mean, I really, really do I tell people about it. I tell people about it all the time, because I think it’s, it’s the first software I’ve encountered that, allows you to very easily create a sequence. And, you know, you can I tell people, I say like, if you want to think about it, you could unspool Tolstoy’s war and peace. If you wanted, like you could, every week you could give like a little section and you can start at the beginning and it takes the pressure off needing to constantly have every email be a first impression. So you can really get, let people to get, to know you in a much deeper, more personal way, because you create a sequence of letters to them that [00:54:23] Nathan: Right [00:54:24] Kimberly: Over time. [00:54:24] Nathan: Well, I think that’s a really important point about starting at the beginning, because when you’re sending these one-off emails to your newsletter, you don’t know where people are joining. Some people for years and other people that is the very first thing. And so every time I find myself adding these caveats are like, Hey, if you’re new here, you know, any of those things and with a, an email sequence, you know, the automated series, it starts at the beginning every time and it works people through it. And so I’ve had that. I’ve had so much fun creating those because you can chip away at them. Like I have one that I’m kind of writing now on, I guess it’s on personal finance, you know? And it’s just things that I wish that I had known as like, Moderately successful creator. Like, Hey, you’re now earning a full-time living, what what’s next? And so I can just write about that when I feel like it and add to this, that’s now like 10 or 12 emails long. [00:55:20] Kimberly: And what’s your frequent. [00:55:22] Nathan: That one I said to every week, but if I don’t write for it, everyone just kind of pulls up at the end and weights, you know, for the next email. So it’s 10 emails And then I add to it. And so like last week I didn’t add a new one. And so now there’s like a hundred people that are all the way at the end and they didn’t get an email last week, [00:55:41] Kimberly: Yeah, no, I have that situation. I have a two year sequence [00:55:45] Nathan: Oh, wow. [00:55:45] Kimberly: I mean, I know like I sound, I probably seem super extroverted and voluble and everything like that, but like, I, I, it’s very difficult for me to sell. It’s very, it’s very not. It’s not cool for an artist to be. So like, I mean, it’s just hard. It’s also just hard for me. It’s my personality. Like I even posting on Instagram is like a stressful thing for me. It’s like, did I get everything that, you know, like I just, it’s just not, I’m not one of those people that just casually throw stuff out there. I just, I’m very thoughtful and I want it, you know, it to be meaningful. And, but anyway, I was having trouble announcing that a workshop was over. Like serious trouble. Like I would put it off and I’d say, I can’t do it. I can’t press the send button. Like I just, even though you have the schedule feature on the broadcast, I was like, I can’t do it. I can’t do it. And you know, I, I can’t remember the name of the marketing guru who was, have the five day sequence or, you know, basically a launch sequence is a series of emails where you first email is all about it. The second email might address one’s reservations about it. The third Emile email might be testimonials. And then the fourth and fifth email are like last chance to get it. Like that to me is like, I would rather have needle eyes surgery than do that, you know, so I built it in, so I basically have the sequence where every quarter there’s a launch sequence. Is that crazy [00:57:13] Nathan: No, it’s fantastic [00:57:14] Kimberly: Because then, so, so that way, like I can just set it and forget it, like back to the Crock-Pot thinking like, you know, like, you know, just set it and forget it. You’re going to sign up. You’re going to get an announcement for a walk shop, a workshop a couple months after you’ve gotten to know me. [00:57:30] Nathan: Do you think that, well actually I guess really quick, the thing that I love about that is you can be completely immersed in your painting, right? And there you are selling a workshop and you’re like, you don’t, you have to think about it or know about it. Cause you did that work once and now you’ve finished a whole day of, of painting. Start something new at the end of the day. Cause that’s the way that you roll. And then also you can say like finish up and check those sales and check that engagement. See, oh, people. [00:57:58] Kimberly: Yyeah, yeah. I mean, it’s, it’s just, it’s I think people before they’re going to buy anything, need to feel. Most people need to feel, you know, a level of comfort about what that person is about. so, you know, I haven’t touched you tube. I haven’t really, I honestly, I haven’t made, I haven’t made a huge effort because I’ve had the book coming out and I F I ha I had a big exhibition in June because, I designed a series of, excuse me. I designed, I painted a series of abstract paintings, for the cover of the book, because I wanted the cover, the book to be stellar and represent like a specified stroke, like hanging in air, like, to just convey the idea of painting and not be like a landscape, because for some crazy reason, if you, if you look up oil, painting, all the books, About oil painting are so poorly designed. It’s like, it’s strange because you would think people who are artists would care about design, but it’s like pink pallet, Tino, bold 14 point font over like a green sunset. it’s [00:59:07] Nathan: Yeah, well, design and painting are not necessarily the same thing you happen to come from a world where you have a lot of this. Even those two worlds have intertwined for you a lot over your career. So it makes sense to [00:59:18] Kimberly: Yes, but, but when, when, but if you get, but the painting books, like if you see a PA a painting book that has like a landscape on it, what if you don’t like the landscape or they all have a landscape, or it has like the, the, you know, a face that’s loosely drawn with, you know, painted with turbine, you know, Alla prima anyway. I’ve had so many exhibitions and like, I have a, I have a show coming up on Saturday and I’ve got to tell people about it. So like, I have to be, I’m already out there as an artist. So I have two different sequences and newsletters. I’ve got like a workshops for people who express interest in a workshop within the main newsletter. Like if, if, like, I’ll say like I have this one great newsletter where the subject line is, who is this gorgeous woman? And then I show a picture cause they used to paint these beautiful renditions of the faces of the Egyptian mummies inside the sarcophagus, like beyond gorgeous. Like if you looked it up, you’d say, oh my God, this most beautiful painting I’ve ever seen. And it looks a lot like Francesco Clemente, which is an artist that like paint uses the same aspect ratio. It’s like, you sort of go, oh, that’s where that guy got that idea, you know? But. I’ll talk about the pigments and that they used to, like, they used to burn mummies and then take the ashes and make a pigment called mummy brown. I know that sounds really kind of gross, but like, but, but they that’s what they did. And I I’ll say like, if this interests you, you might be interested in like a workshop. then if they say yes, then they’ll go into my workshop sequence and they’ll get notified when I open them. [01:01:00] Nathan: Are there other things that you do with email and with your newsletter [01:01:04] Kimberly: Yeah. Like I, like, I really want, I really want people to easily update their preferences. So I created a jot form like that simple select, you know, check box check if you’re no longer interested in, workshops. No problem. Let me know. And I don’t get enough work. Ominous, but hopefully, hopefully you’ll put that feature in soon. [01:01:30] Nathan: We’re actually working on building that feature now. So, [01:01:33] Kimberly: Are you kidding? When does it come out [01:01:34] Nathan: It’s one of those asking where the paintings are done. It’ll be done when it’s done. [01:01:40] Kimberly: The other thing that I do is I really think gifts are important. And I think the marketer, the marketing community is really cheesy about it. Like they always do like outtakes from friends for reaction shots. And it’s just so horrible, but I mean, it’s just corny and you know who I’m talking about, but, you know, anyway, a gift is a beautiful thing because it’s a movie that plays automatically and it doesn’t have sound and. it can be so beautiful and subtle, you know, so every time I make a news that I usually have like an, it’s like a work of art to me, you know? And sometimes if I want to emphasize a word, I’ll paint a picture of that word and I’ll integrate it in it. So like I really spend, I really love making them special. Yeah. I have one about the creative process and about not, not the Ted talk that you saw, but like I have one that’s on the lead up to talking about the masterclass. Where it’s called the curse of perfection. And I show, I talk about how, when I was a kid, my mother used to always like, she would sometimes wear like super smudge makeup and it was psych, it was called the smoky eye. I mean, they still do it now, but now the beauty people make it super specific, but then it was not that it was a little bit more like, woo. And I found a beautiful GIF of like a smokey eye, like slowly opening and closing. And I then go off on this whole subject about how, you know, it’s as a painter, you have to let go of that, of the chains of perfection. You have to let it go in order to. [01:03:22] Nathan: Yeah. Well, I love that you’re taking a medium that you know, of email or gifts or any of these things that a lot of people use in one way. And you’re bringing those styles in that like class and sophistication and really just the level of effort. I think a lot of people are like hearing. Oh, I’m supposed to have, images or gifts. I’m supposed to be funny. And so they just look for something and slap it in there. And there’s a level of effort that’s not happening there, but because you’re doing these automated sequences and you know that if you put this effort into it, it will last and work for you for years, then it’s worth it. You can do a custom painted, you know, word or something like that to illustrate a point. [01:04:04] Kimberly: I mean, I have the luxury of having hundreds of paintings, and pieces of paintings, and video of—there’s nothing sexier and more beautiful than watching somebody mix paint. There’s literally nothing more gorgeous than that—So, I’m lucky. And I understand that other creators have to find other things, but there’s a way to do things that have like a metaphorical—I here’s what I would say. I would recommend that people seek to enhance their ability to think in metaphor when they write. So if they’re gonna talk about a subject, and they’re talking about a roadblock, instead of drawing a boulder on a road, find some other image or GIF. I use a lot of GIFs from ballet. You can find beautiful GIFs just by searching “Swan Lake” GIF, and it implies a physical movement. It goes back into that empathetic mirroring, where you feel that your own body is doing these movements that are surrounding this idea. It’s not directly about what you’re talking about, but it’s like a little bit to the left, or it’s just kind of a metaphorical version of it. It creates the space in between what you’re literally saying, and what you’re actually seeing that ignites the imagination and the view. [01:05:35] Nathan: Yeah. I love that. Just putting that extra bit of effort into defining the thing that’s adjacent, rather than blatantly the first thing that came to mind. I think that makes a huge difference. [01:05:46] Kimberly: Yeah, [01:05:46] Nathan: We need to do a part two, because I have like 25 more questions to ask you, and we’re out of time. [01:05:52] Kimberly: I’m in. I’m in. [01:05:54] Nathan: This has been amazing. Where should people go to subscribe to the newsletter? [01:05:58] Kimberly: They should go to KimberlyBrooks.com. The newsletter’s right there in the footer and on the top. I really love communicating this way, and it’s been an honor to be on this podcast, because I really love the product you’ve created. I really couldn’t do it without you—without ConvertKit. So, I just, I’m such a fan, and I’m an evangelist, so kudos to you. [01:06:19] Nathan: Wow, thank you. Well, we’re excited to host Craft and Commerce again in 2022, and we can have a reunion then. It’ll be great. [01:06:28] Kimberly: Fantastic. Thank you so much. [01:06:30] Nathan: Yeah. Thanks for coming on.0 comments0
- 052: Jay Gilbert - Newsletter Insights From an Entertainment Industry VeteranMy guest on this episode is music industry veteran, Jay Gilbert. Jay wears a lot of hats. He’s a musician, photographer, marketer, speaker, and music executive. Jay has worked as a creative consultant to many record companies and artists. He hosts The Music Biz Weekly Podcast, is a Co-founder of Label Logic, and runs the weekly music newsletter Your Morning Coffee. Label Logic helps artists, managers, and labels grow their audience and optimize their presence across all platforms. Jay’s newsletter is curated to give a weekly snapshot of the new music business. It’s everything you need to know, delivered to your inbox every Friday morning. I talk with Jay about his shift to being a content creator. We talk about life as a musician, working in the music industry, and being a photographer. We also talk about his management company, and his advice for creators wanting to build their audience. Jay also shares some behind the scenes stories, and much more. In this episode, you’ll learn: Simple hacks to grow your newsletter Defining and reaching your target audience Low-budget tricks to instantly add new subscribers Jay’s #1 metric for becoming a successful creator Links & Resources ConvertKit Ben Barnes People Jeff Moscow Travis Tritt Ali Abdaal ConvertKit’s Creator Sessions Music Connect (MRC) Chartmetric Viberate Soundcharts Pollstar Cherie Hu Amber Horsburgh Glenn Peoples Bobby Owsinski Bruce Houghton Hypebot Sound & Vision Music Technology Policy Nancy Wilson Roblox Jay Gilbert’s Links Follow Jay on Twitter Your Morning Coffee newsletter Ben Barnes 11:11 on People.com JayGilbert.net Label Logic The Music Biz Weekly Podcast Episode Transcript [00:00:00] Jay: The harder I work, the luckier I get. You make your own luck. You see these people, and you’re like, “Wow, that guy just blew up on TikTok or, Twitch, or on Spotify, or Apple Music!” Sometimes that happens. Not very often, and it usually it’s a lot of hard work. [00:00:26] Nathan: In this episode, I talk to Jay Gilbert. Jay’s a music industry veteran. He’s been at it for a very long time. What I love is that he’s also made this shift into being a content creator, as well as being a musician and a photographer. So many incredible things. He’s got this newsletter about the music industry called Your Morning Coffee, and he’s grown into over 15,000 subscribers. It’s the thing that everyone in the music industry is reading every Friday morning. We talk about how he grew that, his passion for the music industry, how the industry has shifted, what’s working, what’s not. He also runs a management company called Label Logic where they’re partnering with, artists and managers, and doing these album releases, and so much else. He’s got all these behind the scenes stories, and a lot of advice that is not only for the music industry, but also for any creator looking to build an audience, and endure long enough to get noticed, and to build a brand and everything else. It’s really good towards the end. I also sneak in some selfish questions about what would he do to grow ConvertKit; what’s his advice for ConvertKit entering the music industry. Jay, welcome to the show. [00:01:39] Jay: Hey, thanks for having me, Nathan. Good morning. [00:01:41] Nathan: Good morning. We’ll dive into some of your background, what you’re working on now, but you actually had a pretty big project launch today. What did you launch today? [00:01:54] Jay: Well, when you launch a big project, sometimes it’s like a wedding. You have all this planning, planning, planning, and then boom, there it is. It was pretty exciting this morning. We’ve had to keep quiet about this project. It’s Ben Barnes, who is a pretty famous actor, but most people don’t know he’s a brilliant singer songwriter and pianist. We’ve recorded this really great record. We’ve got some amazing videos, given his relationships in that area. They’re quite special. We launched a window of exclusivity this morning with People Magazine. So, if you go to People.com, you’ll see. the video is debuting. It’s pretty special, and we’re really excited about it. It gets released tomorrow. The song’s called 11:11, by Ben Barnes. It’s pretty cool. I think you’ll dig it. [00:02:53] Nathan: Nice. Yeah. If anyone doesn’t recognize the name, Ben Barnes, he plays Prince Caspian. I’ve been a fan of the Narnia series and all that for a long time. I think my kids actually just rewatched Prince Caspian two weeks ago. [00:03:09] Jay: Have you seen shadow and bone yet? You got to check out shadow and bone. My, my wife and I binged watched it. And he’s, he’s brilliant in that, but it’s a really cool series. [00:03:21] Nathan: Nice. Okay. So maybe with that, of like a snapshot of, of what you just launched, Let’s talk about, a little bit about, logic [00:03:32] Jay: Sure. [00:03:33] Nathan: You know, what types of projects you do. And then we can go back to like the road to get. [00:03:38] Jay: Yeah, well, Label Logic was born out of my partner, Jeff Moscow, and I working in the major label ecosystem for years and years. And we finally got to a point where we were meeting one day for coffee and said, you know, we started our own. So we both worked at universal for a long time. He was there 20 years. I was there 18 years. I worked at Warner music, for five years managing Amazon’s business for we at ADA, globally, which was fantastic. but we decided to do our own things. It’s about seven years ago, give or take, [00:04:16] Nathan: Yeah. [00:04:17] Jay: We started talking to. Some clients that we had at universal and we sort of became the label infrastructure for some management companies. One of our long-term clients and friends is doc McGee, who you might know, manages kiss. And he managed, you know, Motley, Crue and Bon Jovi and Diana Ross and the Supremes. Anyway, doc is a mentor, a friend and a client. And we came in and one of our first projects was working with him and his stable of artists. And what was exciting about that is that you’d have some artists that were new developing artists. They’re never played live before all the way to people filling up arenas. And so the release cycles would change out and it was very dynamic and very exciting. So. That’s what Label Logic is all about. We typically are sort of the label infrastructure, for managers, some artists, you know, we also work with some labels and distributors. I think one of our most exciting projects was taking and creating this thing called resilience music Alliance, with the principals there and they signed the artists. We did, you know, the marketing and digital strategy and help them get all the planes flying in formation. And w you know, we won a Grammy last year, so it was really exciting just going from zero to 60, you know, just building something with your own two hands. [00:05:46] Nathan: Yeah. So what is the, for someone who’s outside the music industry and they’re like this. Just magic. Somehow you find artists and then somehow that goes all the way through to your album releases. When he grabbed me, things like that, like, what are the specific things that, that you’re helping out on and playing in? What, what’s your role there? [00:06:06] Jay: Yeah, good question. It really is the unsexy nuts and bolts things about setting up a release, everything from securing ISRC codes to shooting the album cover to making sure the, the album is recorded and delivered on time. It’s all the creative surrounding it. You know, all of the banners and videos and press release and bio, and there’s so much of this to do. That we organize it all. And then we help, excuse me with partners. You may need a publicist. You may need somebody to work sync licensing. You may need somebody for March, right? There are all these different things that you need to do. And we basically, we like to say that we’re planners, but we’re also problem solvers because every single project is different and has different needs. We recently launched a new album by Travis Tritt. Fantastic record. His team is button. They are experienced. So we took on really more of a, more of a planning role putting together the marketing plans. But then we have some artists that have never released music before. So it’s a little more handholding, you know, all those certain things, because it’s not about gaming the system today. It’s really more about optimization. People always come to us and they say, well, I got to get on this plane. or I want my YouTube numbers to be up and we have t-shirts printed that say a playlist is not a marketing plan, right. Because our playlist important. Sure. They are, but that’s down the road. There’s so much to do before that. And really when I talk about optimization, when it comes to YouTube or DSPs like Spotify, apple music, Pandora, Deezer, it’s not about gaming the system. It’s about optimum. Right. And when you do that optimization, whether it’s with your website, DSPs, press, any of that good things typically happen. [00:08:02] Nathan: What’s an example of some of that optimization that, works rather than, you know, maybe what people are latching onto is is a magic bullet. [00:08:12] Jay: Yeah, couple of obvious ones. Let’s take YouTube and Spotify, Spotify, because you can do more with Spotify than any other DSP. As far as you can change out your image, your banner image, your, your avatar, your artist image. You can add, I think 140 images. to your profile, you can put your social links, you can put your bio, there’s, all these things that you can do that you can’t do. Other places, not all of them. [00:08:38] Nathan: Yeah. [00:08:38] Jay: So, you know, you’d be surprised how many times we’ll go look at somebody’s Spotify profile and it’s an old image and there’s somebody in the photo that’s not even in the band anymore, or it’s just, it’s just dated. And you look at the bio and it’s, it’s dated one of the first places we look, is someone’s Spotify profile. Is it updated? YouTube is a really great example. Optimizing for YouTube is so easy and yet a lot of artists miss it. YouTube is not just a place to go drop your music. YouTube is something that, you know, through their community, through your, your artist page. So many things that you can do with that, the common mistakes we see is an obvious one. You know, the name of the videos should be artists titled. Artists title version, and they’re mixed up and they’re all over the place you want to optimize for that search, right? You want to, for example, the thumbnail, sometimes you go in and look at people’s videos and there’s literally a picture of somebody blinking is the cover of the video. [00:09:44] Nathan: Right. Cause this is what will, what YouTube selected randomly. [00:09:47] Jay: Yeah. And, and as you know, you can, they’ll give you like three or four choices and you can pick one of those, but you can upload any image you want to be on though. And so we have actually a deck that we put together on YouTube and we show these examples of like, here’s Lizzo and look at this. It’s perfect. It’s a beautiful photo of her. And it’s, and then you look at the description, you know, is there a smart URL in there? You know, so. I don’t recommend people put Spotify, apple, Pandora, Deezer, Amazon music, just put a smart URL in there. Have somebody click on that and then they can choose the platform, whether it was. Downloads, probably not physical, digital, YouTube website, all of that stuff. It’s so easy to do. And then also in that description, anything that somebody might care about, who, who shot it, who produced it? Show me the lyrics, you know, give me put all that information in there. So it’s, it’s searchable. there that’s, those are a couple of simple examples of optimization. [00:10:44] Nathan: Yeah. You know, it’s interesting. one of the earlier guests that have the show, his name’s Ali doll, and he’s a YouTuber and he’s got 2 million subscribers who’s channel and he’s just built this incredible, business. And I always think about YouTube as like him optimizing, you know, video like thumbnails and all of those details. Like obviously Lizzo is doing the same thing or really her team is doing that. Right. But it’s, it’s the exact same. game just in two different industries. [00:11:13] Jay: Yeah, it is. And another way to optimize YouTube, for example, and you can watch what you know, Justin Bieber’s doing, and you can learn a lot from those things. one of my favorite writers and marketers is Amber Horsburgh and she did kind of a breakdown of. Some of these marketing campaigns, including Justin Bieber. And one of the things that you see is something we stress all the time. YouTube optimization. You don’t just post your concept video or whatever your music video, you still have like five videos, six videos, meaning, you know, you want to have that concept video, but you also may want to lyric video. You may want a stripped down video. You may want a live video, right? there’s so many like a pseudo video. It goes by a bunch of different names, but I know you’ve seen these where it’s just the album art. And the audio bed. And sometimes people look at those and go, well, why that’s not a video? Why is that on YouTube? Well, that’s because YouTube is the number one destination to listen to music. It’s not Spotify. Right? It’s, it’s YouTube people create playlists from those, you know? so it’s really important to. Optimized for all of these platforms. And that, that means socials, you know, Facebook, Twitter, Instagram, YouTube, as well as the DSPs, as well as all of these. And again, it’s not gaming the system. The problem we run into sometimes is people will come to us and they’ll say, oh, well, you know, I, I bought these spins or I bought these lights. Well, now you’re in trouble because number one, you can get pulled off of Spotify, right? in January 750,000 tracks were pulled off of Spotify for using bots and spin farms. Right. So [00:13:05] Nathan: Quickly, [00:13:06] Jay: Very careful [00:13:07] Nathan: Someone spinning up a whole bunch of computers and bots to go listen to the song on Spotify to be like, look, I now have a million plays. [00:13:17] Jay: Right? [00:13:18] Nathan: Um [00:13:18] Jay: Yeah. But they’re not real, right. [00:13:20] Nathan: Yeah. Okay. I I’ve definitely seen that on Instagram, Twitter. But like, yeah, it makes sense that, that it exists on [00:13:28] Jay: Yeah [00:13:29] Nathan: First thing that you look at when, when I, like, when we’re looking to book an artist for a creator sessions or, or some, one of our other projects, you know, you’re, you’re, it’s that first source of credibility of like, oh, wow. That has two to 2 million plays this. Person’s getting a lot of traction. [00:13:44] Jay: But what we look at instead of looking at those numbers, we look at engagement and when you look at engagement, sometimes you see the audience grow and that’s going up, up, up. But if you don’t see the engagement growing along with it, Then you know, that those aren’t real people, because when you use bots and spin farms to Jack up these numbers, yes, it’s dangerous because it can get you in trouble, but it screws with all of your, data, which is so important, right? The, what you really want. is Engagement. You want people to like, yeah, you want people to follow, but you want people to listen, share comment. That’s real engagement, man. You get that. Uh that’s that’s the prize. [00:14:29] Nathan: Yeah. So let’s go back. as you’re getting into music, what, like, in the, in the early days, what was the hook for you? What, what brought you to the whole industry? [00:14:39] Jay: Oh, my gosh. Well, my, my family’s musical, you know, my brother, you know, he’s a Writer record producer, graphic design artists. my mom played piano. My grandfather played sax and big band. You know, I started a little high school band and ended up, you know, touring in bands and playing, writing, recording. So I kind of got to know how the sausage was made and, and I loved working in record stores. I worked for an indie record store. I worked for tower records for five years. There’s so much fun. Um and [00:15:08] Nathan: Been in the industry. [00:15:09] Jay: Yeah, I’ve always been in music and, working at universal was just such a joy. learned so much. yeah, I’ve always been surrounded by, by music ever since I was little kid. [00:15:21] Nathan: What’s something as a, [00:15:24] Jay: Oh [00:15:25] Nathan: If you’re talking to an outsider, maybe a common misconception they have, know, someone who’s a fan of music then you’re like, oh, this is actually how it works that you find yourself explaining or, [00:15:37] Jay: Oh, my gosh, we could talk for days. [00:15:39] Nathan: Yeah. [00:15:40] Jay: I wish people understood that the harder I work, the luckier, I get, you make your own luck. You know, you see these people and you’re like, wow, that guy just blew up on TikTok or, you know, Twitch or on Spotify or apple music. Sometimes that happens not very often. And it usually it’s a lot of hard work, you know? I asked an ANR person before the. You know, how do you choose who you signed to your label today with all of this data? And he said the same way. I always do. I look for that line up around the block for people to see him play, right? So it’s, it’s a new music business and we can now see with all this data what’s going on. But I think the common misconception is there’s a similar. There isn’t a silver bullet, you know, it’s, it’s a lot of hard work and it’s a lot of finding your tribe. And I say that a lot because you need to find your audience. I talk to people all the time about finding that audience and they think they know who their audience is. If you talk to any manager, artists, they, they they’ll have a sense. Like, well, my demo, my artists or my, my fan base, I mean is 25 year old. But there are three audiences, right? There’s one sales streams and downloads. So the commerce side to the butts in the seats. So when you’re touring, who’s actually out in the crowd, right. And then three, you know, kind of the social side of it. Facebook, Twitter, Instagram, those three audiences, rarely aligned completely. And there’s always something to learn. I was talking to an artist recently who thought that. Their crowd was 25 year old, females, because that’s who they saw in the crowd. But if you look at the other data, that’s not who’s quote unquote consuming their music. So there are a lot of misconceptions, but, I heard this really great line about data and analytics. It’s like a lamppost. You can use it to aluminate or you can use it to lean on. And most people use it to lean on, like, see, I told you that’s, that’s what I thought my data is. But really, if you go in and look at all this, analytics, you’ll find that there’s always something you can learn in there about your audience and how to reach your audience. [00:17:57] Nathan: I like that because I catch myself doing that of like, Let me go dig for the data that proves the point that I already my existing worldview and that they were having that debate. Yeah. See, this is what proves it. And you can go back and, and [00:18:14] Jay: Right [00:18:15] Nathan: The data say almost whatever you want. If you come at it with that [00:18:18] Jay: Yeah, absolutely. And today there’s so many great places to find data like real great data. Like for example, you know, it used to be called SoundScan right now. It’s called MRC connect. Same thing. You can get real numbers for sales, streams, and downloads. That is so helpful. And you can see data from previous releases and kind of get a sense of that. There are these great platforms like chart, metric and vibrate and sound charts, where you can go in and see what playlist was I added to which ones, where I dropped off of what position was I in? How many times was it skipped? You know, there’s so many great data platforms out there, but it’s almost like there’s too much, you know, you need to kind of focus on what, what do you want to do? You know, some people want to route a tour, So that’s really easy. You can kind of see what markets you’re over-performing in. You can download data from Pollstar and see if you played in those markets before, you know, how did you perform? So we’re really big on data, but you kind of have to look at it carefully and decide what you’re trying to learn from it. If that makes sense. [00:19:30] Nathan: How do you think about the intersection, between the different platforms? Like, if you’re actually say we’re promoting it to her or, a new album release or something like that, what are you recommending as far as where artists build, you know, build their audience. and then, yeah. How do you think about the intersection when it actually comes time to drive? [00:19:49] Jay: Yeah. And that’s, that’s a great question because it’s so different for every artist in every release, right? So you kind of have to look where, where is my. You know, they may, maybe they’re still buying physical. Maybe you’re a jazz artist and that’s a, still a, an album format. So you want to look at Amazon. You want to look at places, indie retail, where people are buying the full album and they want to experience that way. then you look at maybe EDM or country, every kind of genre and mood has its own nuances. I think it’s really important to find out who your audience is, what their behaviors are. And then a real simple thing is when it comes to social media, so many artists today, they have so many choices and it’s not just writing and recording and touring. Now they got a post on socials and create videos and comment. I mean, it’s so much, so what we tell people is take a step back. What are you killing? Yeah, right. And a lot of them it’s Instagram, right? Some of them it’s TikTok focus on that. You don’t have to be all things to all people, you know, find out where that crowd is, where your audience is and really work that, and then kind of grow it from there. And hopefully you’ll get to a point, like we were talking about Lizzo, where you have a team surrounding you that can attack all those different platforms. [00:21:16] Nathan: Yeah, think there’s a tendency. I see this in founders and entrepreneurs and marketers, like all across the board. I’ve, we’re so used to failing at things like trying things and failing. They like tried this didn’t work and in order to continue to be a founder or a marketer and you have to try the next thing tried that didn’t work tried that didn’t work, this, it worked. [00:21:38] Jay: Yeah [00:21:39] Nathan: So then I tried this and it didn’t work and this, and it didn’t work. And you’re like, hold on. But what about the thing that did work and, you know, we move on so quickly and we see like every case study of [00:21:49] Jay: Yeah. And it’s so different per artists. So the thing that you just described as spot on, but let’s say we did that for Ben Barnes. Well, our next artist, we got to start from scratch because the things that worked for Ben probably aren’t going to work for Travis Tritt. There they’re totally different animals. So I love trying things. I love trying new platforms and, you know, there are a handful of things that really work across everything. And so you kind of start with those in your marketing plan, like. Tools is bands in town. Now everybody knows bands in town. It’s got like 55 million people have this app on their phone and it says, Hey, Nathan, you know, the accidentals are coming to your town in a couple of weeks and you’re like, oh cool. And then you can buy your ticket and stuff. They look at your music library, but what a lot of people don’t know is that you can go in there and look at how many people are attracting. Right. And usually it’s thousands. You know, you look at these artists, they don’t even know they have thousands of trackers and bands in town. Well, you can reach out to them for free and say, Hey, I’ve got a new release coming out. or I’m going to be in a, there’s a tour and I’m going to be in your area. But what’s really exciting about bands in town is that I can look at like competitive artists fan bases. So if I know that my artists. You know, then maybe there, they would appeal to the Chainsmokers crowd. I, for 5 cents an email, I can target them and say, Hey, you guys dig the chain smokers. You, you might dig this too. So there are a lot of little platforms like that, like you were talking about, which is so important. You got to try. All the time. And you know, as Paul Stanley said, the road to success, isn’t from here to success. It’s failure, failure, failure, failure, success. [00:23:37] Nathan: Yeah, for sure. Are there any trends going on in the music industry now that concern you things where like, as, as you’ve watched it develop, you’re like, I’m not sure where this is headed and I’m not sure that it’s going to be good for the artists. Good for the fans and any of those things. [00:23:51] Jay: Not a lot. I think it’s, it’s changed while we’ve been having this conversation. The music business is evolving so quickly and you know, I do a weekly podcast and newsletter for the music industry and we break down the stories every week and it’s so fascinating to me. How quickly it’s evolving. And, you know, for example, you see companies like hypnosis and primary wave and BMG buying up all of these rights. And you’re wondering like, well, they’re paying these huge multiples what’s going on here. And some of these heritage artists are getting hundreds of millions of dollars. And then in the last couple of weeks, you’ve really seen these stories about interpolation. Coming out, meaning that instead of using a sample, they’re just using the melody of a Olivia Newton, John or Taylor swift song in a new song. And it, no one’s getting sued because they’re crediting the writers and they’re paying the publishing and you may find two or three interpolations in one song. Olivia Rodriguez recently, there’s so many. Of these things that are evolving so quickly, TikTok, it just blows my mind sometimes how fast you can gain an audience there, but it’s one of the hardest platforms to gain real engagement. So you can gain those numbers, but how do you hold onto them? It reminds me of some of these artists that are on these talent shows, you know, American idol, the voice America’s got talent, whatever you got to grab that audience. Once they’re off that show, you have to engage them quickly or it’s gone. cause you’ll have huge numbers from being on those shows. But if you don’t engage with that crowd and keep them interested in, you’ll still have those big numbers of YouTube subscribers and followers. But the engagement just drops right off the cliff. So as far as the trends that concern me, I think the biggest thing we touched on, you know, people who try to buy likes, follows spins. I just, I think that’s horrible and it’s so dangerous for their career. we always tell people. We manage 20 careers. you’re, you’re managing one yours. You need to take that really seriously. And, we, we advise against trying to game the system. I have a friend of mine who’s really big in SEO search engine optimization and, he’s very good at it. And he always tells me. These people come to me and they’ve messed with their website, for example, to get it to come up in search. And he laughs and he says, look, Google’s got, Google has like 200 highly trained engineers working on this stuff. And you think you’re going to trick them with your little, you know, metadata trick, you know, maybe for 10 minutes, but it’s always best to have a plan, have a marketing plan. Optimize for everything. you do that and avoid some of these pitfalls. Yeah. Those are the things that concerned me. It’s just people trying to, find a shortcut. [00:26:58] Nathan: Yeah, that makes sense. you dropped a bunch of things in there that I, I want to talk about and dive into, but maybe starting with the music back catalogs that are being purchased, those rights, I’m always super curious about things like that, because. You know, as a creator, you’re working on things that feel like they’re in the moment. And I have a few friends who are successful authors who are pretty prolific, like they’ll write a book year, a book every other year. one friend said like, basically like putting out annuities where you have this, this thing and add you as you add to your catalog. It just. Let’s say this book is going to sell $50,000 worth copies its long tail every year. Like clockwork, time you come out with a new one, it adds that there’s another 50,000 a year, plus it gives it a little bump. And so you see creators who are these big spikes, and then that’s kind of it. You also see creators who are continually adding to the back. [00:27:54] Jay: Yeah. [00:27:55] Nathan: Like explain more for anyone who doesn’t understand on the music side, why these catalogs are so valuable and why, you know, people are paying [00:28:04] Jay: Yeah. [00:28:04] Nathan: Of millions, hundreds of [00:28:05] Jay: Yeah Well, it’s just math at this point. What’s happened is with streaming. Now there’s some predictable. There’s some planning involved. So if you have a catalog, you know, you look at like Stevie Nicks sold hers, or at least a big portion of it. And Bob Dylan, there’s a predictability now that there wasn’t before on how much revenue that’s going to generate on, on two sides, one the publishing, right? For the, for the songwriters and then the master, you know, so with that predictability comes, some of them are just banging. You know, they come in there and they say, okay, this catalog is worth this much money. And this is how much it makes over a year. Let’s say it makes a hundred thousand dollars a year. Well, we’re going to pay you for 10 years or 20 years worth and cut you a check right now. So we call those multiples and some of these companies are paying super high multiples and almost jacking up the price. It’s kind of a land grab in some respects. So. It really doesn’t help a new developing artist a lot right now. But if you’ve co-written songs with people and you’ve got music out there, There, there is money to be had there. If you want that big payoff, some people are selling off their publishing. Some people are selling it off for a term. Some people are selling their masters off and it makes sense for somebody let’s say Stevie Nicks, cause she’s in her seventies. Now it’s a state planning and she can, you know, get all of that money and help her family and whatever. So I’m not necessarily against. At all. but what I really love is watching how these companies are now going to exploit that catalog. And I mean that in the best possible way, exploited, how are they going to generate the right revenue? And that interpolations that I talked about a minute ago. That is one way, you know, there was a story last week, and they talked about primary wave having, you know, these writer’s camp. And using their top 40 or 50 tracks that they have the rights to, and having these writers write songs surrounding those melodies. And again, those writers will be credited those writers and the publishers and all of that, but that’s kind of the new trend too. So yeah [00:30:35] Nathan: Yeah that’s fascinating. it’ll be interesting to see how it keeps developing Another thing that you talked about a little bit is, uh your newsletter, which I want to get into, what, like so many people consume content, what was the thing that made you switch and say Hey, I want to be to be one of the, people on the creator side, commenting on the industry and building an audience [00:30:58] Jay: Yeah [00:30:58] Nathan: That’s like, it feels like you’ve been more of a behind the scenes guy for a long time. And now there’s a little bit of at least you’re going to be a front of house for all the behind the scenes people. [00:31:11] Jay: Yeah, no, that’s, that’s a good point. I think what happened was I had left Warner music group and I was deciding do I want to start my own company. Do I want to go back working for a major? And I got this email from Sean Rakowski who used to be the head of sales for ADA. And all it was was about a dozen of. These songs and albums that he had found that were really good. And he was sharing it with a hundred people. So I called him up and I said, this is cool, but you know, why are you doing this? And he said, well, I’m kind of between jobs. I don’t know where I’m going to go right now. And I just don’t want people to forget me and the light bulb went on and I went, I’m going to do that. So I did something you’re not supposed to do. And that is, I created an email and just basically sent it to a couple hundred people in my. my contacts, you’re typically supposed to ask for permission, but I just decided, you know what, I’m just going to do this and what do I love Well I love music and technology. So I’ll just do a recap, every week and what I knew at the time. was that People don’t like to read. I love reading stories on technology and music, but not everybody does, but they want to know what’s going on. So I put an image and then just a two, to three sentence blurb. So even if you don’t read those top dozen stories in your morning coffee, you can read that little blurb and go, oh, okay. Well, this is going on. You know, here’s some changes that here’s some platforms that are coming up. This is what’s going on with the music modernization act or NFTs or whatever. And. All of a sudden. It started to grow. And that little newsletter to a couple hundred people is now over 15,000 people and we have advertisers and now we have a weekly podcast, we’ve been doing for a year where we break down the stories. So I didn’t have this grand plan of, I’m going to create this newsletter for the industry. And no, I just didn’t want people to forget me while I was deciding. What my next career path was going to be, and it was a happy accident. I just stumbled into it. And then next thing you know, some of my favorite artists subscribed to it. Some of my favorite managers subscribed to it and they’ll send me notes. What do you think about this? And then. The last thing I’ll say on it is it wasn’t intended for business. It wasn’t intended for me to make money from, but what’s happened is people will read your morning coffee and then they’ll call me up and they’ll go. I think I need to hire Label Logic to be my label infrastructure for this. And so it’s brought us business, but that, wasn’t what it was intended for originally. [00:33:43] Nathan: Yeah, it’s fascinating how that worked. Cause you, you position yourself as the expert, the person with the pulse on the industry I mean, it’s not even like a deliberate thing. You don’t have to say that you just. Are the [00:33:56] Jay: Cool [00:33:57] Nathan: Sent, like sending out the content and people are like great, thanks for doing that. So I didn’t have to go compile it from different sources. And, and you find that you have your own platform. [00:34:07] Jay: Yeah [00:34:07] Nathan: Some, what are some of the things that worked as far as, growing it, maybe deliberate things that you put in, beyond the, organic growth and sharing [00:34:17] Jay: Yeah, I think that, the thing that really helped us is really like, if you’re a wedding photographer or a real estate agent, all of your business practically is word of mouth. And a lot of the growth that we have for your morning coffee comes from people just getting it, and forwarding it to their staff, you know, I’m saying, Hey, have you seen this? And that’s where we’ve seen that growth. I think the things that I did that really. helped Keeping it to those blurbs and not trying and having that image. People are very visual. I’ve seen other newsletters that are just a mountain of text. [00:34:53] Nathan: Yeah [00:34:53] Jay: Not many people are going to dig through that. So I wanted to make it. Very accessible to somebody who’s really busy at an airport. They can just look at it on their device and and get a sense of what’s going on. The other thing that, again, by accident, I started reaching out to some of these writers, like you had mentioned earlier, speaking with Sherry who, I reached out to Sherry, you know, I’ve had her on the podcast, we’ve had conversations. I have a great deal of respect for her in her writing people like, You know, Amber horsepower. I mentioned, Glen peoples, Bobby O Sinskey, you know, Bruce Hoten over at Hypebot. After a while I started developing these conversations in relationships and I would be on their Podcast. They would be on mine. I would write articles for Hypebot Hypebot would promote your morning coffee of the newsletter, a very symbiotic kind of relationship with all of these writers. And the level of debate and the level of communication has just enriched my life. Having these conversations with people, you know, like Amber and Glen peoples and saying, well, what do you think of this? I dunno, what do you think of this? You know, for example, I, I met this really smart young marketer, Maddie Elise, who runs her own company and she was doing some really great analysis on bots and spin farms. Like how can you tell if you’ve been bonded and we got into these conversations and she posted some really great articles online. I put them in your morning coffee. It’s been a wild ride, but it’s, it was unexpected that I would have these conversations. [00:36:36] Nathan: Well, It’s amazing how Yeah. Like in any industry, Like working in sales, the music industry has all connections and relationships. [00:36:45] Jay: Yes [00:36:46] Nathan: Could spend forever people one on one Hey I’m I’m coming to your city I’m in LA I’m in Nashville I’m in Atlanta Like now we’re in a you know like trying to get one connection into the next and coffee and everything else to try to build up that now. Or you can kind of take take a step back and say, all just going to start a newsletter and then get like, thousands and then people that follow it. And then [00:37:10] Jay: Yeah [00:37:11] Nathan: You would like really slowly be like working up relationships to get to the point that you’ve talked to is like oh, Hey, I wrote this thing. Would you mind throwing it in the newsletter And like, [00:37:22] Jay: Yeah [00:37:23] Nathan: Also come on on my podcast, let’s chat. And it’s just this shortcut to relationships and amazing. [00:37:27] Jay: Yes, absolutely. And I’m a big fan of networking, music business association conference, one of the best on the planet. You know, you go there. The, the great meetings are the ones, while you’re waiting in line at Starbucks, you know, you meet all of these people. And it’s then like at the last music business association conference, I was standing in line talking to some publicists. Well, publicists are so great because they’re on the pulse of everything. There are people like, you know, over at shore fire or the great team at rock paper, scissors who matches technology and music in their publicity campaign. And now they’re sending things to me. Hey, have you heard about this new platform? Hey, you might want to interview this person because they’ve got this new thing. And so it, it becomes this thing, but you had mentioned like sitting down and having coffee with people. That’s what I did with Amber Horsburgh I’ve. I read some of her deep cuts, things that she has online. She has done marketing at a high level. My partner, Jeff and I have done marketing at a high level. We called her up, met at the one-on-one coffee shop and just had an amazing. Chat, as you know, when you sit down with somebody who’s enthusiastic about the same things you are, whether it’s music, sports, whatever, you can talk all day. Right. And I love meeting these people and that’s kind of how, like the, your morning coffee Podcast. My, my cohost is Mike Etchart, who did sound envisioned radio. He and I can sit and talk for hours about. This, these stories. So every week we do the podcast, we record it Sunday morning at nine 30 and it goes live on Mondays. We talk for a half hour to an hour before we hit record. We just sit there and, oh my gosh. Did you see that documentary on 1971? No. Hey, have you heard that new record by, you know, Ben Barnes, whatever it is. And because we have such a passion for it. And I think that comes out in the newsletter. It’s not a dry kind of thing. and the last thing I’ll say on that is the other side, these relationships I’ve developed are like with attorneys who write stories. There’s this one guy, Chris castle, who has a website called music technology policy. And I. You know, put some of his great articles in your morning coffee, cause they’re really smart ass, you know, sassy stuff and had him on the podcast. And now I’ll call him up from time to time, you know, like what do you think of this? And it’s just, this whole kind of network is it’s really. [00:40:02] Nathan: Yeah, that’s amazing. Is there a favorite moment or something like that, where, uh or opportunity that the newsletter has created for you? Like, we talked about a lot of connections and stuff like that, but one where, you know, you’re like, Oh wow, this is, this is a fantastic opportunity that wouldn’t have come. If I hadn’t built it. [00:40:20] Jay: Oh my gosh, so many of them, but I’ll tell you, at a high level, getting to speak to people that I admire respect that that’s thrilling. But one great example recently was for our one-year anniversary of the, your morning coffee Podcast. we had Nancy Wilson from heart on and did an hour long interview with her. Now I grew up in. I grew up on heart, Nancy and I shopped at the same record stores. I saw them play live many, many times, huge fan. so that was pretty cool and knowing her as well as I do her career, her music, all of that. Mike and I had an amazing, interview with her and that’s something that we just wouldn’t have had, without this via. [00:41:10] Nathan: Yeah, that, that kind of thing is so fun of like, almost getting to have a conversation, you know, as peers and all of that with someone that you’re like [00:41:21] Jay: Yeah. [00:41:22] Nathan: However many years ago would be freaking out Right. now [00:41:25] Jay: Right. I was in the, I was in the crowd, right. Cheering along, and now we’re having a conversation about things and that’s probably the most thrilling part of your morning coffee. The newsletter and Podcast is the level of debate. The level of people that will call me and say, I disagreed with that piece. Or I’d like to write an op ed or, you know, Th that’s pretty thrilling because look like we said, this music industry’s changed while we’ve been on this call. So if you want to keep up with it, you can follow some of these great, writers. And, you know, you mentioned Sherry who, you know her, I subscribed to her Patrion. I love the research that she does. And I’ve learned so much from that. But if you don’t want to read everything by all of these marketers, then there are. Vehicles like your morning coffee, where you get it for free every Friday, you just glance at it and get a sense of what’s going on. And then if there’s, there’s something that really interests you, you click on it and you can read deeper. [00:42:28] Nathan: Yeah. Yep. I like that. Um what are some of the things that you’re looking to do next for your morning coffee of how to, how to grow it further? What’s sort of the milestone. [00:42:37] Jay: Yeah, we’re I really want to grow it. and we’re looking at, you know, networks that we could be a part of. we’ve got advertisers now, which is nice. you know, we’re not going to get rich from it, but it’s nice that we have, and we can pick and choose, you know, who those advertisers are. We’re not going to advertise for baked beans. We have some really great digital music sponsors my goal. Two things. One, I really want to grow the audience. I’m thrilled with the growth that we’ve had. and the quality cause I use MailChimp. So I can go in there just like constant contact or any of these other great platforms. And I can see who’s who’s subscribing which ones they opening, you know, what are they clicking through? What device are they on? And I love it when people who I admire and respect are. And I want to grow that as well. So grow it, grow the quality of it and, you know, just continue to build that audience. [00:43:39] Nathan: Are there specific activities that you’re thinking of to grow it where you’re like, oh, this was working. So I’m going to do more of that, whether it’s ads or promotions or, any of those things [00:43:49] Jay: Yeah, I, it sounds pedantic, but we always say you do more of what’s working and less of what doesn’t And I know that sounds silly, but we do that with every platform. You look at YouTube or you look at your socials and go, wow, that post really over-performed, Well do more of things like that. And I’m looking at like with your morning coffee, there are certain articles that I just know are going to get high clicks. People love lists. You know, here are the seven things that Nathan thinks you should do. People love bullet point lists, but I try not to, do the cheap applause thing, I could do the whole thing full of that, but there also has to be something in there for you to eat your vegetables. There has to be a little bit of analysis. You know, the one that comes out tomorrow, there’s a breakdown of, you know, the first half of the year versus the first half of last year. Not everybody wants to dig into the data like that. So I try to make. it You know, balanced that way. the other thing I’d like to do is partner with. Other people, for example, one of the reasons I have such a high, you know, viewership is the folks over at Hypebot every week they put my newsletter and Podcast in their newsletter that goes out to a lot of people. so they’re, a great partner for us. We love, we love HighSpot, but if I can get more people, you know, you’re standing on the shoulders of giants, so to speak, I would love to have, the. Orchard Ingrooves ADA, you know, Warner music group, Group use your morning coffee and send that out to their artists, labels, and managers, that sort of thing. That would be the next step. [00:45:33] Nathan: Yeah, that. makes sense. like those partnerships end up being so big. And I’ve seen that with a lot of newsletters where they’re doing cross-promotions or they’re saying, [00:45:42] Jay: Yeah. [00:45:43] Nathan: Hey do a takeover Where, like, [00:45:47] Jay: Right. [00:45:48] Nathan: You know, Jay’s writing the entire newsletter for us this week. If you want to follow more of what he does, you know, and you need to this newsletter swap or a bunch of things. [00:45:57] Jay: Yeah, those takeovers are really important. I did one last week with symphonic distribution, I did a little Instagram takeover and immediately had, hundreds of new subscribers to the newsletter. we always tell people there’s two reasons why nobody is buying or streaming your new release. One is they’ve never heard. of you Two they’ve heard of you, but they didn’t know it was out. Those are two things that you can correct with proper marketing, touring advertising, those types of things. And it’s the same with the newsletter is I need to get it in front of people because, every week I get a note from somebody like, oh, I just discovered your podcast, or I just discovered your, newsletter. You know, and I don’t have big budgets to advertise, you know, put it in billboard magazine or, whatever. but that’s my goal. [00:46:54] Nathan: Yeah I like it. some of my favorite podcasts interviews are Witten. The host starts asking really selfish questions like [00:47:02] Jay: Okay [00:47:03] Nathan: Direct advice that they want. So I’m going to do that now. So uh ConvertKit right So we’re creating a marketing platform, email marketing platform for creators where Uh like quick context We’re 70 people on the team [00:47:19] Jay: Wow [00:47:19] Nathan: Year in revenue, in like mostly in the blogger podcast or newsletter space, but then the last year has been this push into, into music. So we’ve got a whole range of artists from Leon bridges to Tim McGraw. we bought, a platform called fan bridge, at the beginning of this year, but we’re like new to the space And so coming in. What advice would you give either to, you know, ConvertKit or to any of these, you know, I’m sure there’s plenty of other players who are, trying to come into the music industry, really serve artists, be good citizens of the community. Like what advice would you give as far as how to grow, How to get more artists on the platform and [00:48:02] Jay: That’s a great question. I think the first thing you do is you collaborate and we tell people all the time, if, when we’re taking an artist in to meet with a digital service provider or a platform you listen first and you say, How can we partner? How can we collaborate? Not what can you do for me? So some of the obvious things, right, would be, the music business association, right? Portion, her team over there are phenomenal. You have conversations with them, you sponsor their events, you get involved in their live streams and that community. Right. I think that’s, that’s kind of where you start, as you become. A partner, you know, you collaborate, people who, all these people that you mentioned that have these great, you know, newsletters, whether it’s, you know, Sherry who, or Amber Horsburgh or, you know, Bobby, Osinski, all of these things. You, you reach out to them as you’re doing you partner with them, you see, like, how can we collaborate together? How can we work together? How can I help you to grow your audience? And once you become. Part of that network, part of that community. Let me back up. my old boss used to tell me, everybody wants to give you advice. Nobody wants to give you a job. So when you go to somebody, don’t ask them for something, right? And this isn’t directed at you. This is at the larger audience. Don’t go in and say, Hey, I need this. Can you do this? For me? People are busy, right? They’ve got a thousand emails that they’re, they need to respond to. But if you ask somebody for their advice, they’re like, well, hold on a second. What was that? You need my advice. I’ll give you my advice. I found, and I speak at colleges all the time and I mentor and I have interns. And one of the things I tell college students all the time is find someone who’s doing what you want to do. Whether it’s be an engineer, producer, tour, agent, whatever, find the people that are doing it, reach out to them and say, Hey Nathan, I’m a college student. Can I just get 15 minutes of your time? Chat. I need your guidance. I need your advice on something nine times out of 10, they’ll say. Sure, absolutely. And that’s at your fingertips right now. And as a company and as a platform, you need to let this community know what problems of theirs are you going to. You know, not your capabilities, not like the business speak while we’re a full service platform that, you know, these KPIs and blah, blah, blah. No, it’s gotta be, we’re going to help you grow your audience by doing this, we’re gonna help you, spend less money on your marketing and advertising by doing this, we’re going to help you put more butts in the seats by doing this. If you can solve their problems and communicate that. quickly and easily, that’s a challenge. but joining all of these, like, like music business association, You know, and going to these panels, like at music tectonics and some of those, that’s where those people live and breathe. And, and let me just tie it up in a bow by saying that one of the things we did over the pandemic was we formed this artist management collective and there’s, I don’t know, give or take 25 managers and on any given zoom call, we’ll have probably half of that. We, we talk about what, what publicist are you using now? What video editor are using now, you know, do you use it? Who, who should I call for a tour agent for Americana, you know, and we, we help each other, but we also will bring somebody on from TikTok or bring somebody on from roadblocks and tell us about your platform. You know, w how can you help these artists managers? So that’s a long-winded way of saying there’s no silver bullet, but. Those relationships, those, those conversations, then that word of mouth will spread and that’ll help you build your platform. [00:52:06] Nathan: Yeah Well, I mean, it’s exactly what we’ve been talking about of relationships in the community That’s what all of this comes down to and and you know podcasts are especially big for that right Because we have to have conversations like this, and that’s what you’ve seen on, on your Podcast. [00:52:24] Jay: Yeah [00:52:24] Nathan: Makes me wonder, do you think If you’re talking to a newsletter creator? Who doesn’t have a Podcast. What’s the, message that you would say to them of, you know, you’re like, Yeah. the Podcast has been good because of these things. Or are you like, what are you doing? Like start [00:52:43] Jay: Yeah [00:52:44] Nathan: Newsletter, go hand in hand. He got us started both. What, what do you think? [00:52:47] Jay: It depends. I think here’s the thing. I was reading this article the other day, that the average Podcast, this is average, right? There’s 850,000 podcasts out there, but the average one is seven episodes long. That’s it. And reaches about 175. people That’s an average thing. I mean, yeah. You’ve got the New York times daily that has a staff of 75 people and it’s crazy. And then you’ve got the Joe Rogans of the world that have these huge audiences, but that’s the outlier. That’s an anomaly. So I tell people are you really in this? Do you really want to do this? And do you enjoy doing it? So I do, two to three podcasts. every week And I love it. I absolutely love the conversations. It’s something. I have a passion for most of the newsletters that I read. There is a Podcast, you know, Sherry who has a podcast, Amber Horsburgh has a podcast. Mike Warner, has a great podcast. Then you look at how often do you want to do it? You know, like your morning coffee is every single week music biz, weekly that I co-host is every single week. You may not have the time to do that. So maybe you do one every two weeks or one every month. I’m a big fan of podcasts. I think that people go for walks, they exercise, they travel, they commute. They do a lot of things where they couldn’t necessarily read a newsletter. And this is kind of, you’re reading the newsletter to them. So it’s so easy to get syndicated. But the only thing I would suggest for somebody who’s going to start that is stand on the shoulders of giants with us. We partnered with Hypebot So immediately out of the gate, we’ve got an audience. We didn’t have to start from zero So if you can partner with a brand or partner with another outlet to grow your audience, that’s the way to go. [00:54:44] Nathan: Yeah. Yep. I like that. Some of that you said to kind of touched on the idea of longevity, you know, of the average Podcast being seven episodes long. sad, but not surprising, like [00:54:56] Jay: Yeah, [00:54:57] Nathan: What’s your message to, creators about longevity. And it’s both the artists you’re working with, you’re giving advice to those college students who hit you up for the 15 minutes of advice all the way through to those building an audience online, in a newsletter type environment [00:55:14] Jay: Yeah. That’s a great question. I think the bottom line is you need to find what lights you. up And I tell, not just college students, but I tell professionals this all the time. What is that thing that you wake up in the morning and you just can’t wait to do, and you’d do it for free. If you could, is it photography? Is it, it engineering or being a, you know, a manager, whatever it is. There’s some There’re things that are Personal to you that you love to do. And I always tell people, you have to do more of that. The money will come, but you have to add value first and then the money comes. You don’t go looking for the money. That’s a common mistake. A lot of people make, I I started your morning coffee without any expectation of any business, money, ads, anything, and it’s just been a joy. And I look forward to doing. it Every single week, I’ve got it, like 90% ready to go. Cause it goes out at 4:00 AM on Friday. So tomorrow, I’ll be up with my coffee and I’ll hit that. Send button to those lists. that’s not work to me. That’s I can’t wait to do that. And then Sunday morning, Mike Etchart and I are going to record the podcast. I can’t wait to do that. So if you can find something in your jobI love coaching. I love teaching. I love working with developing artists and showing them what’s worked in the past what hasn’t workedand to your point earlier, trying a lot of different things See, see what’s working. and What’s not, you know, I think that’s key because so many people are chasing the dollars and they’re miserable. You know, find what lights you up. [00:56:53] Nathan: Yeah, cause chasing the dollars, especially cause they tend to take a long time to come. Any creative business is slow going. So, if you’re looking at the dollars as the metric that’s going to keep you going, then you are going to end up giving up after the seven episodes. [00:57:12] Jay: Yeah. [00:57:13] Nathan: Something in that [00:57:15] Jay: Yeah. [00:57:16] Nathan: I realized, we should start to wrap up, but I didn’t even ask you about photography. That’s a huge part of who you are as a creator. We don’t have time to get into it a lot, but I just love to hear how photography intersects with the rest of your creative work. [00:57:31] Jay: I’ve been shooting since I was a teenager. What happened was I went to a concert. I shot it and the images didn’t turn out well at all. And that put me on this quest of “Why don’t my photos look like the ones in the magazine?” [00:57:45] Nathan: Yeah. [00:57:46] Jay: I got my own darkroom, started reading books. Long story short, I’ve been doing photography my entire life. I have a photo studio here. I’ve shot album covers from the Temptations, and John Wayne, and Rick Springfield, and many, many others. I absolutely love it. It’s my creative outlet. I can go in on the weekends, shut the door, turn off the phone. My partner, Chris Schmidt and I, we do these shoots and we absolutely love it. It’s also intersected with the business. So, photo shoots for clients. We’ve done videos for clients. It’s a labor of love. It’s like you find what lights you up. Photography lights me up. I would do it for free if I could. I absolutely love shooting live shows. I love shooting studio shoots. If you check out JayGilbert.net, you can see some of my work over the years. You’ll see photos from shooting Van Halen in 1978, all the way to shooting stuff last week with the immediate family. So, thank you for bringing that up. I certainly have a passion for it, and I hope that your viewers and listeners know what their passion is. Even if they can’t do it for a living, continue to do it. Life is short. [00:58:59] Nathan: Yeah, I love it. Well, I had a great time going through your whole collection over the years. [00:59:06] Jay: Thank you. [00:59:07] Nathan: There’s some that are really, really fun. [00:59:10] Jay: Thank you. [00:59:11] Nathan: Listeners should definitely check that out. Where else should people go to subscribe to the newsletter? Listen to the podcast? All of that? [00:59:17] Jay: It’s the easiest URL on the planet. It’s YourMorning.coffee. You can sign up for the newsletter. It’s free. You can sign up for the podcast. It’s free. If you ever want to dig deeper into what Label Logic’s all about, it’s Label-Logic.net. It might be kind of fun just to look through there. Jeff and I have been doing this for decades, so you’ll see some of your favorite artists that we’ve done some campaigns with. [00:59:48] Nathan: Yeah that’s good. Well Jay, thanks so much. [00:59:51] Jay: Yeah, it’s my pleasure, Nathan. Thanks for having me.0 comments0
- 051: Sean McCabe - Launch a Successful Business by Starting With WritingSean McCabe is the founder and CEO of seanwes media, and Daily Content Machine. Sean is a prolific and successful creator, author, and influencer. His course, Learn Lettering, made $80,000 in the first 24 hours. For nearly a decade his podcast, blog, and courses have helped creators grow their brands, content, and skill sets. Sean’s website is a treasure trove of courses and resources for anyone looking for business knowledge and creative support. Sean’s book, Overlap, shows creators how to turn their passion into a successful business while working a full-time job. His podcast includes almost 500 episodes on content creation and entrepreneurship. His latest venture, Daily Content Machine, turns creators’ best content into clippable moments they can share across their social media accounts. I talk with Sean about what it’s like being a successful creator. We talk about growing your audience and connecting with them. We cover how to learn new skills fast, and about developing a growth mindset. We also talk about managing stress as a founder, how to handle burnout, and much more. In this episode, you’ll learn: Why good writing is the foundation of great content How to connect better with your audience Leveraging short-form content to grow your brand Pricing at full value without feeling guilty How to avoid burnout, and what to do if you’re already there Links & Resources Sean McCabe on The Nathan Barry Show episode 003 Craft + Commerce conference ConvertKit Enough Ryan Holiday James Clear Marie Forleo Ramit Sethi Sean McCabe’s Links Follow Sean on Twitter Check out Sean on Instagram Sean’s website Daily Content Machine Episode Transcript [00:00:00] Sean: If you are a founder, you should be in therapy. Full-stop. You need a therapist. I thought I didn’t. I had a great upbringing. I’m all good. Everything’s healthy. I don’t have any problems. The problem was I didn’t know the problems that I had. I didn’t realize what I was stuffing down. I didn’t realize what I was avoiding. There is so much to unpack that you don’t know you need to unpack. [00:00:30] Nathan: In this episode I talk to my friend, Sean McCabe. We’ve known each other for seven years now. It’s been a long time. We’ve been in a mastermind group together. He’s actually been on the show before. Sean is a wildly talented designer. He got his start hand-lettering. I think last time he was on the show, years ago, we were talking about that aspect of his business and how he built this substantial course business. Selling courses on hand-lettering, on marketing, on writing. He’s spoken at our conference Craft + Commerce, all kinds of things. Sean is one of the most prolific creators that I’ve ever known. It’s also super fun that he’s a friend and lives right here in town. We just have a great conversation. We talk about how you create content, which is one of those things that it’s not even how you create content, it’s why. Where that comes from. The internal drive in what you use. Where you choose to have as a source of fuel and energy to put into that creative output. How some sources are really good and productive, and others can be kind of like a house of cards, and it can be harmful. We also talk about scaling teams as a creator. How do you know when to build out a team around your business? He’s done that two different ways. So I get to ask him about some of the things he’s learned and applied differently. I’m going to stop there. There’s a lot of good stuff. So with that, let’s dive in. Sean. Welcome to the show. [00:01:59] Sean: Hey, Nathan, just saw you recently. We were playing volleyball, or something. [00:02:03] Nathan: Or something, like two days ago. You moved to my city. It’s kind of… [00:02:08] Sean: Yeah. It’s horrible. It’s a terrible place. Boise. Don’t move to Idaho. [00:02:15] Nathan: You mean Iowa? Boise, Iowa. [00:02:17] Sean: Iowa. Yeah. Don’t, yeah. Did I do okay? [00:02:21] Nathan: Yeah. That’s exactly what you’re supposed to say. If you Google something about Boise, Google has the accordion of extra questions, or things you might want to know. One of them is, “Does Boise smell?” and it’s just like auto complaints in there. And I was like, what is up with that? I clicked on it, and it’s this satirical article that has 12 reasons you shouldn’t move to Boise. One of them is the city dump is right in the middle of the city. Another one is like that the Ebola outbreak hasn’t been fully contained yet. So it’s not really safe. I think there was something about lava. Anyway, it’s just an article about all the reasons to not move to Boise. So I think you’re right in line. [00:03:08] Sean: Stay, away. That’s what they tell me to say. [00:03:11] Nathan: Yes, but if someone were to ignore that and move to Boise, they could come to our weekly volleyball game on Wednesday nights. [00:03:19] Sean: It’s casual. It’s open. [00:03:21] Nathan: Let’s try it. Yeah. It’s been so fun having you and Laci here. It’s also been fun because you started a new company. Your company is producing and editing and creating all the clips for this podcast. So, connections on so many levels. [00:03:37] Sean: Yeah. We produce this show, like the video show, the audio show, and then find clips and make those clips for social media. It’s been great. We love this show. Our team’s favorite content. So, I’m a little biased, but it’s fun to be on. Because my team’s going to work on this. [00:03:58] Nathan: Yeah, exactly. I made sure to spell your name correctly in the setup, and I know they’ll get it all. I wanted to ask what sparked—like maybe first give a summary of Daily Content Machine, since that’s what you’re spending nearly all of your time on. More than a normal amount of time on. So, what sparked it, and what is it? [00:04:19] Sean: Fun fact. This is not the first time I’ve been on the show. The last time was episode three, 2,624 days ago. [00:04:30] Nathan: Give or take [00:04:32] Sean: I was doing different stuff then. It’s been a crazy journey. Right now the newest iteration is an agency. We produce video clips. We turn long form video shows. If you have a video podcast or other kind of long form video content, we found that the hardest part is finding all the good moments in there, and turning those into short clips. That’s what we do. I designed it for myself, really. I wanted it to be where you just show up, you record, and, everything just happens? What is your experience, Nathan, with having a video and audio podcasts made, and clips and all that published? What do you, what’s your involvement. [00:05:14] Nathan: Yeah. So I think about who I want on the show, I email them and say, will you come on the show? And then I talked to them for an hour, and then I read no, either way. I don’t even do that. Yep. That’s my full involvement. And what happens is then really what I see is when the show comes out, which I don’t touch anything from that moment on. I actually probably notice the show coming out like, oh yeah, that’s the episode that we post this week. Cause we have a three week delay on our, production schedule. And so I noticed like, oh yeah, I had a David Perell on the show when I get the Twitter notification of like, David, Perell just retweeted you. And I’m like, oh, what did oh, right. Yeah. Because his episode came out and then every, I mean, David was especially generous. Right. But every clip that week seven in a row, he retweeted and posted to his, you know, hundreds of thousands of Twitter followers. Right. Cause it makes him look really good. It’s clips of him delivering these, you know, soundbites of genius, perfectly format. And he’s like great retweet share with my audience. I think that one, I picked up like hundreds of new Twitter followers, just, you know, maybe more just from, from, that. So it’s a, it’s a great experience. The side that I haven’t done as much with that I really want to. and you and I talked about this a lot when we. Like early days of Daily Content Machine and what could it be? And, and then, getting my show set up on it is the transcripts in the show notes that you all do. cause first you found the most interesting points of the show and then second there’s text versions of all of that. And then they’re all like neatly edited and, and everything. And so, [00:07:01] Sean: A lot of re-purposing options. [00:07:04] Nathan: Yeah, so like if you ask the same question or a similar question, like, Hey, how’d you grow from a thousand subscribers to 10,000. Tell me about that process. If you ask that consistently, which I’m not great about asking the same questions consistently, but then over the course of 20, 30 episodes, you have this great library of answers to that question and you could make like compile it all, write some narrative and it’s like, oh, there’s an ebook that would be 15 pages long and could be a free lead magnet or a giveaway or anything else. It’s just a total by-product of the podcast and Daily Content Machine. So I’m a huge fan. That’s my experience. [00:07:42] Sean: Well, it’s great to hear. yeah, we wanted to make it, I wanted to make it, so I just show up. I record myself doing a podcast with the camera on, and then I walk away. Like I don’t have to, the footage sinks. It goes to the team. They produce it. They made me look good. They make me sound good. They find all of the best things. I said, things my guests said, they think about my target audience. What are their struggles? What are their goals? What do they want, what do they need? How would they search for it? How would they say it themselves? And they work together to come up with good titles for them, then produce it, flawless captions, you know, do the research, how’s the guests build their name. How does their company name capitalize? Like make sure it’s, it’s all polished and then publish it everywhere. So I just show up once a week for an hour and record, and then I get to be everywhere every day. That’s that’s at least the goal. And I’m hearing you say like one of the benefits, but one of the benefits of finding clips out of your long form shows to post on social media is you give your guests something to share. And there’s kind of two, two ways of approaching podcasts. And one is kind of the old school way, you know, People used to blog and the used to subscribe to RSS feeds and like, you know, that’s how they consumed their content. And definitely you still want to build your own platform, have a website, have a blog, you know, definitely have an email newsletter on ConvertKit but now we’re, we’re posting Twitter threads. We’re posting more content natively and people are consuming more natively on the platforms. So there’s the old idea of, I have a podcast, here’s a link, go listen to my podcast, go watch my podcast, go watch my video shifting from that to, Hey, why don’t we deliver the best moments of the show? Because people are consuming short form content, and that’s how they’re evaluating whether they want to subscribe, whether they want to spend an hour listening in depth to that interview. We’re giving them all of these entrance points and just providing value natively on the platform. Instead of asking them to go off the platform and interrupt their experience, it’s here you go. Here’s some value here’s where you can get more. And, and that that’s such a great way to. Bring new listeners on as well as to give the guests something to share, because think about the experience between a guest, being told like, Hey, your episodes out, will you, will you share a link to it? And they’re like, Hey, I was on a show, go listen to the show. It’s such a great interview. You know, we, we do it. We want to help out that, that person with the podcast. But imagine if the best moments that, where you said that the smartest things with all of your filler words remove and your tangents remove was tweeted, and there’s a video right there. All you have to do is hit retweet. It’s free content for you. It looks good. But then also for you as the show host, it promotes your show and gives you a new awesome. [00:10:28] Nathan: The other thing in it, like the retweet is fantastic, but a lot of people want that as original content on their social channel. And so having like the, the deliverable that I get from you all is, is. Yeah, it just shows up in Dropbox of here’s all the videos for all the platforms and everything, you know, from my archives and all that. And I’ve sent those on to the guests when they’re like, Hey, can I post this? Not every tweet. Like I want to post it with my own, title or tweaks on that. And so I can just share that whole Dropbox folder and they’ll, they’ll go find the exact thing they want to share and, and use it in their own softens. Like, yes, absolutely. Because the pre-roll or like the, or the post roll on that video is like, go subscribe to item newsletters. It’s like, yes, please. [00:11:14] Sean: And it’s not like Nathan, that you would have trouble getting guests, but if one had trouble getting guests for their show, or you want to get someone that’s like really big, really busy, they get all kinds of requests all the time. Well, imagine if they’re evaluating between these different shows, you know what, what’s the audience size? What am I going to get out of it? You know, especially if you don’t have millions of downloads on your podcast. Well, if you’re providing these additional assets, like, Hey, we’re going to make clips of this. You’re going to get content out of this. It can help people make that decision to come onto your show as opposed to maybe another. [00:11:46] Nathan: Yeah, totally. I want to go, so somebody different directions. This is, we talked about an agency and the business that you’re starting. I have a question that I’ve kind of asked you one-on-one sometimes. And I want to know why build a business with a team and like build this X scale of business rather than go the indie creative route. Right? Because if we want to, if you wanted to say independent, no team, you could probably make a business doing $250,000 a year. Work on it, maybe 20 hours a week, something like that, you know, hanging out in the studio, you’d still have your podcast. You could sit down and like, you’re one of the most prolific writers I’ve ever met. so you could do a bunch of those, those things. And yet you keep trying to do and succeeding in doing these much harder businesses of building a team. And I have to know why. [00:12:39] Sean: Nathan, I don’t know. I don’t know why. I kind of know why, uh it’s it’s like it’s going to get deep. I mean, it, it probably really goes back to childhood and being, being the oldest of 13 kids feeling like. I don’t know if my parents are watching, but like, I felt this, this pressure to be successful, to be a good example, to be, to be a leader, you know, like to be productive. And, you know, I’m working through a lot of that stuff in therapy, like learning, like where did my motivations come from? And like, you know, it is this healthy because, you know, you know, my, my background of extreme workaholism for like 10 years, like, Nope, no joke. It was really bad. Like 16 hour days, seven days a week for 10 years, like all I did was work and like that’s, that’s my tendency. And I think something beautiful came out of that, which is this sabbaticals idea where since 2014 now I’ve taken off every seventh week as a sabbatical. So I work six weeks and I, I take off a week and we do that with our team and all of our team members. I paid them to take off sabbaticals and it’s just been beautiful. The heartbeat of the company. And like, it’s been really good for me as well in terms of, you know, burnout prevention and just unlocking my best ideas, but that’s, that’s my tendency. And, you know, th there’s, there’s all kinds of reasons. And, you know, there there’s messages that we hear that maybe were said or implicit, you know, growing up that we internalize. And so I think, honestly, Nathan it’s, it’s probably just like chasing, like, I’m going to be dead honest, like, like it’s, it’s just like, I think of your post that post that you titled about enough, you know, and, you know, thinking through it, like, like if I were to just think of a number, you know, it’s like, no, that’s not enough, you know, and I know that’s not healthy. So like, yeah, I could totally, I could totally do the solo thing. I could totally make 600. Work part-time, have less stress and maybe I should, you know, maybe I will eventually, but there’s something in me that wants to build something bigger, but at the same time, it’s just so much fun. Get it, like, I just love processes and systems and like, you know, building things that can scale. And so, yeah, it’s. [00:15:08] Nathan: Well, let’s lean into it more because I have the same thing on two different sides. Like I made the same leap from a solar creator to having a team. and there’s sometimes I miss aspects of the solo creator thing. Like there’s a level of simplicity and like, I look at somebody’s product launch or something, and it does $25,000 or $50,000. And I’m like, oh, I remember when that amount of money was substantial in that it moved the needle for the business and like, and drove real profits. Now, like 25 or $50,000 gets eaten up by that much of expenses, like immediately, you know, cause the, the machine is just so much, so much bigger. And so I have the same thing of, of pushing for more and trying to figure out what. Like, what is that balance? And, and, yeah, I guess, how do you think about the balance between gratitude and enough and drive and ambition? [00:16:08] Sean: Yeah, that is a great question. It is. It is a balance. And as someone who has a tendency towards all or nothing thinking like, I’m, I just get obsessed. Like if I’m, if I’m about something like, I’m just all in, or I don’t care at all. Like I’m really not in between. And that I think is a double-edged sword. Like it’s a reason for my success, but it’s also a reason for all of my downfalls and like, you know, going years without exercising and losing relationships and friendships, because I was so consumed by what I was building, you know, it is very much a double-edged sword. And so I think the answer is balance, you know, in what you’re saying, w what do you, what do I think about the balance? I think it is a balance. It has to be, you have to be operating from a place of enough and then have things that are pulling you forward. You know, something that you’re working towards having goals I think is healthy. You know, it’s. Something that gets you out of bed in the morning. You’re excited about what you’re doing. You have this vision for where you’re going, but it’s operating from a healthy place of, I’m not doing this to fill a void in my soul. Right? Like I’m not doing this because I believe I’m not enough because I believe I’m not worthy of something. But, but because I know, yes, I matter I’m worthy. I’m important. And I’m excited. Like, I think that’s the, I’m not saying I’m even there. I just think that’s the balance to strike [00:17:34] Nathan: Yeah. I think you’re right in this. It’s interesting of the things that you can do in your, I guess, life, maybe the creative Dr.. I think there’s a tendency of using that insecurity to drive creative success that can work really, really well for an amount of time. Like if you need to finish a book, grow your audience to a thousand subscribers, you know, like accomplish some specific goal. And he used the chip on your shoulder and the feeling of like, this person doesn’t believe in me and that like triggers those deep insecurities on one hand, it’s wildly effective and on the other, it can be super destructive and it’s such a weird balance and place to sit in. [00:18:21] Sean: Yeah, a double-edged sword, for sure. Like it can, it can be what helps you succeed? And it can be your downfall. So you have to wield it wisely. unintentional illiteration you ha you have to be careful with that because it’s so easy to just get consumed by it, to drown in it, to let this, you know, whatever it is, this, this, this drive, this motivation, the chip on the shoulder, whatever it is to let it take you to a place where you’re just like, along for the ride, you know, on a wave, going somewhere on a, on a, you know, a tube floating down the river, right. You’re just being taken somewhere, but are you being taken where you wanna go? [00:19:05] Nathan: Well, yeah. And then realizing, like, it might feel like you are up into a point, but then I guess if you’re not aware of it and you’re not in control of it, then you’ll get to the point where the thing that you were trying to succeed, that the book launch, you know, hitting $10,000 in sales or whatever else, like that’s not going to have any of the satisfaction and. [00:19:25] Sean: If I can take an opportunity here just to speak very directly to a point. If you are a founder, you should be in therapy. Full-stop like you, you need a therapist. I thought I didn’t. I was like, I had a great upbringing. I’m all good. You know, everything’s healthy. I don’t have any problems. The problem was, I didn’t know the problems that I had. I didn’t realize what I was stuffing down. I didn’t realize what I was avoiding. There’s so much stress, you know, being a founder or even any, any C level executive in a company, like there’s just so much going on, and you’re responsible for so many things it affects your personal life. It affects your relationships. It affects how you see yourself. There is so much to unpack that you don’t know, you need to unpack. And there’s probably also stuff that, you know, you need to unpack. and Maybe you don’t want to, but I went my entire life until the past year. Never going into therapy, never went to therapy. I’m like, yeah, that’s great. You know, if you have some serious problems or a really bad childhood or whatever, like yeah. That’s, you know, I support, it like positive, you know, like golf clap and I’m like, oh my gosh since I’ve been going on. I’m like I didn’t know why I was doing the things I was doing, what my reasons were, what my motivations were, the ways that it was unhealthy to me, the way that it was affecting my relationships. So I just want to encourage everyone to go to therapy. I promise it’s going to be beneficial [00:20:53] Nathan: Yeah. I cannot echo that enough. I’ve had the same experience and just having someone to talk through whatever’s going on in your life, whatever, like even just interesting observations. When someone said this, I reacted like that. And that doesn’t quite add up. Like, can we spend some time digging into that kind of, you know, and you realize that like, oh, that wasn’t, that wasn’t a normal, like healthy reaction. And it had nothing to do with what the person said or who they are or anything like that. I had to do it. This other thing, the other thing that I think is interesting about therapy is when you’re following people online, you’re partially following them for the advice and what they can do for you and all of that. But I think the most interesting creators to follow are the ones who are on a journey and they bring their audience, their fans, along that journey with them. And a lot of people are on a really shallow journey or at least what they put out online is a really shallow journey of like a, I’m trying to grow a business from X to Y I’m trying to accomplish this thing. And it’s like, Like, I’m happy for you. There’s like tips and tactics that you use along the way. And that’s moderately interesting, but I think if you’re willing to dive in on therapy and why you do, or you make the decisions that you do and what really drives things, it makes for as much deeper journey, that’s a lot more interesting to follow. And all of a sudden the person that you followed for like learning how to do Facebook ads is talking about not only that, but the sense of gratitude that they were able to find in the accomplishments that they made or how they help people in this way or other things that’s like a really authentic connection. And I think that, even though like growing a more successful business is not the goal of therapy and, and all of that. Like, it has that as a by-product. [00:22:42] Sean: It does. It definitely does. Although I’m, I definitely look at things the way that you’re saying, which is like, what is. Productive output of doing this thing. And it’s like, yeah, that’s why I need to be in therapy to understand why I apply that lens to absolutely everything. but I I’ve found it immensely helpful. I would say I would echo what you’re saying. in terms of sharing your journey, both the ups and the downs. I think that the highs of your journey are only as high as the lowest that you share, because otherwise it’s just kind of it’s, it’s flat, you know, there’s nothing to compare to like th th in the hero’s-journey-sense you know, we we’re rooting for the underdog who is going through challenges, and then we’re celebrating with them when they have the wins. If you know, if you’re not sharing the, the, the low points, it’s not as relatable. Now that doesn’t mean you have to share everything you’re going through. You don’t, you know, you can keep some things, you can keep everything personal. I’m just saying, if you have the courage to share what you’re going to find is that you’re not alone. You’re not the only person going through these things. You’re not the only person feeling these things. And sometimes the biggest failures or, or the things that, that hurt the most or the most difficult to go through when you share those, those can actually resonate the most. That can be where your, your community really steps up. And you, you feel that, more than any other time. [00:24:07] Nathan: Yeah. I think that, like I wrote this article a few years ago, titled endure long enough to get noticed, and it was just actually wrote it, it was off the cuff. I was on a plane just like needed to get something out that week. And it was an idea about serum on my head and I wrote, wrote it out, send it off. And, just the replies from it, because it took a more personal angle and it was talking about some of the struggles and a bunch of the replies were like, oh, that’s exactly what I needed in this moment. Like, I was about ready to give up on this thing, you know? And, and that was that bit of encouragement. It ends up being this thing that feeds both ways. If you’re able to take care of your audience and then if you let them, your audience can take care of you of saying like, oh, that that was really, really, meaningful. [00:24:49] Sean: Can I turn it around on you for just a second and, and ask, I, I know Nathan, you’ve been writing recently, you’re on a bit of a streak and for those. Following your journey for a long time. They know you’ve, you’ve gone on streaks for periods of time. You made an app to log those things. We’re talking about this recently. And I was just curious, what, what made you start writing again? And it may be, if you can touch on like the identity piece that you were sharing with me. [00:25:17] Nathan: Yeah. So most good things that have come in my business. Many of them, at least for a whole period of time, he came from writing. I wrote a thousand words a day for over 600 days in a row. And like, that was. Multiple books, a 20,000 subscriber audience, like just a whole bunch of things so I can work it from and everything else. And I’ve, I’ve tried to restart that habit a handful of times since then. And yeah, you were asking the other day, I’m trying to think, where are we out of the brewery? Maybe? I don’t know. [00:25:51] Sean: Yeah. Something like. [00:25:51] Nathan: Well, I’ve all something. And you’re just asking like, Hey, you’re restarting that what what’s driving that. And the thing that came to, I actually came to it in a coaching therapy conversation was like, I’m a writer. That’s who I am. You know, it’s part of my identity and yes, I’m also a, a creator and a startup founder and CEO and whatever else, but like, realizing that. I’m most at home when I’m writing, that’s not what I’m doing. Writing is my full-time thing. And like, here’s the cadence that I put out books, you know, obvious thing of like Ryan holiday, he’s super prolific, like a book or two a year, you know? I’m not a writer in that way, but I, I have things to say and, words have an impact on people in the act of writing has such an impact on me that I realized that I feel somewhat of this void if I don’t exercise that muscle and stay consistent of not just like teaching and sharing, but also taking these unformed thoughts that bounce around in my head and it, and like being forced to put them out in an essay that is actually coherent and backs up its points and like, Yeah, it makes it clear. So anyway, that’s the, that’s why I’m writing again. And so far it’s been quite enjoyable. I’m only on, I think, 20 days in a row of writing, writing every day, but it’s coming along now. I have to look. 21 today will be 22. [00:27:19] Sean: Nice. Yeah. Right. Writing is so great for clarifying thinking. And I love the, the identity piece. It’s like, I’m a writer, you know, that’s what I do. And I think it’s interesting to think about whether it’s kind of chicken and the egg, right. Maybe, maybe James clear would, would disagree, but like, does it start with a belief that you’re a writer and therefore you write, or is it the act of writing that makes you a writer? And if you, if you aren’t writing, then you’re not. [00:27:50] Nathan: Yeah. I wrote something recently and maybe it’s a quote from somebody of, if you want to be the noun and you have to do the verb, you know, and so we’re looking for, how do I become a writer? How do I become a painter? How do I become a musician An artist, any of these things? And it’s like, if you want to be a writer? Yyou have to write, you know, like, and I think we, we get so caught up in the end state that we start to lose track of the, the verb, the thing of like writers, write painters, paint, photographers, take photos, you know? And so if you’re not seeing progress in that area, then it’s like, well, are you actually doing the verb? And yeah, that plays a lot into identity and, and everything else. [00:28:37] Sean: I like what James, James clear says about like casting a vote for the person you want to [00:28:43] Nathan: Yeah, I think I referenced James on. So it’s the, I reference you probably every fourth episode. And then James, maybe at like, just on alternating ones. So the thing that I quote you on all the time is the show up every day for two years, like I always had create every day as a poster on my wall, and I really liked the for two years, angle. And so I I’d love for you to share where does the for two years part come from and why, why that long? Why not for two months or two decades or something else? [00:29:16] Sean: Right. It really, the whole show up every day for two years, idea came from me, drawing letters, hand lettering. You know, you think of the Coca-Cola logo. That’s not a font. That’s, you know, customer. That’s what I would do is draw letters. Like, like what you have behind your head, that type of style of lettering. And I just enjoyed doing that and I, it wasn’t a job or anything, and I really didn’t pursue it seriously for a long time, even though I enjoyed it as a kid, because I thought I could never make a living at this, you know? And it’s that like productivity filter again, what can I be successful at? You know, as opposed to like, Hey, what do I enjoy? You know? And, it took an artist telling me, Hey, if you enjoy it, just create. because cause you enjoy doing it. Just create. I was like, yeah, I don’t know why I needed that permission, but I did. And I just started creating and I was creating for me, like, because I loved it. And I was sharing on Instagram and Twitter and places like that, the drawings I was making, but nobody really cared or noticed for the first two years. And it, it, it, that was okay with me because I was doing it for myself. I loved the process. I love the act of. But somewhere right around two years, it was just this inflection point. It’s kinda like you say, you know, like do it until you’re noticed, right. And people started asking for custom commissions, do you have posters? Do you have t-shirts? And the reason I recommend that people show up every day for two years is it’s not going to happen overnight. You know, hopefully in that time you find the reason for yourself that you’re showing up. and the two years part is arbitrary for some people within eight months, they’re on the map and people notice their work and maybe they could quit their job or, or whatever. Right. But two years is really just to give people a mark, you know, to, to work towards. by that time they figure out like, oh, it’s not actually about two years. It’s about showing up every day. [00:31:16] Nathan: Yeah. And a lot of what I like about two years is it since your time horizon correctly. and it helps you measure your like past efforts. I think about, you know, if you’ve thought about starting a, like learning a musical instrument or starting a blog or any of those things, you’re like, eh, I tried that before, you know, and you’re like, yeah, I showed up most days kind of for two months, maybe, you know, like when you look back and you analyze it, you’re like, oh, I didn’t show up every day for two years. And there’s also sort of this implicit, I guess conversation you have with yourself of like, if I do this, will I get the results that I want? And cause the, the most frustrating thing would be to put in the effort and to not get the results and how the outcome you’re. Like, I tried it for so long and I didn’t get there. And so I believe that if you’re doing something like creating consistently showing up every day, writing every day for two years and you’re publishing it and you’re learning from what you, you know, the results you try and consistently to get better, you almost can’t lose. Like, I don’t know of examples of people. Like no one has come to me. I actually emailed this to my whole list and said, like, what is something that you’ve done every day for two years, that didn’t work. And people came back to me with story after story of things that they thought would be that. And then it like started working a year or year and a half in, or at some point in there because it’s really hard to fail when you’re willing to show up consistently for a long period of time. [00:32:54] Sean: And I think there’s a point of clarification there kind of a nuanced discussion where some people might say, well, you know, where where’s, where’s the other end of the spectrum, where you’re just continually doing a thing that doesn’t work, you know, doing the same thing and expecting different results. And I don’t think that’s what we’re talking about here. Like when we say show up every day, Showing up everyday to your craft, you know, for yourself to better yourself, whether that’s writing or drawing or working on your business. This doesn’t mean never course-correcting, this doesn’t mean adapting or adjusting to find product market fit. We’re talking about showing up for yourself. This doesn’t mean even posting every day. It’s not, it’s really not for others. Like share what you want. If you want to tweet every day, if you want to blog or post your art every day, go for it. I actually tried that and, you know, it was pretty exhausting and that’s part of why I made Daily Content Machine. I was like, how about I show up one hour a week and you turn that into Daily Content for me. but still on all the other days, I want to show up for myself. And, and often for me, it starts with writing as well. I think it all starts with writing, whether it’s a business idea or a course or a book or content like writing is just the seed of all of that. So I like writing, not because I. It was born a rider or anything. I just see results from it. So for me, it’s showing up in writing, even if I’m not posting that, or I’m not posting it now, you know, it’s just for me. [00:34:19] Nathan: Yeah. And that’s an important point because a lot of the time my writing is just chipping away at some bigger thing. Like some of the long essays that I’ve written have been written over the course of three or four months, you know, it’s not like I got it together and like published it and it was ready to go. It was like an ongoing thing. What, like, what are some of your other writing habits? Because you’re someone who has written a ton, I’ve seen you consistently write like 4,000 words a day for an entire month and stuff like that. yeah. When someone asks you, how do I become a better writer? How do I write consistently any of that? What are some of your tips? [00:34:55] Sean: Yeah. I’ll tell you how not to do it, which is how I’ve done it, which is back to our earlier discussion. Just kind of all or nothing. my first book I wrote in 14 days, 75, 80,000 words, and my, my second book, which I still haven’t edited and published. I was like, I want to show people that things take, as long as the amount of time you give them, how long does it take to write a book a year, 10 years a month? You know, two weeks, I was like, I’m going to try and write a hundred thousand words in a single day. So I live streamed it, and my idea was to speak it and have it dictated, right. Have it transcribed. I made it to 55,000 words. And these are like, it’s, it’s all you, you can find it. it’s, it’s coherent words like this. Isn’t just feel like, like the book was in my head. I made it to 55,000. My voice was going and I’m like, I think I’ve got most of the book. I’m not going to kill my voice. And that’s, as far as I made it. So I failed on the goal, but still got 55,000 words. But then for the next, like three, three or six months or something I hardly wrote. Cause I was just like, oh yeah, you know, look what I did. You know, I wrote all those words and it’s like, no, that’s not the right way to do it. Like I actually, I think there was a point to what I was doing and it was, it was a fun stunt or whatever, but I kind of regret that, you know, I wish I just stuck to, you know, you had that, that idea of like write a thousand words a day and this is something I would share with people as like an idea for starting out, Hey, try and read a thousand words a day. And I found out people would get stuck on that. They’d be like, I wrote 830, 2 words. I’m a failure. I’m just gonna give up and wait until the weekend when I have more time. And it’s like, no, that’s not the point. The point is to just show up and, and put some words there. So maybe for you, it’s a time like write for 20 minutes, write for 15 minutes, write three sentence. And maybe you keep going, you know, but like put in the reps, show up, you know, put on the running shoes and go out the front door. If you don’t run the five miles, that’s fine. You know, walk around the block, but show up. And so I I’ve done it both ways and I don’t prefer the stunt way where I write 50,000 words in a day. I prefer the, the, the ones where I write 400 words every single day, that week [00:37:06] Nathan: Yeah, I think that’s absolutely right. And I’ve, I’ve, had that a lot of times where I was like, oh, I can’t write today because I, I wouldn’t have time to hit 500 or a thousand words. And so that’s something I’m doing differently this time around of like, look even a hundred or 200 is a, is a success, any amount of, of doing the reps as good. [00:37:26] Sean: I want to lean in on that idea of defining success as less. What I mean by defining success as less is, and this is especially helpful. If you’re going through a hard time, if you’re feeling burned out, if you’re feeling depressed, w with remote work, growing and growing, you know, w we’re commuting less, we have more time. We have more flexibility in our day, but we, we tend to fill that time with just more and more work. And it’s really easy to get to the point where you feel overloaded. And you, you go into your day just too ambitious thinking. You can get too many things done and ending with disappointment. Like I didn’t get all the things done, you know, and you’re just on this perpetual cycle of disappointment every day, setting yourself up for disappointment, trying to do too much. And instead of defining success as less. And so if you’re, if you’re feeling depressed, I mean, this gets as small as today as a success. If you brush your teeth, like today’s a success. If you shower, today’s a success. If you walk around just your block, that’s it not run a mile, you know, not come up with a new business plan or outline a whole course or something. Less defined success is less, when I would do podcasts, I, you know, a podcast is what an hour, maybe two hours or something like that. But it takes a lot of energy. If you’ve never been on a podcast, you know, it takes energy to record. And I would feel bad after I record a podcast, not getting as much done afterward, you know, like, oh, I didn’t get that much done. I mean, I recorded a podcast, but then I was supposed to have this and this and this, and just beat myself up. And I realized like, Hey, that, that podcast I recorded, that’s going to be heard by thousands of people. That’s really high leverage work. And I brought my best self and I really showed up and I really delivered. And that was good work. And you know what, on days where I have a podcast, I’m going to define that day as a success. If I show up and record that podcast, anything else is a bonus. And, and you just make that smaller and smaller and smaller until it’s accessible to you until it’s attainable for you. So maybe it’s like write three sentences. If you show up at all to your writing app and write three sentences, the days of success. And what you’ll find is more often than. You’ll keep going. [00:39:34] Nathan: I think that’s so important in, and I imagine most creators have been in that position of no motivation feeling depressed. And then you beat yourself up because you didn’t get anything done, like deriving yourself worth. This kind of goes back to the earlier conversation, driving your self worth from what you create can both be very powerful in that it can feed itself really well. And then it is also incredibly fragile. And I’ve gotten to that point where if you end up in the downward spiral version of that, then like not creating, not accomplishing something. Leads you to feel more upset and depressed and so on. And it like when it works, it works well. And when it stops working, it fails spectacularly. And I think you’re right. That the only way out of it is to lower that bar of success to something crazy low that you can’t consistently. And then, you know, gradually you’re way out of it from there. [00:40:34] Sean: Yeah, you, you are more than what you do. You are more than what you create. You are more than what you produce. You are more than your job. You are not your company. You’re not the money in the bank. You’re not how much you make each month. You’re not the decline in revenue from this month compared to last month. Like you’re none of those things. You’re a person you’re a human outside of that with independent work. And that’s such a hard thing to internalize, but, but if you can, I mean, you, you, you just become impervious to all the things that can come against you. You know, you just become unstoppable. Nothing’s going to phase you. Like you can embrace the highs and embrace the lows and just ride the rollercoaster. And I’m just describing all the things that I don’t know how to do, but I’m working. [00:41:20] Nathan: Yeah. It’s all the things that we’re trying to, like lean in on and remind ourselves of, in those, in those tough times, I have a friend who has his game, that he played his, a few little kids, and his sort of a little game that he plays with them over time. And he like in a playful, joking voice, he asked them like, oh, what do you need to do to be worthy of love? And it’s like turned into the thing for they, like, they’re like nothing, you know? And he’s very purposefully trying to counteract this idea of like, oh, I need to earn worthiness. I need to earn love. If, if I like show up for my parents in this way, if I take care of my family in that way, if I’m not a burden on other people, then like, Then I’ll be okay and I’ll be worthy of love and all of that. And so he’s just playing it, like making it a playful thing with his kids from a very young age to basically instill this idea of like, you are a complete whole person and you can’t, like earn worthiness of love and you also can’t lose it. [00:42:19] Sean: I’m just thinking of the titles for this episode, that my team’s going to come up with, like how to be a founder worthy of love. [00:42:26] Nathan: Yes, exactly. [00:42:28] Sean: Don’t use that title. [00:42:31] Nathan: Okay. But I want to go, you’ve built a, a team twice, for first for Sean West, as a business, you know, of the course and content, community business. And then now for Daily Content, I want to get into, like what you like, how you built the team differently between those two times and what you learned. but before we do that, let’s talk about as a solo creator. When you’re thinking about making that leap to something where you need a team to build it to the next level, maybe you’re at a hundred thousand dollars a year in sales, and you’re looking at maybe the roommate’s eighties and the Marie Forleo’s of the world where like a few, rungs above you on the same ladder. And you’re like, okay, that would require a team. What are some of the things that you think people should consider in that leap? [00:43:22] Sean: My biggest mistake was applying the right advice at the wrong time. Like I’m not a, I’m not a reckless person. Like I’m going to do my research and learn and like get all the smart people’s advice. And so every, every big mistake I’ve made was as a result of applying great advice from smart people at the wrong time. And so it’s, and, and I don’t think I’ve ever heard anyone really, really talk about this. There’s a lot of people slinging advice who should really be asking questions, but at the same time, you can’t even blame them. Cause like Twitter, there’s no room for nuance. Like you tweet fortune cookie tweets, you know, with, with advice and like, hope that people apply it at the right time. Like, that’s just kind of how it goes. But like, you know, to, to your point of like looking to other people and what they’ve built and like, oh, that’s what I would need and stuff, you know, I, I heard things. Delegate, you know, you don’t want superhero syndrome. Like you need to empower other people and delegate the things you’re not good at delegate the things you don’t like to do, delegate the things you’re good at. And you like to do, but you shouldn’t do because you’re the founder and you need the vision, you know, like, so it’s like delegate, delegate. And so, okay. All right. Hire. This is going to sound really stupid, but no one told me that you need to make sure the thing that you’re doing is working before you hire, because hiring is scaling, which means to make something bigger. And if you’ve got a bucket at the beach and the bucket has holes in it, and you scale that bucket, you have a bigger bucket with holes. Like th th that’s not better. That’s like, do you, do you like the stressful problems you have now? How would you like problems with another zero on that? Like you have $30,000 problems. Do you want $300,000 a month problems? Like, you know, it’s not fun. so nobody’s told me that and looking back, it’s like, it’s so dumb. Like, do you think making this big. Automatically makes it better. It’s just going to automatically make the problems go away. No, you need to, you need to scale. What’s working, do more of what works and, and, and slow down and hold off and make sure the thing you have is working before you grow it. I don’t know if I answered the question, but I’m just speaking to my past self. [00:45:32] Nathan: You totally did. So what are the things that, like, how does that play out as you’re building Daily Content Machine, versus the previous team? [00:45:40] Sean: The difference here is my, my previous business required me to function and I hired people around me, you know, to support me. So I wasn’t doing all the work, but I had to show up. I had to, you know, whatever I had to write, I, you know, come up with an email or blog or. Or live stream or podcast or whatever. It was like, it was built around me and there’s nothing wrong with that. Like, that’s totally fine. You can build a business where you do what you love and you’re supported by your team. I just found that you can, you can do something that you love and burnout, like after you do that for years and years and years, it’s not even that I don’t like podcasting or I don’t like writing cause I actually do what it ultimately came down to is that I don’t like having to do it. And if I don’t, if I don’t, then everything falls apart. And so with this new business, the agency, it was like, okay, like the first thing I want to build from is this can’t require me to function. It has to be built in a way that the team can run things where it’s like, I don’t have to be on the strategy call. I don’t have to do the marketing. Like my face isn’t necessarily the reason people are coming to. and that, that really shifted how we build things. [00:47:01] Nathan: Yeah. I mean, that, that’s a huge thing. And like, I imagine you defining all of these roles and early on, you might be doing a bunch of them to test if it works and to build out the systems, but none of them are like defined by your own unique skillset. Like you actually I’ve loved watching your systems and the, as you’ve shown me behind the scenes, because you’re breaking it down and you don’t need one person who is a fantastic video editor and copywriter and project manager talking about that, actually, because I think so often we’re trying to find the employee or the team member. That’s like the, the unicorn perfect fit. And you’ve made a system that doesn’t require. [00:47:42] Sean: Exactly. And we did start out that way, where, when, when I was initially hiring for, you know, this Daily Content Machine service that we have, what’s involved in that process and we talked. Clients and prospects all the time that like the Mo one of the most common things they try to do is either build a team in-house that can find all the best moments scrubbed through the long form content, edit it. Well, you know, titles, research, all of that, the build that team in house, or hire a freelancer and the problems with either of those is like what I’ve identified as it comes down to the person doing, doing content repurposing well requires nine key skills among them like copywriting and marketing and design and animation and rendering, and like, you know, SEO and all of that stuff. And I’m not saying there’s, there’s no one out there with all those skills, but, but those people are doing their own thing most of the time, [00:48:38] Nathan: I think I’m a pretty good Jack of all trades. And I think if we get to five of those, probably maybe on a [00:48:45] Sean: You could probably do most, I can do most too, but I don’t scale, you know, so I’m trying to, I’m trying to scale me. and the first thing I tried to do was hire someone who could do all the things like, okay, you need to be able to, and that very quickly was not the way that was not going to work. So we realized we need specialists. We need people who are really good writers. We need people who are really good animators. People who are good editors, people who are a good quality assurance, reviewers, people who are good project managers, you know, all of that. And that’s, that’s what probably sets us apart. You know, the most unique thing is like, we learn about your audience and we find all of the moments and like teaching people, I’ve talked to people who have their own teams, or they’re trying to build teams for doing this. And that’s the hardest part is how do you teach someone how to find those moments? Like video editing is commoditized. You can find a video editor anywhere, but what happens when you try and get a freelancer who can just chop up clips and animate it and put a slap a title on it? Yeah. Th they’re not, they don’t care about the quality. They’re not capitalizing the book titles and the company names and spelling the guests. Right. You know, and the titles of the clips, that’s like half of it, you know, like half of it is the title, because that’s going to determine whether someone sticks around and clicks or watches or whatever, and they’re not thinking the right way, or they’re not finding the right moments. And so the person who’s outsourcing, they’re trying to go from, I’ve been doing this myself. I’ve been editing my own video. I’ve been scrubbing through my own long form content to now, okay, you have got this freelancer, but now you’re a project manager and a quality assurance reviewer because their work isn’t up to par. And so I have people asking me like, how do you teach people how to do this? Well, how to find those moments, what’s going to provide value to the audience. How do you title it all? and that part, I’m not giving away because that’s, that’s our home. [00:50:33] Nathan: Yeah. And that, that makes sense. So you described Daily Content Machine as an agency and it is, but I was like, great. You’re an agency. Here’s my other idea for a show where. Like a dream it up and produce it. Or actually we build my website for me, like your, your designers on all that. Right. And your answer would be like a flattened and I think that’s really important for the business. So can you talk about the difference between the agency that you’re running in productized services and how you think about making that scale versus like a, an agency of, Hey, this is our hourly rate. These are the projects we’re best at, but we’ll kind of take on anything. [00:51:11] Sean: So maybe I’ll I’ll I’ll title the clip of this moment, how here’s, how you will try it like this. Here’s how you create a six figure agency. And for. It is by saying no to almost everything and getting really specific about what you offer and to whom. So my previous, the previous iteration of my business, I was out of a scale of one to ten I was working at a level 11 effort, you know, to bring in six figures with this version of the business. It’s like a one or two in terms of, you know, getting people to give you vast amounts of money. And the difference is in what you’re providing and, and to whom. So you’ve kind of got this, this matrix of products or services that either make money for your clients, or they’re just nice to have. And then on the people side, you have, it’s a generalization, but people who have money and people who don’t, and I was always playing on hard mode, you know, I was trying to sell like kind of more premium stuff to people who didn’t have money. And I’m like, you know, feeling bad about not being able to give stuff to the people who don’t have money. And it’s like, you know, what a really great way to do this would be to provide premium services that make money for people who have. So I decided I’m going to start with six to seven figure business owners. What is it that they need? And what is it that, that I’m good at, you know, core competencies. And that’s where we came up with this idea. And the hardest part has been not giving into shiny object syndrome. All of the things that we could do, all of the services that I want to build. And it’s like, no, there’s so much more juice in this one thing. If we just stick to this and just become the best at finding, identifying, and producing and distributing clips from long form content and just be really, really good at that. There’s enough complexity in that, you know, and just see that as the game, like, how can we get really good at this? How can we sell this better? How can we deliver it better? How can we increase the quality and just getting really focused and aligning what you offer the value of that to the people you’re offering it to within four weeks with just a page and a form. This was a six figure book. [00:53:16] Nathan: When I think about the price of the offering. So I think I have. for what I pay for and Daily Content Machine paying about $5,000 a month. Is that right? I think somewhere in there. [00:53:28] Sean: So, what we didn’t say is you, you kind of talked me into, adding another service, which is, we also do the video and audio show notes, transcript, like podcast production piece. So like, we’ll produce the full thing. You just show up and record sync the footage to us. We’ll produce the show and we’ll make the clips. That’s actually been a really nice bundle, but I’m like, okay, that’s it, that’s it. You know? So you kind of have some extra services in there. [00:53:53] Nathan: Yeah. To be clear, you don’t want to let your friends, even if they live in the same town, as you convince you to like change your agency, [00:54:00] Sean: Nathan’s very convincing. [00:54:03] Nathan: I distinctly remember. I even invited you over for dinner and convinced you of it, [00:54:07] Sean: How am I supposed to say no, [00:54:08] Nathan: Exactly. [00:54:10] Sean: You made an offer. I couldn’t refuse. [00:54:13] Nathan: But in that, so you’re talking about like what you’re selling to someone who might not be able to afford it, or like you might make a course that you charge $5,000 for that is absolutely worth every bit of that when in the right person’s hand and apply it in the right way. But you’re going to have a bunch of people trying to buy it, who like, aren’t that person who’s going to get the leverage to make it a clear 10 X value or something like that. And so you might have in this position where someone’s like, oh, $5,000 is expensive. Should I buy it? I don’t know. And you’re like, honestly for you, I don’t know if you should buy it. Like you’re not in the target market and that’s, that’s $5,000 one time in the case of this. And this agency, this productized service, I guess, $5,000 a month. And so actually two of those clients, and you’ve got a six figure a year agency business. And it’s just interesting. The thing that you said made me really drove home the point of, there’s not necessarily a correlation between effort and income and, and effort and output. And so you found a model and kept, kept tweaking until you found one where it was like, look, there’s a ton of work that goes into this, obviously. And there’s a bunch of really smart people working on editing and transcribing and captioning and everything in the show. but like, it, it doesn’t have to be crazy complicated, whereas some of the other business models that you and I have both tried have been way more effort for way less. [00:55:40] Sean: Yeah. And what can really hold you back is not realizing who you’re trying to market to. And. getting Talked down in your prices by accidentally catering to the wrong people. So like people who can’t afford your services, you could get on call consultation calls with them. And they’re just like, I just don’t have this much money and can you do discounts? And you, you almost start to feel bad. Like, you know, how can I charge this much? I must be charging way too much. And it’s like, or maybe you’re serving the wrong customers. Like, you know, when you talk to the right people, that may actually be really cheap. I remember when I started designing logos, this is like a decade ago. My first logo, I charged like 150 And then, once I sold that I got enough confidence to charge 300. And then I was like, I, you know what, instead of doubling again, I’m going to charge $750 [00:56:30] Nathan: Ooh. [00:56:31] Sean: I did that. And you know, I’m like slowly building on my portfolio and I got up to like, $1,500 and clients were paying that and right around there, you start to get people resisting. Now you’ve got a price with a comma and it gives people. pause And they’re like, can you come down? Can you do a little bit cheaper? And it’s so tempting. You, you want to do that because you want the job. You, you want them to be happy. It could be a good portfolio item. And I remember just kind of fast forwarding through this, but like, you know, just mindset shifts and stuff. Eventually I got to the point where there was this startup out of San Francisco they wanted a logo. And I was like, this would be really valuable for this company, you know? And I somehow mustered up the courage to charge $4,000. And I found out later from a friend of a friend, you know, from someone that worked there that they thought I was like super cheap because someone else they knew or some other agency was going to charge $25,000 And I was like, wow, like I’m over here. Just like feeling bad about my prices, thinking I’m going so big. And really I’m. I was just serving the wrong code. [00:57:34] Nathan: Yeah. And it’s so interesting because the person who’s only able to pay $500 or only thinks the logo is worth $500. It’s not that they’re wrong or they’re devaluing your service or something like that. It’s that maybe it’s for a side project or it’s for a business that just got off the ground or any of that. And so it’s not worth getting offended over or something like that. It’s like, we just don’t have product market fit, like product customer fit. It’s not a thing here, you know, and my services are better for, you know, bigger, more established companies. So the saying no to, to, services, occasionally getting talked into specific services by your somewhat annoying local friends. but then where does it go from here as far as what are you looking to, to, to add more clients and, and keep scaling and growing? [00:58:30] Sean: Yeah. That’s what we’re trying to figure out right now is it’s always tricky. It’s a blessing and a curse when you have an audience, because it can kind of create false product market fit. Like you, you think you have something and then you exhaust your audience and then you’re like, oh, like I kinda need to figure this out. You know, that’s like, we’re experiencing that right now because like, I was getting like 40% close rates on consultation calls on sales calls, and now we’re not, and it’s. Oh, no, like what’s happening. And it’s like, well, I think those people probably knew me for several years, you know? And then like, there’s just all this trust and still Nathan we’re a year in and we don’t have, like, we don’t have a proper website for, for the agency. It’s like a page with a form. That’s it? There’s no, there’s no examples. There’s no case studies. There’s no portfolio item and we’ve made it this far. but you know, when people don’t know you, they need that social proof and they want the examples and they’re looking for past versions of success. And like the sales cycle is a little bit longer. And so that’s where we’re at right now is like figuring out kind of like Mar marketing channel fit. And I know well enough to know, like it’s better to, and back to right advice, wrong time. it’s a good idea to be everywhere if you can, you know, cause different people consume on different platforms. Even if you don’t use Instagram. Other people do, even if you don’t use YouTube, other people do it’s. Beyond LinkedIn, even if you don’t, you know, that like there’s, there’s some, there’s some sound reasoning to that at the same time. You don’t want to try to do all of that all at once, you know, and, and spread yourself too thin, like pick one channel, do one channel. Well, and when you’ve got that down and it’s easy and you have systems and it’s not taking too much time, then expand to another channel with the goal of like, ultimately diversifying kind of like investments. You don’t want to just diversify all at once. You know, like, like try some things out, you know, focus on one thing at a time, see what works for us. I, at least I know that much. And so it’s like, okay, I’m not trying to do every version of marketing, you know, like, oh, do we do affiliates? Do we do ads? You know, do we do content? Do we do cold outreach? You know? I’m trying not to do everything at once. So we’re kind of dabbling in one thing at a time and seeing what fits. [01:00:48] Nathan: So how many clients do you have now for the agency that are the consistent tenders? [01:00:53] Sean: Not a lot. It’s still very small. And we’ve had like, I it’s under a dozen cause like some, we had like several accounts, like not renew and stuff. So it’s still very small. And for three or four months, I stopped marketing and sales completely because I did not want to break this thing with scale because I notice things in operation that were the operations that were not going well. I’m like, this is going to be really bad. Like if we just sign more clients, it’s going to be really bad. So, I had clients pay upfront for like six months or 12 months of service, which kind of gave us time to focus on operations. And now everything’s humming along smoothly. Like the systems we’ve built can support like dozens or hundreds of accounts, even like, we don’t need it right now, but it’ll support where we want to go. But it’s still a very, it’s actually very small, like again done, like almost no marketing a year end, still don’t have a website. Like it’s pretty much just been all internal focused. [01:01:52] Nathan: One thing that I’ve respected a lot about how you’ve set it up is like, as a client, I could see it produce that they could see it as a client. And then, as, as a friend and, you know, business peer and all that. It was the times that you’ve tried things and then been like, oh no, we can’t do that. We can do this version of it where like, well, I came, remember what we shifted in, in the production of this podcast. Right. But we, we added the, like the video service, because most people who come to you, you know, have their show being produced already. And, and then they’re bringing it and say, Hey, can you make clips? And, and all of that, of this. And so, you know, we added things and then you, then you tweaked and changed it because you’re like, yes, I can totally make this work for this client. And maybe even five more, but like at 50 clients at a hundred clients, there’s no way that this will ever work. And so we’re not going to do it now. And I have a ton of respect for that. [01:02:42] Sean: I’ve scaled a bucket of holes before, and it’s like, I don’t want bigger problems. No, thank you. [01:02:49] Nathan: Yeah. okay. Something that you also preach a lot that I really appreciate is. this specifically, if you’re doing a podcast, like turn on the camera, why? [01:03:01] Sean: Yeah. If you’re doing a podcast, you’ve got to film it. There’s so much more you can do with this. We’ve just found when you try and repurpose audio files, it just doesn’t perform as well. On Twitter. People resonate with people’s faces and they connect with humans. So just turning on your camera for your own show, even if you don’t want to post it yet, even if you’re not repurposing it, at least you have it. We have a lot of clients that have just a backlog. They had a podcast, it goes out audio only. They don’t even produce it video, but behind the scenes, they recorded the zoom calls. So they’ve got all the zoom recordings in the cloud and they’ve just got this massive backlog. And now we can repurpose that and resurface it and put it on the different plans. It just gives your content legs. It’s like thinking of like a wood pallet and you, you know, you, you build something on it and you want to move that. It’s like, it can’t go anywhere. It’s like, it puts wheels on that pallet, you know, your content. So even if you’re on someone else’s podcast is what I tell our clients. If, if they’re like, I don’t know if I record enough content, it’s like, you probably do. And you’re just not like making use of it. Like anytime you probably get, podcasts, interview requests, sometimes you’re like, I don’t know if I have time for this is the audience big enough? I feel bad asking that question, but you’re thinking about it, right? And like a way that will help you create free content and justify going on. Maybe those smaller shows and building those relationships is even when you’re on an audio only podcast interview, turn on your own. And record yourself, use your webcam, use your iPhone. Don’t overthink it. Don’t do the external DSLR, Thunderbolt HD, my convert. Like I know it gets complicated. Don’t go down the rabbit hole, but just film yourself. And now you’ve got video. You can do stuff with that. You can repurpose because you’re probably already recording the content that. [01:04:51] Nathan: Yeah. And that, that’s something that I think about all the time, because exactly we talking about, when you go on that show, you’re like, can I justify the time for the size of the audience or any of those things? And it’s like, yeah, you can, if you’re going to reuse that elsewhere, like you told a story on that random podcasts, it’s going to go out to maybe a hundred people or something like that. And if you can pull that story back and say like, oh yeah, but I’m going to have it, you know, turned into clips and transcribed and it’s going to turn into a, a, a, another blog post or another idea then it’s totally. [01:05:26] Sean: And here’s a free idea. I tell my clients this as well. I’ll give you two. One is a live-stream Q and A. There’s just such a win. You’ve got the live engagement. You’ve got people asking you questions, which essentially writes the titles for you. It’s reading their minds. But then you’re also maximizing your input. You’re leveraging your time where you could show up for 30, 40 minutes, answer 21 questions, and then there’s three weeks worth of daily clips that you made in like half an hour. So, Q and A, even if, if you don’t have a big enough audience for live, do async. Send out an email to your list, add it to your “welcome” auto-responder. “Hey, what’s the biggest struggle around X?” Put that in a spreadsheet, show up with an outline, and just knock it out. A week’s worth of Daily Content for you right there. The other idea is, I was talking to someone who coaches founders, and he had a rate for every-other-week calls of a certain length, and access to a Slack and stuff like that. It was like maybe $850 a month. What you could do is charge $1,200, but say, “I can do $850 if I can record this,” and repurpose the content. Maybe you could come up with some arrangement where it’s pinned on your video, and it doesn’t show the person, or you edit out sensitive details, but you’re already giving advice on your coaching calls, on your consulting calls. You’re creating content. All it takes is just like a little tweak to expectations you set with your clients, and then you don’t have to create more. You have content, right? [01:07:03] Nathan: Oh, there’s so much good stuff. It really just takes this idea of creating content, being a huge hurdle that you’re trying to carve out time and trying to make it happen, and turns into something that you can show up pretty consistently and make it happen, in a somewhat meta sort of thing. Your team has mentioned that they’d like episodes to be between 50 minutes, and an hour and 10 minutes, just for finding the right amount of content. So we’ll try to stick with them that. So, I think you might be the only one of the only guest that has come on the Nathan Berry show twice, in his relatively short run of, I don’t know what we’re at, 45 episodes or something like that. [01:07:43] Sean: Yeah, I think you’re over 50. [01:07:44] Nathan: Over 50. Alright. See, I like that. You noticed that side of it, but we’ll have to do this again because it’s just so easy, and we can riff on whatever we want and it’s it’s great content. [01:07:56] Sean: Well, thanks so much for the opportunity. Nathan always love getting to chat with you. [01:08:00] Nathan: Yeah. So where should people go to learn about Daily Content Machine to follow your stuff? Are you podcasting? What what’s going on? [01:08:08] Sean: Yeah. DailyContentMachine.co. That’s going to take you to our page with a form on it that’s not very fancy. I have a video there. If you’re listening in the future the website’s awesome. The transition to the animation. The illustrations. It’s beautiful. You got to check it out. No, I’m just kidding. But you can follow me on Instagram, Twitter, that kind of thing @SeanWes. So S E A N W E S. [01:08:37] Nathan: Sounds good. Well, thanks for joining me.0 comments0
- 050: Dave Pell - Lessons From Two Decades of Publishing OnlineDave Pell has been writing online for almost as long as the internet has existed. His popular newsletter, NextDraft, has over 140,000 subscribers. NextDraft covers the day’s ten most fascinating news stories, delivered with a fast and pithy wit. Dave has been a syndicated writer on NPR, Gizmodo, Forbes, and Huffington Post. He earned his bachelor’s degree in English from U.C. Berkeley, and his master’s in education from Harvard. Besides being a prolific writer, Dave is also the Managing Partner at Arba, LLC. For more than a decade, Arba has been angel investing in companies like Open Table, GrubHub, Marin Software, Hotel Tonight, Joyus, and Liftopia. In this episode, you’ll learn: How Dave merged his two writing passions into a successful product The key to building a strong relationship with your audience How Dave dramatically increased signups to NextDraft Links & Resources Flicker Unsplash Fareed Zakaria Jim Rome The Skimm Morning Brew The Hustle Spark Loop Sam Spratt Dave Pell’s Links Dave Pell on Twitter NextDraft newsletter Dave’s new book: Please Scream Inside Your Heart NextDraft app PleaseScream.com Episode Transcript [00:00:00] Dave: If you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it. So, that’s pretty powerful and still excites me. I still press publish with the same enthusiasm now than I did when the internet first launched. [00:00:23] Nathan: In this episode I talk to Dave Pell, who has been writing for basically as long as the internet has been around. He’s been an investor since the early days. He’s been writing since the.com bust, and even before then. He writes his popular newsletter with 140,000 subscribers called Next Draft. We have this really fun conversation about writing. His writing process. How he grew the newsletter. Bunch of other things that he cares about. Even a few things that I was interested in, like he doesn’t have his face in photos on the internet very much. He has his avatar instead. So, just getting into why that is. He also has a book coming out soon. It’s called Scream Inside Your Heart, which is a fun reference to some memes from 2020. So, enjoy the episode. There’s a lot in there. Dave. Welcome to the show. [00:01:12] Dave: Thanks a lot for having me on. [00:01:14] Nathan: Okay. So you’ve been doing this for a long time. You’ve been writing on the internet since the .com era. So, I’m curious maybe just to kick things off, what have you seen—I realize this is a giant question. What have you seen change? What are some of those trends that you’ve seen, that you either really miss from the early days, or some of those things that you’ve held onto from the early days of the internet, that you’re really still enjoying? [00:01:46] Dave: Yeah, that is a pretty huge question, but I’ll give it a shot. The thing I miss from the early days of the internet is that our democracy was not being destroyed by the internet in the early days of the internet. So, everything we thought we were building, basically it turned out to be the opposite of what actually happened. The part about the internet that I still feel is there, although a little bit less so because of the big companies have sort of taken over all the platforms and stuff, is just the idea that someone can have a passion or a creative output that they want to share with the world, and they can mold internet tools to fit their skills, and then use the internet to broadcast that out, and still become sort of pretty popular withour the “OK” of some gatekeeper at a publication, or at a television studio, or whatever. The indie spirit of the internet still lives on. It ebbs and flows, and has a lot of different iterations. But that was the thing that excited me the most when I first played with the internet. And that’s the thing that continues to excite me the most now. [00:02:57] Nathan: I always think of the newsletter, and your newsletter in particular, is that indie spirit. Is that what you see most commonly in newsletters? Or are you seeing it in other places as well? [00:03:10] Dave: I see it in podcasts. I see it in newsletters. I see it in people sharing their art, sharing their photography on Flicker, and up through the more modern tools. I go to a site called Unsplash all the time to look at images, and it’s just basically regular people sharing their images. Some of them are professional photographers, some aren’t, and they’re getting their work out there, and then some of them probably get jobs out of it and stuff like that. So, just the idea that you can have some kind of creative output and have a place to share it. And try to get an audience for that is really inspiring. It’s a lot harder than it used to be because there’s a few billion more people trying to get attention also, and because there are more gatekeepers now. So, you have to, hope that your app meets Apple’s guidelines, or that different products you might want to share on the internet have to meet certain classifications now, whereas they might not have in the very early days of the internet. But in general, if you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it. So, that’s pretty powerful, and, still excites me. I still press published with the same enthusiasm now that I did when the internet first launched. [00:04:32] Nathan: Yeah. So let’s talk about the main project that you have right now, which is Next Draft. Give listeners the 30-second pitch on Next Draft, of what it is. [00:04:46] Dave: Sure. Basically I call myself the managing editor of the internet. What I basically do is a personality-driven news newsletter where I cover the day’s most fascinating news. I cover 10 stories. A lot of times in each section there’s more than one link. I give my take on the day’s news, each individual story, and then I link off to the source for the full story. When I first launched it, I called it Dinner Party Prep. I provided enough information for you to sort of get the gist of the story. And if there’s topics you want to dig deeper, you just click and, you know, go get the story yourself. So that’s sort of the overview of it. [00:05:27] Nathan: Nice. And you said that you’re obsessed with the news maybe in a somewhat, even unhealthy way. why, where did that come from? [00:05:36] Dave: Yeah. Well, nothing, nothing about my relationship with the internet is only somewhat unhealthy. it’s all extremely unhealthy, but, both my parents are Holocaust survivors and, when I was growing up, news was just a very big part of our daily lives, especially when my three older sisters moved out and it was just the three of us, that was sort of our mode of communication. We talked about the news. We watched the news together. Fareed Zakaria is basically the sun my parents always wanted. but so I got really into the news and being able to connect the news to, our everyday lives, which of course my parents had experienced as children and teens and Europe during world war II. And also reading between the lines about why certain politicians might be saying something, why stories are getting published a certain way. So I just got really into that and I’ve always been into a and college, you know, I, I majored in English, but if we had minors at Berkeley, I would have minored in journalism. I took a bunch of journalism courses. I’ve always been really into the media, but not so much as quite an insider where I go to work for a newspaper, but more observing, the news and providing sort of a lit review of what’s happening and what has momentum in the news. So I sorta got addicted to it and, Also as a writer. My favorite thing to do is counter punch. I like to have somebody give me a topic and then I like to be able to quickly share my take, or make a joke or create a funny headline about that content. So I sorta took those two passions of the way I like to write. I like to write on deadline. I like to write fast and I like to counter punch and the content that I like, which is news, and I sort of merged those two things and created a product, and a pretty cool suite of internet tools to support that. [00:07:35] Nathan: Yeah. So that makes sense that you’ve identified the constraints that match your style and made something exactly that fits it. the deadline, like having, he, you know, coming out with something on a daily basis, is more than a lot of creators want to do. so what’s your process there? [00:07:55] Dave: Yeah. I mean, I should emphasize that I do it every day. Not because I think it’s some incredible draw for readers to get Daily Content. I do it every day because I’m addicted to it. If my newsletter had five stories in it, instead of 10, it would do better. If my newsletter came out three days a week instead of five days a week, I’m sure it would do better. If it came out once a week, it would do even better then you know, also if I had a more marketable or not marketable, but a more, business-oriented topic that was more narrow, it would do better. I used to write a newsletter that was just on tech and it was. Really popular in the internet professional community back in the first boom, I had about 50,000 subscribers and there were probably about 52,000 internet professionals. So I just like writing about what I want to write about and I’m addicted to pressing the publish button and I’m just addicted to the process. So I do it because of that. I’m not sure that would be my general advice to somebody trying to market or promote a newsletter. [00:09:01] Nathan: Yep. Are there other iterations, either ever before or things that you tried that you realized like, oh, that’s not a fit for your personality, your writing style? [00:09:09] Dave: Yeah. When I first started it, I actually, I’m an angel investor also and have been since, probably right after Google and Yahoo launched. so a while, and I used to, my passion has always been writing, so I wanted to mix writing into that, process. So I would send out 10. Daily stories, but they were all tech news related to the CEOs of the companies I worked with and a few of their employees, so that they wouldn’t have to spend their time reading the news or worrying about competitors or worry about what the latest trends in tech, where I would give it to them. And they could focus on doing their jobs and that sorta got shared and got out. so I did that for a few years. really, that was my iteration. I should’ve kept the brand. It was called David Netflix. not that it was a great name, but I’ve shifted brands about 40 times in my life. Cause I love branding and naming. I that’s another, maybe this is more of a cautionary tale than a lesson and newsletter marketing. I would stick with a brand if anybody has the possibility of doing that, that was a big mistake I’ve made over the years is having multiple brands. But when the bus came, the first internet bust, I basically was writing an obituary column every day and about companies that had failed. So I just decided, I wanted to expand it and I knew I was interested in much broader topics than just tech news. So I expanded it to all news, a critical point that, really changed Next Draft and got it to catch on and become more popular was when I decided to focus on making it more personality driven and less, less overwhelmingly, providing an overwhelming level of coverage. I used to think that I had to provide all the news in the day because people would sort of, depend on me to provide their news. I was sort of selling myself as your trusted news source. So I would include a lot of stories that I didn’t have anything to say about because they were huge news, you know, an embassy closed in Iran or whatever. That was huge international news, but I didn’t necessarily have anything to say about that that day. So after a while I decided, no, I’m not going to do that. I’m just going to limit it to 10 items. And I’m going to focus that on what I think is the most fascinating and think of it less like a curation tool and more like, a, modern day column. I think if the column newspaper column were invented today, it would look a lot like Next Draft people would sort of share their takes and then provide links off for more information. once I did that, it was a big change. People started signing up much more readily and, once I stopped trying to be exhaustive. [00:11:56] Nathan: That makes a lot of sense to me. I think that that’s something you see from a lot of creators is that they’re, they’re trying to find some model. That’s like, this is my idea of what people should want, you know, rather than what they end up doing, eventually it’s coming to, it’s like, okay, forget all of that. This is what I want. And I’m going to make that. And then people like me can find and follow it. And people who don’t can, you know, do their thing. Can you go find one of the other million sources on the internet? [00:12:21] Dave: Yeah. When I think of the people that I like to follow or have followed forever on the internet, all of them are that ladder. They just do it their way. They have a design, they want, they stick to their guns. They say what they feel like saying. they decide. what the personality of the product is. And, they move within that. I always find that to be the most interesting thing, especially when it comes to something like newsletters. I really think newsletters are more like a radio talk shows than they are like other internet content, podcasts to a certain degree as well. But I always feel like I listened to are used to listen a lot to this radio, sports caster named Jim Rome. And whenever he would have a new city that he was launching and he would always give the same speech on the Monday that they launched saying, just give me a week. You might not. Get the vibe of what we’re doing today. You might think it’s okay, but not great, but just give it a week and listen, and then decide if you like it or not. And I sort of feel like that’s how newsletters are your relationship with your readers sort of creates this, sort of insider-y voice and communication that, you, it takes a little while to get into the rhythm of getting it. But once you do, then it’s like this familiar voice or this familiar friend that you feel like, even if you didn’t read it for a few weeks, you can start a conversation with that person right away easily. That’s how I think the voice of a newsletter is most effective. So that’s why I’ve always thought of it. More of what I do is sort of a textual talk radio, more so than a blog or some other format [00:14:01] Nathan: What do you think, or what would you say to someone who maybe had 10 or 20,000 subscribers and felt like their newsletter had gone a bit stale and maybe their relationship to it had gotten a bit stale or they’re in this, this position of writing things that no longer have their voice, how would you coach them through like bringing their voice and personality back into it? [00:14:22] Dave: I mean, it’s definitely hard. it’s hard doing something that you do alone and, something that is often hard to really get off the ground or get to grow, especially when you’re on a platform like the internet, where every day, somebody does something and 10 seconds later, they’re like internet famous and you’re trying day after day. So, I mean, the first thing. Is that you really have to be interested in what you you’re passionate about. and focus in on that, because that will alleviate a lot of that stress. Like, do I feel like sending it today? I’m a too burnt out. What’s the point? I mean, not that those feelings don’t happen. I had those feelings as recently as an hour ago, when I press publish, I have those feelings and disappointments constantly, you know, that’s part of being a creator of any kind. Maybe that word is sort of, sort of goofy, but anybody who’s putting themselves out there and putting content out, you know, you have that feeling all the time. If you’re an indie, and you’re doing it all day in front of the computer by yourself, then that’s even more powerful because, you know, if you work at a big company or everybody’s working on the same goal, or even in a small group, you can sort of support each other and, maybe even bullshit each other at some cases where, oh, no, this really matters. You know, where, if you’re by yourself, that has to be pretty self-sustaining or self-sustaining. I do have a friend or two that I always share blurbs with who, one of my friends Rob’s, he proves almost all of my blurbs, so it’s nice to have that virtual office mate. He’s not really officially part of Next Draft, but you know, I don’t think I would do it as easily or as, for as long if it weren’t for him because he’s like my virtual friend on the internet that says, oh, come on, let’s get it out today or whatever. So I think that’s helpful to have a support team or a couple people you can count on to sort of give you a boost when you need it. But the key really is, is that it’s gotta be something that you are passionate about, both in terms of the product and in terms of what you’re focusing on, because if you feel strongly about it, then it really. I don’t want to say it doesn’t matter if people enjoy it, you should take cues from your readers. What are they clicking on? What are they reading? What are they responding to? But at the core, it’s gotta be you because that’s what gets you through those down points? you know, I had a weird thing because I write about news. The general news, world basically benefited dramatically from the Trump era because everybody was habitually turning on their news, 24, 7, and refreshing and Whitey and Washington post and checking Twitter every two seconds to see what crazy thing happened next. And we’re all poor sorta, [00:17:01] Nathan: Wreck to watch. [00:17:02] Dave: So everybody was really into it and it created. Unbelievable platform for people to become media stars. You know, Trump was bad for democracy, but he was great for media. Great for creating new voices out there. whether we like it or not. for me, it was different because I wrote about all news. I wouldn’t say I was apolitical, but I wasn’t heavily political. The Next Draft had plenty of readers from both sides of the aisle. when Trump came around, it was like one story every day, basically. So it really limited. I would get emails from longtime readers all the time that said, Hey, can’t you cover something other than Trump every day? And I say, Hey, if you can find the story for me, I’ll cover it. This is what every journalist is on. Now, the people who used to cover the secret service around Trump, the people who used to cover sports are not talking about Trump because of a pandemic relation ship to it. The people who aren’t entertainment are talking about Trump because they can’t believe that anybody voted for him, whatever the issue was, every dinner party was about Trump. So it was really a bummer for my brand and my product. Actually, it became boring in some ways to me to have the same story every day. And it became, I think frustrating to my readers. But during that era, when it was happening, I had to make a decision. Do I become more political and go full on with this? Or do I sort of try to. Do what I would call a falsely unbiased view or a, you know, false equivalence view that we saw in the media where there’s both sides to every story. And you have to pretend they’re both accurate, including one guy saying to put disinfectant into your veins. And the other person’s saying to wear a mask and take a vaccine, but those things get treated as equal somehow because the president said it. And I really decided, you know, more important than keeping readers is that I’m true to my own sort of ethical standards. In a moment that called for it, at least for me. So I became more political. went into it and I said, what I believe and still believe is the truth, you know, about what was happening with Trump and Trumpism and our slide towards authoritarianism. And I know that this is a podcast more about newsletterish than it is about politics or news, but I’m just sharing that because that’s the kind of thing that kept me going. and the people who really cared about what I was writing, appreciated it and would email me and say they got something out of that. And most importantly, my mom would say, yeah, you made the right call. Or my dad would say, yeah, you got that. Right. And ultimately, When it became a sort of a bummer period for me, which I would say 2020 was because of all the horrible news. And, I was writing a book about the year. So I was like living, July of 20, 20, well writing about March of 2020, which I don’t recommend for anybody’s emotional health. And I just had to think like, what’s really important to me. Yes. I want to be funny, which I try to be in my newsletter every day. I want to be read my narcissism is as strong as ever, but ultimately I want to be able to look myself in the reflection of the, darken screen on the rare times that it is dark and say like, yeah, you told the truth and that kept me going there. So I think whatever your brand is, you know, it can be a newsletter about guitars, but if you have that sort of passion, And you have something you want to say, and you think is important to say it sort of gets you through those levels and your motivation. And if it’s not getting you through the lows and the motivation, there’s nothing wrong with saying, Hey man, this is not worth it. I’m going to go try to make something else. You know, it doesn’t have to be, you don’t have to beat a dead horse. [00:20:51] Nathan: On the political side. Are there specific things that you felt like it costs you opportunities that it lost you? Because I think a lot of creators, whether they talk about, you know, finance or photography or whatever, I’ll see these things. And they’re like this either directly relates to me and my audience and I feel like I should take a stand on it. Or it’s like a broader macro issue that I feel like we should talk about. And when you do, then there’s immediately, you know, somewhere between three and 300 responses of like, we didn’t follow you for the politics, you know, or like something like that. And your Instagram, DMS, or newsletter replies or whatever. [00:21:24] Dave: Yeah. it costs me a lot. Definitely it costs me readers or subscribers. It costs me, psychic pain because I was locked into a story that was just overwhelmingly, emotionally painful, really, and shocking and difficult to understand all the things that cause you sort of emotional exhaustion. We’re in the Trump story, especially in 2020, when it became a story about our own health and our kids’ health. And the frustration level just went through the roof. for me, professionalizing that content actually helps create a bit of a barrier to the feelings about it. Some of my good friends were probably more bummed during 2020 than I was because when the latest crazy story or depressing story would happen, I felt I had to. Ingest that content and then come up with, something cogent to say about it. And maybe hopefully funny to make it a little bit of sugar to take the medicine and then get it out to people. So I’ve always felt that being able to do that, sorta created a barrier between myself and actually feeling something. So that’s another thing I like about the newsletter probably at least unconsciously. but yeah, there was a lot of costs in terms of readers, for sure. Hate mail. but there always is, you know, Today. I would say I get much more hate mail from the far left. If that’s what you want to call them. People who feel like every joke is like an incredible triggering a front to their existence or any hint that you mentioned somebody as attractive. I’ve gotten hate mail because I implied that Beyonce is appearance was part of her brand. I mean, it’s totally crazy, but, It’s those extremes. You have to be able to turn off. You know, a friend of mine used to work at a major, be the editor of a major American newspaper. And he said every Friday they would get together and they would play the craziest, calls to the editor. They had a call line. In addition to, you could send a letter or you could call, leave a voicemail about something you were upset about in the coverage. And they would just gather around and have drinks on Friday. Listen to this because of course the people who are calling this line are almost self-selecting themselves as a little bit wacko and their takes were usually pretty extreme. The internet, Twitter, social media, Provides, greases the wheels for those people to be more prevalent in our lives. But I think it’s really important to know that that’s a real minority of people, somebody who sent you a hate mail, that your joke was so offensive, or they can’t believe you mentioned that people ever watch pornography on the internet or any of these other things, it’s this tiny minority of people. And then it’s one step crazier that they felt like they had to contact you. So that’s a really hard thing. I think about being split, particularly the newsletter game, because anybody can hit reply and you’re going to get many more replies from people with crazy complaints, than you are from people with really thoughtful responses. Not that those don’t come and those are valuable and I love getting those, but you get many more from people that just have really bizarre. I mean I could list probably for hours to crazy things that people send me that they’re mad about, you know, [00:24:50] Nathan: Is there something specific that you do? Like one thing when I get those replies, if they’re just like completely off the wall or abusive or something like that, I just scroll down and then click their unsubscribe link because, you know, they’re never going to know, and then I just have to show up in their inbox [00:25:07] Dave: Right. [00:25:08] Nathan: There’s something that you do. [00:25:09] Dave: That’s not a bad strategy. I like that. I do do that occasionally for sure. occasionally I’ll just go to Gmail and just, create a filter for that email to automatically go to my trash. if it’s like a hardcore right-winger, that’s telling me how stupid I am about ivermectin and that, you know, people should be taking horse dewormer and I’m just not getting the truth. And that Trump is awesome and that, Whatever. I usually just delete, honestly, because I don’t see a big benefit to replying to somebody, especially if it’s like a rabbit email, you know, they’re looking for a reply, they want the conflict. A lot of people sleep easy with conflict. That’s one of the lessons of the internet that I learned when I was first starting on the internet, you know, David edix sort sorta became popular because somebody that had a blog with a similar name, that I hadn’t heard of, complained that I sort of stole his name because his name was also Dave. And I had got like, probably about three or 400 emails saying, you know, with expletive saying what a horrible person I was. And I also got about 3000 subscribers and at the time I had about 30, so. I didn’t know how to respond. I felt like, wow. Number one, I didn’t know that guys had the product with the same name. Number two. My name was different enough. Number two or three were both named Dave. I mean, who cares? You know, and plus I don’t want to be attacked by anybody. So your first reaction is to respond and a slightly older, although not noticeably these days with my gray beard, slightly older friend of mine who had been in tech a little longer, said, don’t respond. This guy lives for conflict. You guys are going to fight. There’s going to be this public thing. You’re going to be up all night and he’s going to never sleep so easy. So, I took that to heart and didn’t respond. And I, I think about that a lot when I get rabid emails from people, Mike exception, actually probably my weak point really is from, more my side of the political spectrum, where people who are generally liberal, but are just so extreme for me. In terms of being triggered or having a joke, be every joke, be inappropriate. That those people, I actually do feel like I want to respond to because, I, I don’t think I can really motivate or move, somebody who was on the opposite end of the spectrum and is sending me hate aggressive, hate mail, but maybe I can move somebody who’s just a little bit different than me, or a little bit more extreme. I will respond to those, although I’m usually sorry. The one other thing I always respond to is if people have been reading, they say, oh, I’ve been reading you for years. And, I wanted to ask you a couple of questions about this book that you wrote before ordering it. And I’m like, just order the damn book. that’s probably my most common email to people these days. It’s actually remarkable how many people says, wow, I I’ve been reading you for years. I share you with all my friends. something, when my sons come home from college where it’s always talking about, Dave said this, Dave said that, before I buy your book, I just wanted to ask you a couple of questions to make sure it’s going to be for me. I’m like I worked on something for an hour and it’s like, your family is talking about it. What, just by the thing I worked on for a year, you know? So those kind of things, personal frustration, I respond. [00:28:37] Nathan: Yeah, that makes sense. okay. I’d love to talk about the book some more, but before we get into that, there’s two things I want to talk about. The first one is like, how do you measure success for the newsletter? What’s the thing that you’d like to, cause I don’t think it’s, you’re pursuing the monetary side for this. It sounds like the monetary side comes from investing and, and then what’s success for the newsletter. [00:28:59] Dave: I mean, I have had right now, I I’m just marketing my, my own stuff. And during the pandemic I marketed non-profits, but, that had to do with either the pandemic or, the democracy issues that we were facing. but I have made decent money from selling straight sponsorships. Year-long sponsorships to people, which I highly recommend. I think some of the ads that people put into his letters that go by clicks or whatever, unless you have a massive audience, it’s hard to make much money, but if you pitch to some company that is a like-minded brand, Hey, you’re going to be my only brand for a year. And anytime you have special events, I’m going to mention it. Then you can say, okay, you have like, you know, 20,000 readers or a hundred thousand readers that can make a difference to a brand to say, yeah, it’s like a rounding air show. We’ll give you 20 grand or a hundred grand or wherever it comes in there that you can actually make a decent. Living in terms of writing. So that always worked better for me, but no, my, my internet life is really all about narcissism and, clicks, you know, the dopamine, I just want reads. I’d rather you subscribe to my newsletter than pitch me your startup company. I just, that’s what I want the most. So more numbers, more opens, more reads, more subscribers. And unfortunately that’s probably the hardest thing to get also, especially in a product that is sort of viral. I think newsletters are sort of viral, but it’s better if you have a team and some tools to really get it going. That’s, you know, sites like the Skimm morning brew and the hustle. They have teams that are really growth hacking and focusing on that and having rewards programs and ambassador programs. The reason you see that is because. Newsletters themselves are not really inherently that viral. Yes. Somebody can forward it to one person or whatever, but it’s not as viral as a lot of other forms of content where you can click a button and share it with all of your followers, like a Facebook post or a tweet. So yeah, the thing that matters to me most is probably the hardest to get in the newsletter game, but that’s the truth [00:31:10] Nathan: Yeah. Well, I think the, the point on like newsletters don’t have a distribution engine. There’s no Facebook newsfeed, YouTube algorithm equivalent for newsletters. And so it really relies on either you posting your content somewhere else, whether it’s Twitter or YouTube or medium or something that has an algorithm or your readers saying like, oh, I read Next Draft. You should too. There’s not really something else in there. Have you looked at, or I guess if you have thoughts on that, you comments on it, but then also have you looked at launching an ambassador program or, or an actual referral program? [00:31:44] Dave: Yeah, I’ve thought about him. And now over the last year, there’s been a few tools that have come out a few. I think X people from sites like morning view Ru, and some other sites that have sort of perfected some of these marketing programs have, sort of come out with these tools. I’ve messed around with them a little bit. Some of them still require I find, some technical ones. so I, I have like an engineer who works with me on Next Draft, like as a freelance basis every now and then, but it’s not always easy for me to launch stuff that requires a lot of a moment to moment technical support, and management, because it’s just me using a lot of, they’re customized, but they’re over the counter tools. So I’ve thought about a lot of them, but I really haven’t tried it that much. I want to though I do want to do that. I would like to do one of those programs, especially where you get credit for referrals. I think that’s the best kind of model. So there’s one called spark loop. [00:32:51] Nathan: Yeah, we actually, I invested in spark loops, so we [00:32:54] Dave: Okay. [00:32:55] Nathan: Decent portion of that business, so good. [00:32:58] Dave: Oh, nice. Yeah. That one, if it was just slightly easier, I know that it’s probably difficult to make it easier because, there’s so many pieces. They have to have your subscribers. I have to have my subscribers, but that is, does seem like a good product. And especially if they can, I think expand into like letting a person sell a product or whatever, get credited for sharing products that can be even bigger. But yeah, that kind of stuff is really powerful for sure. And I, I do want to get into that. it’s more just inertia that I it’s just a matter of sitting there for the, an amount of hours that it requires to get it going. But I do think that’s a great thing for newsletter writers to do, and I’m pretty surprised that more newsletter platforms don’t build it right in. I think that’ll probably change over time too. Maybe you guys will get acquired by. [00:33:48] Nathan: Yep. No, that makes sense. I know for convert kit, we wanted to build it in, it looks at the amount of time that it would take and then said like let’s invest in a , you know, and then roll it into our offering. [00:33:59] Dave: Yeah, it’s hard. It’s hard not to take that stuff personally, too, you know, for people that do newsletters, you think you’re going to put a thing on there and say, Hey, you know, it’s just me here and you always read my newsletter and click. I know you love me so much. Can you just do this to get a free whatever? And it’s, you know, sometimes not that many people click, you know, or other times like they click just as long as there’s the free item. So there’s a lot of ways to get depressed. Like I had things where I say, Hey, the first a hundred people who do this, get a free t-shirt or whatever next strap t-shirt. And those hundred people will literally do what I asked them to do in like 34 seconds, you know? And then it like stops after that. The next time you ask them, if there’s not a t-shirt. But it’s not you, you know, if you go to a baseball game or a lawyer game or whatever, you know, people sit there, they don’t even cheer as much for the team as they cheer when the guy comes out with the t-shirt gun. So it’s like, people love t-shirts more than they’re ever going to love you. And you have to go into these things with that in mind. there’s no way, even if it’s, even if you’re XX large and the t-shirt is, you know, petite, it’s still worth more than you are. And the average mind of the average person. So you have to go into all of these things thinking, I hope this works like crazy, but if it doesn’t tomorrow, I open up the browser and start writing. [00:35:19] Nathan: Yeah. That’s very true. I want to talk about the growth of the newsletter. I was reading something, which I realized later was back in 2014, that you were at around 160,000 subscribers. I imagine it’s quite a bit larger than that now. And then I’d love to hear some of the inflection points of growth. [00:35:35] Dave: Yeah, I’m not, I’m not sure. I might’ve, I don’t know if I lied in 2014, but now I have about, [00:35:41] Nathan: Quoted it wrong. [00:35:42] Dave: No, you might’ve got it right. I might’ve exaggerated. Maybe that was a including app downloads and a few other things. Yeah. I have about 140,000 or so now, so that would be making that a pretty horrible seven years now. You’re depressing me. Your listeners should just stop, stop writing newsletters. It’s not worth the depression [00:36:02] Nathan: Just give up now [00:36:03] Dave: Yeah. And by all means if Nathan goals do not pick up. no, yeah, I probably have it 140,000 on newsletter. Made my newsletter. It’s hard to believe in this era of newsletters actually, but when I first launched Next Draft, I noticed that even people who would send in testimonials or that I would ask for testimonials would say, basically something to the extent that even though email is horrible, this is the one newsletter I I’d sign up for whatever. And I kept thinking, man, that’s a bummer that I’m starting out at this deficit, that people have a negative feeling about the medium. So I, since then I’ve always made it my goal to. Have the content available wherever people are. So the newsletter is certainly the main way that people get next job, but there’s an app for the iPhone and the iPad there. That’s the first thing I launched because I wanted to have an alternative for people who just hate email too much. So now you go to the landing page, it’s like, Hey, if you don’t like email, here’s another version. I have a blog version. I have an apple news version. I have an RSS version. I’m lucky enough to have a really good, WordPress custom WordPress install that I just push one button and it pushes it out to all of those things. But I am, I’m a big proponent of just meeting people where they are. even, as an example, I recently launched a sort of a substance. Version of my newsletter under the radar. but when I redo my site, I’m going to make that more clear because if people already subscribed to like 10 sub stacks and they’re using their aggregator and they already have their email saved and they can just click a button, it’s like, I don’t care. You know, it takes me five extra minutes to paste my content into sub stack. So I just want the reads. I don’t really care about how they read it or whether they read it. [00:37:55] Nathan: Yeah. That’s fascinating. So then let’s shift gears a little bit. I want to hear about the book. first I wanna hear about the title. Would you have it on your shirt? [00:38:03] Dave: Yeah. That’s pretty embarrassing. I swear. I didn’t know it was video today, but I do have a shirt [00:38:06] Nathan: You’re good. [00:38:07] Dave: Otherwise I wouldn’t have worn. This would have worn my Nathan Barry’s shirt. [00:38:12] Nathan: That’s right. It’s in the mail actually. It’s [00:38:15] Dave: Oh, good, good. [00:38:16] Nathan: Big photo of my face. [00:38:17] Dave: Yeah. Convert kit. My wife converted to Judaism before we got married. So I have my own convert kit. [00:38:23] Nathan: There you go. Exactly. so I want to hear like what the book is about and then particularly where the title came from, [00:38:30] Dave: Sure. [00:38:31] Nathan: It made me laugh a lot when I heard it. [00:38:33] Dave: Oh, cool. That’s good. That’s a good start then. yeah, the title comes from, in July of the, of 2020 when the pandemic was really setting in and becoming a reality for everybody. this amusement park outside of Tokyo in the shadow of Mount Fuji called the Fuji queue. amusement park reopened. And they found that even though everybody w everybody was wearing masks, people were screaming so much on some of the rides, especially the Fujiyama roller coaster, which was their scariest ride, that they were worried about germs spread. So they sort of put signs around the amusement park saying, no screaming, you can come, you can ride and have fun, but keep your mask on adults scream. And it sort of became a little minor social media thing in Japan, where people were sort of making fun of them like, oh, they’re telling us not to scream. How can anybody not scream on the Fujiyama roller coaster? So in response, the, park management had to have their executives with perfectly quaffed hair and tie and colored shirts and masks on ride the roller coaster with a webcam facing them the whole time without moving a muscle. Cracking a smile or grimacing or screaming. And then at the end of the ride, when the rollercoaster stops, it says, please Scream Inside Your Heart. And that was always my favorite meme of, 2020. It went really viral. There was like t-shirts. aside from mine, there were posters memes. It sort of went crazy for about a week or two, which by 2020 standards is a pretty long time for a meme to last. And I just thought that made sense as a title for the book, because that’s sort of how we felt, all year that I dunno if we were screaming in our heart, but we were certainly screaming into a void. Like no matter what we sat or yelled on social media or complained to our family members or friends, it just kept getting worse. The year just kept getting worse. And, so the idea is that this book sort of, now you’re free to sort of let out the scream. And the book is it’s about 2020, certainly, but it’s really about the issues that led us to 2020. There’s a ton about our relationship to media and including my own relationship to media and how that got us into trouble. Some of the stuff we’re talking about today, how, technology has impacted our lives stuff. I’ve been sort of thinking about it, writing about for the last few decades, and a lot of the political hate that emerged. and, but it’s all within this time capsule of the craziest year. [00:41:12] Nathan: Yeah. Yeah. And so that’s coming out early in November, November 2nd. so you’re, it looks like you’re just starting the, you know, mentioning the promotion tour and all of that. is there a big, big push that comes with it or are you kind of, I, I’m always curious with people’s book launches, what strategy they take. [00:41:30] Dave: Yeah. I mean, I’m a newbie, so it’s, the whole process has been interesting to me working with a publisher, working with others, is not my forte. so I got used to that or I’m getting used to that and they’re probably getting used to it also because working with grouchy 50 something in these is probably not ideal, but, yeah, I’ve just been promoting it so far in Next Draft, but I’ve been doing, I have a PR company that’s helping me and I’ve been doing a ton of podcasts and I’m marketing it to my own readers. And then as it gets a little bit closer to the November 2nd date, I have a lot more stuff planned rut, a lot of influencers have early copies of the book, and hopefully they’ll promote it. And, I’ll call out a few favors from bloggers and hopefully newsletter writers. I feel like that should be my in theory. That should be my secret weapon because, in addition to being fun and creative, nothing moves traffic, except maybe Facebook, nothing moves traffic more than newsletters. I know a lot of people who run e-commerce companies and newsletters are always second, if not first, in terms of traffic drivers. So, I really think that, if some of my friends out there at morning brew in the hustle and the scam and all these other sites that sort of, have surpassed my size by quite a bit, put the word out that, one of their fellow warriors is, has a book out. That’ll probably move the needle even more. The media, I’m hoping to get stuff like that, but I really don’t know. I’m trying not to get my hopes up too much because, unlike a newsletter, it’s not just one day’s work, you know, you like worry about one word or one sentence in a book for like three weeks and then you put it out there and people are like, oh yeah, I’ll check it out sometime. Thanks. So, you know, that’s, you know, whatever that’s life as a, you put yourself out there, that’s how it goes. So I’m hoping it sells well. And, the more people that get it, I think some people, their first reaction is, oh my God, 2020. I don’t want to relive that again. But, hopefully people who know my brand and those that they share it with, know that it’s, you know, there’s a lot of humor and there’s, it’s probably 30 pages before we even get into the first event of 2020. So it’s, there’s a lot more to it and it’s sort of fun and crazy and tries to have the pace of a roller coaster. that was the other thing I took from the Fujiyama roller coaster. [00:43:59] Nathan: Yeah. So one thing that I’m always curious about with people who have like a prolific newsletter, you know, in your case of writing every day, and then like, for a lot of people, that would be a lot to handle of staying on top of a daily newsletter. And then you’re writing a book on top of that. How did you schedule your time? Were you blocking off like, oh, these afternoons are specifically for book, book writing. Cause you turned it around relatively fast. [00:44:24] Dave: Yeah. the newsletter is sort of like a full-time job. People always ask me, you know, when do you work on, or how many hours do you spend on it? I mean, I’m, I’m always looking for news, whether it’s on Twitter or friends, emailing me stuff or texting me stories, or just in conversations with people to see what they’re into or what stories are interesting them or what I’m missing. In terms of actual time spent like where I’m dedicating time. I probably do like about an hour every night, because the story has changed so quick. So I’ll do an hour of looking for stories every night. And then the next day I sort of lock in from about nine to one, usually, or nine to 12, where I’m finding stories, saving those stories, choosing what stories I want to go with and then actually writing the newsletter. All of that takes about anywhere from like two and a half to four hours, depending on the day I go pretty fast. When it came to the book, that was tricky. It was actually more emotionally tricky because like I said before, I was like, had to go back and write about, you know, Briana Taylor while I’m living another horrible act, you know, or even more so the Trump, you know, one crazy Trump thing and another crazy Trump thing and seeing the pandemic getting worse and worse. So that was stressful. But I found at the beginning I would try to write a lot at night and that was okay. But I found actually if I just kept going, in the day when I was already rolling and had written the newsletter and I was already in the group just to add on an hour or two to that was actually easier and more effective for me than trying to get going. But that’s just me. I mean, I just go by my it’s almost like my circadian rhythm or something like that, I almost never eat or consume anything before I’m done with next job except for coffee. I would keep that going, you know, once I would like, sort of have a sandwich or whatever, then it’s like, oh, let me just take a quick nap and then whatever. So, yeah, I tried to just keep it going. I always find the more consistently busy I am, the less I procrastinate. And if I take a day off or I take a few hours off, even then, between writing, it just, it takes me longer to get going. [00:46:37] Nathan: Yep. That makes sense. The habit that I’m in right now is starting the day with 45 minutes to an hour of writing and that’s working much better for me than like slotting it in somewhere else. So I think like w what I hear you saying is like, experiment and find the thing that works well for you. [00:46:54] Dave: Yeah. I mean, if you’re going to start experimenting almost every writer, I know not like newsletter writers, but just general writers, all do what you just described. They sort of pick a time in the morning and they get their output done. then the rest of the day, if ideas come to them or whatever, they jot it down, but they’re sort of powering in that morning hours. [00:47:13] Nathan: Yeah. [00:47:14] Dave: That’s probably a good one to try. Although, you know, some people just do it better at different hours. I’m sure. [00:47:19] Nathan: Yeah. another thing I realized, I’ve always you for years, and until we got on this video call, I had no idea what you looked like. and which is kind of an interesting, [00:47:28] Dave: Well, I’m sorry. It’s by design. I have a face for Panda. [00:47:32] Nathan: Tell me more about, well, I guess two sides, one, has there ever been an interesting interaction? You know, because you’re like, Hey, I’m, I’m Dave and people are like, I wouldn’t have ever recognized you. Or has there been any other benefits and thought behind, you know, why it have an avatar? [00:47:49] Dave: If by interesting you mean horrible? Yes. There’s been many interesting interactions with people. I mean, before, before I had my current, avatar, which is, pretty awesome, actually, a guy named Brian Molko designed it. I had this incredible drawing of a character that looked like me that, had sort of ether net, Machinery and cord going into his head and it was like me, but my head was actually lifted. The top of my head was lifted off and you could see all this machinery and it was an incredible graphic, by this guy named Sam Spratt. Who’s now done, album covers and book covers. He’s like a super talent. If you want to follow somebody fun on Instagram, he’s just incredible. And it was a drawing, even though it looked photo realistic. And I used that for a while and then I would go places and people would be like, you are so much fatter and grayer than I imagined. And so instead of having Sam sort of ruin his artwork, I went back with the more, cartoonish or animated, avatar. So since then I don’t get too much of that, but, that was a good move. Although that’s the best thing about avatars and the internet is that your avatar never ages. It always looks the same. It stays the same weight. My avatar never overeats he exercises right here. Angie really gets along well with others and doesn’t have any kind of social anxiety either. So he’s pretty cool. Yeah, it goes a little downhill with me in person. So [00:49:21] Nathan: Yeah. So is it, that’s something that like, it gives you some distance between you and readers, or it gives you some anonymity that, you know, you don’t want to be recognized in the streets? [00:49:32] Dave: No, no, it’s, it’s, basically just what I described. It’s like, I literally prefer the, the attractiveness of my avatar versus me, but also actually my avatar is really awesome. my logo, so it’s also iconic and scalable. so it looks awesome on t-shirts even people who don’t know what Next Draft is when they see, by son wearing his t-shirt, whatever, it just looks awesome. So that that’s that’s as much of it as anything. I thought your response was going to be mad. You seem perfectly attractive to me. I don’t know what the issue is, but no, you went with, am I doing that for some other reason? Yeah. So, I get this all the time. Cause my wife is a very attractive person also. So when people meet me, they’re always like, whoa, we were once a very famous celebrity came up to me and I said, oh, I’m Gina’s husband. And she was like, wow, you did well. Oh, you know? So I’m like, thanks a lot. That helps. So just gave her a picture of my, my icon and walked away. [00:50:31] Nathan: Then that worked. I’m sure that she has it framed in her office, from now on. it’s just interesting to me. You’re you’re sort of at this intersection between personal brand and, like media brand. And I think the avatar helps push you over into the media brand side. and I don’t have any real commentary on it other than I find it interesting. [00:50:53] Dave: Yeah, no, I think there probably is some of that. I I’ve never really been a fan of using my actual face, or my actual person as a logo. I love the process of designing or working with people to design logos and taglines and all that. But yeah, probably at some point there was a, a goal with Next Draft to make it seem bigger than it is. I know a lot of people that are solo operators. They regularly say we, when they’re talking about their brand to make it seem bigger, I actually think that’s sort of been flipped on its head though. in the last few years where so many people are coming into the space, it’s very clear that what they’re doing is leaving a big brand, leaving a we and going to an eye. And I think it’s actually a selling point in a lot of ways. So, I mean, I, I still get a lot of emails that say, I don’t know if anybody at Next Draft is going to read this email, you know, or if you do, can you get this message to Dave? He’s an asshole or whatever. And it’s like, I’m the only one here, you know, or the other one I always get is when I email back to people that go, oh, I can’t believe you actually emailed back. I didn’t think this would get to anybody. It’s like, you hit reply. And it had my email, like where else would it go? Exactly. You know? But I think actually having people thinking of you as a person, instead of a brand, Is a benefit today. Whereas if you would ask me when I was younger, I probably would have said, make it seem like you have a big company behind you. [00:52:24] Nathan: Yeah. And I think that that indie shift overall, like people are looking for that. [00:52:29] Dave: Yeah, [00:52:29] Nathan: Want to ask about the intersection between your investing and the newsletter. like, are you still actively investing today and doing author. [00:52:38] Dave: Yeah, yeah, no, I, I still invest a ton. I usually follow along with people who are a little more in tune with today’s companies than I am. I don’t really go out there and brand myself as an investor much, but I’ve been really lucky. I have very little intersection actually, if any, with my newsletter and my investing and I definitely want people to. To think of me as a writer first, for sure. Not as an investor who has this hobby, because that’s definitely not in terms of time or passion, the reality. but I’ve been really lucky over the years that, I’ve invested with people or co-invested with them that were cool with me. branding myself as a writer first, but still looking at deals that came through their brands because they were branded as BCS or investors or angels. That’s probably a bigger deal now than when I first started. There were like five angel investors, basically. Nobody really did small, early stage seed deals. you know, I mean, we all knew each other that did it and now there’s like thousands of them. So you really have to be either a really pretty well-known entrepreneur or you have to. Sort of attach yourself to our organization or two who are really branding themselves well, getting out there and building a stable of companies, [00:53:58] Nathan: Yeah. [00:53:59] Dave: It’s pretty different, more, much more has changed about that than the newsletter game, actually, which is pretty much the same as it was the day I started actually. [00:54:07] Nathan: Are there a few of those I’m curious who are a few of those, people that you would tag along with, you know, when they’re investing where like, oh, this person puts money into something I’d like to be right there with them. [00:54:19] Dave: I mean, I have some people that are like entrepreneurs and former entrepreneurs that do it, and if they like it I’ll do it. but generally I co-invest with, at any given time, a different group of people, used to be a larger group. When I first started out, my whole investing career, I’ve co-invested with this guy named Bob zip who’s much smarter and much wiser than I am about all things business and. Startup world. So that was really great. And he used to work at a company called venture law group in the first boom, and they represented Google, Hotmail. eGroups all the big, huge, early internet companies, and so he really knew the space well. And when he became, I used to get deals from him. That’s how you used to get deals actually was by a couple of law firms that focused on startups. I’ve been co-investing with him all along and he’s been generous enough to, he left the law firm a long, long time ago and became an investor primarily. And he had a fund and was well-known guy and well-respected guy. So I got to sit in when he would hear pitches. and we sort of, we weren’t investing together out of the same fund, but we would sort of make our decisions together. And we still do that a lot. these days, I almost always follow along with a guy named run-on barn Cohen and a really good friend of mine. He was for many years at WordPress, basically, most of the things that make money at WordPress, he did. and now he’s a investor at a VC called resolute. If anybody’s looking for a good VC, he’s like incredible, like Bob zip much, much smarter than I am about this stuff. Unbelievably ethical, great business sense. Great technical sense. so I mostly just follow him. So if he does something that’s usually good enough for me. And if I see something that I think it’s good, I’ll pass it along to him, but it’s mostly that, but I’ve been really fortunate. I can’t express that enough, that I’ve been able to invest in companies without having to spend all of my time, branding myself as an investor. That’s just been unbelievably lucky. So, I’ve been able to focus a ton of my energy on my six. [00:56:31] Nathan: That’s right. I’m writing a newsletter about the news. I guess, as you’re looking to grow and continue on, right? Like the next phase of readers and, and all of that, since we can just say directly that we’re all narcissists and we do this for the attention. what’s what’s sort of that next thing that you’re looking for, it’s going from 140,000 subscribers to say 200,000 and beyond. [00:56:54] Dave: Yeah, well, I’m, I’m hoping that, I’m not just trying to sell my book here. I’m hoping that the book and the newsletter will sort of have, a coexistence with them because the new the book is really an extension of the brand and the brand is that icon to Next Draft. So I’m hoping that the tricky part about writing about marketing a newsletter, like we discussed earlier, there’s not really a natural virality to them. So. You Have this piecemeal growth from people telling each other or their friends or forwarding it to somebody or maybe occasionally tweeting or sharing a Facebook link. Oh, you should check this out. But it’s all sort of small little blips. If you get a news story or a big blog story about it, or another newsletter recommending you, that’s probably the fastest way people grow these days is by, co-sponsoring each other’s newsletters or co-promoting them. Those big hits are more rare and they usually require like, I’ve had a ton of stories written about Next Draft, but most of them a long time ago, because it’s basically a similar product to what it was when they wrote about it the first time. So they’re like, Hey, I’d love to write about it, but what’s the hook. What’s the new thing, you know? so I’m hoping that the book provides that emphasis. It’s like, we’re doing now a ton of people who may by either been on a podcast in the past, or they’ve wanted to do a podcast with me say, okay, now’s a great time. I’d probably want to move your book and, we can set something up. So it’s sort of as an impetus. So I’m hoping that that will be the next big newsletter thing that most, most people who write about the book will also write about the newsletter and the two things can sort of grow together. [00:58:35] Nathan: I think that’s spot on. [00:58:36] Dave: That’s in terms of, you know, marketing and promotion, otherwise, I do want to try, one of these referral programs because people definitely do like products. And, I am lucky that my icon looks really good on shirts so that people actually really want them. And I have a great designer named Brian Bell who makes all of my shirts. [00:58:58] Nathan: There’s something like when creators thinking about products, often if you spread yourself too thin, you’re like into the newsletter, the book, the podcast, and like the 14 other things that you could make all at once you sort of hinder the growth of each thing, but then if you really build one of them up to a significant level, then at that point it can start to stall out and by shifting to another medium or have it like launching another product in this case, the newsletter to a book, then that book can have a bunch more momentum that feeds back into it. And so there’s just sort of this interesting balance of like, no, When to like, keep pushing on the thing that you have versus when to add the next thing that like, then they feed off of each other and go from there. So I think you’re doing it with good timing. [00:59:45] Dave: Hopefully it’ll work. All that kind of stuff is the tricky part of doing this stuff. Especially stuff like podcasts and newsletters that are—it’s really a ton of word of mouth, unless you get lucky and get some press, and word of mouth is just slow. There’s some point where you’re going to hit a tipping point where you’re going to go from five or 10,000 to like 50,000 much quicker, more quickly because instead of three people going home and saying, “Hey, did you ever hear of this newsletter?” there’s like 30 people going home and saying that. But, even with that they hit a plateau, and then you figure out what’s the next thing. That’s why doing something you’re into is so important. And I don’t think it’s bad to try those other mediums or stretch yourself out, because you never know you might’ve been writing a newsletter three years, and then you do a podcast and it catches on. For some reason, you’re like awesome. Less typing, more talking, let’s go. So, but it’s tricky. I wish I was better and had better advice for people on promotion and marketing. I’m not awesome at it, and it’s not in my nature. So, begging for favors or telling people, even in my own newsletter, to buy my own book is very painful for me. I’m very sensitive to criticism about it. So, if people just all bought it and then made everybody else buy it, that would be a huge relief for me. [01:01:13] Nathan: That would be great. Well, along those lines, where should people go to subscribe to the newsletter, and then follow you on your preferred channel, and then ultimately buy the book? [01:01:24] Dave: I don’t want like two or 300,000 people taking my site down. So let’s go with if your last name starts between A and M you can start by going to NextDraft.com and sign up for the newsletter there. Or, you can also just go to the App Store and search for Next Draft. If you’re N through Z, you can start with the book, and that’s at: PleaseScream.com. It has links to all the various audio, and Kindle, and hardcover versions. [01:01:50] Nathan: That’s good. I liked how you split the traffic, that way there’s no hug of death, and we’ll do well there. [01:01:57] Dave: I don’t want to get fireballed. [01:01:58] Nathan: That’s right. Dave. Thanks for coming on. This was really fun. [01:02:01] Dave: Yeah, thanks a lot for having me.0 comments0
- 049: Jessica DeFino - Using Musicality and Rhythm To Dramatically Improve Your WritingJessica DeFino is a freelance beauty journalist living in Los Angeles, California. For the past seven years Jessica has been writing, researching, editing, and publishing about the beauty and wellness industry. Her work has appeared in Vogue, The Cut, Fashionista.com, Cosmopolitan, Marie Claire, Business Insider, SELF, HelloGiggles, Harper's Bazaar, and more. Before starting her career as a freelance journalist, Jessica worked as a beauty writer for The Zoe Report. She was Director of Communications at Fame and Partners, and worked as a ghostwriter for Khloé Kardashian and Kendall Jenner. Jessica earned her bachelor’s degree in Music/Business Songwriting from the Berklee College of Music. Jessica’s music degree brings a unique perspective to her writing. It infuses each piece with lyrical qualities of storytelling, flow, and connection to her audience. Jessica also publishes a bi-monthly beauty newsletter called The Unpublishable, where she shares “What the beauty industry won’t tell you — from a reporter on a mission to reform it.” In this episode, you’ll learn about: Making lasting connections with your audience Why understanding music and rhythm makes your writing better Capturing and keeping your readers’ attention right from the outset The dangers of cross-posting your content across social media Links & Resources Vogue Magazine Allure Harper's Bazaar Ursula K. Le Guin RhymeZone Ali Abdaal Jessica DeFino’s Links Follow Jessica on Twitter The Unpublishable Jessica’s Instagram Episode Transcript [00:00:00] Jessica: I started writing as a songwriter. The musicality of something is very important to me. So I’ll read my own stuff out loud sometimes. I feel when people can read something and there’s a clear flow and rhythm to it, and the words melt into each other sound nice next to each other, it locks them into the content early on. You want to keep reading because if you stop reading it’s like you’re breaking this rhythm that you’ve started. [00:00:34] Nathan: In this episode I talk to Jessica DeFino. She’s a journalist covering the beauty industry, but she tends to take an approach that’s not as popular with sponsors and publishers, because she’s anti a lot of their products and a lot of the nonsense that is put into the products and the marketing behind it. She’s taking a critical angle and she’s well loved by her readers because of it, but maybe not so loved by the big brands. We talk about how that came about. We talk about her writing style, her approach of using her background in song writing and going to school for songwriting to have a better, more interesting writing style. She gives some tips along that angle, talking about how she launched a newsletter last year and growing that to 9,000 subscribers. How that is a backbone for the rest of her work she does in journalism. It’s a great conversation. So, let’s dive in. Jessica, welcome to the show. [00:01:28] Jessica: Thank you so much for having me. [00:01:29] Nathan: We’ll jump around a whole bunch, but I want to start on the launching of your newsletter. What was the moment when you started to think, okay, I want to actually run a newsletter and start to control my own audience? [00:01:44] Jessica: I had been toying with the idea for a while, and then I think it was, April, 2020, right after the pandemic, where I had gotten into a situation where—I’m a freelance reporter—I had four freelance stories out when March happened, and Coronavirus lockdowns happened and everything was up in the air. The company severed ties with all of their freelancers and basically gave these four unpublished stories back to me, and gave me a kill fee. So it was like I had reported out these whole stories. I had spent months on them, and now I had nowhere to put them, and I gave it about a month of pitching it out to other alums. There weren’t any takers because media was in such a precarious position at the time. Finally I was like, maybe this is the opportunity I’ve been waiting for to launch a newsletter. and I decided to call it The Unpublishable because I couldn’t get anyone to publish this. And yeah, it’s been going, almost like every other week. [00:02:50] Nathan: Nice. Yeah. It’s interesting how these unfortunate moments result in something that’s like, okay, this is actually either a good thing now, or hopefully going to be a good thing soon, but it starts with difficult times. [00:03:05] Jessica: Yeah, exactly. I wanted these pieces to be big. They were stories that I thought were important to tell, and I really wanted them to be in a major outlet. Sometimes with media, you can’t sit on things for very long. It was like, I maybe have two more weeks before they stopped becoming relevant. [00:03:23] Nathan: Yeah. So for context, for anyone listening, what were some of those stories as an example? [00:03:27] Jessica: The first story I published with a piece called “Where are All the Brown Hands?” It was a look into the overwhelming whiteness of the top nailcare companies in beauty. If you would look at their Instagrams or if you would look at their websites, everything was modeled on white hands. As a beauty reporter, when I have to source images for the stories, I don’t want to just be showing white hands. If I’m writing about nail trends or whatever, and it would take me hours every week to comb through places and try to find the trend I was speaking to on a person of color. At one point, I was like, why is this happening and how come it’s so hard? This should not be hard. So, I wanted to do an investigation into it, and just like that the whole process had already taken six months. I was like, you don’t know what’s going to happen in this story. It might be scooped. It might be written by somebody else. It might be irrelevant in another month or so. So, I really wanted to get that out there, and that started it. [00:04:31] Nathan: When you publish a story like that, and you’re used to publishing for a major beauty publication, but you’re publishing it for yourself. What did that look like? What was the process of saying, I have this story that I’ve worked on for a long time, and I have a brand new newsletter and all at once. How did you bring that to life and pull the audience together? [00:04:52] Jessica: Well, luckily at that point I had a mask, a little bit of a social media following just from my work on work, like major publications. Like I had been writing for Vogue and allure. Harper’s bizarre. And I had been pretty diligent about building up a social media audience. So I had a pretty sizable, amount of readers just from Instagram. And a couple of years prior, I had like tried starting my own beauty content platform, but I never really had the time to dedicate to it. But I had a small email list from that, from when I was still doing it. So I kind of like funneled all of that together under this new umbrella of this is going to be like my personal reporting newsletter and I kind of got the word out on Instagram. So it ended up reaching like a surprisingly large audience for something that was like a first-time newsletter. [00:05:44] Nathan: Yeah. So if you don’t mind sharing how many subscribers were like to that first article? [00:05:49] Jessica: I think that first article probably went out to like 1500 subscribers [00:05:53] Nathan: Okay. Yeah, but that’s you’re right. That, that is a surprisingly of like, here’s the first thing that we’re doing. And I guess it goes to show from right. Spending a whole career being known and, and building it in this space. And then, you know, you’re not starting from scratch when you funnel entity. [00:06:10] Jessica: Yeah, it, it had always been important to me to, not as important, but it was something I thought about to collect email addresses and to get social media followers, because my goal had always been to write a book. And I know that when publishers are looking at whether to buy a book from you, it matters what kind of audience you have and how many people you have on an email list. So even though I wasn’t sending things out prior to finally launching the newsletter, Collecting emails here and there. Just, just to have for the, for the book pitch one day. [00:06:42] Nathan: Yes. That’s something that I’ve always heard is, you know, from agents and friends who are authors and all of that, as they talked about the, the email as being the thing that the publisher is looking for, they’re like, Yeah, that sounds good. First question. [00:06:57] Jessica: Yeah. [00:06:57] Nathan: I mean, they use it as a proxy for how many copies can you sell? [00:07:01] Jessica: Exactly. Yeah. When I was pitching out my book, it was all about, Instagram. I, this was probably like two years ago now. and I couldn’t get an agent to talk to me until I had 10,000 Instagram followers. So that’s like, all I cared about for maybe a year, I was like, I don’t care. I’m not going to put effort into anything else. I just need these Instagram followers. [00:07:23] Nathan: Yeah. So you have 35,000 followers on Instagram now. what were the things that worked for you as far as growing that, that audience on it? [00:07:32] Jessica: Honestly, in the beginning, when I was like, I need to get to 10,000 followers, I was a little scammy about it. I did a lot of the like follow unfollow. So I followed a ton of people who were following accounts that were similar to mine. And kind of, and what you do with that is like, they see that you followed them, they check out your page. Hopefully they follow you back. If they don’t follow you back, you can like unfollow that person to keep your ratio looking good. [00:08:00] Nathan: So is that like going through and following like 50 people a day kind of thing or hundreds [00:08:05] Jessica: Yeah. I mean probably 50 to 200 people. Like I would spend probably an hour or two hours a day just doing. Stupid stuff like that, but I didn’t really care about, but I was like, I’ll do anything to get a book deal. If it’s following 200 people a day, that doesn’t bother me. And if at the end of the day, they’re looking at my profile and saying, Hey, this is somebody whose content I care about. I’m going to follow them. It doesn’t feel like bad or wrong to me. So I just did a lot of that [00:08:34] Nathan: Yeah, it’s a very small way, like small and non-intrusive way to be like, Hey. Do you want to pay? Like, you’re just sort of raising your hand and people either go like no, or they go, oh yeah, I’ll look at that for a second. What’s interesting is I think that a lot of creators started in that way, but probably now when they tell their story, they’re like, yeah. You know, I just, I just put out good content and then the content itself. And before you know it, I was, you know, internet famous, you know, [00:09:01] Jessica: I think that worked, it worked like 10 years ago, maybe even five years ago, but right now there’s just so much content out there on every platform. And I don’t think it’s fair to say that if you have great content, you will be successful on that alone. Like, I think you need more than that today. [00:09:18] Nathan: Yeah. So, so the following, people in the space, which we’d recommend, you know, regardless, what are some of the other things, on that quest to 10, that will. [00:09:27] Jessica: Yeah, I was falling up a storm. I was liking a ton of stuff cause that’s kind of the same strategy. Like sometimes Instagram too will phrase your account. If you like too many things or you. follow too many people. So I was getting into that. I did a ton of hashtagging at the time. luckily the, the area that I write to to beauty has like a very big and dedicated community on Instagram. So there are a ton of like beauty community hashtags out there that I was following and getting involved in and commenting and just really making my presence known in this community while at the same time posting my own content. That I thought had a very different point of view that would be intriguing to people. So once they saw that I was engaged, they were like, who is this person? And there was, you know, a lot of content there for them to, to delve into. [00:10:18] Nathan: Yeah, that’s good. In the last, episode of this show, I had a YouTuber on his name’s Ali doll and he’s got, you know, he’s built up to 2 million subscribers on YouTube, but he talked about that like back catalog that you have of when someone comes across your work for the first time, like seeing the back catalog and seeing it have a unique point of view. And I feel like. That would be the experience, you know, when you pop up in some little way. Okay. Another, you know, beauty, Instagram account, and then you come in like, oh, this is actually different. Has a unique point of view. So, I’d love for you to share. I don’t know what the, the short version of like the different perspective that you’re bringing to the beauty industry and what someone would notice when they come to your Instagram or your, newsletter. And they’re like, this is different. This is a, you know, [00:11:08] Jessica: Yeah. [00:11:09] Nathan: Challenging. [00:11:10] Jessica: I think the easiest way to put it that most beauty content out there is very fluffy. and very positive and very product heavy. and my stance is very beauty industry critical. and I, I say that I’m pro skin anti product. So I’m much more interested in how beauty applies to like your actual skin and your actual body and like the human itself, rather than this external product, you can apply some very focused on the science of how human beings work rather than the science of like a skincare and. [00:11:44] Nathan: Right. Okay. Is there an example that comes to mind of something where you’re like, do this? Not that. [00:11:50] Jessica: Yeah. I mean, probably the biggest example is just, I mostly tell people to stop using skincare, you know, period. End of story. Just, you don’t have to, our skin does all of that for us. You know, humans have survived millennia without pre bottled products, and there’s no reason why. In the past 30 years, our skin has suddenly evolved to need a 10 step routine. It doesn’t so, yeah, I just tell people, stop using it. And they’re shocked at the results all the time. [00:12:20] Nathan: I like that. I could see a conflict in. Message and business model in the industry. and your interaction in this. there’s a lot of money in the industry of obviously selling, I mean, any product, but especially a product that you need to buy every month or every three months or something like that. Like that’s a very good business. So have you had any, any conflict of publications not wanting to pick up your stories or any of those things as the publication is. You tell your people to not buy our sponsor’s products, you know, or something like that. [00:12:55] Jessica: Oh yeah. I mean, there’s been a ton of pushback and depending on what platform I’m writing for, I. See my work being edited in a certain way or softened in a certain way or a brand name being taken out. I’ve had articles be published and then the platform takes them down almost immediately because an advertiser has complained. I’ve had legal action threatened against me while I’m reporting for a story just for asking questions. yeah. Yeah. It’s that kind of stuff happens all the time because in beauty journalism, there is a huge. Conflict between what you’re supposed to be writing about and who’s footing the bill for that content, which is products and advertisers. And I think in the beauty industry in particular, there’s this extreme lack of objectivity where, you know, editors and journalists and influencers are all gifted product or taken on press trips. And. And given money to review products in a way that in any other industry, you wouldn’t be able to call that journalism. You know, there’s always gotta be some sort of separation there. Like a typical journalist is not allowed to accept gifts in the beauty industry. It’s the complete opposite. It’s like, well, how can you write about our product if we don’t gift it to you? So it’s, it’s a very weird space that is very reliant on gifts and money and advertising. [00:14:18] Nathan: So how has that changed as well as you’ve launched your own newsletter? I imagine you’re still doing plenty of freelance writing. Is that. [00:14:27] Jessica: Yeah. Yeah. I’m still, my, my thing is, is I try if I have a story I want to tell, I obviously want to tell it to the biggest platform possible. And then if I can’t get the story placed somewhere else, I will, I will tackle it for the news. [00:14:43] Nathan: Okay. So yeah. How has like, has the news that are helped? Like, for example, you’re trying to get us started placed and they’re like, sure, we’ll place it. But could we do this version of it instead? And, and you know, maybe you’re saying that like, no that’s okay. Whereas before the paycheck might’ve mattered more or how’s That. relationship? [00:15:01] Jessica: Yeah, that’s pretty much spot on. I, I didn’t really push back too much before, but now that I have. platform that like actually brings in, okay. Money for me. It’s not like if I say no, I don’t want that story published this way. It’s really not like I’m losing out on a paycheck anymore because I will make that up from my own subscribers. So, I think since I’ve launched the newsletter, there have been two instances of that where I’ve written a story for a platform have been uncomfortable with the edits and actually. And was like, no, I don’t, I don’t want to publish it this way. And that feels really good to have a little bit more control over, over what I want to say and the information I want to put out there. [00:15:45] Nathan: Yeah. I mean, you have even more, I mean, you, you always had agency, right. But now it’s like, you have an alternative instead of like, I’ll keep pitching it to someone else who might have the same objections or, or that kind of thing. On the business side what’s well, actually, maybe if we dive into the newsletter today, right? So that we talked about where I was at a year ago when we launched to, I just said, we, when you launched, I had nothing to do with my launch. There’s no Royal we in that are taking credit later. when you launched, you know, a year and a half ago, there was at 1500 subscribers. where’s it at today, [00:16:24] Jessica: I’m at 9,000 subscribers now. [00:16:26] Nathan: Right? [00:16:28] Jessica: But, I mean, I have a model where some of it is free and some of it is paid, so there are like different cohorts within the subscriber-based too. But like, I’m, I’m pretty happy with how it’s grown on the free side so far. [00:16:41] Nathan: Yeah. And so on the paid side, you’re charging $7 a month, or 77 a year. What was the thinking on the pricing there? Was that something that you like agonized over a lot or was that a, like, we’ll just go with something and see how it works. [00:16:54] Jessica: Yeah, I didn’t agonize over it too much. I started out at $5 a month and, after I got maybe my first hundred or 200 paid subscribers and I felt really good about like, wow, that feels like a lot. That’s like a good chunk of change I didn’t have before. And then when I was looking into the fees that were taken from like Stripe processing, from sub staff, I was taking home like closer to $3 per subscriber. And I was like for the time and attention that I want to give this project, I’m just not going to be making it. At $5 a month until I hit a certain number of paid subscribers. so I decided to bump it up to seven, just to sort of motivate myself to put the time and attention into it that I wanted to give it because if I wasn’t going to be bringing in like, actually $5 to me, it didn’t feel worth it. So by pricing it at seven, I get more like $5, which felt like a, okay, I’m happy with that number. now that I do have more paid subscribers, I am toying with the idea of, of lowering it because I feel like I feel like from, at least from my perspective, when I am subscribing to a newsletter, I subscribe to a ton of them. I’m much more interested to click. I’m much more likely to click pay and subscribe if it’s $5. And if it’s like six or seven or eight, [00:18:21] Nathan: You think about [00:18:22] Jessica: Eh, that’s kind of a lot. Do I care enough about this content to pay that much? But personally for me, $5 is like a whatever I’ll I’ll subscribe kind of thing. So I, I think I’m getting closer to the point where I feel like I have enough of a base that I can do that and hopefully reach more people. [00:18:42] Nathan: Right. Okay. I have so many questions here, but diving into the psychology side of when you’re deciding to subscribe to something, right? Cause everyone listening is Ryan newsletter and asking these same questions. Like, should it be $5? Should it be $20? Should it be free? Shouldn’t be $2. You know, like any of these things. And then they’re analyzing their own buying habits. And they’re like, but what if it’s a business versus a fitness versus, you know, any of these, like what category I’m in and what are those other things that you notice beyond price? When you as a newsletter consumer, I go to like instant subscribe versus like, well, think about this. How many articles have I enjoyed from the recent layer? Like that, tips it over to the other side. [00:19:25] Jessica: Right. Oh, I don’t know that there are that, like my personal revelations will be. relevant to people. I personally, just because I run a newsletter, I love to support. So if it’s anything that I’m like vaguely interested in and it’s like $5 a month or less, I don’t know why $5 is my cutoff, but also subscribe. And I’ll just see what it’s like for a couple of months. And if I don’t like it, Whatever I can always unsubscribe, but I just really love the idea of putting that abundance out there into the universe and just being like, I’m a little bit interested in this and I want to support this creator because I know what a, like a hustle it is. I’m sure the average, like newsletter consumer doesn’t really doesn’t really think that way. but for me, I don’t know. I love a good headline if it’s like a good quippy, funny headline, like I want to be reading. fun, critical content. There’s a lot of like heavy, critical content out there. and I love something that’s like fun and critical, so that’ll get my [00:20:27] Nathan: Yeah. There are things wrong with the world and we could get depressed about them, but that doesn’t [00:20:32] Jessica: Yeah, [00:20:34] Nathan: About fixing the things that are wrong with the world, [00:20:36] Jessica: yeah, exactly. Like turn it into a little bit of a, like the state of the world I feel is so bizarre. [00:20:43] Nathan: Right. [00:20:44] Jessica: Just so wild that we have set up the world the way we’ve set it up. Like everything that, that exists is just something that like some guy made up one day and we were like, okay, we’re going to go along with it. And I feel like there is a lot of humor in that. so yeah, I, I love looking at the depressing state of the world for like a bit of a jokey lens. So if I find anything like that, I’m like immediate. [00:21:09] Nathan: Yeah, that makes sense. And I think that’s where for anyone writing their content, like having that voice really matters. So it’s not just, you know, this is what you’re teaching or this is, the educational side. Or present the entertaining side. It’s like, okay. But how can you, how are you gonna make me feel as I read and consume this. [00:21:29] Jessica: That’s a great way to think about it. I think the difference, when I’m consuming like a newsletter versus the news is I don’t really know. I don’t concern myself with like tone or voice when I’m reading an article from like the New York times or the Washington post. but a newsletter is so much more personal. It’s like you’re getting into people’s personal inbox, it’s more of a one-on-one relationship. and I think it’s a great opportunity to play with your voice in a way that you really sometimes can not when you’re writing for a media plan. [00:22:04] Nathan: Yeah. So what are the things that you’ve done to practice that obviously you’ve had a whole career as a writer. And so, you know, as you’ve found your voice and the things that you play with, are there yeah. Little exercises or things that you play with or try on, or anything like that? Any, any tips for someone who’s also looking to like craft their own way? [00:22:26] Jessica: It’s as much of a tip, but I started writing as a songwriter. I went to school for songwriting. So I feel like a lot of my writing takes that into account. Like that’s the musicality of something is very important to me. So I’ll like read my own stuff out loud. Sometimes like flow of a sentence is very important to me, the rhythm of a sentence, the like intonation, the, Continence and assonance and all of that alliteration, I, I feel like when people can read something and there’s a clear flow and rhythm to it, and the words like melt into each other sound nice next to each other. I personally feel like it locks them into the content early on. Like you want to keep reading because if you stop reading, it’s like you’re breaking this rhythm that you’ve started. So, yeah, I would say rhythm is very important to me and reading things out loud helps me make sure that what I’ve written is what I’d like envisioned and felt [00:23:35] Nathan: Yeah. [00:23:36] Jessica: Mind and my heart when I was conceptualizing the thing. [00:23:39] Nathan: Yeah, reading out loud is a really good tip because there’s so many things where I’ll find myself starting to read what I wrote and then like finishing it in a much more like in my head in a much more conversational way, and then realizing the sentences or the following sentences that I had. We’re not conversational. They were like stilted. The version that I wanted to auto finish in my head is like, oh, that’s better. Let’s let’s say that instead. [00:24:05] Jessica: I love that. And I think, I think newsletter subscribers are like ready for more. Conversational writing. Like I don’t, I think you can be like professional and say something that has weight and has merit and has value and still be kind of, you know, casual about it. [00:24:23] Nathan: Yeah. [00:24:23] Jessica: As a strategy to connect with people. [00:24:26] Nathan: Is there a poster or a piece that you’ve written that you felt like. Maybe you struggled to find that balance of like, it was a, maybe a weighty piece or something like that. And you’re like, oh, maybe this one I shouldn’t be playful with or, you know, finding [00:24:41] Jessica: Yeah, there are definitely times when I take a break from the jokey conversationality I think the last big piece that I wrote, was about, anti-Asian racism when like all the news came out that like anti-Asian hate crimes were at an all time high. there’s a lot of the beauty industry tends to take a lot of its concepts from Eastern culture, from Asian cultures. So, there was a lot to say there about racism within the beauty industry that, you know, happens in ways that you may not even realize. So for a piece like that, I think there were some moments of, of humor within it, like a dark humor within it, but for the most part, for, for things like that, I take that very seriously. I think my readers take that very seriously and I. It’s less conversational then, because it’s like, no, I have something that’s like very important and clear that I want to get through to you. And I don’t want it to be muddled with any sort of, uh jokingness. [00:25:46] Nathan: Yeah, that makes sense. So let’s say you were a writing coach, coaching someone, Ryan newsletter, that sort of thing. You don’t have to become a writing coach after this. Just. [00:25:59] Jessica: Thank God. [00:26:00] Nathan: But like, you know, you have a friend, maybe they’re writing the newsletter, they’ve got a couple of thousand subscribers they’re getting going in. And they’re saying like, you know, they, they hear what you’re talking about of the, the musicality and the, the flow of, of writing. And they’re like, okay. Short of going to songwriting school, like, what’s the, what, you know, is there, a book or another thing that you would recommend of where to start to, to sort of dive into the flow of what you write? [00:26:29] Jessica: There is a great essay, by Ursula K Le, is that how you say her last name? [00:26:37] Nathan: I’m not sure. [00:26:37] Jessica: Read it and I’ve never said it out loud before. [00:26:41] Nathan: Yep. I have so many things like that in my life where I’m like, I don’t know how to pronounce this word. [00:26:46] Jessica: It’s so embarrassing writing about skincare, because there are these huge, like long skincare ingredients that I write all the time. I can spell them for you off the top of my head, but then I tried to like say them out loud on a podcast, for example. And I’m like, I don’t know how to say this at all. I’m looking for this, this essay it’s from her book. No, no time to spare [00:27:10] Nathan: Okay. [00:27:10] Jessica: And there’s this. And she writes a lot about right. but she has this beautiful essay about rhythm, and how it’s different in poetry and how it’s different in pros and how to kind of like sort out the rhythm of your piece. and I would say that was hugely helpful to me when I, when I first read it. So I would recommend doing that and. Yeah, I don’t know. I use things like, I mean, I, I use it the sores all the time, but I use rhyme zone a lot for like fun phrasing and plays on words. It’s just rhyme zone.com and you type in the word that you’re you’re playing with. And it’ll kind of like, you know, [00:27:50] Nathan: Oh, interesting. Yeah. That’s exactly the kind of, kind of that’s good. Yeah. A lot of people, you know, they come to newsletters from kind of two different sides, either from the journalist, professional writer side or the, you know, hobbyist, maybe even, I never thought I’d be a writer, but I have this skill or something to teach or behind the scenes in this industry. And like writing maybe as a slog or a chore. And so it was always interesting when these two worlds meet and either, you know, one group might be really good at marketing because they knew they came from that world and another group. [00:28:27] Jessica: Yeah. [00:28:27] Nathan: Really good at writing and they each hate the other’s job, but [00:28:31] Jessica: Yeah, [00:28:31] Nathan: Like they pick the job. That’s the intersection of both of those worlds. [00:28:35] Jessica: Yeah, no, you’re so right. I think there is this like sort of misconception in the journalism and reporting space that any reporter who is on sub stack has decided to go in all in on the newsletter. Because there have been some very high profile journalists who are no longer writing for like the times or the posts and they’re just doing their newsletter. But I think for the large majority of, of reporters and journalists who have, who have started newsletters as well, it’s like a both and kind of thing. [00:29:06] Nathan: Yeah. [00:29:06] Jessica: Sill freelancing and we have this, this sort of personal platform. [00:29:11] Nathan: Yeah. So how do you think about your career developing over the next couple of years? Is it, is there a specific milestone in mind, where you’re trying to grow the newsletter to, to do that full-time or is it always trying to place a piece to the biggest possible audience? What’s that like? [00:29:29] Jessica: Yeah, I would say my goal, like I very much, this is kind of earnest and nerdy, but like, I very much want to change the beauty industry. I see so much that is wrong with it and I see how it like emotionally impacts people. in terms of anxiety, depression, mental disorders, eating disorders, like there’s a lot of heavy stuff that comes out of the beauty industry. And I like, I’m very passionate about actually measurably changing it. So for me, the number one thing is always, I want to reach the largest audience possible with an unadulterated message. So if I can do that in a place like the New York times, of course, I’d rather place it there than my own news. if I can do that through a book, of course, I’d rather write it in a book then in my own newsletter. So the newsletter has been sort of like a nice foundation for me to have and a nice fallback for me to have. And I, I truly love fostering it as its own little separate entity, but I would, I would say I almost try harder to place things elsewhere because I want As many people as possible to be able to, to read the things that I’m writing. the newsletter I’m I am writing my first book right now, and it’s definitely been hard to juggle book writing with like reporting for other platforms and deadlines. So I will say like juggling a book and my own personal newsletter has been much easier than trying to juggle a book and reporting. So I think, I think there will be times in my writing career while I’ll lean a little bit more heavily on the newsletter. And times where I’ll lighten up on the newsletter. I’m always seeing it as sort of like a supplemental tool to my like greater mission. [00:31:13] Nathan: I think, I don’t know what publication they were writing for. but someone was telling me about, was that in each of these publications, they’re watching the view counts, you know, for every story. And they had gotten the newsletter. I think they were maybe at 20, 25,000 subscribers. And they would, when they placed a piece with a fairly major publication, they would email it out. And they, it was enough direct traffic to that individual piece that they could get it to move on. Some of these internally watched leaderboards and stuff like that. And so editors were paying attention to that of like, they didn’t necessarily know like making things up that, you know, Jessica was the one who drove a bunch of traffic to this, but they’re just like, wow, Jessica’s stories are consistently resonating. And so they were wanting to pick up more pieces in that. and so I was always wondering about that, of how you can, it’s not gaming an algorithm or anything like that. [00:32:08] Jessica: Hmm. [00:32:08] Nathan: Just saying like, look, here’s my story. And I bring an audiences. [00:32:12] Jessica: Oh, I love that. I might try to do that. I always do. Like I do these little roundups every other week for my paid subscribers. And if I have something that comes out, I’ll always put, drop the link in there, but I’ve never done like a strategized push like [00:32:28] Nathan: Right. [00:32:29] Jessica: Be interesting to experiment for sure. [00:32:31] Nathan: Well, cause it’s like, if someone is following you that they’re following you for. Your content and your ideas and your perspective. And they probably don’t really care if it’s, you know, in your sub stack, you know, on your Instagram or, you know, [00:32:48] Jessica: Right. [00:32:48] Nathan: Major publication, there’s like, look, I want to read your, your content. And you’re like, oh, today’s article is [00:32:54] Jessica: Yeah. [00:32:55] Nathan: Here on Vogue. Or, you know, [00:32:57] Jessica: Kind of nice to hear, because I think that’s something that I do worry about pretty often with my newsletter is I feel like a ton of my newsletter readership has come from social media. And so I’m like very conscious of cross posting. Like I don’t, I don’t want someone to get my newsletter and say, I already saw this on your Instagram, so I don’t need to subscribe. I don’t need another email in my inbox because I’m seeing it on Insta, you know? And I don’t know if that’s like a legitimate concern or how much people see when they subscribe to you on different platforms. but that has been. You know, something that I’m very mindful of, where if it’s like a meme that I’m posting on social media, or just like a one-off Instagram post, I’m probably not going to repeat that content, even if I think it’s good or important on the newsletter. Just because I don’t know, I’m aware of like how precious it is to allow someone into your email inbox, because at least for me, like email is very annoying. The worst part of my day is trying to like go through my inbox and file it away into folders. And I never want my newsletter to be like, oh, I’ve seen this already. I’ve seen something very similar from her already. [00:34:09] Nathan: Right. Yeah. I don’t know that I have a perspective on that. I’m just thinking about it. I don’t have the same concern. but I don’t know that. You know whether I should or not. I think probably my approach would be that if you’ve already seen something, let’s say there’s five or six things in the newsletter and I’ve already seen one of them on Instagram, but I just skipped past that one. [00:34:30] Jessica: Yeah. [00:34:31] Nathan: And so my focus would be on making sure that everything is high quality, more than making sure that everything is, completely a unique [00:34:40] Jessica: Yeah. That’s I mean, that’s encouraging to hear, and I think that that might, change how I approach my like every other week [00:34:49] Nathan: Yeah, [00:34:49] Jessica: Maybe I’ll experiment and I’ll see, I’ll see if people are like, Hey, I saw that. [00:34:54] Nathan: The other thing that I would do is I would ask, one of my favorite things to do is to ask for replies to my newsletter, which has a downside of that you get a whole bunch of emails, but they can often be really fun cause they’re, No, the people who are reading every day and like they’re following your stuff. And, and so they’re usually not pitching you things. They’re just saying, like, here’s the thing that I, and so in that case, just say, Hey, you know, if I share something on Instagram, would you also like it here? Or do you feel like, keep those worlds more separate? Like don’t I want everything to be unique. And then I would just like, say hit reply and let me know. [00:35:34] Jessica: Yeah. [00:35:34] Nathan: And it’s. Yeah, but you know, out of 9,000 subscribers, I’d bet you’d get at least, I dunno, 20, 30, 40 replies or something. [00:35:42] Jessica: Yeah, that’s a good point. Okay. Oh, you’re inspiring me. I have so many ideas now. [00:35:48] Nathan: Perfect. I love it. okay. One thing that I want to know more about is growing that. That newsletter from the pieces that you’re, I assume subscribers are coming from Instagram. And then also from the pieces that you’re publishing, [00:36:04] Jessica: Yeah. [00:36:04] Nathan: Seen like spikes? when it came from an Instagram post that did really well or some other promotion to drive subscribers, [00:36:13] Jessica: I mean, I definitely get new subscribers every time I post about it on Instagram or Instagram stories. So I would say that’s been like a main driver for me, but my two biggest, like surges of subscribers came from, All of the newsletter press that’s been happening lately. Cause you know, like the newsletter revolution is here. So, I got a little write up in New York magazine and then one in the UK Sunday style magazine and both of those were amazing and totally unexpected. I had no idea they were coming. so now I’m like, damn, how do I, how do I facilitate some more press for myself? Because this is where that. [00:36:55] Nathan: Like what would a spike like that look like? Cause that a couple of hundred subscribers, 500 a thousand from one of those [00:37:01] Jessica: I would say from New York magazine, it was probably close to a thousand. And then from the UK, Sunday times was probably between like 500, 600. [00:37:11] Nathan: Yeah. That that’s substantial. [00:37:14] Jessica: Yeah. It was, it was really exciting. and it definitely goes to show like the power that these publications have. It’s interesting to see that power as applied to like inherently, anti large publication platform, like a personal newsletter, you know? [00:37:35] Nathan: Yeah. So how do you, how do you think about it when it’s like. More press would be nice. You’re like, Hey, this, this is a big boost, you know? I’d 10% lift in total subscribers or something from a single thing. And then knowing what you know about journalism and being in the space, like, is that something that you craft a strategy around and say, okay, I’m going to intentionally pursue, placements in these publication. [00:38:02] Jessica: No, in terms of just the newsletter, I, I don’t think I’ll ever like strategize and try to do that. I think, I mean, the, the reason that I got those two placements is just because I. In the beauty space, my newsletter does offer something that’s really different that you’re not getting anywhere else. and so it becomes inherently interesting to write about or call out because this is the only place you can get that kind of thing if that’s what you’re looking for. So I think it’s just more of like striving to figure out, like, how can I create more, very original content that actually. Gives value to the reader in a way that’s going to create that kind of buzz. I don’t want to like manufacture the buzz so much as I want. Like my condoms would be good enough for people to actually talk about it. But that being said, when my book comes out eventually like, hell yes, I plan to like strategize and try to get the shit written about me everywhere, which will hopefully we get to the newsletter as well. But yeah, I feel like I’m going to save all of that, like smarmy, you know, networking for book launch. [00:39:14] Nathan: Yeah, that makes sense to me. I want to push back on it a little bit, because so much of the success of the book is going to be dependent on a lot on a lot of things, but a big factor is going to be the size of your platform. When that book comes out. [00:39:29] Jessica: Yeah. [00:39:29] Nathan: And so if you wait to be self promotional until the book comes out, then like, that’ll get this far, but let’s say you were self promotional in a tasteful way. We’re going to be tasteful about all of this. you know, but along the way, and that 9,000 subscribers turned into 25,000. Right. And it’s that much bigger of a platform to launch from. So I’ll say that with the caveat that I think the same thing. [00:39:51] Jessica: Yeah. [00:39:52] Nathan: We have, I’ve lots of friends who have big platforms and I’m like, oh, I could guest post on them. You know, with them, or like ask, Hey, can I come on your podcast or something like that? And I’m like 90% sure that they would say yes, but then I think, oh, I should save that for when my book comes out. Right. Cause you know, you have that, maybe that, just that one ask. So I think it’s something that a lot of creators struggle with of like when to promote. And so intellectually I’m like promote early enough. [00:40:21] Jessica: Yeah. [00:40:22] Nathan: And then emotionally, what I’m actually doing is I think exactly what you’re doing, but I’ll save that for when I really need it. [00:40:28] Jessica: Yeah, I think for me, there’s also this, this sort of inherent struggle with what I write about and getting press, because I am pretty critical of beauty media coverage. and I’m aware that I have made some enemies in the beauty media space. Like I’m not the most well-liked person, in some of these circles. So I do feel like I only have like a certain amount of rope that I can, use up like a certain amount of leeway in these spaces. and then also I, yeah, I don’t know. I think it’s something I have not sat down to really work out my feelings about. But there is some sort of ethical dilemma there where if I’m critiquing the way a certain platform has covered this beauty trend or whatever it is, I’m critiquing. And then I’m sort of like asking for press at the same time, like ethically, what does that say about me and my participation in these systems? You [00:41:30] Nathan: Right. [00:41:31] Jessica: Which is a big question and not one that I’m going to be able to answer here. [00:41:36] Nathan: Yeah. Are there publications outside of the beauty space that would have less of the, maybe sponsored ties or other, you know, issues [00:41:47] Jessica: Yeah, [00:41:48] Nathan: The main publications might have, but that would find your story. [00:41:52] Jessica: I think so. I think the path that I am trying to follow in beauty coverage right now. the path of sustainable fashion coverage, like I feel like fashion and beauty have been so intertwined in their coverage and they’re, they’re both sort of seen as these like less serious pursuits. They’re both seen as like inherently female interests. And they’ve struggled to be taken seriously, I think. but with like the push towards sustainability content and, you know, the inevitability of climate change, I think. Sustainability and fashion is getting a ton of like serious quality coverage all over the place, even from platforms that wouldn’t normally touch fashion. And I see beauty as being very behind that. Like there are still these huge global issues in the beauty industry and beauty production and just the way that we consume and beauty, that hasn’t been touched. But I see it starting to be touched by these larger, serious. News organizations. And I feel like there’s such an opportunity there. And that those are topics that I’m super passionate about and super interested in. So I’m, I’m trying to carve out a space for myself there to say, look, we’re taking fashion seriously for the impact that it has culturally societaly environmentally. Like we have to start taking beauty justice seriously because it’s just as big of a person. [00:43:17] Nathan: I like, I like that angle on that. That makes a lot of sense. And just seeing trends in a neighboring industry. I think you’re right. I hope that I hope that you’re right in, that plays out in there. [00:43:28] Jessica: Me too. [00:43:29] Nathan: One of the things that I’m curious about is kind of the rise of newsletters in the journalism space. I don’t come from that world. I very much come from the newsletter world. And so seeing, you know, so many people either make the switch full-time, or get to the point where they’re like, Hey, I’ve been writing these pieces everywhere. And like, my byline has just directed people back to Twitter or Instagram or. And now it’s directing people back to my own audience. What are you seeing in like in your friends and colleagues and all of that is, are a lot of people starting newsletters or is there this overwhelming trend of some are starting it, and maybe it’s getting hyped more than is actually happening. [00:44:12] Jessica: Yeah, I think that’s what I’ve noticed. I don’t think as many people within my like, sort of direct. Community of journalists and reporters are starting newsletters. And I think it’s gotten so hyped. Like we’re in such a moment of coverage right now that it almost like, seems like a little lame to start a newsletter now. Cause like everyone’s doing. But the reality of the situation is that everyone is not doing it. And I think there’s still a lot of opportunity and a lot of room to grow and to move into and to create your own kind of thing. like I mentioned, I think there is a big misconception that if you’re starting your newsletter, that means you’re done with journalism and you’re just doing this now. It’s like, no, you can very much do both. And you can do your newsletter once a month. You can do it, you know, once a week you can do it. However, often you have time for it. Like you said you could use it as a tool just to send out your journalism, pursuits to a wider audience. but yeah, I think sort of the hype around newsletters has sort of, created this little, Ooh, I don’t know if I want to do a newsletter too. Cause I might get to see them. Like, I’m just doing what everybody else is doing. [00:45:23] Nathan: Right. Yeah. The, the newsletter hipster trend is sort of passed and it’s gone mainstream. I can’t do it [00:45:31] Jessica: Exactly. I mean, for the record, I don’t believe that that’s true, I think that’s how people are perceiving. [00:45:38] Nathan: Well, it’s so funny to me because, I’ve been doing E you know, email and email newsletters and that kind of thing since I guess, 2013. and you know, very excited. They got into all of that. And I was telling people like, email is amazing and friends that have me, who’ve been doing it since like 2001 were like, yeah, like good job, discovering it. Do you want to go and start? Like what a pat on the back, what are you hoping for here? And watching is, you know, these trends as they come, if you had a friend who, you know, is in the space who comes to you and says like, oh, I’m going to start a new. You know, what are the things, I don’t know, the three or four things that you would tell them right away of here’s what they should watch out for is strategies that they should employ any of those things. [00:46:25] Jessica: I mean, my number one piece of advice that seems really obvious. Isn’t always is just to find your niche. Like I would say hone in on something as specific as you possibly can, within your space so that people have a reason to subscribe. I would say to have, like, especially if you’re doing sub stack or a place where you can view past newsletters, like have a healthy backlog before you actually start soliciting people to sign up so that they can see what your content is like. And then this is a big thing that I think is missing from a lot of the journalism to newsletter side, because like he said, there are people who are coming from marketing and people who have never done marketing in their life. something that I do is that when I’m sending something out to my paid subscribers, I send a shorter version out of it to my free subscribers. Click to continue. And then it brings them to the paid subscriber thing. And I convert between 30 and 50 people every time. And when I sign up for free newsletters, which I sign up for a ton of them, I have never once got in that. I’ve never once gotten an email. That’s like the intro of the article. And then it, you know, sort of leads me into that paid funnel. And I used to work in marketing. I used to work in fashion marketing. That was just like a no, duh of course I would do that sort of thing. but I’ve never seen any other like journalists to newsletter convert, use that very easy tool. so I would say, take advantage of that for sure. [00:48:07] Nathan: Yeah, that’s interesting of the things that in one industry, like you’re right in the marketing industry, everyone’s like, obviously, you know, of course you would do that. And then you get into another space and it is this exciting, new thing. I started in, in design and, like user experience and interface design. And so I brought a lot of design ideas to marketing and then a lot of like direct response marketing ideas into the design world. And it needs to circle. Everyone was like, whoa, this is amazing and new. [00:48:35] Jessica: Yeah, [00:48:36] Nathan: You did it in the original circle, people are just like, obviously there’s nothing novel about it. [00:48:41] Jessica: Exactly. I think people really, underestimate. The skills they learn on the way to get to where they’ve, they’ve gotten to. Like, I never would have thought the job that I hated in fashion marketing would have served me in, in, any way. Cause I sort of wanted to get away from all of that. Like marketing bullshit, lack of a better word, because at least at the company that I was at, it mostly felt like lying and just like squeezing money out of people. I think you can use those tools for good as well, which is what I’m trying to do. [00:49:15] Nathan: Yeah. So a lot of creators struggle with that transition where they feel like either from a past experience or something that they’ve seen where they’re like, oh, I can never ask for money for this or charge for it or, that kind of thing. Or they’re very, very hesitant to sell in any, anything. what would you say to them? Or what’s your journey been like in saying like, no, this is what it costs. This is why you should subscribe. [00:49:40] Jessica: Yeah. I mean, I think it’s important to have, to have a reason, you know, make it very clear that it’s reader funded or user funded. for me, all of my content is very clear that I blame the media advertisement model for so much of the misinformation and bullshit that’s out there in beauty. So me saying that my newsletter and this content is completely user funded, so that I’m loyal to you. The reader rather than an advertiser, is very like, you know, quote unquote on brand for me. And I think people who are interested in my content are more than happy to pay for it. It’s solving a problem that I am pointing out in my reporting, you know? and then I would just say also like allow yourself to be surprised at how much people want to support you. I have been so pleasantly surprised by people who are just, they just liked my content and they’re happy to pay for it. And I think one of the, the biggest, the biggest ways that I’ve seen that happen is that, on substance. They let you do like the page, so you can do monthly or a yearly rate, or you can do something called a founding member, which is just somebody who pays a little bit more to support and they don’t really get any extra benefits at all. And I am shocked at the amount of people who give me 50 more dollars than they need to, just to support, And that’s like, every time I get that email, that’s like someone signed up for the founding member level. It’s heartwarming because it’s like, there are a lot of people out there who want to support great creator, led content. [00:51:23] Nathan: Do you have a percentage or numbers on that? Like I’m curious, every time I see that I’m like how many people select that [00:51:29] Jessica: Yeah. [00:51:29] Nathan: Know from doing multiple prices or packages, that it’s one of the best ways to increase revenue is to just have a higher price option available. [00:51:38] Jessica: Yeah. [00:51:38] Nathan: confirming that, but I want to know any [00:51:40] Jessica: Yeah. I have not like crunched the numbers on anything, but just from, so I sent out a paid newsletter, on Thursday. So between Thursday and today from like my conversions of free [00:51:55] Nathan: Yep. [00:51:56] Jessica: Sign up, I’ve gotten, I think 56, new signups. I would say maybe 10 of them were the yearly membership and maybe five of them were the founding member. [00:52:08] Nathan: Okay. Wow. So half of the year, the ones being the like yeah. I’ll pay you $50 more just to support your work. Even [00:52:17] Jessica: Yeah, [00:52:18] Nathan: Because the yearly membership is supporting your work, but even just [00:52:21] Jessica: Yeah, [00:52:21] Nathan: Above and beyond. [00:52:23] Jessica: Yeah, exactly. I mean, that’s just what, roughly, from what I remember from the email. I’m not like super concerned with, with stats and strategizing right now. I’m just like ecstatic. Every time I get the ding on my phone that says somebody new signed up. [00:52:39] Nathan: Yeah. That’s super fun. So, what are the things that you’re thinking about next for the newsletter? Is it slow, steady, growth, and maintaining that while working on the book? Is there a big milestone that you’re working towards any of those things? [00:52:52] Jessica: There is not a huge milestone, but I think when I first started it, and this is, I think maybe just a personal hangup, but I was very conscious of not bothering people too much, like not being in their inbox constantly. So, it was like one big story a month, and then every other week for paid. Now I’m toying with the idea of doing more, short form content and where weekly content. I’m going to be launching a new feature for paid subscribers that’s gonna be, like an advice column, but more like, how do I navigate the industry? How do I divest from these marketing tactics? How do I like stay smart and know what’s alive and what’s not? So, I’m going to be launching that within the next month. Then, for everybody, I’m going to be launching weekly or even twice a week, just like little, like a little tip newsletter. Because what I do in my newsletter a lot is critique the beauty, and point out what’s wrong with it. People are always like, okay, sure, but how do I apply that to my own life? Like how do I get over the fact that I know it’s marketing, that I don’t need to have big lips to be beautiful, but how do I stop feeling that way? So, it’s going to be more practical tips for, I guess, sort of healing from all of the beauty industry shit that they put us through, but it’s going to be very short, quick hits, like, you know, five sentences, a paragraph tops. So, I’m going to experiment with a couple of different, forms of writing and a couple of different frequencies and see, see what people. [00:54:38] Nathan: Yeah, that sounds good. Well, if anyone wants to go subscribe to that and follow you on Instagram and other things around the web, where should they go? [00:54:46] Jessica: My sub stack is JessicaDefino.substack.com, and you can sign up for The Unpublishable there. And then on Instagram, I’m @JessicaDeFino_. [00:54:56] Nathan: Sounds good. Well, thanks so much for coming on. This has been fun to [00:54:59] Jessica: Yeah. [00:54:59] Nathan: learn about a whole side of the newsletter industry that I’m less familiar with, and just hear your story, and your writing tips, and everything else. [00:55:08] Jessica: Yeah, thank you so much. I feel inspired. I’m going to go send more newsletters. [00:55:13] Nathan: Sounds good.0 comments0
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