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 lifeSubscribe to Morning Brew!Sign up for free today: https://bit.ly/morningbrewytFollow The Brew!Instagram - https://www.instagram.com/morningbrew/Twitter - https://twitter.com/MorningBrewTik Tok - https://www.tiktok.com/@morningbrewYouTube - https://www.youtube.com/@TheCrazyOnesPodFollow Our Hosts!Alex Lieberman (@businessbarista)Jesse Pujji (@jspujji) Learn more about your ad choices. Visit megaphone.fm/adchoices

Jonathan Swanson, founder of Thumbtack, and John Kobs, founder of Giant and Apartment List, discuss the evolution and challenges of marketplaces. They explore untapped market potential, technology integration, and building liquidity. The conversation touches on creating marketplaces for new behaviors, future opportunities, and the impact of innovative advertising. They share insights on evaluating markets, pivoting startup ideas, and connecting talent through marketplaces.