Show Notes
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Dan Nathan sits down with Paul Costolo, former CEO of Twitter and current VC. They start with Dick's early comedy days (Second City alongside Steve Carell, two SNL auditions that didn't pan out) and his stint writing for HBO's Silicon Valley, before diving into his path from founding FeedBurner to running Twitter through its IPO — including candid stories about the culture shift from private to public company life, and a surreal late-night run-in with Jack Dorsey in Paris in the middle of Elon Musk's takeover drama.
From there they get into Dick's venture firm, 01 Advisors, and his thesis on investing in the AI "enablement layer" (the infrastructure sitting above the models) rather than chasing the flashiest apps. Dick shares his read on today's eye-popping valuations — including Stripe's $7 billion acquisition of OpenRouter and a leaked investor letter claiming "the singularity happened on New Year's Day" — and gives his predictions for the coming wave of AI IPOs, arguing Anthropic and SpaceX are well positioned while OpenAI could face a tougher road given its executive turnover and messaging challenges. They close by talking about prediction markets (and the striking gap between how well people think they're doing on platforms like Kalshi versus reality), before wrapping up with a plug for Dick's own podcast, the Dick and Paul Show.
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