600 People, $66 Billion: The First Major Cash-Out in the Era of Large Models
The first systematic "big cash-out" of the AI era occurred in October 2025, when over 600 current and former OpenAI employees sold a total of $6.6 billion in shares via a secondary market. Approximately 75 individuals maxed out a $30 million per-person sale limit, while around 525 others cashed out an average of $8.3 million each. This event, exceeding the scale of any 2024 US IPO, functioned as a "shadow IPO." It marked a radical departure from the traditional Silicon Valley path of waiting for a public listing, instead allowing employees to convert equity to cash after just two years of tenure—a direct retention tool in a fiercely competitive talent market where rivals like Meta have offered packages worth hundreds of millions.
This massive liquidity event presents a dual-edged sword for OpenAI. While it helps retain talent, it also risks triggering a brain drain as newly wealthy employees may depart. Furthermore, it creates a dilemma for those who sold: they forfeited potential future gains as the company's valuation soared from $400 billion to $852 billion within months. In stark contrast, employees at rival Anthropic demonstrated greater reluctance to sell during their own secondary offering.
The financial narratives of the two labs also diverge sharply. OpenAI, while achieving over $20 billion in annualized revenue by 2025, faces massive projected losses (up to $14 billion in 2026), a long path to cash flow positivity, and significant revenue-sharing payments to Microsoft. Anthropic reports rapid revenue growth, improving gross margins, and a faster path to profitability. OpenAI's trajectory is thus balanced precariously between skyrocketing valuation based on funding narratives and the pressures of sustained financial losses post-cash-out. The event underscores that the AI race has evolved into a capital and human experiment, where immense wealth crystallizes the complex calculations of greed, fear, and ambition within the industry.
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