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.

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