Billionaire Chamath Palihapitiya says the real signals of the AI future are hiding in plain sight, and they are not where most investors are looking.
In a new episode of the All-In Podcast, the billionaire investor says deal size itself reveals whether a transaction is about the past or the future, using recent tech investments to explain why billion-dollar bets matter far more than eye-catching mega-valuations.
“Whenever you see deals, it’s important to look at the amount of money that is at risk. And that is the best tell about whether this is important for the future or not. $100 billion deals are typically about things in the past. What is the future? Billion-dollar deals.
When Facebook bought Instagram for a billion dollars, that turned out to be a huge bet about the future. It was right. When Google bought YouTube for a billion six, that was a huge bet on the future. They were right. When Microsoft invested a billion dollars in OpenAI, that was a huge bet on the future. It was right.”
By contrast, he says massive valuations often reflect backward-looking assumptions built on leverage rather than genuine foresight.
“When you look at assets that trade at $100 billion plus valuations, they’re so undergirded by debt. All of that debt is only ever bought by looking at the past, meaning how much money they have made, and then it’s a best guess about how much money they could make in the future.”
Applying that lens to Disney’s reported $1 billion investment in OpenAI, Palihapitiya downplays its strategic impact on the media landscape, arguing that structural shifts in content creation matter far more than any single partnership. He adds that as short-form and creator-driven media accelerates, traditional intellectual property may lose relevance faster than many expect.
“The reality is that the future is unscripted, uncontrolled, user-generated content. You see it on YouTube. It is already the 800-pound gorilla in the space.
And then separately, it’s now becoming about shorter-form video. And you see that with things like Instagram reels, and TikTok. None of that landscape will change based on this deal. If anything, if those trends accelerate, the value of historic IP is going to erode even faster, meaning this generation of kids will have no idea or care about the Marvel Cinematic Universe, about Star Wars, and that may upset those of us who are nostalgically tied to it.”
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