The AI lottery is paying out early

TL;DR: Around 75 current and former OpenAI employees became overnight multimillionaires last fall after each cashing out the maximum $30 million in company stock, the Wall Street Journal reported this week. They were among the 600-plus workers who collectively pocketed $6.6 billion in what was likely the largest pre-IPO liquidity event in tech history. And it could be the warmup to even bigger windfalls if OpenAI and Anthropic go public later this year.

What happened: That $6.6 billion means that, on average, each qualifying OpenAI employee walked away with about $11 million last October—putting them near the top 1% of wealth in the US. For many, it was the first chance to cash out, as OpenAI requires a two-year hold on shares. After maxing out the sale cap, some employees reportedly parked their remaining shares in donor-advised funds, a charitable giving account that lets them take tax deductions and also swerves the capital gains tax, according to the WSJ.

The AI era has already minted plenty of billionaires, mostly founders and VCs. But such share sales are creating a class of AI nouveau riche who were, until recently, just salaried workers.

Now or never: What’s also eyebrow-raising is how much cash cleared before OpenAI even goes public—atypical in Silicon Valley. But just a glance at recent history could hint at why. During the dot-com boom, many employees had to wait to sell even after their company went public—and lost much of their paper fortunes when the bubble popped. (See also: crypto and NFT wealth that looked fat in that digital wallet and then largely vanished overnight.) And the sell-off comes amid a growing anxiety that if you don’t set yourself up financially now, you’ll be left behind in a “permanent underclass” as AI replaces jobs.

The coming flood: Per the WSJ, this is just a “sneak peek” of what’s coming once OpenAI and Anthropic IPO. OpenAI is now worth around $852 billion and could reportedly target a $1 trillion-plus valuation upon going public. Meanwhile, Anthropic is in talks to raise funds that would value it at around $900 billion pre-IPO.

AI wealth has already infused the Bay Area, with housing prices jumping 14% in the past year—not so surprising when Meta offers $300 million pay packages for top talent and OpenAI lists salaries that exceed $500,000. (AI stock is so in-demand right now that one investment banker is trying to swap his Bay Area mansion for Anthropic shares.)

Bottom line: With such record-breaking IPOs on the horizon (ones that would let employees sell beyond any company-set cap), we might see a new class of haves and have-nots for the AI era—and it won’t just be the people running the firms. —WK