More or Less · Topics · Episode #163

OpenAI Chose Consumer, Anthropic Chose Microsoft -- and Only One Bet Is Paying Off Right Now

From #163 — Stripe Buys OpenRouter, OpenAI vs. Anthropic & the AI Backlash · August 21, 2026 · 6:31 min · Jessica Lessin, Dave Morin, Brit Morin, Sam Lessin

Clip from the full recording, 27:26–33:57 · download mp4 · watch at this point on YouTube

With OpenAI reportedly struggling to convert enterprise customers away from Anthropic despite $40B in revenue, Dave argues the two labs simply built different bodies with different organs -- and Sam warns neither company's growth can be trusted to compound in a straight line.

Jess raises the uncomfortable question hanging over OpenAI: despite the company not starting from zero in enterprise, she keeps hearing anecdotally that it’s struggling to win customers off Anthropic even on attractive terms. Dave’s framing is stark – Anthropic chose to become “Microsoft,” building deep relationships with its largest enterprise accounts and largely ignoring press and small business, while OpenAI has always been a consumer company first, now awkwardly retrofitting an enterprise motion the way “Meta trying to get into hardware” never quite works. Brit pushes back gently on the “OpenAI is failing” framing: revenue is still growing to a reported $40 billion, they’re targeting a public listing by 2027, and that’s not a company to count out – though Dave notes CFO Sarah Fryer has been signaling the IPO timeline earlier and earlier in the press.

Sam widens the lens to the real problem: nobody can actually forecast these companies. He argues everyone’s instinct is to pattern-match Anthropic and OpenAI to the early internet giants – Google, Facebook – but that comparison breaks down because those companies could reliably project and control their growth, while the AI labs are accelerating, decelerating, and reaccelerating in ways that make revenue guidance meaningless. His verdict on OpenAI’s stumble: “it’s like if Uber got hit by a Lyft” – a reversal nobody’s growth-story framework predicted, and one that shows leads in AI simply aren’t secure, no matter what the current quarter says. He still credits Sam Altman with running “the greatest fundraising story in the history of the world,” built on a narrative of AI-scale inevitability that Anthropic’s narrower, coding-and-enterprise-focused strategy has now temporarily eclipsed.

Key points

• Dave's framing: Anthropic chose to be "Microsoft" (deep enterprise focus, ignoring press/small business); OpenAI stayed a consumer company trying to retrofit enterprise -- "two completely different bodies with different organs."
• Reports say OpenAI is struggling to convert enterprise customers away from Anthropic even on favorable terms.
• Brit's counter: OpenAI's revenue is still growing (reportedly $40B) and it remains on track for a public listing; not a company to write off.
• Dave notes CFO Sarah Fryer has been signaling OpenAI's 2027 IPO timeline earlier and earlier in press appearances.
• Sam: comparing AI labs to early internet giants (Google, Facebook) is a flawed pattern-match because those companies could reliably project growth; AI labs can't.
• Sam calls OpenAI's stumble against Anthropic "like if Uber got hit by a Lyft" -- proof that no lead in AI is secure.
• Sam still credits Sam Altman's fundraising execution as historically unmatched, even as Anthropic's narrower enterprise/coding strategy currently has momentum.

Where they landed

Quotes

“They decided to be Microsoft, build an enormous enterprise business, and have done a great job doing that... OpenAI chose a consumer strategy.”— Dave

“I think OpenAI missing massively on quarter and getting so eclipsed is just... it's like if Uber got hit by a Lyft.”— Sam

“What matters is that no lead is secure, right? And the projections don't mean anything.”— Sam

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