OpenAI just closed the largest venture round in history: $122 billion in committed capital at a post-money valuation of $852 billion. The round was anchored by Amazon, Nvidia, and SoftBank. Revenue has crossed $2 billion per month.
By every traditional metric, this is a triumph. By the one metric that actually reveals investor sentiment — secondary market demand — it's something else entirely.
Bloomberg reports that OpenAI shares have fallen out of favor on the secondary market, with institutional holders struggling to unload roughly $600 million in shares at current valuations. In some cases, the shares are "almost impossible to move." The reason? Investors are pivoting to Anthropic.
Ken Smythe, founder of Next Round Capital, told Bloomberg his secondary marketplace was seeing a clear drop in demand for OpenAI shares even as the company was raising tens of billions. The smart money, it appears, is moving toward Claude.
Meanwhile, Forbes cataloged OpenAI's growing graveyard of dead products and incomplete deals — from the Sora shutdown to hundreds of billions in announced partnerships that haven't materialized. And OpenAI itself published a policy reminder that all equity is subject to transfer restrictions, warning that unauthorized sales — including SPVs and tokenized offerings — are void and may violate securities law.
Why it matters
This is a story about two things happening at once. On one side: a company raising more money than any startup in history, with revenue growing faster than almost any enterprise software business ever has. On the other: secondary market investors voting with their feet, signaling that the valuation may have outrun the reality.
The contrast is unusual. Normally, a record funding round generates secondary demand, not a sell-off. The fact that investors are struggling to exit even at $852 billion suggests the market sees real risk — product cancellations, executive departures, competitive pressure from Anthropic's Claude Code, and the basic question of whether any company can grow into a near-trillion-dollar valuation on AI revenue alone.
For the broader industry, this is a signal. The era of "raise at any price" may be ending. Capital is still flooding into AI, but it's becoming more selective — and the winners and losers are diverging fast.
Also in the news
- Oracle cut thousands of jobs to fund AI data center expansion. Employees found out via email. Analysts say the layoffs will free up cash flow for the company's aggressive AI infrastructure buildout.
- The Claude Code leak deepened. Developers mapped the entire 1,893-file, 517K-line codebase, surfacing 53+ tools, 95+ slash commands, and unreleased features including persistent memory, multi-agent worktrees, and a Tamagotchi pet.
- Q1 2026 global venture funding hit $297 billion — a record quarter driven almost entirely by AI infrastructure and model companies.
- A peer-reviewed Science study confirmed AI sycophancy is harmful — chatbot flattery across 11 state-of-the-art models actively decreased users' prosocial intentions and promoted dependence.