After more than 15 years sitting at trading desks and corporate treasury tables, I learned a rule that almost never fails: when the buyer, the seller and the bank financing the deal are, underneath it all, the same half-dozen companies, somebody —sooner or later— ends up without a chair when the music stops. That’s exactly what’s happening in artificial intelligence right now, and this week made it clearer than ever.

Here’s What’s Real

Anthropic, the company behind Claude, is in the final stretch before going public at a valuation that, according to investors cited by the Financial Times, could reach $2 trillion —double what was being discussed at the start of the year—, in what would be the largest IPO in history, bigger even than SpaceX’s listing. Reuters reported that marketing would kick off in mid-October, with the goal of closing the Nasdaq listing before November’s midterm elections. Anthropic is also lining up a $15 billion credit facility right before going to market: not even the company gearing up for the biggest IPO ever wants to rely solely on its own cash.

It isn’t alone. OpenAI closed a round this year north of $120 billion, with Amazon, Nvidia, SoftBank and Microsoft as the main backers, at an $852 billion valuation —we go deeper on it today in the Daily Briefing #0039—. They are, literally, the same companies, moving among themselves.

Here’s What Nobody Says Out Loud

Since August, investor Michael Burry —the same one who called the subprime mortgage crisis— has been circulating a diagram worth more than most analyst reports: Microsoft, Amazon, Google, Meta, OpenAI, Anthropic, Nvidia and AMD trading equity stakes and cross purchase commitments worth hundreds of billions of dollars. Nvidia sells chips to OpenAI; invests in OpenAI; OpenAI buys cloud capacity from Microsoft and Amazon, who in turn invest in OpenAI and in Anthropic. The money doesn’t disappear —it travels in a circle among ten names, and every lap gets booked as “revenue” or “demand” somewhere on a balance sheet. That doesn’t mean AI is smoke —the products exist, people use them, they generate real value every day—. It means a chunk of the demand propping up these valuations isn’t coming from an outside customer paying for something they need: it’s coming from the same group of investors paying each other.

The Real Opportunity

It isn’t guessing whether Anthropic lists at $2 trillion or $1.5 trillion, or fighting for an allocation in the year’s hottest IPO. It’s something far more boring and, over time, far more profitable: before adding a single AI stock to your personal portfolio or your company’s treasury, ask yourself three questions any serious trading desk asks before sizing a big position. First: does this company generate real free cash flow today, or does it live round to round? Second: who’s the end customer for what it sells, and are they someone other than whoever’s financing it? Third: if the next round or IPO prices lower than the market expects —which already happened once this year with Anthropic’s own number before it climbed back to $2 trillion—, what happens to my position?

If you’re investing from Colombia, with the peso strengthening against the dollar and appetite for hard-currency assets on the rise, the temptation to jump on the AI wave without asking these questions is even stronger: betting on something that climbs every day feels free. It isn’t. It never was.

Warren Buffett said it best: you only find out who’s swimming naked when the tide goes out. Nobody knows when this tide turns —it could take years, or it might never turn in the catastrophic way some predict—. But you can decide, today, what you’re wearing when you walk into this story. That’s the difference between speculating and applying judgment. Have you asked yourself those three questions about your own AI exposure yet, or are you still waiting for someone else to answer them for you?

If questions like these interest you, we keep following this story —and plenty of others— every day in the ViSFI Daily Briefing. And if this was useful, share it with anyone thinking about jumping on the next AI IPO.