The OpenAI vs Anthropic Battle for the Enterprise artwork

The OpenAI vs Anthropic Battle for the Enterprise

AI to ROI

September 9, 2026

For the first time, the two leading model companies can be compared on an apples to apples basis. In Q2 2026, Anthropic booked $11.6B against OpenAI's $6.7B, and posted roughly $300M in operating profit while OpenAI's operating loss widened to $12.3B.
Speakers: Ray Rike, Peter Buchanan

Topics: Management, Business, Technology

**Ray Rike** (0:08)
Welcome back to the AI to ROI The Big Story episode. I'm Ray Rike, Founder and CEO of Benchmarkit.

**Peter Buchanan** (0:17)
And I'm Peter Buchanan. I am the managing partner of NewPlan. And Ray, this week we're going to cover the contents of our September 1st AI to ROI newsletter. It's entitled, OpenAI and Anthropic Wage an Epic Battle for the Enterprise.

**Ray Rike** (0:34)
I'm actually really excited to have this discussion because I think who wins the enterprise may win this battle. But before we get into it, let's hear a word from our sponsor.
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It's the first time that I've seen their financials on an apples to apples basis.
Based upon this, it bodes very well for Anthropic, but I'm not so sure how it bodes for OpenAI. I already know how it bodes for the GTM executives at OpenAI because of the turnover.

**Peter Buchanan** (2:59)
Right. Well, she got fired after eight months, and she had actually tremendous revenue growth. It's not like their number was shabby. They went from 5.7 billion in the first quarter to 6.7 billion, so 18 percent quarter-over-quarter growth, which is pretty fantastic. But Anthropic had a seven or eight X growth over last year's second quarter, so it's just basically a thumping.

**Ray Rike** (3:27)
But Peter, revenue wasn't the whole story, was it?

**Peter Buchanan** (3:31)
No, the revenue is not the whole story. So Anthropic also posted a small operating profit of about $300 million. It's the first time they've been profitable. OpenAI's operating loss widened, I didn't think that was possible, but it did, to $12.3 billion. So Anthropic's growth combined with profitability tells you maybe what's ahead for them.
Doesn't say who's going to be the winner over time. I think the long-term winner, frankly, in the top of enterprise AI is not going to be apparent for 24 to 36 months. I think there are a lot of chips to fall, and there's frankly no guarantee that either of these companies will be at the top of the stack. They will, however, make lots of noise between now and then.

**Ray Rike** (4:16)
Yeah, that's fair, especially from a financial performance metrics perspective. But I'd add that that profitable quarter paired with now superior revenue leadership is a really good signal that enterprise buyers like to see to de-risk multi-year purchasing decisions. I mean, when a CFO is signing off on a large AI model platform contract that's becoming foundational to their business, I think seeing a partner, a vendor with such operating discipline carries as much weight as the growth rate.
But once again, it's one quarter, Peter, and the AI industry is evolving too fast. Anthropic, like OpenAI, had hundreds of billions of dollars in infrastructure obligations. I think these profits may be temporary.

**Peter Buchanan** (5:13)
Yeah, which is basically the thesis of the whole newsletter edition. OpenAI and Anthropic are basically running very similar playbooks on the surface.
They have very similar model products, model lineups. Their products line up as peers from top to bottom. They have similar coding products, they have similar vertical market pushes, they have similar distribution. That's the differentiator over the next two years isn't about who has a better strategy or products because they on the surface are quite similar. It's about who executes their strategy better with fewer unforced errors because they're both actually really good at unforced errors. And so, they've got to attack a market that's enormous, right? In order to meet their numbers, that enormous has to be big. So that market has to be big. So before we get to the two companies and really break them down, Ray, how big is the prize that they're actually chasing?

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