E1152: Keith Rabois on leaving Silicon Valley for Miami, Roaring Twenties 2.0, IPO spree & more

15 Dec 2020 · 97 min
1:37:00

In this interview, Keith Rabois and Jason Calacanis discuss a wide range of topics spanning California’s political climate, the role of macro crises in driving policy change, the impact of high‑tax states losing wealthy residents, and the dynamics of the Prop 22 referendum. They examine the significance of IPOs versus acquisitions, noting that public listings often signal long‑term durability for companies like Palantir, Airbnb, DoorDash, and Square. Rabois shares his venture‑capital mindset, emphasizing the psychological reward of backing unpopular founders, the necessity of tolerating failure, and the shift toward larger funds that require multi‑billion‑dollar outcomes. The conversation also touches on the evolving landscape of SPACs, the migration of talent and capital to Florida and other low‑tax jurisdictions, and the cultural implications of tech leaders buying sports franchises. Throughout, Rabois reflects on personal anecdotes about founders’ eccentricities, the importance of founder‑investor chemistry, and how he stays sharp after years of investing. The dialogue blends political analysis, investment strategy, and personal philosophy, offering insight into the future of tech ecosystems and venture capital.

Chapters

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