From YC to Initialized and back

In this episode of Out of Office, Lightspeed Partner Michael Mignano joins Y Combinator CEO Garry Tan for a walk through his home turf: San Francisco. Garry reflects on growing up in the Bay Area, learning to code as a teenager, and how those early experiences led him from founder to investor to one of the most influential figures in tech. The conversation spans seed investing, Y Combinator’s evolving model, and why Garry believes abundance, resilience, and taste matter more than ever in the age of AI. They also dive into Garry’s outspoken involvement in San Francisco politics and his investment in shaping the city, from public safety and education to housing and self-driving cars, and what it really takes to move the needle locally. Michael gets to know the real Garry Tan as they check out some of his favorite local spots. Along the way, Garry opens up about faith, community, and why bringing people together offline has become central to his life.

Episode Chapters

00:00 Introduction to San Francisco's Tech Scene

01:04 Meeting Gary Tan: A Journey Through San Francisco

02:22 Gary's Early Days in Tech

04:09 The Impact of San Francisco on Tech Aspirations

06:16 Political Awakening and Local Involvement

18:38 Saunagate and Garry’s Personal Life

22:36 Relationship to Faith and Technology

30:32 Reflections and Future Aspirations

31:05 Rejection and Resilience in YC Applications

31:32 Handling Public Criticism and Rejection

32:13 The Journey of Building a Startup

34:06 Transition from Initialized to YC

35:59 YC's Investment Strategy and Success

37:52 Changes and Future of YC

49:32 Community Involvement and Local Impact

50:45 Future of San Francisco and Tech

52:40 Future of YC and Venture Capital

56:13 Personal Insights at the Bar

56:31 Conclusion and Farewell

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Out of Office is produced by Lightspeed in partnership with Pod People.