The AI Power Play: OpenAI's Valuation Under Siege

In a move that has sent shockwaves through the tech industry, OpenAI’s $852 billion valuation is facing unprecedented scrutiny from some of its own investors. The company’s struggles to pivot towards enterprise customers and fend off the rising star, Anthropic, have led to concerns about its lofty valuation. As reported by the Financial Times, the skepticism stems from Anthropic’s impressive revenue growth, which has jumped from $9 billion at the end of 2025 to a staggering $30 billion by the end of March.

The primary concern lies in the fact that OpenAI’s valuation is not justifying itself in the secondary market. The demand for Anthropic shares has skyrocketed, while OpenAI shares are trading at a discount. This disparity raises questions about the sustainability of OpenAI’s valuation, particularly when compared to its competitor’s more impressive financials. For investors who have backed both companies, the doubts are even more pronounced. One such investor, who has invested in both OpenAI and Anthropic, told the FT that justifying OpenAI’s round requires assuming an IPO valuation of $1.2 trillion or more – making Anthropic’s current $380 billion valuation seem like a relative bargain.

This situation is not without precedent for Altman, the co-founder of OpenAI. During his tenure leading Y Combinator, he witnessed aggressive valuation inflation that left some portfolio companies financially stranded, while others proved worth every penny and then some. This experience will undoubtedly inform his perspective on the current dynamics between OpenAI and Anthropic.

The battle between these two AI heavyweights is not just about financials; it’s also a question of competitive positioning. Iconiq Capital partner Roy Luo, whose firm has invested over $1 billion in Anthropic and holds a smaller stake in OpenAI, articulated this tension when he told the FT that there is “fundamentally a number one and a number two dynamic, and the number one will win disproportionately.” In essence, Luo believes that only one company can emerge as the dominant force in the AI landscape. His firm has clearly bet on Anthropic being that winner.

OpenAI’s CFO, Sarah Friar, pushed back against these concerns by highlighting the company’s massive $122 billion raise – the largest private fundraising in history. This significant injection of capital underscores investor confidence in OpenAI’s vision and strategy. However, this narrative is unlikely to quell the doubts surrounding OpenAI’s valuation without a more convincing demonstration of its financial performance. As the AI landscape continues to evolve, one thing is clear: only time will tell which company will ultimately emerge as the leader.

Source: https://techcrunch.com/2026/04/14/anthropics-rise-is-giving-some-openai-investors-second-thoughts/