President and CEO of YCombinator Garry Tan sits down with Tyler & Sterling and recounts his time as an early hire at Palantir, starting his company Posterous and becoming an investor of dozens of well-known startups. The companies Garry has worked with are worth a combined $226 billion. Garry gives valuable advice on cofounder dynamics, doing your inner work, and startup strategies for both Investors & Operators. Chapters: 00:00 Intro 05:55 Garry's $200 Million Mistake 13:00 Why Posterous Stopped Growing 14:30 Why You Should Pay Attention To The Competition 21:10 A Healthy Cofounder Relationship Means Having Conflict 29:38 Adverse Childhood Experiences & Why You Should Heal Them 32:45 A 'B' is an 'F' in Startups 37:07 Users Lie To You Until They Are Paying For Something 43:40 Culture Radiates From The Founder 49:30 Startups Fail Because They Build Something People Don't Want 54:30 Why SF Is The Best Place to Find PMF 1:03:45 Tyler & Sterling's Takeaways Connect with Garry: YT: https://www.youtube.com/@GarryTan LI: https://www.linkedin.com/in/garrytan X: https://twitter.com/garrytan More on Garry: Current President and CEO of YC, Garry was a partner at Y Combinator from 2011 to 2015, where he built key parts of the YC experience for founders including Bookface and the Demo Day website. Garry is the co-founder of Initialized Capital and Posterous (YC S08), a blog platform acquired by Twitter, and prior to that, he was an early designer and engineering manager at Palantir (NYSE:PLTR), where he designed the company logo. Garry holds a BS in Computer Systems Engineering from Stanford.