OpenAI Mints Over 300 Billion-Dollar Billionaires Before Its IPO

Scale of internal share sales

According to The Information , OpenAI and Anthropic have conducted multiple internal share‑sale rounds over the past five years, allowing employees and early investors to cash out roughly $14 billion (≈¥1 trillion). The payouts created more than 300 “billion‑dollar‑net‑worth” individuals.

Largest single payout

In October 2023, 600 OpenAI employees sold shares in a single day, receiving a total of $6.6 billion . The average receipt was about $11 million per person (≈¥80 million). Seventy‑five employees hit the personal cap of $30 million, taking home roughly ¥200 million each.

Tax‑driven liquidity

U.S. equity‑tax rules require employees to pay income tax on the fair‑market value of vested shares even if the shares are not sold. For many senior staff the tax bill can reach tens of millions of dollars. Companies therefore open a “controlled liquidity window” that lets employees sell a portion of their holdings to cover the tax liability.

Retention and compensation

Internal share sales are used as a retention tool because keeping top AI talent is more expensive than training models. OpenAI’s per‑employee equity compensation in 2025 was reported at $1.5 million , which is:

7 times the historic record for technology startups;

≈30 times the average equity grant of large‑cap tech IPOs a year before the offering.

OpenAI’s annual revenue is now roughly half spent on equity compensation for its staff.

Valuation rivalry

Anthropic, founded in 2021, has a reported valuation of $965 billion , surpassing OpenAI’s $850 billion . Both firms have filed IPO prospectuses in secret, creating a “you‑go‑first‑I‑go‑too” standoff. The first mover could lock in a higher IPO price, while simultaneous listings risk splitting institutional demand and depressing valuations.

Compute spending as the primary cash burn

Anthropic signed a ten‑year compute contract with Amazon valued at > $100 billion . OpenAI’s internal “Stargate” project is estimated at $500 billion . Such scale makes public‑market financing essential.

Employee decisions at Anthropic

Anthropic’s revenue grew from <$1 billion at the start of 2024 to $300 billion by April 2026 – a >300‑fold increase in 27 months. When a share‑sale round was offered at a $3.5 trillion valuation in early 2026, many employees chose not to sell, expecting a higher price after the IPO. After a subsequent $650 billion financing round lifted the valuation to $9.65 trillion, the non‑selling employees saw their paper wealth triple.

PitchBook labels this behavior the “champagne problem”: shareholders are reluctant to sell while the stock is still appreciating.

Who buys the pre‑IPO shares?

Secondary purchases by investors such as SoftBank (which bought at least $1.7 billion of OpenAI shares outside the formal financing round) demonstrate strong demand for the limited liquidity.

Caplight CEO Javier Avalos noted that the pressure on employees to monetize their holdings “forces companies to provide a liquidity outlet.”

Controlled vs. uncontrolled liquidity

Internal share sales give the company control over price, buyer identity, timing, and amount, avoiding the fragmented shareholder structure that can arise from private sales through shell companies. This controlled approach helps manage the cap table ahead of an IPO.

Retention costs versus compute costs

While equity compensation is a major expense, the dominant cash burn remains compute. Anthropic’s $100 billion+ Amazon contract and OpenAI’s $500 billion “Stargate” project illustrate the magnitude of capital required to stay competitive in the AI race.

Strategic implications

The $14 billion already cashed out by employees is a small “drop of oil” in the larger AI funding flywheel. Internal share sales act as a pressure‑release valve but do not eliminate the fundamental drive toward an IPO and the massive capital needed to sustain compute growth.

As Next Round Capital’s Ken Smythe observed, “internal share sales are just a pressure‑release valve; they do not remove the incentive to go public.”

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