**[OpenAI and Anthropic Employees Cash Out $14 Billion in Five Years]** According to monitoring by Dongcha Beating, as OpenAI submits its initial public offering (IPO) draft, the company is planning a new round of tender offers for employees at a pre-money valuation of $730 billion. Based on estimates from *The Information*, 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. In the past five years, OpenAI has conducted at least eight tender offers, providing employees with cash-out opportunities totaling over $9 billion. In contrast, its competitor Anthropic, founded five years ago, has had a lower frequency of equity buybacks. Anthropic completed its first employee equity buyback in May 2025, a few months after reaching a valuation of $58 billion, and conducted another multi-billion-dollar equity cash-out earlier this year following a funding round that valued the company at $350 billion. As startups remain private for longer periods, employees face tax pressures on vested equity, making company-initiated tender offers a primary channel for liquidity. Meanwhile, SoftBank, after leading OpenAI's $330 billion valuation funding round last year, also purchased at least $1.7 billion in existing shares through private transactions. Due to widespread employee expectations of an IPO, some shareholders have opted to wait for the public offering, which caused Anthropic's cash-out scale earlier this year to fall short of investors' expectations of $5 billion to $6 billion. Currently, both companies are tightening compliance restrictions, cracking down on unauthorized secondary market equity transactions through special purpose vehicles and other means. [*Original Link*]