Episode 97: On this episode, I talk with Sahil Lavingia about his 2019 essay titled “Reflecting on My Failure to Build a Billion-Dollar Company.” Sahil is the founder & CEO of Gumroad, an e-commerce platform for creators. Gumroad does nearly $20m per year, is highly profitable, and has no full-time employees. In the essay, Sahil talks about leaving Pinterest as its second employee in 2011, to build his life’s work…a company called Gumroad that would be worth billions of dollars, IPO one day an employ hundreds of people. But that’s not what happened. In 2015, Sahil laid off 75% of Gumroad’s staff to keep the company alive. Of course firing some of his best friends was heart-wrenching. But possibly just as difficult for Sahil was the death of his dream to build a venture-backed unicorn. The heart of this article & much of what you’ll hear Sahil talk about during our conversation is the emotional journey post-layoffs & the decision to build a profitable “boring” lifestyle business.

Reflecting on My Failure to Build a Billion-Dollar Company: https://sahillavingia.com/reflecting

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