Jonathan Swanson on Building a Unicorn and Delegating 90% of Your Life

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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Alex Lieberman (@businessbarista)

Jesse Pujji (@jspujji)