Key Points
Anthropic has become an enterprise AI powerhouse, with Claude Code emerging as a dominant tool for software developers and helping drive explosive revenue growth.
OpenAI still owns the strongest consumer AI brand and benefits from its deep partnership with Microsoft, but its path to profitability remains much longer.
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Two artificial intelligence companies are likely going to ask public markets to buy into them at valuations in the vicinity of $1 trillion this fall. Both are unprofitable. Both are spending money at a rate that would terrify CFOs at any other company on earth. And yet the race between Anthropic and OpenAI to go public sets up one of the most consequential investment decisions individual investors will face in the next 12 months, because despite their similarities, the two companies are not the same bet.
Here’s why: Anthropic filed its S-1 confidentially on June 1 following a $65 billion Series H round that valued the company at $965 billion. This briefly made it the most valuable start-up in the world, ahead of OpenAI. Anthropic’s annualized revenue run rate hit $47 billion in May, up from $4 billion just 14 months earlier. More importantly, Anthropic management has offered guidance predicting that it’s headed for its first profitable quarter.
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OpenAI is valued at approximately $852 billion, with an annualized revenue run rate of roughly $30 billion. That sounds similar. But OpenAI’s internal documents project it will book a loss of $14 billion in 2026 — roughly three times its 2025 loss — driven by compute costs, research hiring, and infrastructure expansion. The company’s internal forecast is for cumulative losses of $44 billion through 2028, with profitability not arriving until 2029.
These are not small differences. One company is approaching its first profitable quarter. The other is on pace to burn $14 billion this year.
How Anthropic won already without anyone noticing
The story that matters most isn’t valuation — it’s where the money is coming from and why it keeps accelerating.
Anthropic’s Claude Code — a terminal-based artificial intelligence coding tool — now holds 54% of the enterprise AI coding market. OpenAI holds 21%. That’s not a close race. Coding accounts for 51% of all enterprise AI spending, and Anthropic collects the majority of it. Claude Code crossed $2.5 billion in annualized revenue as a stand-alone product. That single product line is larger than most public SaaS companies.
This matters for IPO investors because enterprise software is sticky in a way that consumer products are not. When a company’s engineering team builds its entire development workflow around Claude Code, they aren’t going to change tools because a competitor runs a campaign. Switching costs are real, and Anthropic is accumulating them at scale.
The case for OpenAI
None of this means OpenAI is a bad investment. ChatGPT remains the most recognized AI brand in the world, with a far wider consumer footprint than Anthropic’s. OpenAI’s partnership with Microsoft (NASDAQ: MSFT) — which through a complex structure holds a significant stake in OpenAI — gives it a distribution channel that reaches virtually every enterprise on earth through Microsoft 365 and Azure. When OpenAI goes public, it will do so with brand recognition in the consumer market that Anthropic lacks, and a commercial relationship with Microsoft that keeps enterprise doors open regardless of what Claude Code is doing.
The problem is that brand recognition alone won’t reduce its losses. OpenAI introduced ads into its free ChatGPT tier this year. This is a clear sign that the path to monetizing its consumer base is proving harder than the early growth suggested.
Which one could deliver bigger returns?
This is the honest answer: Neither is guaranteed to deliver gains, and anyone who tells you otherwise isn’t reading the same S-1s you are.
But if I had to pick one heading into an IPO, I think Anthropic is the far more interesting investment right now. It grew its revenue run rate from $4 billion to $47 billion in 14 months, has captured the majority of the market for the highest-value AI use case, and is approaching profitability, which OpenAI isn’t.
OpenAI may still win. It has more capital, a powerful brand, and its Microsoft relationship as a structural backstop. But Anthropic is winning the enterprise battle where it counts, in the tools engineers reach for every day.
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Micah Zimmerman has no position in any of the stocks mentioned. The Motley Fool has positions in and recommends Microsoft. The Motley Fool has a disclosure policy.
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