Jan 25 • 1HR 4M

Sahil Lavingia: Independent Thinking + Pricing Changes at Gumroad

How do we make hard calls when we know there will be pushback?

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Helping product leaders scale up effectively without burning out. Build a product that matters, an org that is effective *and* healthy, and a fulfilling career.
Sahil Lavingia

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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