OpenAI just raised $122 billion, the largest private funding round in history. By most measures, that’s a stunning achievement. But according to Financial Times reporting, some of the company’s own investors aren’t convinced the $852 billion valuation is justified.
That’s not skepticism. That’s a red flag the size of a billboard.
The Math Doesn’t Add Up (Yet)
Here’s what makes this awkward. According to the Financial Times, one investor who has backed both OpenAI and Anthropic told the publication that OpenAI’s valuation only makes sense if you assume an IPO valuation north of $1.2 trillion. That’s not a projection. That’s a requirement just to break even on the current round.
Compare that to Anthropic, which just hit a $380 billion valuation. On paper, that looks cheap. But there’s a reason the secondary markets are pricing them differently.
Anthropic’s annualized revenue jumped from $9 billion at the end of 2025 to $30 billion by March 2026, largely driven by demand for its coding tools. That’s a 3x revenue jump in four months. The company is printing money. Meanwhile, OpenAI is scrambling to reorient around enterprise customers and fend off Anthropic’s advances.
The secondary market reflects this reality. Anthropic shares are in high demand. OpenAI shares are trading at a discount.
The Netscape Problem Nobody Wants to Say Out Loud
Jai Das, president of investment firm Sapphire Ventures, said something in the Financial Times that probably kept some people up at night: he views OpenAI as “the Netscape of AI.” For anyone old enough to remember the 1990s, that comparison lands like a punch. Netscape was dominant. It was the browser. Then Microsoft came along with Internet Explorer bundled into Windows, and Netscape got absorbed into the wreckage of its own obsolescence.
The parallel isn’t perfect. OpenAI isn’t going anywhere overnight. But it raises an uncomfortable question: in a race where your competitor is growing revenue faster and capturing market share more aggressively, can valuation stay decoupled from fundamentals forever?
Sam Altman’s Track Record
There’s irony in this dynamic. Sam Altman has seen valuation bubbles burst before. During his time leading Y Combinator, aggressive valuation inflation left some portfolio companies stranded while others lived up to the hype. He knows how this story goes.
OpenAI CFO Sarah Friar pushed back against the skepticism, telling the Financial Times that the $122 billion raise itself proves investor confidence. Technically true. But confidence in what? That investors will keep the money flowing, or that the company will actually deliver returns that justify a trillion-dollar-plus exit? Those are two different things.
The Business of Technology Cycles
The real issue isn’t whether OpenAI is a good company. It clearly is. The question is whether it’s a $852 billion company and whether it’ll be worth $1.2 trillion in five years. Those aren’t given answers just because you raised the biggest check in history.
Anthropic’s explosive growth suggests the AI market isn’t a winner-take-all game. It’s not even clear who the winner is yet. In a crowded field where your competitor is capturing market share and growing faster, the burden of proof falls on you to show you’re worth the premium valuation. Raising more money doesn’t answer that question. Revenue growth does.
The secondary markets seem to understand this better than the headline valuations suggest. When investors have a choice between Anthropic shares and OpenAI shares at current prices, they’re picking Anthropic. That’s not noise. That’s a signal worth listening to.
