Anthropic’s rise is giving some OpenAI investors second thoughts

OpenAI’s $852 billion valuation is facing skepticism from some of its own investors as the company scrambles to reorient itself around enterprise customers and fend off Anthropic, according to the Financial Times.

Anthropic’s annualized revenue jumped from $9 billion at the end of 2025 to $30 billion by the end of March, driven largely by demand for its coding tools. One investor who has backed both companies told the FT that justifying OpenAI’s round required assuming an IPO valuation of $1.2 trillion or more — making Anthropic’s current $380 billion valuation look like the relative bargain.

The secondary market tells a similar story right now, where demand for Anthropic shares has grown nearly insatiable while OpenAI shares are trading at a discount.

Altman has been here before. During his tenure leading Y Combinator, aggressive valuation inflation left some portfolio companies financially stranded while others proved worth every penny and then some.

Iconiq Capital partner Roy Luo — whose firm has invested over $1 billion in Anthropic while holding a smaller stake in OpenAI — told the FT where he stood. “There’s room for both, but there is fundamentally a number one and a number two dynamic, and the number one will win disproportionately,” he said. “We picked.” OpenAI CFO Sarah Friar pushed back, telling the FT that the company’s $122 billion raise — the largest private fundraising in history — was evidence of continued investor confidence.