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

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Reflecting on My Failure to Build a Billion-Dollar Company