the 6 traits of people who can’t stop making money

Shaan introduces the term “natural moneymaker” for someone who repeatedly finds, brokers, or inserts themselves into deals and has built multiple businesses ranging from $100 million to many billions across different fields. He distinguishes this person from a strong founder, CEO, or entrepreneur: a conventional entrepreneur may have vision, recruit well, and understand markets, while a natural moneymaker adds an unusually cold, logical, and rational relationship with money. Shaan says he is a decent entrepreneur but not a natural moneymaker, and Sam immediately thinks of their friend Suli as an example. The key difference is hit rate. Most entrepreneurs fail repeatedly before succeeding; the natural moneymaker supposedly has a pattern closer to “succeed, succeed, fail, succeed, succeed.” They often cannot explain their decisions in elaborate frameworks because they operate through instinct. Shaan calls this having “a great nose”: they sniff out opportunity, detect bullshit, and recognize where money will be made or lost across several industries, even without being the best manager, designer, or technical specialist. Their general skill is the ability to identify and capture value.

Shaan’s first defining trait is emotional distance from business. He says natural moneymakers still feel anxiety, but they use emotion as an input rather than allowing passion or sentiment to control the decision. Founders often rely on emotion to recruit people and rally a team; the natural moneymaker instead asks what the numbers show and acts accordingly. He illustrates this with a story about Carl Icahn, the 1980s tycoon and hedge-fund/private-equity figure. After buying what Shaan believes was a shipping company, Icahn visited its office for two weeks, saw 12 floors of employees whose purpose he could not identify, and fired everyone immediately. Four or five months later, he asked his team whether removing those employees had harmed the company. When they said they had not even noticed the people were gone, the decision was confirmed. Shaan’s point is not that every company should fire staff indiscriminately, but that a natural moneymaker can see organizational nonsense and remove it without becoming emotionally attached. Sam and Shaan later describe this attitude as maximizing: even a small or inconvenient return is still a return.

Shaan presents Nick Kokonas as an unusually clear example. Kokonas studied philosophy, liked math, and wanted to become a trader rather than take a conventional banking job. As a trader, he could win or lose roughly $300,000 in a day while working with only $600,000 to $1 million, so he had to make rapid decisions under large emotional and financial swings. He ultimately made tens of millions as a trader, including a year in which his company earned $100 million from one arbitrage. Kokonas noticed that newly popular exchange-traded funds could be priced slightly differently from the real-time value of the underlying stocks. He used options and future contracts to capture the spread, then arranged for fiber-optic connectivity between the New York and Chicago exchanges so his firm could receive quotes faster than traders still relying on phone calls, paper slips, and shouted instructions. He later moved into restaurants, partnered with chef Grant Achatz, and created Alinea, which became the first Michelin-starred restaurant outside New York and was ultimately ranked America’s number-one restaurant. Despite restaurants being notoriously difficult businesses, Alinea reached about $26 million in annual revenue with almost 20% profit. During COVID, the team pivoted to roughly $35 takeaway dinners and continued making money. Even after the interview, Kokonas was discussing a wine-collection arbitrage: buying a $1 million collection for $150,000.

Shaan connects Kokonas’s behavior to another wealthy friend who, while out with them, discovered that defaulted or soon-to-be-defaulted credit-card debt could be purchased and collected through a specialized firm for roughly a 14% return. Sam thought the opportunity was too small and too much trouble for someone already wealthy. Shaan says that reaction separates ordinary investors from natural moneymakers: they do not decide that “enough is enough.” Their rule is that “diminishing returns are still returns.” He gives Jay Gould as an extreme historical example. After Gould’s wife had died, while he was suffering from tuberculosis and believed to have about a year to live, his family urged him not to pursue another railroad deal because the family was already financially secure. A week later, he told them he had decided to return to his “first love,” making money, completed the deal, and died about six months afterward. Shaan places Charlie Munger in a similar category because Munger kept investing and doing deals late in life, while also making money through Berkshire Hathaway, real estate, and a law practice. The hosts then debate whether the trait is nature or nurture. Shaan thinks it may be encouraged by growing up around financial conversations, but also suspects an inborn competitive drive and a desire to conquer. He says natural moneymakers tend to have high IQs and unusual comfort with complicated arrangements, contingencies, and compounding. Sam pushes back slightly: the people they know often prize simplicity. They agree that these people may see a complex execution process as simple because the reason for doing it fits “on a fortune cookie,” and they find ways to reduce complexity by locating experienced suppliers, buying proven machines, or outsourcing management.

Shaan identifies Syed Balkhi as another natural moneymaker. Balkhi began with a relatively unglamorous WordPress blog, used its profits and influence to buy WordPress plugins, and expanded into real estate, public stocks, and privately held companies. Sam recalls being puzzled that someone worth hundreds of millions would buy a $200,000 gas station. Balkhi’s answer was essentially that the gas station still offered a good return and could be made simple: buy a hard corner in a good area, rely on its track record, and use a triple-net lease so there is little to manage. They discuss a related principle Balkhi learned from a mentor: “only spend the second derivative.” In practical terms, if someone earns $100,000, that $100,000 is not the discretionary spending pool. It should be invested, and only the returns—perhaps $10,000 at first—can be spent on optional lifestyle upgrades. As the invested principal compounds, the spending pool grows without consuming the principal. The hosts describe it as “don’t touch the principle; only live off the interest,” while acknowledging that “interest” is shorthand for investment gains. Sam says his own version is to keep annual spending below 3% of liquid net worth. They reject the assumption that people who live this way must be miserable misers. Shaan points to Brian Johnson, who says he is happy with an unusually disciplined lifestyle, and to a generous, family-oriented friend named Val. At the same time, they acknowledge that some natural moneymakers are unpleasant or unhappy; the money-making trait is separate from being well-rounded or kind.

Shaan argues that people who love the sport and status of business can continue making money long after additional money no longer improves their lives. They trade valuable hours for “useless dollars”—money they will never spend or need—and then justify it as being for their children or as a model of hard work. Shaan says children are more likely to want their parents present than to watch them work constantly. Sam agrees that people often dismiss disciplined financial behavior as “no fun” because they feel defensive or guilty, rather than becoming curious about whether they could borrow part of the strategy. Shaan also says high-performing businesspeople often avoid areas where they are inexperienced. He compares this with his own tendency to read another article or make another slide deck instead of exercising. The same pattern applies to his marriage: improving the relationship could produce more life benefit than adding another amount to an already-large portfolio. To counter that tendency, he deliberately became a beginner piano player, accepting that he would be bad at it, spend money rather than make it, and receive no status from it. Learning music still added a different kind of joy. The hosts conclude that “natural moneymaker” is only one way to win, not a ranking of human worth. Sam admires some of the trait’s strengths without wanting every natural moneymaker’s lifestyle. They endorse asking what tools can be borrowed from people with different strengths rather than assuming one archetype is the only successful path.

The hosts expand their informal taxonomy of founders. A missionary is devoted to a long-term purpose that others might dismiss; Shaan gives Brian Chesky as an example, saying Chesky appears committed both to making Airbnb excellent and to improving travel. An “extreme balancer,” represented by Jesse Itzler, pursues family, vacations, and adventures with the same intensity used in business. A tank is a relentless operator with high pain tolerance, a large span of control, and the ability to lead an army forward; they compare this to video-game characters such as Reinhardt and mention operators such as Frank Slootman. The trickster is different: fragile if directly hit but difficult to hit because they exploit odd gaps and create viral or novelty products. They cite Alex Tew’s Million Dollar Homepage and Calm’s initial “do nothing for two minutes” product, weighted blankets, star-naming registries, and Eric Ryan’s products including Method Soap, OLLY vitamins, and Welly bandages. The trickster’s apparent randomness is actually lateral creativity—the ability to make an ignored object or idea valuable. They also describe the fierce nerd: a highly intelligent, intensely competitive, possibly socially unusual person who treats business as a game played on their own battlefield, with Mark Zuckerberg and Travis Kalanick as examples. “Deep students,” such as Dan Carlin or David Senra, win through extraordinary endurance for studying history and other people’s games. Finally, a sniffer such as Austin Rief or Vishal identifies non-obvious trends and people before consensus forms. Rief reportedly spotted multiple opportunities early, while Vishal introduced Shaan to Bitcoin and predicted the importance of stablecoins, privacy coins, and prediction markets. Unlike quieter natural moneymakers, sniffers are often enthusiastic and eager to share their conviction. The episode ends with the hosts joking that their archetype names sound like sexual positions or slurs, while agreeing that the framework could help people work with their nature rather than fight it.