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Sahil Lavingia

Sahil Lavingia sahillavingia.com

No meetings, no deadlines, no full-time employees

Once again, Sahil Lavingia shared proof that we can think differently about the future of work. Sure, not every company should operate the way Gumroad is operating, but there are plenty of insights to be drawn from their experience.

Recently, I pitched the whole company about going full-time, because it felt wrong to grow any larger without full-time staff.

Nobody accepted.

I realized then that I was trying to copy the status quo–to try and fix something that wasn’t broken–so that I could feel better about doing things the “normal” way. But the deal we already had in place was better for what our people prioritize: freedom over growth, sustainability over speed, life over work.

I recently spoke with Sahil on Founders Talk #66 about failing to build a billion-dollar company. I highly recommend that episode.

Founders Talk Founders Talk #66

Failing to build a billion-dollar company

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.

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