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 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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Featuring:

Sahil Lavingia – Website, X
Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X

Show Notes:

Gumroad.com
Sahil’s Medium post titled “Reflecting on My Failure to Build a Billion-Dollar Company”
From Bubble to Bubble on Medium
Jack Dorsey’s 11 biohacks

Something missing or broken? PRs welcome!

Failing to build a billion-dollar company 01:12:01 Share

Founders Talk: Startups, CEOs, Leadership

Shownotes Transcript

Failing to build a billion-dollar company