Ex-Twitter CEO gave Musk the Bird, 01A AI investments & IPO Landscape

Ex-Twitter CEO gave Musk the Bird, 01A AI investments & IPO Landscape

August 21, 2026 · 1h 40m · Episode 298

About this episode

Dan Nathan interviews former Twitter CEO Paul Costolo about his career, venture capital insights, and the future of AI investments and IPOs.

WATCH 'The Dick & Paul Show' on YouTube: https://youtu.be/LtLBhBp5T40 This episode is sponsored by Fidelity Investments and the all-new Fidelity Trader+ platform. Try Fidelity’s most powerful trading experience yet: https://Fidelity.com/TraderPlus Fidelity Investments and MRKT Call are not affiliated. Views, opinions, products, services, and strategies discussed are not endorsed or promoted by Fidelity Investments. Fidelity Brokerage Services LLC, Member NYSE, SIPC. 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…

Sponsors

Fidelity Investments

More episodes of RiskReversal Pod

Explore listener stats, chart rankings, contacts and more on the RiskReversal Pod podcast page.