Sahil Lavingia is the founder and CEO of Gumroad, a platform for creators to sell the things they make. Since 2011 Gumroad has sent over $200 million dollars to creators. That’s a big number. Sahil’s ambitions lead him to believe that Gumroad would become a billion-dollar company, have hundreds of employees, and eventually IPO. That didn’t happen.

…we were venture-funded, which was like playing a game of double-or-nothing. It’s euphoric when things are going your way — and suffocating when they’re not. And we weren’t doubling fast enough to raise the $15M+ Series B we were looking for to grow the team. For the type of business we were trying to build, every month of less than 20 percent growth should have been a red flag. But at the time, I thought it was okay…

We talk through Sahil’s journey with Gumroad, why it failed to meet his goals, the path he’s on today and the things he now values…but to understand why Gumroad didn’t live up to his expectations, we really have to understand the backstory of Gumroad.