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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