Early employees and investors at OpenAI and Anthropic have cashed out an estimated US$14 billion in private share sales over the past five years, a tactic easing retention pressure for firms whose staff cannot sell vested stock. The estimate, reported on June 14 by The Information using its own reporting and PitchBook data, noted that both AI developers have arranged company-sponsored sales allowing current and former staff to turn illiquid holdings into cash. OpenAI has completed at least eight share sales in five years, delivering more than US$9 billion to its employees, and began planning a fresh tender offer pegged to its March valuation of US$730 billion. Anthropic ran its first buyback in May 2025 after a US$58 billion valuation, arranged another sale after a US$350 billion round, and most recently raised US$65 billion at a US$900 billion valuation, with annualised revenue past US$30 billion. Citing Carta data, The Information reported that staff at private companies sold roughly US$1.7 billion in shares in 2025, more than US$200 million above their combined 2024 and 2023 totals, as Stripe, Databricks and SpaceX delayed going public. The core HR concern is that long private company stretches can turn equity into frustration, as employees may owe tax on stock compensation before selling.