More or Less

Stripe Buys OpenRouter, OpenAI vs. Anthropic & the AI Backlash

August 21, 2026·56 min
Episode Description from the Publisher

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 trailer1:00 Episode start4:00 This week in AI5:00 Stripe buys OpenRouter8:30 Is OpenRouter actually worth billions?11:00 The agentic commerce bet14:00 Why Google could own the AI assistant17:30 The DOJ investigates Andreessen Horowitz22:00 Anthropic vs. OpenAI26:00 Why OpenAI is struggling in enterprise28:30 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 capitalism37:30 Grok enters the AI race41:00 AI makes software increasingly disposable45:00 The AI data center backlash47:30 “The backlash is that AI sucks”48:30 Did we build too much AI infrastructure?53:30 Josh Kushner, Thrive and the Lakers55:30 Travis Kelce enters the NIL businessWe’re also on ↓X: https://twitter.com/moreorlesspodInstagram: https://instagram.com/moreorlessYouTube: https://youtu.be/Xwzl-Ihyyr0Connect with us here:1) Sam Lessin: https://x.com/lessin2) Dave Morin: https://x.com/davemorin3) Jessica Lessin: https://x.com/Jessicalessin4) Brit Morin: https://x.com/brit

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