OpenAI just filed its IPO paperwork, and the company is planning a new tender offer for employees at a pre-money valuation of $730 billion. According to an estimate from The Information, employees and early investors at OpenAI and rival Anthropic have collectively cashed out roughly $14 billion over the past five years.
Over that period, OpenAI has conducted at least eight tender offers, providing employees with more than $9 billion in total liquidity. Anthropic, which was founded five years ago, has been less frequent with buybacks. It completed its first employee stock repurchase in May 2025, just months after hitting a $58 billion valuation, and then completed another multi-billion-dollar cash-out earlier this year following a funding round that valued it at $350 billion.
As startups stay private longer, employees face tax pressures on vested equity, and company-initiated tender offers become a primary liquidity channel. Meanwhile, SoftBank, after leading a $330 billion valuation round for OpenAI last year, also bought at least $1.7 billion in existing shares through private transactions. Many employees are holding out for an IPO, which caused Anthropic's cash-out earlier this year to fall short of the $5 billion to $6 billion investors had expected. Both companies are also tightening compliance, cracking down on unauthorized secondary market trades through special purpose vehicles.