Sam Altman Has a Lot of Things Keeping Him Awake at Night

by Dave Lee of Bloomberg News, 9/19/25

What’s keeping Sam Altman up at night?

Talking to the former Fox News host Tucker Carlson recently, Altman, the chief executive officer and co-founder of Open AI, was only half-joking when he said he hadn’t “had a good night’s sleep since ChatGPT launched” in November 2022. On his mind were the “very small decisions” his company makes that can affect millions of people. He was speaking in the context of a flurry of reports on the sometimes tragic consequences of mentally unwell people turning to ChatGPT for help.

But it’s surely not the only issue swirling around in Altman’s thoughts when he lays down his weary head. To put it mildly, there is a lot coming over the hill for OpenAI for the rest of this year and beyond. None of these struggles looks particularly threatening in isolation. Combine them, though, and you start to wonder whether OpenAI’s challenges, the things it needs to solve to remain competitive, are becoming overwhelming.

First, let’s talk structure. Time is running out to turn into a for-profit corporation. Don’t let the recent memorandum between OpenAI and Microsoft Corp. give the impression that OpenAI’s transition into a public benefit corporation, which technically must be completed by the end of the year, is finalized. It is not. The conscious semi-uncoupling, where both OpenAI and Microsoft are seeking to diversify who they work with on AI and rewrite a revenue sharing arrangement, is just one part of the delicate negotiation in altering OpenAI’s structure. It also has to satisfy regulators in California and Delaware that its new structure doesn’t violate charitable trust laws — complications around which have reportedly had some executives pondering whether the company should move out of California (though OpenAI has denied this). Failure to square this circle puts $19 billion of contingent funding at risk, plus untold future fundraising opportunities.

The company’s costs are skyrocketing. OpenAI’s $300 billion deal with Oracle Corp. for cloud computing over roughly five years from 2027 was enough to propel its chairman, Larry Ellison, back to the top of the list of richest people. But his company will see that money only if OpenAI’s extremely lofty revenue goals are met and its costs drop sharply. By 2030, reports The Information, OpenAI is projecting $200 billion in annual revenue, which is highly ambitious compared with what could be around $13 billion in total revenue this year. How will it make up that difference? More subscribers won’t be enough; it’ll take different revenue models, such as advertising, to fill in the gaps. That’s a great, great uncertainty. While it figures things out, OpenAI estimates it will burn through $115 billion in cash through 2029. Unlike the other companies in the race, like Google and Meta Platforms Inc., there is no highly profitable legacy business underneath it all to keep the lights on. A public listing will surely be needed to buy time.