Jan. 25, 2023

Sahil Lavingia: Independent Thinking + Pricing Changes at Gumroad

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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

Related episodes:

#42 ARM: A mental model for fulfilling work

People & orgs:






Daniel Vassallo tweet about money he’s made Gumroad

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


The Minimalist Entrepreneur


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)?

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