Sahil Lavingia, the founder and CEO of Gumroad, shares his journey transitioning the platform from venture-backed growth to profitability. He reveals the story of how Kleiner Perkins sold their stake for just $1 and discusses how he automated contract reviews at the VA, identifying $1.6 billion in cuts. Lavingia also highlights the rise of AI coding tools and their impact on the hiring landscape, and he advocates for radical transparency as a competitive advantage in business.
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insights INSIGHT
AI Raises Senior Engineers' Value
AI tools shift the value of engineers towards senior roles that understand architecture and tools.
Junior engineers face tough markets because basics can be quickly automated by AI coding assistants.
volunteer_activism ADVICE
Interviewing Engineers Post-AI
Interview engineers by discussing their experience and problem-solving, not just coding challenges.
Look for alignment with your mission and general intelligence over coding speed.
question_answer ANECDOTE
Sahil's 60-Day Doge Engineering Stint
Sahil Lavingia joined the Department of Veterans Affairs with Doge for a 60-day stint as the only software engineer.
He helped automate contract reviews and worked on software projects as a pro bono engineer.
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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
Founders in Arms 