Dick Costolo (Former Twitter CEO) on Elon, AI, and What's Next

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. 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. Timecodes 0:00 - Intro 3:30 - Silicon Valley 9:15 - Feedburner & Twitter 29:40 - VC Landscape 48:45 - IPO Market 56:30 - Dick & Paul Show — FOLLOW US Instagram: https://www.instagram.com/riskreversalmedia/ Twitter: https://x.com/riskreversal LinkedIn: https://www.linkedin.com/company/riskreversalmedia #investing #stocks #stockmarket The financial opinions expressed in Risk Reversal content are for information purposes only. The opinions expressed by the hosts and participants are not an attempt to influence specific trading behavior, investments, or strategies. Past performance does not necessarily predict future outcomes. No specific results or profits are assured when relying on Risk Reversal. Before making any investment or trade, evaluate its suitability for your circumstances and consider consulting your own financial or investment advisor. The financial products discussed in Risk Reversal carry a high level of risk and may not be appropriate for many investors. If you have uncertainties, it's advisable to seek professional advice. Remember that trading involves a risk to your capital, so only invest money that you can afford to lose. Derivatives are not suitable for all investors and involve the risk of losing more than the amount originally deposited and any profit you might have made. This communication is not a recommendation or offer to buy, sell or retain any specific investment or service.