Sahil Lavingia is the founder and CEO of Gumroad, a web platform where creators can sell products directly to consumers with quick, simple links. Sahil was the second-ever employee at Pinterest before starting Gumroad with the goal of making it a billion-dollar company. Gumroad got off to an explosive start, but it eventually imploded. Sahil managed to keep the company afloat and made it independent, healthy, and profitable. Although Gumroad isn’t the billion-dollar company Sahil originally imagined it would be, it has created tremendous value for creators who’ve generated nearly $190 million from selling their creations on the website.

You can say hello to Sahil on Twitter and read his viral article on his failure to build a billion-dollar company at this link.

Sahil and I discuss:

  • Why he dropped out of college only after a semester
  • What it was like to be the second-ever employee at Pinterest
  • The critical difference between one-way and two-way decisions
  • Why Silicon Valley is far less risky than people assume
  • How he ended up with $8 million in his bank account as a 19-year-old founder of Gumroad
  • Why Gumroad eventually imploded after an explosive start
  • What it was like for Sahil to navigate this public failure and what advice he would have given himself
  • How Sahil finally turned the company around
  • Why he believes his definition of success as building a billion-dollar company was flawed from the very beginning
  • Why you should start a company if you’re thinking about it.

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