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.

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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

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Related episodes:

• #42 ARM: A mental model for fulfilling work

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People & orgs:

• Gumroad

• USC

• Patreon

• BandCamp

• Substack

• Daniel Vassallo tweet about money he’s made Gumroad

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

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Books:

• The Minimalist Entrepreneur

• Essentialism

• Only the Paranoid Survive

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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)?

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