OpenAI and Anthropic employees and investors cash out $14 billion within five years

Over the past five years, OpenAI and Anthropic have allowed employees and early investors to cash out approximately $14 billion. OpenAI plans to arrange a tender offer with a pre investment valuation of $73 million, providing employees with over $9 billion in cash out opportunities through at least eight tender offers over the past five years. Anthropic completed its first repurchase after a valuation of $58 million in May 2025, and completed another round of multi billion dollar realization after raising $35 million earlier this year. After leading OpenAI's $33 million financing, SoftBank purchased at least $1.7 billion worth of shares through private transactions. Anthropic's expected monetization scale at the beginning of this year did not reach $500000 to $600000.