Reflecting on My Failure to Build a Billion-Dollar Company

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By Chris Castiglione and Learn to Code. Discovered by Player FM and our community — copyright is owned by the publisher, not Player FM, and audio is streamed directly from their servers. Hit the Subscribe button to track updates in Player FM, or paste the feed URL into other podcast apps.

This week I chat with Sahil Lavingia (Gumroad.com Founder) who spent years running a profitable business with millions of adorning customers — only to be told again and again that he was a huge failure.

In this episode, Sahil and I discuss the expectations of taking VC money, and the metrics for success (and failure) that startups must answer to.

Sahil begins,

"In 2011, I left my job as the second employee at Pinterest — before I vested any of my stock — to work on what I thought would be my life’s work. I thought Gumroad would become a billion-dollar company, with hundreds of employees. It would IPO, and I would work on it until I died. Something like that. Needless to say, that didn’t happen. Now, it may look like I am in an enviable position, running a profitable, growing, low-maintenance software business serving adoring customers. But for years, I considered myself a failure. At my lowest point, I had to lay off 75 percent of my company, including many of my best friends. I had failed. It took me years to realize I was misguided from the outset. I no longer feel shame in the path I took to get to where I am today — but for a long time, I did. This is my journey, from the beginning."

Reflecting on My Failure to Build a Billion-Dollar Company

Episode Show Notes and Full Transcript

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