Sahil Lavingia

What defines success in business and relationships? Making a shit ton of money? Investing in the right company? Providing value? Writing 1000 words a day for a week? Having the most meaningful interactions you can on a day to day basis?

Sahil Lavingia, the guest on this week’s episode, has defined success differently at different stages in his life. As a teenager into his early 20s, Sahil lived in Silicon Valley, the home of cutting edge startup culture. He was the second employee at Pinterest and then left to start his own company called Gumroad, an online platform that enables creators to sell products directly to consumers.

In 2011, At 18 years old Sahil raised 8 million dollars for Gumroad and declared his mission to build his first billion-dollar company. Things did not go as planned. In 2015, Sahil laid off 75% of the company, was no longer venture-funded, but today Gumroad is strong as ever. What happened? To quote Sahil’s blog post, Reflecting On My Failure to Build a Billion-Dollar Company, he writes,

“For years, my only metric of success was building a billion-dollar company. Now, I realize that was a terrible goal. It’s completely arbitrary and doesn’t accurately reflect impact. I’m not making an excuse or pretending that I didn’t fail. I’m not pretending that failure feels good. Everyone knows that the failure rate in startups — especially venture-funded ones — is super high, but it still sucks when you don’t reach your goals. I failed, but I also succeeded at many other things. We’re simply focused on building the best product we can for our customers. On top of all that, I’m happy creating value beyond our revenue-generating product.”

In this podcast, Sahil shares what triggered this change in the mentality of how he views success, moving from Silicon Valley to Provo Utah, the most conservative and religious city in America over 100,000 people, painting with retired moms, the DNC debate format and more. Without further ado, here is our wide-ranging conversation with Sahil Lavingia.