$100M hedge fund manager: Do not make the mistake of dying rich

Bill Perkins says his first pool of capital came from trading natural-gas derivatives. He began as an “assistant assistant peon” clerk on the New York Mercantile Exchange floor, became an over-the-counter broker, and disliked brokering even though it paid six figures. When deregulation arrived in 1995, firms recruited New York professionals for Houston derivatives desks, so he moved to Texas and became a trader. He compares brokering to being a real-estate agent and trading to buying and selling the houses: he wanted to be the principal taking the risk, and that is where he became rich.

Sam admits he does not understand commodities and asks whether Bill literally buys oil and resells it. Bill explains that traders are “glorified insurance agents”: they price the distribution of outcomes, identify theoretical fair value, and sell protection when customers want to hedge. Before winter, natural-gas buyers feared prices would rise, so Bill sold them futures and accepted exposure to a price increase. In practice, the winter premium usually bled away and prices fell, making his long-term money by staying short. He was not simply outsmarting every other trader by forecasting prices.

Bill says he helped generate nearly a billion dollars in profit for his employer, but personally could have made much more by investing more of his own money in the fund. His younger self believed it was acceptable to have no money with a job or no job with money, but not both no job and no money. He now considers that logic wrong for a young person: at that age, he was likely to find another job, so he should have been fully concentrated and “bet the farm.” Independent hedge-fund traders generally “eat what they kill,” receiving a share of profits.

Shaan identifies three common ways investors win: superior temperament, informational advantage, or pure arbitrage. Bill says his fund relied on the first two, not arbitrage. Traders may understand supply and demand better than gamblers and hedgers, but that knowledge is useless if losses trigger panic; when the amygdala is going crazy, the prefrontal cortex stops working. Bill’s fund could fall 50% or rise 250% on roughly $100 million to $200 million. He calls it a product for getting rich rather than staying rich and says the central rule is to survive long enough for the market’s edge to compound.

The hosts ask whether Bill’s Texas-cowboy, risk-on image is accurate and whether he nearly lost everything. He says the apparent recklessness was a calculated response to a high-volatility product and admits he almost lost it all a couple of times. He also confirms that trading demanded years of obsession: every open position kept him mentally working, with many moving variables and capital at risk. He now wishes he had gone into equities instead, because the market is vastly larger, more capital is available, and large funds can charge roughly 1% to 1.5% fees on billions with relatively ordinary track records.

Bill wanted to become a millionaire before 30, then quickly exceeded that goal, but never had a specific wealth number at which he would quit. His early ambition was conventional: money, girls, and a rock-star lifestyle. In his thirties, after reading Your Money or Your Life, he began defining money as hours of life exchanged for other people’s hours. He concluded that net-worth peak is a date, not a number, because the body’s ability to turn money into fulfilling experiences declines with age; eventually, extra money has little value.

Shaan reads an excerpt from Die With Zero comparing life to pumping a well: people keep filling it and take only tiny sips, ending up thirsty after a lifetime of work. Bill says death and several books gradually forced him to ask what capital, health, and time were for. The experiences of pursuing romance, partying, or adventure have age windows, so postponing them can destroy the opportunity. He says his dominant fear is not losing money or status but wasting his life, because money is merely a tool for obtaining fulfillment.

Bill argues that people usually avoid starting businesses or taking opportunities because their ego cannot tolerate a status drop, not because they cannot tolerate financial risk. They fear looking foolish to friends, parents, or society if they try and fail. He calls the underlying behavior cowardice, while acknowledging that awareness alone does not create action. Bill repeatedly has to challenge his own ego too—by apologizing, admitting he is wrong, or doing something that might make him look foolish. His blunt feedback can sound abrasive, but he sees it as giving people a truthful mirror rather than performing social niceties.

A college teammate, Dwight Sistrunk, once told Bill he did not want a suburban, corporate “cookie cutter” life, and the comment stayed with him. Bill later realized that many preferences were cultural programming rather than innate desires, using fried crickets as an example: they seem repulsive only because he did not grow up eating them. He did not reject every inherited preference, but began testing each reaction against his actual goals. Instead of assuming that anger is the correct response when someone steps on his shoes, he asks which response serves the life he wants.

Shaan connects Bill’s ideas to Daniel Negreanu’s account of a self-help exercise: rewrite an event that went wrong while taking complete responsibility for one’s part, rather than narrating it as victimhood. Bill says he has done similar exercises and treats accountability as a permanent practice, not a one-time breakthrough. The hosts identify an internal locus of control as one of the few traits they consistently see among successful people. Bill agrees that the principle is maximum accountability: people cannot control every event, but they can control their interpretation, response, and subsequent action.

Sam asks how Bill combines ambition and unconventional living with a family. Bill says his children are now 22 and 19, and he has traveled with them while designing family life around shared preferences; he and his wife may take their younger child to live in Japan. He rejects the idea that every day, month, or decade must contain equal portions of work and leisure. Life swings between intense work, travel, partying, relaxation, and spiritual effort. The goal is to get buy-in from family members and make the chosen life work, not to prove that one lifestyle is universally superior.

Bill says people do not experience one death but many transitions: college ends, single life ends, young children grow up, and careers change. Each period has experiences that fit its age and may not transfer well later. Skiing 500 times with friends, for example, probably belongs earlier, before friends marry and responsibilities accumulate. He compares life to Tetris: the order matters if someone wants a high fulfillment score. Bill and his wife actively discuss three- to five-year periods, including living abroad while their child is under five, rather than postponing everything to an abstract retirement bucket list.

Asked what dissatisfaction remains in his life, Bill identifies health adherence. He says he was once at 8% body fat with a top-1% VO2 score, but is now around 16%–18% body fat with a VO2 score near the middle for his age. He blames tiredness from caring for a baby, pregnancy-related eating, and other explanations, then calls those stories “bullshit” masking laziness. His doctor’s Centurion Olympics asks which activities he wants to perform in his final decade; at his current trajectory, Bill estimates he could lose the ability to do 80% of his chosen activities. He hires trainers and plans to outsource accountability.

Bill explains that Die With Zero means spending resources during life rather than leaving an unused surplus, while also meaning dying with zero regret. His regrets come from times when he did not do his best, not merely from unfortunate outcomes. He cites inheritances as an obvious case: parents often wait until death to give money to adult children who could use it at 30 or 40, even though they no longer need a bequest at 60. Readers have changed estate plans, moved retirement dates, spent time with grandchildren, and reconsidered how they allocate wealth, health, and time.

Bill still runs a hedge fund and two startups—SkyFi, a satellite-imagery platform, and SimMax, an intelligence firm—but says he will stop working when another dollar no longer produces fulfillment. He also spends on yachting and private travel, while envisioning a modest future garden with bees, grandchildren, and friends. His largest recent purchase was Ernie Barnes’s Sugar Shack for $15 million. The painting depicts Black joy in the segregated South, appeared on a Marvin Gaye album and in Good Times, and had been sought by Bill for years. At Sotheby’s, he battled an art consultant and paid far above his expected $3–$5 million, believing the purchase signaled Barnes’s importance to the market.