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Reflecting on My Failure to Build a Billion-Dollar Company

Medium no longer allows this article to be read easily, so I’ve moved this article to be available directly on my website. Sorry for the inconvenience!

Credit: Zdenek Sasek/iStock/Getty Images Plus

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.

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Marker
Marker

Published in Marker

Marker was a publication from Medium about the intersection of business, economics, and culture. Currently inactive and not taking submissions.

Sahil Lavingia
Sahil Lavingia

Responses (235)

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Gumroad is a product of many people’s hard work, including our alumni: Leigh McCulloch, Sidharth Shanker, Anish Bhayani, Kathleen Warner, Heather Whiles, Benjamin Nguyen, K. Tighe, Stev...

I like the fact that you acknowledge the people behind Gumroad. People who have made contributions and are likely still providing contributions to it. Just shows the kind of leader you are. Kudos.

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“Failures” like Gumroad are “Failures” like Lucas Films. I love your service. I make thousands through it every month for _exactly_ the reasons you initially created it. Selling a product shouldn’t require a website (or, to be more precise, each…

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Sahil, nothing but respect for the decisions you’ve made, and for telling this story with such clarity and honesty.
I was inspired by your work in designing and building out Aer.io’s commerce capabilities, and will always remember that companionable…

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