Anthropic’s rise is giving some OpenAI investors second thoughts

OpenAI's staggering valuation of $852 billion is now under scrutiny from some investors, as the company works to pivot towards enterprise clients and contend with the rapid rise of its competitor, Anthropic. Recent reports indicate that Anthropic's annualized revenue skyrocketed from $9 billion at the close of 2025 to an impressive $30 billion by the end of March, largely fueled by the increasing demand for its coding tools. An investor with stakes in both firms expressed concerns to the Financial Times, noting that justifying OpenAI's valuation would necessitate an IPO valuation of at least $1.2 trillion, which casts Anthropic's current $380 billion valuation in a more favorable light. This shift in perception is echoed in the secondary market, where enthusiasm for Anthropic shares seems insatiable, while OpenAI shares are reportedly trading at a discount. This scenario isn't new for OpenAI's CEO Sam Altman. During his time at Y Combinator, he witnessed how inflated valuations could leave some portfolio companies struggling, while others thrived beyond expectations. Roy Luo, a partner at Iconiq Capital, which has invested over $1 billion in Anthropic and holds a smaller stake in OpenAI, shared his insights with the Financial Times. He pointed out the competitive landscape, stating, "There’s room for both, but there is fundamentally a number one and a number two dynamic, and the number one will win disproportionately. We picked." In response, OpenAI's CFO Sarah Friar defended the company’s position, asserting that its record-breaking $122 billion fundraising round—the largest in private equity history—demonstrates ongoing investor confidence in OpenAI's future.