OpenAI Can’t Hold a Lead, Stripe Buys OpenRouter & AI Hits a Wall

Stripe buys OpenRouter for billions, which naturally raises the question: did Stripe just buy critical AI infrastructure, or a very expensive router with great distribution? The original squad is back to debate why $7B acquisitions somehow feel normal now, whether Google already has agentic commerce won by owning your inbox, calendar, and Drive, and why Anthropic vs. OpenAI might be less about who has the best model and more about who built the right company. Sam makes the case that OpenAI pulled off the “greatest fundraising story in history,” Dave argues Grokbot might officially make AI a three-player race, and everyone tries to figure out how you price any of these companies when no lead seems to last. Plus, is AI a great investment or just a great trade, does the data center backlash actually have anything to do with data centers, have we built trillions of dollars of infrastructure before finding enough use cases for it, and, naturally in pop corner, Josh Kushner bought into the Lakers. Chapters: 0:00 Episode trailer 1:00 Episode start 4:00 This week in AI 5:00 Stripe buys OpenRouter 8:30 Is OpenRouter actually worth billions? 11:00 The agentic commerce bet 14:00 Why Google could own the AI assistant 17:30 The DOJ investigates Andreessen Horowitz 22:00 Anthropic vs. OpenAI 26:00 Why OpenAI is struggling in enterprise 28:30 Can anyone actually price AI companies? 30:00 OpenAI’s “greatest fundraising story in history” 33:30 Is AI a great investment or just a great trade? 36:00 SpaceX, Moderna and narrative capitalism 37:30 Grok enters the AI race 41:00 AI makes software increasingly disposable 45:00 The AI data center backlash 47:30 “The backlash is that AI sucks” 48:30 Did we build too much AI infrastructure? 53:30 Josh Kushner, Thrive and the Lakers 55:30 Travis Kelce enters the NIL business We’re also on ↓ X: https://twitter.com/moreorlesspod Instagram: https://instagram.com/moreorless Spotify: https://podcasters.spotify.com/pod/show/moreorlesspod Connect with us here: 1) Sam Lessin: https://x.com/lessin 2) Dave Morin: https://x.com/davemorin 3) Jessica Lessin: https://x.com/Jessicalessin 4) Brit Morin: https://x.com/brit

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