Sahil Lavingia: Why Building A Billion Dollar Business Is A Terrible Goal, Thoughts On Dave Chappelle, and Painting With Retired Moms

2019-10-20

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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 le...

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.

Follow Sahil on Twitter: https://twitter.com/shl

Follow Sahil on Instagram: https://www.instagram.com/slavingia/

Gumroad: https://gumroad.com/

Medium Post by Sahil: https://bit.ly/2p1GauG

The Aux (podcast): https://apple.co/2m0GBUb

The Aux (newsletter): https://www.auxoro.com/theaux

**Intro/Outro Music: Produced by David Grossfeld

Intro song: The London by Travis Scott, J.Cole, Young Thug

Mixed and Mastered by Dbsound on Fiverr

Sound Design: Matt Grossfeld

Episode Art: @shl

Auxoro main site: https://www.auxoro.com/