Rory O'Driscoll

Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated

Aug 27, 2026 · 1:26:44

Jason Lemkin, Rory O’Driscoll and Harry Stebbings say the AI boom now depends on Nvidia and hyperscalers financing frontier models, as shown by Nvidia's $6B Poolside purchase and $1B at a $12B pre-money valuation. They dissect OpenAI's promised 2027 IPO, arguing it has no choice as Anthropic outraces it and 'it's all about code'; they call Anthropic's $30T TAM claim delusional and OpenAI's $200 plan a losing consumer business. Also covered: Mercor's $20B round, Hugging Face's $13B sale risk, Citadel unwinding 80% of Leopold's fund, Stripe's 41% growth, agents' data leaks, and why customer support, humanoid robotics and AI services are the dumbest categories. Their verdict: we're less than a third of the way through the cycle and addicted to tokens.

Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?

Aug 20, 2026 · 1:17:47

Harry Stebbings, Jason Lemkin and Rory O'Driscoll analyze SpaceX's $60B Cursor takeover, Stripe's $7B OpenRouter deal, Anthropic's first profit, Silver Lake's $43B Workday bid and Lovable's $13.3B round, arguing all reward speed and growth over margin. Musk got Cursor at ~10x forward revenue; Microsoft, not Meta, is the real loser. OpenRouter is a niche that may vanish in five years, yet could become 20-30% of Stripe revenue. Anthropic's first profit on $11.5B Q2 revenue was inevitable at ~40% gross margin; only 2027-28 projected revenue matters for its IPO. Workday is a 5.3x-revenue system-of-record LBO baseline versus 70x trailing for OpenRouter, and Higgsfield's $5.5B and Lovable's $13.3B are compared to Cursor, with Lovable 'not radically off' as AI apps accrete moats.

Frontier Labs Threatened by Kimi? Should the US Ban Chinese Open-Source Models & Stripe Buys PayPal

Jul 23, 2026 · 1:27:39

Harry Stebbings, Jason Lemkin, and Rory O'Driscoll debate China's near-frontier open-weight models Kimi and Quan, arguing the US should not ban them but compete. They discuss OpenAI's 'AI Communism' tweet, the commoditized inference market leading OpenRouter to consider sale while Fireworks AI hits $1B ARR at $17.5B valuation. The panel notes the application layer has not arrived, with infrastructure spending far exceeding app revenues. They analyze the Stripe-Advent bid to take PayPal private at ~$60B, predicting a 35% premium deal. Finally, they touch on Databricks' $188B Series M, nuclear energy progress, and the strange inversion of private and public markets.