Episode 17: Today, hosts Alex Lieberman (@businessbarista) and Jesse Pujji (@jspujji) are joined by fellow startup entrepreneur Jonathan Swanson. Jonathan is the co-founder and chairman of Thumbtack—a massive technology leader building the modern home management platform. In this episode, Jonathan tells Alex and Jesse all about how he and his co-founders came up with the idea for Thumbtack, the turning points and oh-sh*t moments of growing the business, and his genius delegation tactics that save him hundreds of hours over the course of a year.
Time Mapping:
(00:50) - Intro
(01:51) - Start of Jonathan Swanson interview
(04:04) - What keeps Jonathan motivated, even after all of his career success
(05:21) - Jonathan Swanson’s upbringing and background
(06:20) - Why Jonathan decided to pursue entrepreneurship
(09:23) - The early days of starting Thumbtack
(15:48) - The moment that changed everything for Thumbtack
(17:09) - How Jonathan navigates his co-founder relationship
(22:00) - The event that almost killed Thumbtack
(27:00) - The overseas employee that changed Jonathan’s trajectory
(30:20) - Jonathan’s career path after Thumbtack
(33:40) - Jonathan’s tips for how to delegate as a leader
(41:21) - Jonathan’s other businesses
(45:00) - How Jonathan hacks his personal life
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53m ·
Jonathan Swanson on Building a Unicorn and Delegating 90% of Your Life
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The Crazy Ones
Founders, friends and fellow builders Alex Lieberman and Jesse Pujji know what it is to be a founder. The irrational confidence, relentless grind and creative ecstacy needed to build something. In this show, they dole out unfiltered opinions and advice on how to build businesses, and how the current state of the world helps or hurts founders.
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