Today, we're doing something I do every day: talking to Paul Graham, who as well as being one of the founders of Viaweb and Y Combinator is also my husband. Paul has been involved with startups since 1995; before he invented the accelerator, he invented the web app. So there's a lot of information in this episode, but it was also, as you'll see, one of the funniest.

In today's episode, we're talking with Brian Chesky, cofounder and CEO of Airbnb. YC funded Airbnb in 2009, when the company was at death's door. During YC we watched the founders work frantically to get growth started and turn Airbnb into the rocketship that it is today. Learn what it takes to come up with an idea so weird that it seems like it will never work, and then make it work.

In this episode we walk down memory lane with Steve Huffman, co-founder and CEO of Reddit, who was in Y Combinator's very first batch of startups in 2005. In those days Steve was a programmer fresh out of UVA. He had no idea that the site he was creating would become the forum of forums, still active and growing 18 years later. Hear about Reddit's eventful early years and how they affected what it eventually became.

Today we're talking with the fabulous Tracy Young, one of the most successful female startup founders so far. Y Combinator funded her company, PlanGrid in the winter of 2012. PlanGrid revolutionized the construction industry by getting blueprints off paper and onto tablets. You’ll hear about how they found their idea, how they lost a cofounder to cancer in the first few weeks of YC, how they sold the company for almost a billion dollars in 2018, and how she’s now gone on to start a new startup called TigerEye, with her husband and PlanGrid cofounder, Ralph Gootee.

In this episode we’re talking to Garry Tan, the president & CEO of Y Combinator. We go full circle with Garry as we chat about his path from turning down a job with Peter Thiel, to founding a YC-backed company in 2008, then starting his own multi-billion dollar fund in 2011, and finally returning to run Y Combinator in 2023. Garry knows about programming, design, running startups, and investing in them, so there are lessons and stories for everyone in this episode.

In this episode we catch up with Tony Xu, founder and CEO of the food delivery service, DoorDash. Tony and his cofounders were students at Stanford when they first launched DoorDash as a class project. Y Combinator funded them as part of its summer batch in 2013. In this episode, Tony takes us through version 1 of their idea to what is now a public company (DASH) operating in 27 countries across the globe.

In this episode we’re talking to David Lieb, creator of Google Photos. Back in 2009, YC funded his startup, Bump Technologies, which had a cool technology where you transferred your contact info from one person to another by literally bumping phones. He’ll share Bump’s ups and downs as they went from business school side hustle to hot new iOS app. He’ll talk about getting acquired by Google and ultimately transforming Bump into the wildly popular Google Photos. David recently came back to Y Combinator as a visiting group partner.

In the premiere episode, Jessica & Carolynn sit down with Paul Buchheit. Paul created Gmail in 2004 while he was employee #23 at Google. They do a deep dive into the history of Gmail, including the fact that it might never have launched if it weren’t for a leak to the New York Times. After Google, PB went on to found a startup called FriendFeed, which was a social media aggregator, and where the first “like” button was created. It was acquired by Facebook in 2009. After that, he joined Y Combinator as a partner and also became one of the most successful angel investors in Silicon Valley.