Anthropic's Rise Sparks OpenAI Investor Doubts

OpenAI's substantial $852 billion valuation is reportedly drawing skepticism from some of its own investors, particularly as the company intensifies its focus on enterprise clients and competes aggressively with rival Anthropic, as reported by the Financial Times.

Anthropic, meanwhile, has demonstrated significant growth, with its annualized revenue surging from $9 billion at the close of 2025 to $30 billion by the end of March, primarily fueled by strong demand for its coding solutions. An investor with stakes in both AI firms indicated to the FT that validating OpenAI's latest funding round necessitates projections of an IPO valuation reaching $1.2 trillion or higher, which consequently positions Anthropic's current $380 billion valuation as a comparatively more attractive prospect.

This sentiment is mirrored in the secondary market, where demand for Anthropic shares has become almost insatiable, contrasting sharply with OpenAI shares, which are currently trading at a discount.

This scenario isn't entirely new for OpenAI CEO Sam Altman. His previous experience leading Y Combinator saw aggressive valuation inflation leave some portfolio companies in precarious financial positions, while others ultimately justified their high valuations and exceeded expectations.

Roy Luo, a partner at Iconiq Capital, whose firm has allocated over $1 billion to Anthropic while maintaining a smaller investment in OpenAI, articulated his perspective to the FT. "There’s room for both," Luo stated, "but there is fundamentally a number one and a number two dynamic, and the number one will win disproportionately. We picked." Countering this, OpenAI CFO Sarah Friar asserted to the FT that the company's recent $122 billion fundraising round — marking the largest private capital raise in history — serves as clear evidence of sustained investor confidence.