Anthropic’s rise is giving some OpenAI investors second thoughts.

According to the Financial Times, OpenAI’s $852 billion valuation is being viewed with skepticism by some investors as the company pivots to focus on enterprise customers and struggles to defend Anthropic.

Anthropic’s annual revenue surged from $9 billion at the end of 2025 to $30 billion at the end of March, driven primarily by demand for its coding tools. One investor who backed both companies told the FT that justifying OpenAI’s round would require assuming an IPO valuation of more than $1.2 trillion. So Anthropic’s current valuation of $380 billion seems relatively cheap.

The secondary market is now telling a similar story, with OpenAI stock trading at a discount while demand for Anthropic stock has grown to an almost insatiable level.

Altman has been here before. During his tenure leading Y Combinator, aggressive valuation inflation caused some portfolio companies to struggle financially and others to turn out not to be worth a penny.

OpenAI CFO Sarah Friar countered by telling the FT that the company’s $122 billion fundraising, the largest private round in its history, was evidence of continued investor confidence. Not everyone will be convinced. Jai Das, president of investment firm Sapphire Ventures (which has no stake in either company), told the FT that he sees OpenAI as the “Netscape of AI”. This meant that the once dominant browser was overtaken by Microsoft and eventually absorbed by AOL.

Update: This article has been updated to remove investor quotes published by the Financial Times and later removed.