For two months, I interviewed people with extreme wealth, asking them how money had changed the way they think — how their view of the world shifted once financial constraints disappeared. How did becoming rich alter their perceptions of status, friendship, obligation, and maybe even reality itself?
I sent many requests, offering anonymity. Many said “no.” (“We’re going to pass this time,” said a rep for a well-known hedge-funder. “Not my jam,” replied a famous entrepreneur.) Even more just ignored me.
But some said “yes.” One founded a large company. Another had made millions on his own and then married into hundreds of millions more. Another multiplied his family inheritance many times over by buying into the investment firm where he worked. Another was Mark Cuban.
At first, few of them would tell me outright that wealth had changed their thinking. But almost none could say it hadn’t, either. They deflected and hedged and resorted to hypotheticals. The former CEO said his perspective “hasn’t shifted that much” but then admitted “I might be deluding myself.” An acquaintance of mine who married into old money joked that “other people I know might regale you with the various ways I have dramatically and reprehensibly transformed,” but he couldn’t name one.
Meanwhile, ask pretty much anyone without money what wealth does to people and the answer is usually more straightforward: It makes them worse. Resentment of the rich now powers politics both left and right for slightly different reasons but with the same math: A tiny few control staggering amounts of wealth while ordinary people struggle to pay for rent and groceries. The number of billionaires has tripled since 2010, and the most visible among them are often the most obnoxious, many of them building the very AI companies that threaten to automate everyone else out of a job and into a permanent underclass. Hollywood has received the memo; every prestige-TV show now seems to be about affluent people who are either evil or dumb or both and who seldom make it through an episode without cheating on a spouse, defrauding a business partner, or murdering a poor person with their bare hands. Then, in January, into this already charged atmosphere dropped 3 million pages of Epstein files, exposing hidden depths of our elites’ depravity and also how often they have dinner with Woody Allen. The reputation of the rich has rarely been lower.
But the people I spoke to didn’t seem evil or dumb. None of them had emailed with Jeffrey Epstein. These weren’t the billionaires building bunkers in New Zealand or trying to buy the U.S. Constitution. Anyone willing to have this conversation is, by definition, self-selecting and probably an unrepresentative sample. All were willing to engage with my occasionally awkward questions and to struggle, in good faith, toward some kind of honest self-accounting.
However reluctant they were to draw conclusions about themselves, the people who agreed to talk often had plenty to say. In several cases, I asked for a short phone call or Zoom and they went for an hour, sometimes two. What surprised me most was how many of them, despite undergoing one of the most dramatic life changes possible, told me they were discussing this topic for the very first time. “I’ve actually never talked about this with anybody,” one said. “And it feels strange to do it with you.” Said another, “These are things I haven’t really thought about. I probably should.”
Not everything they told me was a revelation. A lot of their thoughts were tentative, the kind of things a person comes up with when they’re working it out as they speak. People contradicted themselves, changed the subject, and started stories they couldn’t finish. A question about money would turn into an answer about marriage, then into a long silence. Only some of it resolved into clean, quotable points. Still, in the accumulation of half-formed ideas and accidental admissions, a portrait took shape.
Early on, one source warned me that writing this story may be difficult because there is no universal experience of wealth. “I know a lot of very wealthy people,” he told me, “and you see some who are just epicurean hedonists. You see some who try to pretend that they don’t have it and feel quite guilty about it. Then you find some who either find a balance or keep working because they want more.” And yet, he said, just as studies have shown that poverty creates a scarcity mind-set — shaping how people think about things like risk and time — there must be something like an inverse effect. “There are probably some behavioral trends that can be pulled out.”
What emerged was less a unified theory than a cluster of variations. Wealth seemed to work differently on different people, depending on who they were and how the money arrived. A software developer whose start-up sold to a tech giant for nine figures — making him very rich, if not quite ultrawealthy — told me that when he got his payday, his first emotion wasn’t happiness but something closer to vindication. “It felt like things were finally as they should be,” he said. He’d grown up with ADHD and struggled in school. The money wasn’t just about money. “It was about showing the world — and my high-school English teacher who didn’t like me very much.” His fortune felt like a kind of scale-balancing, as if the universe had belatedly recognized who he was and compensated him accordingly.
I heard stories like this mostly from the self-made. Inheritors tended to describe their money as a source of gratitude, guilt, or embarrassment but rarely a solution to cosmic injustice. The self-made often believed they could rebuild their fortunes from scratch if they had to. “If you lose all your money today and wake up on the streets tomorrow having nothing but the clothes you’re wearing,” said a European entrepreneur who is both self-made and the son-in-law of a centimillionaire, “knowing that you can yourself build the life that you have is a vastly different feeling than basically having everything thrown into your lap.” He compared it to driving a race car. The self-made person has earned his spot on the team and “can control every tiny movement in that car if anything happens. But if you’re just placed in this fast machine with no training, that’s scary.”
David Roberts was born into money. His maternal grandfather, he told me, made a fortune in oil in the 1930s. As an adult, Roberts grew his inheritance by using part of it to buy an ownership stake in the firm where he worked, which sold for $2.7 billion in 2023. Still, he puts himself in the inheritor camp. “The drive forged in self-made people,” he told me, “is of a different caliber” from his own. The sacrifices someone born to wealth is willing to make, he said, are rarely as challenging. “There’s a resilience you probably only get from confronting scarcity and defeating it.” He was candid about what he saw as his own limitations. “I don’t think I ever had the confidence and risk tolerance” to be an entrepreneur, he said. Even so, he had his own version of striving. As a young father, he remembers worrying about whether he would “ever make enough money to mimic the lifestyle I had been brought up in.”
Ed McCaffery, a tax-law professor at USC who advises wealthy families, told me that among inheritors, the psychology isn’t uniform. In his experience, it splits along gender lines. Female heirs, he said, more often treat the money as something to protect. Male heirs are more likely to invest inherited money in risky ways — active trading, crypto, hedge funds, some aggressive bet that lets them feel they’ve transformed the wealth into something earned. “The son wants to feel like it’s his money, so he’s going to do something with it to make it feel earned,” McCaffery said. “Take the money, put it in bitcoin, claim that you made a fortune in bitcoin.”
For all those differences, certain effects seemed to recur. One of the most common was isolation. For some, it set in almost immediately. The European entrepreneur remembers the exact moment. As a university student, he’d launched a business on his own, and one afternoon he sat in his dorm room refreshing his laptop screen as hundreds of thousands of dollars flooded his bank account. He would go on to make much, much more, but that first infusion was the most destabilizing. “I was like, Fuck, what do I do now?” he says. That night, he went to dinner with schoolmates and said nothing. “My friends would’ve called me a prick.” He also couldn’t tell his parents, who are hippie anti-capitalists. “I couldn’t say, ‘Hey, I made more money in literally one second than you do in years.’ I got what I wanted, but in that moment, I felt totally isolated.”
It became a pattern for him, especially after he married a woman who came from a much wealthier family. He noticed his wife talked less about herself with others than anybody he knew. “You don’t tell your friends in high school about all the exotic places you’re jetting off to because they’re going to be jealous. They’re going to tell stories about you,” he said.
For anyone already inclined toward solitude, money can make it easier to withdraw further. “I’m naturally very introverted, and I don’t like being around a lot of people,” said the software developer who sold his company to the tech giant. “Wealth allows me to just be a little more insulated and less dependent on other people,” which perhaps indicates he recognized that this was not entirely a good thing. “As you move up in terms of luxury and comfort, experiences are always going to be more private,” noted the European entrepreneur. “When you get a bigger house, your neighbors are further away. In a nice hotel, the people that service you are going to be more polite and less personal. And you don’t meet anyone in a private jet.”
Without honest company, even people who suspected that wealth had changed them didn’t always trust themselves to say how, likely because our brains are built to normalize whatever life throws at us. The European entrepreneur had studied psychology and knew the term for this phenomenon: hedonic adaptation, or the human tendency to adjust to new circumstances quickly no matter how drastic the change. “Our senses don’t work objectively,” he said. “We can only see light compared to dark. We can only hear loud sounds compared to quieter ones.” Happiness works the same way. It’s not a fixed target but the gap between what you expected and what you got. He understood all this in theory. Then his expectations rose anyway.
Most of my sources said that buying nice stuff gets old fast. “Having your new car — the anticipation of which model, which style, which color — it really got me excited,” said the European entrepreneur. “But after the first couple of drives, you don’t use any of the features. It is just like your old car, a way to get from point A to point B.” The software developer described something similar. Before he could afford them, he would occasionally splurge on $500 sneakers. “Now I buy myself those same $500 sneakers and I don’t get the same pleasure,” he says. It turned out the pleasure wasn’t in the shoes themselves but in the irresponsibility of the purchase. He said he recently invested a million dollars in OpenAI — and that did the trick.
Not everybody I talked to believed that money changes people in such complicated ways. I sent Mark Cuban a cold email on a Tuesday afternoon, and by that evening he was calling me from his car in Dallas.
Cuban grew up in a working-class family in Pittsburgh — neither parent had graduated from college, and his father never made more than $40,000 a year — and once slept on the floor of an apartment he shared with five roommates. Then, at 40, during the dot-com boom, he sold his company Broadcast.com to Yahoo for $5.7 billion. I asked whether becoming rich changed him, and he said “not really.” “It was an enabler, but not really a change factor,” he said. “If you were happy when you were broke, like I thought I was, you’re going to be insanely happy when you’re rich. And if you were miserable, that doesn’t change.”
So maybe wealth isn’t transformative; it’s an amplifier. It turns up the volume on whoever you already are. When you don’t have money, your personality runs up against friction all day long. You might be generous, but your generosity has a ceiling when you’re living on a fixed income. You might be anxious, but ordinary life forces you to confront your stressors often enough to keep them manageable. Money removes that friction, and whatever it was holding in check is free to run. The generous person can give amounts that change other people’s lives. The anxious person can design a life without any of their old triggers and then fall apart when the smallest thing goes wrong because their coping muscles have atrophied. This might sound reassuring — You’re still you! — but how many people really know who they are when there’s nothing pushing back on them? Plenty of billionaires probably seemed normal when their eccentricities were still bound by everyday constraints.
Even if money doesn’t change a person in major ways, it still introduces new asymmetries into everyday life. In many of my interviews, the conversation found its way to the same topic, usually before I could bring it up myself: the restaurant check. It might be the thing that makes the abstract strangeness of being wealthy feel most concrete. It’s a tiny war over status, pride, and generosity that happens every time the rich and non-rich sit down to eat together.
Here’s the situation: You’re a deep-pocketed person out to dinner with shallower-pocketed friends. The meal winds down. The check arrives. You could easily pay the whole thing and never think about it again. But paying might send a message you didn’t intend — that you think you’re better than everybody else at the table, or that you want to be thanked, or that you’re keeping score. Not paying, or splitting the bill, sends a message too — that you’re cheap or clueless or pretending to be modest. Every option sucks.
A founder of a large company told me he always gets the check and has learned to make peace with the awkwardness. “I think I should always pay,” he said. His close friends push back. “They’re like, ‘No, I need to pay some because I’m not here to mooch on you.’ And I’ll say, ‘I know you’re not here to mooch on me.’ And they’re like, ‘Yeah, but I still need to pay some.’” Over time, he said, you develop codes. When he and friends go on vacation, he’ll cover the hotels and meals; they’ll pay for their own flights. “Usually people always need to protest once, but then when you go out twice, they’ll just let you pay,” he said. “But then sometimes you do wonder how much people are wanting to hang out with you because you’re paying the bill and you actually have no idea.”
The European entrepreneur told me that when he’s out with friends and the check arrives, “in implicit ways it’s suggested that I take the bill because I can. It’s super-subtle but clearly noticeable.” He doesn’t mind paying, but he’s uneasy about the expectation. “There’s a power dynamic that’s not equal.” He’d felt the imbalance from the other side, too, when his in-laws flew the family somewhere by private jet. “I want to say thanks as I would to anyone making a nice gesture. But again it feels like the dynamic is a bit skewed.”
The restaurant check represents a miniature argument about obligation. What do you owe the people sitting across from you? The tax code is the same argument but bigger.
by Lane Brown, Intelligencer | Read more:
Image: Zohar Lazar
[ed. Let me remind everyone again struggling with basic math (me included), a billion dollars equals one thousand millions. Sometimes the scale just overwhelms. For example, the national debt now stands at $39 trillion, so we pay $900 billion in interest each year servicing that debt. This idiot war in Iran is just adding a lot more to that (we used to increase taxes to cover our various military adventures), now we just issue bonds that further increase our debt - a small portion of what we'll pay over time when future veteran's benefits are included (now in the trillions). But, uh yeah... this was about billionaires.]
[ed. Let me remind everyone again struggling with basic math (me included), a billion dollars equals one thousand millions. Sometimes the scale just overwhelms. For example, the national debt now stands at $39 trillion, so we pay $900 billion in interest each year servicing that debt. This idiot war in Iran is just adding a lot more to that (we used to increase taxes to cover our various military adventures), now we just issue bonds that further increase our debt - a small portion of what we'll pay over time when future veteran's benefits are included (now in the trillions). But, uh yeah... this was about billionaires.]