We put a multimillionaire’s portfolio into Claude (the results shocked us)

Sam describes meeting a Hampton acquaintance who had sold his company for something in the eight-figure range and now invested in public stocks. Because Sam was curious, he asked the man to open his brokerage account immediately. The investor had achieved nearly a 22% annual return for roughly the past decade. Sam and Shaan exported the account into Claude and counted each stock purchase or sale as a decision. Although the investor generally owned around 15 stocks, plus or minus five, he made only 2.9 decisions per year. In three of the last ten years he made no decisions at all, and his maximum was six in a year. The account began around 2014 and returned 21.8% annually versus 13.5% for the S&P 500. He beat the market in 11 of 12 years, losing only to it in 2022. A hypothetical $10 million investment could have grown to roughly $60 million, depending on the starting date. His holdings were recognizable businesses rather than obscure bets, including something like a major travel company and a popular clothing company. Sam says the result challenged his own habit of confusing activity with progress: three decisions a year means spending months thinking, waiting, and taking no action.

Shaan asks whether the investor was actively researching every day or simply practicing “set it and forget it” investing. Sam texts the investor for an explanation. The investor says he studies only a few businesses he can understand, studies them very deeply, keeps detailed notes, and waits for an opportunity. As an example, he had researched one company extensively for about six months before COVID, liked it, but considered it too expensive. He documented what he learned, read the annual reports, continued monitoring it, and bought the stock on the day the market made it cheap enough. Sam connects this to Warren Buffett’s approach: spend most of the time learning and make a move only when the opportunity appears. Buffett has described his strategy as “lethargy bordering on sloth.” Sam says the same pattern appears among other people he admires: investors such as Howard Marks and Ray Dalio make decisions within a clear framework, while startup builder Kevin Ryan once said he basically gets one good idea a year. The hosts conclude that high-quality decision-makers often make very few consequential decisions rather than constantly changing direction. They also say reversible decisions should not receive the same level of agonizing as irreversible ones. Shaan says his default is not to care about most things, which makes it easier to discard low-value concerns; Sam admits his own tendency is more neurotic and often treats every detail as meaningful.

Sam identifies two more habits among strong investors and operators. First, they know their circle of competence. His investor friend rejected an idea not because it was necessarily bad, but because he did not understand the industry and therefore would not invest. Second, they write down their reasoning. They make arguments for and against an idea, journal, and use premortems to list what could go wrong. The hosts distinguish this from “resulting,” or judging whether a decision was good solely by its outcome; a decision should instead be judged by the quality of its inputs and framework. Shaan gives Jack Dorsey’s preparation for launching Square as an example. After helping create Twitter, Dorsey could easily have become overconfident, so he reportedly wrote “140 Reasons Why Square Will Fail.” The exercise forced him to confront failure modes before they happened. Shaan compares it to Charlie Munger’s principle of asking where he will die so he knows not to go there. Identifying the ways a company could fail in advance does not guarantee avoidance, but it makes it possible to design around the risks instead of ignoring the obvious problem. The discussion is interrupted by a joke about “Silicon Valley CEOs,” with Shaan saying people had effectively bought real estate on Dorsey’s metaphorical anatomy. The humor reinforces the point that even successful founders benefit from deliberately humbling themselves.

The hosts turn to Mark Zuckerberg’s recent public confidence about Meta’s AI efforts. Shaan says Zuckerberg is on a victory lap, giving interviews and using unusually casual language, even though leadership in AI can change every six months. They joke about Zuckerberg’s awkward first sip of Guinness and his attempt to sound more relaxed, but Sam argues that the reaction was relatable because many people dislike their first Guinness. Shaan says Zuckerberg made a huge, initially unsuccessful bet on virtual reality and the metaverse: Meta reportedly spent around $60 billion, roughly ten times what Apple spent developing the iPhone, without producing comparable popularity or usage. When AI emerged, however, Zuckerberg pivoted. Shaan says Zuckerberg’s philosophy is that entrepreneurs are judged less by their mistakes than by what they get right and how significantly they get it right. This differs from Warren Buffett’s investing rule—“don’t lose money”—because entrepreneurship allows many failed attempts if one successful attempt is large enough to win the war. Jeff Bezos expresses a similar idea by comparing business to baseball: a home run is worth only four runs in baseball, but one correct business decision can produce a thousand or ten thousand runs. Shaan also says Zuckerberg believes Scale AI founder Alexandr Wang is “the guy” because of his strategic clarity, communication, execution beliefs, and conviction that AI teams should be small and talent-dense rather than thousands of merely smart employees.

Sam questions whether Alexandr Wang was being described as an individual technical contributor even though he had led a company valued around $14 billion. Shaan clarifies that Zuckerberg admired Wang’s leadership abilities: deciding what Meta should do, communicating it clearly, and strongly believing in an execution model built around a small, elite, flat team. Wang was not expected to perform every task himself; his value was his strategic mind and ability to lead. Shaan recounts that Meta was a major Scale AI customer, and Zuckerberg would periodically message Wang on WhatsApp with a question and receive a thorough, crisp, almost blog-post-length answer. Zuckerberg also asked many smart people outside his formal board for their views instead of waiting for a quarterly meeting. He did not automatically follow their advice, but used the responses both to gather signal and to assess who consistently offered useful thinking. Sam says he has experienced the same behavior when people vastly more successful than him ask for his opinion, even though he initially thinks they should already know more. They connect this to the Dunning-Kruger effect: people with limited knowledge can be overconfident, while experts become more aware of how much they do not know. The hosts say accomplished people often admit luck’s role, recognize the limits of their knowledge, and remain humble enough to seek insight from people who are less accomplished on paper.

Sam discusses hiring an executive coach and being told he was highly self-critical. He describes feeling inadequate because the podcast puts him in contact with people who are among the best or richest in the world. Shaan says comparison is only useful after identifying the game one is actually playing. He argues that people often pursue success without defining the end state or knowing what they are trying to win. They use athletes to illustrate the idea. LeBron James, at 42, is playing a game of defeating Father Time and catching Michael Jordan in the greatest-of-all-time debate. Another player might be playing a “prove myself” game after being traded, while a less prominent player may simply be trying to enjoy the sport, make a good living, earn a contract, or make an All-Star team. The hosts describe their own evolution: in their twenties, they were trying to “make it,” become successful, and become multimillionaires; in their thirties, they wanted to build families while remaining successful without repeating the same sweaty grind. Shaan cites the book The Score: when someone chooses a game, the game determines what they want and what kind of person they need to be. Charades rewards expressiveness and communication; Mafia rewards lying and manipulation; Twister values mobility. Because games shape behavior, people should consciously decide which game they are playing rather than blindly accepting someone else’s definition of winning.

Shaan tells a story about Elon Musk, presented as an unverified but useful fable. At a private dinner, Musk was supposedly asked what he would do if Tesla and SpaceX both failed and he lost every dollar. The story places this around 2008 or 2009, after three failed SpaceX launches and when Tesla was close to failure. Musk allegedly said he would move into the cheapest apartment he could find, buy a computer, and begin building something new within 24 hours. Losing the companies would devastate him, but he would allow the devastation only one night; he did not need to know the next idea in advance because “the thing finds you” if he is building when it arrives. The hosts connect this to Napoleon’s reported line, “I act and the plan emerges from my action,” and Scott Galloway’s advice to “keep your sails up.” Even in bad conditions, a boat must keep its sails raised so it can catch the wind when it comes. Sam recalls applying this during an early company period in Boulder, when he and Shaan slept on an air mattress, nailed a garbage bag to the wall instead of owning a trash can, and allowed business problems to make their whole lives worse. They changed nothing about the business strategy at first; they hiked the Flatirons, cleaned up, improved their routines, and stacked small personal wins. The improved mood produced better ideas and more productive work.

Sam explains that he had flown for 15 years while taking Xanax because he hated flying. After reading DARE, a book about panic attacks, he learned the sequence “dismiss, allow, run towards, engage.” Instead of resisting panic, he was instructed to dismiss it as unimportant, allow it to occur, actively welcome it, and then engage in a new activity after it peaked. He tested the approach on a trip to Jackson Hole, his first flight without medication in 15 years. The trip also involved leaving both children for four nights, and the flight became unusually difficult: after landing, the plane took off again because its brakes had failed. The pilot said they would divert to Salt Lake City and that fire trucks would meet them, while also explaining that planes have multiple braking systems and would use reverse thrust. Sam panicked but remained medication-free and concluded the technique had worked. He says it reframed the situation from “I am trapped with panic” to “panic is trapped in here with me.” The hosts then discuss exposure and rehearsal. Shaan describes George St-Pierre’s MMA coach preparing him by replicating every detail of fight day: the meal, UFC gloves, clothing, walkout music, lights, and heat around the octagon. Shaan wants to apply the same method to firings, negotiations, and difficult conversations by rehearsing the exact setting and sequence. They conclude that anticipation is often worse than the event, and that acceptance can neutralize fear more effectively than trying to convince oneself the situation is not scary.