Why OpenAI’s $122 B Funding Still Leaves Its Shares Unwanted in the Secondary Market

Bloomberg reports that OpenAI’s stock has become unpopular in the secondary market, with investors rapidly shifting capital to its main rival Anthropic.

In the past few weeks six institutions attempted to sell roughly $600 million of OpenAI shares but found no buyers, while about $2 billion of capital is waiting to invest in Anthropic.

Valuation data shows OpenAI at an estimated $852 billion versus Anthropic’s $3.8 billion. Buy‑side quotes place OpenAI at about $765 billion (a ~10% discount to its financing valuation) and Anthropic at roughly $6 billion, representing a premium of more than 50% over its last round.

Earlier this week OpenAI closed a new financing round with $122 billion of committed capital, bringing its post‑money valuation to $852 billion. Investors include Amazon, Nvidia, SoftBank, Microsoft and Andreessen Horowitz. The company also opened a zero‑fee channel for retail investors, raising over $3 billion and gaining exposure in ARK Invest ETFs.

The zero‑fee retail channel is contrasted with Anthropic deals that typically charge 15%–20% ancillary fees through SPVs, which OpenAI warns investors about.

Fundamentally, OpenAI’s growth remains strong: monthly revenue is about $2 billion, projected full‑year 2025 revenue $13.1 billion, ChatGPT has over 900 million monthly active users, more than 50 million paying users, and enterprise revenue accounts for over 40% of total. However, high compute and personnel costs mean the company is still unprofitable.

To curb expenses, OpenAI has paused certain products such as Sora and is working to integrate ChatGPT, Codex, and agent capabilities into a unified “AI super‑app.”

Anthropic is viewed by some investors as a more “steady” player, with relatively restrained infrastructure spending and stable, high‑margin enterprise business. Nonetheless, it faces challenges: it was placed on a U.S. Department of Defense supply‑chain risk list and is involved in litigation, and an npm package leak exposed roughly 512,000 lines of Claude Code, sparking security‑process discussions.

Both companies are contemplating IPOs, with OpenAI’s process potentially starting as early as this year, while Anthropic has not disclosed a clear listing timeline.

One market‑side explanation suggests that if OpenAI’s IPO is expected (e.g., 2026), rational investors may prefer to wait for the public offering rather than pay a premium in the secondary market, reducing secondary demand. Anthropic, lacking a clear IPO path, sees its secondary market as the primary entry point, concentrating demand.

Overall, the uneven secondary‑market activity may simply reflect normal capital flow across different financing stages, and the fast‑changing AI landscape means a single major product update could quickly reshape market narratives.