Gusto Co-Founders: Josh Reeves, Edward Kim & Tomer London

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.

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.

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.