OpenAI and Anthropic Employees Cash Out $14 Billion in Five Years

According to Dynamic Beating monitoring, as OpenAI submits its initial public offering (IPO) prospectus, OpenAI is planning a new round of tender offer for employees at a pre-money valuation of $730 billion. Based on The Information's estimate, over the past five years, OpenAI and Anthropic, two leading artificial intelligence companies, have cumulatively allowed employees and early investors to cash out approximately $14 billion.

Over the past five years, OpenAI has provided employees with cash-out opportunities totaling over $9 billion through at least eight tender offers. In contrast, its five-year-old competitor, Anthropic, has had a lower equity buyback frequency. Anthropic completed its first employee stock buyback a few months after its valuation reached $580 billion in May 2025, and completed another multi-billion-dollar equity cash-out earlier this year after a funding round at a $3.5 trillion valuation.

As the time that startups remain private extends, employees face pressure from taxes on vested equity, and company-initiated tender offers have become a primary liquidity release channel. Meanwhile, SoftBank, after leading a $330 billion financing round for OpenAI last year, also purchased at least $1.7 billion in existing shares through private transactions. With employees generally anticipating the company's IPO, some shareholders choose to wait for the initial public offering, leading to Anthropic's recent cash-out scale falling short of investors' expectations of $5 billion to $6 billion. Currently, both companies are also tightening compliance restrictions, cracking down on unauthorized secondary market equity trades through special purpose vehicles and other means.