Anthropic Trounces OpenAI with Its Papal Pivot: Value Investing in Our AI Age

“I don’t look to companies to be moral guides. I want them to be good companies. When you invest in the stock market, you want them to be growing fast and making profit. That’s it. There’s nothing more to it.” — Keith Teare If it’s Saturday, it must be our weekly tech show. Before we went live, That Was the Week publisher Keith Teare told me it wasn’t a big news week. He was wrong, of course (as he often is). The really BIG news this week, which Keith conveniently missed, is that Anthropic overtook OpenAI as the world’s most valuable AI startup. Dario Amodei’s AI startup raised $65 billion this week, putting its valuation at $900 billion, way ahead of OpenAI’s last round at $730 billion. Keith says, without any proof, that they’ve cooked their numbers. Which makes this week’s news even tastier. The more interesting story, for Keith at least, is Sam Altman’s latest pivot: that humans need stakes in the AI platforms whose wealth they help create. Rather than Patagonia-style moral corporations (which Keith says would make him “throw up”), it should be the responsibility of the state or government to make capitalism more moral. But even slippery Sam got outpivoted this week by Anthropic, who sent a co-founder to Rome to do a deal with the Pope. Leo XIV’s new encyclical, “Magnifica Humanitas,” is Anthropic’s papal pivot. It’s the smart model for value investing in the AI age. Five Takeaways • Anthropic Tops OpenAI — But the Numbers May Be Wrong: Anthropic raised $65 billion this week at a $900 billion valuation, overtaking OpenAI’s last round at $730 billion. The VCs backing it — Green Oaks, Sequoia, Altimeter, Dragoneer — are credible. Andrew’s argument: they’ve seen the books. Keith’s counter: the VCs are playing a different game. They expect two to three times their money at IPO and they’ll probably get it — not because the revenue numbers are solid, but because the only way is up right now. The real test: the S-1, which requires audited accounts. Keith’s prediction: the revenue numbers will look different when the SEC sees them. • Dario’s Credibility Problem — But Claude 4.8 Is Fantastic: Keith has consistently characterised Dario Amodei as “slightly juvenile” and has long been sceptical of Anthropic’s public positioning. This week he cites Om Malik and the All In podcast in support of the revenue numbers critique. But he is careful to separate the man from the product: Claude 4.8, released two days ago, is “fantastic.” At SignalRank, Keith’s firm, Claude rebuilt an entire agent valuation workflow in an hour that would have taken days manually. Andrew’s observation: Andrew is now Anthropic’s newest fan. He has replaced Spurs with Anthropic as his team. • Altman’s Pivot: From UBI to Ownership: Sam Altman has shifted his public narrative on AI and labour. Previously: UBI — universal basic income — as the answer to mass unemployment. Now: ownership. Humans need to own stakes in the AI platforms whose wealth they help generate. Not welfare. Not redistribution. Ownership. Keith’s verdict: it’s an interesting and significant move. More interesting than Amodei’s continued fearmongering about AI devastation. Andrew notes that Altman seems to have genuinely grown up in the last two months. His tone is markedly different. • Patagonia Capitalism Would Make Keith Throw Up: The week’s interview of the week: Eric Ries on Incorruptible , arguing that great companies stay great by choosing a higher moral purpose — the Patagonia model. Keith’s response: it would make him throw up. He doesn’t want companies to be moral guides. He wants them to be profit machines. Moral guidance is the job of politics. And politics, he acknowledges, is massively disappointing. He does agree with Ries on one thing: Sundar Pichai, as an individual, should care about the future. But Google’s job is to make money. That’s it. • Where Does Moral Guidance Come From? The Populists: Andrew’s closing question: if not corporations, not politicians, not the pope — where does moral guidance come from? Keith’s reluctant answer: the populists. Because the people care. They care about the future. And in the absence of politicians they can trust, they go elsewhere. Keith sees this as inevitable rather than desirable. Populism is the unintended consequence of political failure. The people filling the gap that broken institutions left. It’s not a solution. It’s a symptom. About the Guest Keith Teare is a British-American entrepreneur, investor, and publisher of the That Was the Week newsletter. He is a co-founder of TechCrunch and Andrew’s regular TWTW co-host. References: • That Was the Week by Keith Teare. • Om Malik, “The Copy and the Guru” — the post on Anthropic’s revenue numbers referenced in the conversation. • All In Podcast — referenced for the Anthropic S-1 revenue discussion. • Episode 2921: Eric Ries on Incorruptible — the interview of the week discussed in the show. • Episode 2915: Keith Teare on capitalism and AI — the preceding TWTW, referenced at the opening. About Keen On America Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America , Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,900 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting. Website Substack YouTube Apple Podcasts Spotify Chapters: (00:31) - Introduction: ten days since the last TWTW (01:01) - The big news: Anthropic tops OpenAI at $900 billion (01:53) - Keith’s reaction: both true and BS (02:22) - OpenAI is further ahead on IPO filing (03:15) - Om Malik and the revenue numbers: what does misleading mean? (03:41) - The All In podcast and Dario’s credibility (04:21) - Anthropic’s $65 billion raise: the VCs’ game (04:42) - But Claude 4.8 is fantastic: the SignalRank story (06:16) - Dario vs Sam: who’s more grown up? (07:00) - Altman’s pivot: from UBI to ownership (08:00) - Keith admits he was wrong about OpenAI’s dominance (09:47) - What did Keith get wrong? (10:36) - Corporate vs consumer AI dominance (15:00) - Agentic AI: the big theme in Keith’s newsletter (20:00) - The pope: Leo XIV and AI (25:00) - Moral cap...

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Anthropic Trounces OpenAI with Its Papal Pivot: Value Investing in Our AI Age is an episode from Keen On by Andrew Keen.

This episode is 39:10 long.

This episode was published on May 30, 2026.

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