The most successful investor you rarely think about
Most people know Sam Altman as the CEO of OpenAI. That is the right answer for a trivia question, but it is the wrong frame for understanding how Altman built his fortune and where he is pointing his capital next.
Josh Baylin’s Stansberry Research presentation, which we reviewed in full here, spends a surprising amount of time on Altman’s investment track record rather than his OpenAI role. The reason becomes clear by the end: Altman’s investment pattern is the thesis, and medical AI is the latest expression of a strategy that has worked repeatedly.
The Stripe investment
Before ChatGPT, before OpenAI became a household name, Altman was an early investor in Stripe. Court documents cited in the presentation show he is up more than 4.2 million percent on that position. In plain English, every $1,000 he invested turned into $42 million.
Stripe is now one of the largest fintech companies in the world, processing hundreds of billions in payments annually. But when Altman invested, it was a small startup. The pattern is consistent: Altman identifies a technology trend early, invests before the trend is obvious, and holds through the growth phase.
The unicorn portfolio
The Stansberry presentation lists the companies Altman backed before they became household names: Airbnb, Reddit, Uber Technologies, Pinterest, Neuralink, Asana, Instacart, and DoorDash. The combined value of ventures backed by Altman exceeds $1 trillion, according to the presentation.
Not every investment was a winner, and the presentation does not claim otherwise. But the hit rate is genuinely impressive. Altman has made 100 times his money or more on five separate occasions, a record that puts him in rare company even by Silicon Valley standards.
The pattern matters because it tells you something about how Altman identifies trends. He does not chase the hottest sector. He identifies a structural shift, a technology that changes how something fundamental works, and he gets in before the shift is obvious to the mainstream.
The medical AI bet
This is where the Stansberry thesis connects to Altman’s track record. In 2022, Endpoints News reported that an AI biotech startup called Retro Biosciences had raised $180 million from anonymous investors. BioSpace noted the same day that the investor identities were “notably missing” from the announcement.
MIT Technology Review later revealed that the sole investor was Sam Altman. He personally funded the entire $180 million round. His involvement was, as Josh describes it, “literally a secret” for years.
Retro Biosciences is focused on longevity research, using AI to discover therapies that could extend human lifespan. It is a bet on the same thesis Josh presents in the Stansberry video: that AI applied to biology and medicine represents a fundamentally new investment opportunity, one that is potentially larger than any previous technology shift.
McKinsey, the global consulting firm, estimates this could be 500 times bigger than ChatGPT. ARK Invest says it “will transform our lives and the global economy radically” and could ignite a $200 trillion boom for the U.S. stock market. Anthropic CEO Dario Amodei says we will achieve medical breakthroughs in the next 10 years that would have taken 100 without AI.
The billionaire pattern
Altman is not alone in this bet. The presentation notes that Jeff Bezos, Peter Thiel, and Elon Musk are all investing in the same direction. Peter Thiel, who has made $28 billion as a tech investor and co-founded PayPal and Palantir, is backing the same industry. Musk admits the technology behind Altman’s venture is “the most disruptive force in history” and is putting his own personal money into it.
The framing that all four billionaires backed this one specific project is where the marketing stretches the evidence, as we noted in our review. But the underlying pattern is real. Silicon Valley’s most successful investors are directing personal capital toward AI applied to medicine, and they are doing it quietly.
Josh’s closing advice draws on this pattern: “If you want to know the truth, don’t watch what people say. Watch what they do. Their actions will tell you everything you need to know.”
What the track record means for investors
Altman’s investment history suggests three things for investors thinking about medical AI.
First, he has a genuine track record of identifying major technology shifts before they become obvious. The Stripe investment, the unicorn portfolio, and the OpenAI bet all followed the same pattern.
Second, he is willing to invest significant personal capital quietly, without publicity, and to hold for years. The $180 million Retro Biosciences investment was made anonymously and remained secret for years.
Third, the medical AI bet is consistent with his previous pattern. It is a structural shift in a fundamental industry, it is early enough that most people have not noticed, and it has the potential to be much larger than the initial investment suggests.
Whether the specific stocks Josh recommends in his True Innovations Report will match the returns of Stripe or Airbnb is an open question. But the thesis, that AI applied to medicine is the next major technology shift, is one that Altman’s own capital is backing.
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