Jason Fried on Getting Told He Sucked, His First $20, and Landing a $100K Gig Solo | Very First Win episode artwork

EPISODE · May 28, 2026 · 13 MIN

Jason Fried on Getting Told He Sucked, His First $20, and Landing a $100K Gig Solo | Very First Win

from Very First Win · host Goanna Capital

Jason Fried, founder of 37signals (Basecamp, HEY), joins Robert Hilmer on Very First Win.Jason has built one of the most well-known bootstrapped software companies of the last 25+ years. 27 years of profitability, ~60 people, zero VC money on purpose. In this episode he shares three early moments that shaped how he thinks about building: the rejection that lit a fire under him, his first $20 ever made from software (mailed from a stranger in Germany), and landing a $100K Getty Images project as a solo freelancer.Follow Very First WinSpotify: https://open.spotify.com/show/0cTzEJW3juIZEBnyswNl9c?si=674c885122c64a70Apple Podcasts: https://podcasts.apple.com/us/podcast/very-first-win/id1896315027YouTube: https://www.youtube.com/@GoannaCapitalRobert Hilmer: https://www.linkedin.com/in/roberthilmer/

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Jason Fried on Getting Told He Sucked, His First $20, and Landing a $100K Gig Solo | Very First Win

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