Sahil Lavingia: Independent Thinking + Pricing Changes at Gumroad

Sahil Lavingia has had an epic journey as an entrepreneur: he dropped out of college to become employee #2 at Pinterest and then went on to found Gumroad, one of the largest platforms for creators to sell their work and earn a living online. After the company failed to meet its VC-driven growth timeline and almost died, Sahil had to lay everyone off and build it back up into the resilient, streamlined, and fully distributed company it is today.

We discuss:

• the logic behind his recent, controversial decision to raise Gumroad's prices (takes effect next week)

• the true motivations we each have for making the things we make

• the essential superpower of entrepreneurs

• what it actually takes to run a fully distributed company well, and

• what Sahil would do if he had to start all over

Listen now on Apple, Spotify, Google, Overcast, or Youtube.

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Links & resources mentioned

• Send episode feedback on Twitter @askotzko , or via email

• Sahil Lavingia: Gumroad, Twitter, personal site

  • Book: The Minimalist Entrepreneur

  • “Reflecting on My Failure to Build a Billion-Dollar Company”: essay + talk

  • Sahil’s early stage investment fund

• Related episodes:

  • #42 ARM: A mental model for fulfilling work

• People & orgs:

  • Gumroad

  • Patreon

  • BandCamp

  • Substack

  • USC

  • Daniel Vassallo tweet about money he’s made Gumroad

  • Paul Graham: “You've found market price when buyers complain but still pay.”

• Books:

  • The Minimalist Entrepreneur

  • Essentialism

  • Only the Paranoid Survive

• Other resources:

  • How Gumroad is run: No Meetings, No Deadlines, No Full-Time Employees

  • Video: Gumroad Q4 2022 board meeting - where pricing change was announced

  • “Reflecting on My Failure to Build a Billion-Dollar Company”: essay + MicroConf talk

  • What is a transformer model (AI)?