Make Things That Matter

Sahil Lavingia: Independent Thinking + Pricing Changes at Gumroad

Listen on

Episode notes

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.

Episode web page.

Sign up here to get upcoming essays + episodes emailed to you.

Follow the MTTM journey on Twitter or LinkedIn!

If you haven't already would you do me a favor and take ~40 seconds to rate/review the show on Apple Podcasts ? It really helps. (Scroll to bottom of page for rate/review links.)

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)?

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit