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 downThe remarkable story of Kleiner Perkins selling their stake back for just $1 and the tax implicationsWhy AI coding tools like Cursor and Devin are making senior engineers more valuable while challenging junior developersWhat it's really like working inside the federal government as a Silicon Valley software engineerHow Sahil automated contract reviews at the VA and helped identify $1.6 billion in cutsThe three-pronged DOGE strategy: cutting contracts, workforce reduction, and shipping softwareWhy radical transparency (public board meetings, open-source code) became Gumroad's competitive advantageHow to implement a dividend model for private companies instead of traditional growth/exit strategiesThe challenges and opportunities of bringing private sector expertise to government agenciesWhy cooperation beats disruption when trying to modernize massive bureaucratic systemsIn 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

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