NextFin News - OpenAI’s shares are facing a sudden chill in the private secondary market, where a glut of sell orders has met a wall of indifference from buyers. Despite the company recently securing a massive $122 billion valuation in a primary funding round, institutional investors are struggling to offload approximately $600 million worth of shares. This liquidity trap in the secondary market stands in stark contrast to the frenzy surrounding its chief rival, Anthropic, which currently commands a $2 billion waiting list of eager capital.
Ken Smythe, the founder of Next Round Capital, reported that about six institutional holders—including hedge funds and venture capital firms—have approached his platform in recent weeks to liquidate their OpenAI positions without success. Smythe, whose firm specializes in secondary market liquidity for late-stage startups, has observed a distinct pivot in sentiment. While OpenAI was once the undisputed crown jewel of the AI boom, investors are now balking at its nearly $852 billion post-investment valuation, opting instead for the perceived "room for growth" offered by Anthropic’s $380 billion price tag.
The divergence is visible in the pricing data from trading platforms like Augment and Hiive. Buyers are currently bidding for OpenAI shares at a 10% discount to its latest financing round, implying a market-clearing valuation of roughly $765 billion. Conversely, Anthropic shares are trading at a premium of more than 50% over its previous round. Adam Crawley, co-founder of Augment, noted that the sheer scale of OpenAI’s valuation has made it a "heavy lift" for secondary buyers, whereas Anthropic is viewed as a more nimble play in the enterprise AI sector.
This secondary market fatigue does not necessarily signal a fundamental collapse, but rather a structural shift in how investors view the AI hierarchy. OpenAI’s financial engine remains formidable, with monthly revenue hitting $2 billion and a projected annual run rate of $13.1 billion for 2025. However, the company’s burn rate remains astronomical due to the costs of training frontier models and maintaining a massive compute infrastructure. To manage these pressures, U.S. President Trump’s administration has been monitoring the strategic importance of these AI leaders, even as OpenAI recently paused certain product lines, including the video-generation tool Sora, to prioritize core profitability.
Skeptics of the "OpenAI slump" narrative argue that the secondary market data may be skewed by the company’s own success. With a clear path toward an initial public offering (IPO) as early as late 2026, many rational investors may simply be waiting to buy shares in the public market rather than paying high fees to hold private stock through Special Purpose Vehicles (SPVs). Anthropic, by contrast, has not provided a clear listing timeline, making the secondary market the only viable entry point for many institutions.
The competitive landscape is also being reshaped by regulatory and security hurdles. Anthropic recently faced scrutiny after being included on a U.S. Department of Defense supply-chain risk list, and a minor source code leak involving its Claude model briefly rattled confidence. Yet, for now, the "underdog" narrative continues to favor Anthropic in the eyes of private equity. As the AI sector matures, the secondary market is acting as a high-frequency barometer for valuation fatigue, suggesting that even the world’s most valuable startups are not immune to the gravity of price discovery.
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