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.

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.

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.

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.

Today we catch up with Harj Taggar, who knows as much about startups as anyone of his generation. YC funded two of his startups, Auctomatic in 2007 and Triplebyte in 2015. In between them he was the first partner we hired besides the founders, and now he's a YC partner again. Among other things he happened to have a front row seat for the Damore controversy in 2017, and is one of the few people who know just how extreme things got in those days.

In today’s episode, we chat with all three of the Gusto founders: Josh Reeves, Eddie Kim, and Tomer London. Gusto is a payroll and employee benefits company that YC funded in 2012. The striking thing about Josh, Eddie, and Tomer is their level of commitment: to their customers, their employees, and one another. It's rare to see a startup with 3 founders still being run by all 3 founders 12 years in, but these guys are special.

In Part 2 of our conversation with legendary investor Ron Conway, we chat about how he made one of the most prescient decisions in the history of startup investing when he decided in the early 1990s to focus exclusively on investing in internet startups. It's like being a fly on the wall at the beginning of the internet boom as he takes us through shadowing Sequoia founder Don Valentine and "living" in Netscape's office as it took off.

In this episode, we speak with Surbhi Sarna, founder of nVision Medical, a pioneering company in women's health diagnostics. Surbhi shares her journey from experiencing a personal health scare as a teenager to founding nVision, which developed a microcatheter for the detection of ovarian cancer. nVision was acquired by Boston Scientific for $275 million in 2018. Now a Partner at Y Combinator, Surbhi discusses her transition from founder to mentor, offering insights into the challenges of healthcare innovation. Her book, Without a Doubt, was released in 2022.

We’re back with Tyler Shultz for the second part of his story: the whistleblowing. He’d resigned after noticing potential fraud within Theranos. After he spoke on background to the Wall Street Journal, Theranos retaliated with a series of legal threats, intimidation, and surveillance -- all designed to silence him. Tyler tells us about the nightmare leading up to when the news story broke, and the world found out about Theranos. (Learn more about Tyler at tyler-shultz.com.)

Tyler Shultz went to work at Theranos right out of Stanford and soon noticed that things weren't as they seemed. Lots of other employees knew there was something fishy going on, but Tyler was one of a tiny handful able to resist the mesmerizing and intimidating Elizabeth Holmes and speak out about the fraud that was putting patients at risk. This podcast is a lesson for anyone who wants learn what it takes to speak out against misdeeds by powerful people. (Learn more about Tyler at tyler-shultz.com.)