Heitzman: Circular revenue deals between AI giants are a warning sign
Rick Heitzman · Where Are The AI Startups? — With Rick Heitzmann · Oct 17, 2025 · at 25:53
FirstMark Capital founder Rick Heitzman analyzes mega-deals between OpenAI, Microsoft, and Oracle, comparing them to late-stage froth in previous tech cycles.
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“Well, it depends on who you are, and that kind of goes to the recycling or the circularness of some of these things. Obviously, the OpenAI, Microsoft, or OpenAI Oracle, goes back to the OpenAI Oracle deal. And, you know, I'm gonna give you money that you're gonna invest in our infrastructure, or how, how does this cycle of capital work, which tends to be towards the end of these cycles, right, where you can't generate enough money yourself, you might have exhausted the capital pools externally, so now we're gonna all give each other revenue and cash flow to keep them, keep the train going. So that is actually a little bit of a canary in the coal mine of how this is working.”
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