Sahil Lavingia is the founder and CEO of Gumroad, a platform that helps creators sell digital products and has facilitated over $1 billion in creator earnings. After raising a $7M Series A from Kleiner Perkins, Sahil took the unconventional path of transitioning from venture-backed growth to a profitable, dividend-paying company—and even spent time as a software engineer with DOGE at the Department of Veterans Affairs.
What you'll learn:
- How Sahil transitioned Gumroad from venture-backed to profitable without selling or shutting down
- The remarkable story of Kleiner Perkins selling their stake back for just $1 and the tax implications
- Why AI coding tools like Cursor and Devin are making senior engineers more valuable while challenging junior developers
- What it's really like working inside the federal government as a Silicon Valley software engineer
- How Sahil automated contract reviews at the VA and helped identify $1.6 billion in cuts
- The three-pronged DOGE strategy: cutting contracts, workforce reduction, and shipping software
- Why radical transparency (public board meetings, open-source code) became Gumroad's competitive advantage
- How to implement a dividend model for private companies instead of traditional growth/exit strategies
- The challenges and opportunities of bringing private sector expertise to government agencies
- Why cooperation beats disruption when trying to modernize massive bureaucratic systems
In this episode, we cover:
(00:00) Introduction and Sahil's early Pinterest days
(05:26) The decision to drop out of college for startups
(08:12) Building Gumroad and raising from Kleiner Perkins
(25:26) How AI is changing software engineering and hiring
(39:02) The 60-day DOGE experience at the Department of Veterans Affairs
(50:15) Transitioning from venture-backed to profitable company
(57:16) The Kleiner Perkins $1 buyback story
(1:02:45) Implementing dividends and radical transparency
(1:09:04) Why transparency makes you better at everything
