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:

1. How Sahil transitioned Gumroad from venture-backed to profitable without selling or shutting down
2. The remarkable story of Kleiner Perkins selling their stake back for just $1 and the tax implications
3. Why AI coding tools like Cursor and Devin are making senior engineers more valuable while challenging junior developers
4. What it's really like working inside the federal government as a Silicon Valley software engineer
5. How Sahil automated contract reviews at the VA and helped identify $1.6 billion in cuts
6. The three-pronged DOGE strategy: cutting contracts, workforce reduction, and shipping software
7. Why radical transparency (public board meetings, open-source code) became Gumroad's competitive advantage
8. How to implement a dividend model for private companies instead of traditional growth/exit strategies
9. The challenges and opportunities of bringing private sector expertise to government agencies
10. 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