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Founder Mode: Jake Heller, Founder & CEO, Casetext Aug 29, 2025

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In this episode, Jake Heller talks about how he and his cofounder discovered the perfect product in a weekend of intense experimentation after GPT4 was released, and then changed the whole direction of the company. This was a classic case of founder mode, because Casetext was already 9 years old at that point and it was hard to convince everyone to change course.

Founder Mode: Paul Graham, Founder, Y Combinator Aug 22, 2025

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Paul Graham talks about how the concept of founder mode arose from Brian Chesky's famous talk in 2024, what it means, and the latest things he's observed in the startup world.

Founder Mode: Garry Tan, President & CEO, Y Combinator Aug 22, 2025

Show notes

We spoke with YC president & CEO Garry Tan about the Founder Mode event he organized for YC alumni. He talks about why founder mode matters and how the concept is evolving the the age of AI.

Founder Mode: Brian Chesky, Founder & CEO, Airbnb Aug 22, 2025

Show notes

At YC's first Founder Mode event, we talk with Brian Chesky, whose legendary talk last year was the origin of the concept. Unless you were one of the lucky founders in that audience, this interview is probably the closest you can get to experiencing it.

Ron Conway, Founder, SV Angel Part 4 (Bonus) May 30, 2025

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In part 4 of our series with legendary investor Ron Conway, we get into the story of Napster. Napster was founded by Shawn Fanning and Sean Parker in 1999 and was the first app to let people access music on demand, at scale. Though it ultimately failed amidst a series of lawsuits, Napster blazed the trail for Spotify and Apple Music, leaving in its wake a series of stories as interesting as the founders themselves.

Ron Conway, Founder, SV Angel (Part 3) Apr 09, 2025

Show notes

In Part 3 of our conversation with Ron Conway, he takes us behind the scenes at early Google. Ron was involved with Google almost from the start; he and Ram Shriram arranged their Series A round. So if you want to know what a really, really big success looked like at the beginning, this is the episode for you.

Drew Houston, Founder & CEO, Dropbox Mar 26, 2025

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In today's episode we talk with Drew Houston, founder and CEO of Dropbox. We've known Drew for a long time (YC funded Dropbox in 2007) and he's extremely candid about the many challenges he faced, and overcame, in the journey from building something that solved his own problem to serving as an essential part of the foundation of today's tech infrastructure. If you want to understand what it takes to be the CEO of a public company, this episode is for you.

Sam Altman, CEO of OpenAI Mar 12, 2025

Show notes

Today we catch up with Sam Altman, Founder and CEO of OpenAI. Sam was in Y Combinator's first batch in 2005 and later returned as YC's president from 2014 to 2019, so he's one of the people in Silicon Valley that we know best. In this episode we cover his whole journey from Stanford sophomore to one of the most influential figures in tech.

Eric Migicovsky, Founder, Pebble & Beeper Feb 26, 2025

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In today's episode Eric Migicovsky, the founder of Pebble and Beeper, shares the journey of building one of the first smartwatches. The Pebble watch made history as Kickstarter’s most-funded project at the time, raising $10.3 million. What happened next showed how difficult it was to build a hardware startup in the 2010s, even if you did almost everything right.

Alexandr Wang, Founder & CEO of Scale Feb 12, 2025

Show notes

In today's episode we go down into the engine room of the AI Revolution with Scale AI founder Alexandr Wang. Since 2016 Scale has been supplying training data to most of the top AI models. In fact there's probably no one with a better overall view of the field than Alexandr.

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