At Brox.AI, we're building digital twins of real people, and one cohort we have just done this with is the "rich", otherwise known as HNWIs. These are not sanitised financial profiles or demographic segments, but actual psychological replicas: how they think, what they fear, what they lie about, and what they'd never tell their wealth manager. We have about 80 of these twins so far, built from in-depth interviews with people averaging $24 million in assets, excluding their primary residences (notice the plural).
This post won't be quite as titillating as the recent one about professional dominatrixes, but I think it's almost as interesting, because the only thing as interesting as sex is surely money.
Disclaimer: This substack is written in a personal capacity, it does not necessarily represent the views of Brox or my colleagues (be warned I will be occasionally shilling Brox) and even though many of the findings are powered by our AI, this substack is very much my personal take.
Part I: The Research
At Brox.AI, we interview people across every corner of society to understand what makes them tick. For this particular project, we got 80+ wealthy individuals to do in-depth multi hour interviews about their relationship with money, spending, identity, fear, legacy, and everything in between. These were all very long, unstructured conversations, where people said things they've probably never told anyone else, so that we could make digital twins of them, so that our clients including luxury goods companies, banks, wealth managers, can sell them stuff or services (oh the joys of Capitalism)
The sample spans self-made tech founders, inherited wealth families, immigrant entrepreneurs, real estate moguls, VCs, doctors, a high school dropout turned multi-millionaire, a semi-retired personal trainer, and a woman who describes herself as "almost a Marxist" despite being a very senior banker (if you're reading this just know I think you're great).
Net worths ranged from $5m to $300 million. Ages ranged from 29 to 71. About 30% were women. Roughly a third were first or second-generation Americans.
So what did we find:
Part II: (Almost) Nobody Feels Wealthy. At Least Not Financially
I asked every single person whether they feel wealthy, and most of them said no. A man worth over $10 million, who collects 16th-century halberds and Japanese lacquerware for fun: "No. God, no. I don't think anybody feels wealthy." He referenced the scene in Billions where a character with $40 million says "I'm so poor."
"While I am wealthy, I don't think of myself as wealthy because I don't want to spend it, and I don't know what to spend it on."
An investment banker: "Do I feel wealthy on a normal kind of statistical definition? No, I know the number could always be bigger."
A tech VP worth $15 million: quiet pause, then a deflection about "being comfortable."
A real estate mogul worth $80 million who still drives a pickup truck: just laughed at the question.
The few who did say yes were interesting though, because they didn't point to their bank balance, they pointed to their time. "I feel wealthy because I can spend Tuesday morning with my kids." "I feel wealthy because nobody tells me what to do." "I feel wealthy because I woke up this morning with no alarm and no schedule." When people do feel wealthy, it's almost never about the money, it's about what the money bought them: freedom over their own hours.
The hedonic treadmill is real, everyone knows it's real, and nobody can get off it. "What would you do differently if you had five million, if you had 50, if you had 500? And unfortunately, at least for me, the answer is relatively little for each of those stages."
"I earned more last year than I had in any previous year, but it was probably less exciting than the day I got my job here where I earned much, much less, 12 years ago. Everything becomes normal, doesn't it?"
A bunch of people told us basically the same thing: life gets exponentially better up to about $10-15 million, after that, additional money stops meaningfully improving your day-to-day existence until you get to hundreds of millions, and even then, the step up is marginal. Above a certain point, wealth actually creates new problems. More houses means more staff, more maintenance, more things going wrong. Private jets mean dealing with pilots, hangars, and mechanics. And then you have the stress of managing the people who manage your money. One person put it bluntly: "After a certain point you're basically running a small company just to manage your own life."
Part III: A Lot of Them Are Pathologically Cheap
This probably won't surprise anyone who knows actual wealthy people, but it was striking just how many of our interviewees are genuinely, psychologically incapable of enjoying spending money, not performatively frugal, but properly, deeply cheap in ways that cause real issues in their lives.
One VC partner, worth tens of millions, took his family to Rwanda to see gorillas. Amazing trip, he says. Life-changing. And also:
"I literally don't enjoy spending money. I cringe. To Africa, to Rwanda, to go see the chimpanzees and the gorillas, and it was amazing. And I loved it. It was fantastic. But I was, like, cringing at how much it cost. I went through the seven stages of death. Even though the money doesn't, in the scheme of my net worth, it's nothing. Like, still I was cringing at the cost."
The Bubblegum Slap That Echoes Through Decades
One interviewee traced his entire relationship with money to a single childhood moment: his mother slapped him for putting 25 cents in a bubblegum machine. He's now worth millions and still can't enjoy spending:
"My wife makes fun of me where, like, no matter whether we can quote, unquote, afford it or not, it has to be a deal. It has to pencil out or I just can't enjoy it."
The Blueberry Boycott
One VC still refuses to buy blueberries. Or $8-a-pound grapes. She plans her driving routes to avoid left turns "like a FedEx driver" to save time and fuel, she charges her son for AAA batteries ("batteries don't grow on trees"), she stays at $4,000-a-night hotels but asks for complimentary welcome cocktails rather than buying a margarita. And she's perfectly aware of the contradiction: "$8 grapes. But I'll pay 2 grand to go to LA business class."
But this same woman paid off her first employee's $4,000 in credit card debt without being asked. She started college accounts for her nanny's three sons. She paid for funerals when the nanny's parents died. She paid for a babysitter's coding academy and helped her get a job, that woman is now a head engineer. She was simultaneously the cheapest and most personally generous person in our entire sample.
Part IV: What They Drive (The Anti-Status Symbol)
If you want to spot actual wealthy people, look for boring cars, this was so consistent across our interviews it deserves its own section.
| Net Worth | Car |
|---|---|
| ~$80M (real estate) | Ford F-150 King Ranch |
| $68M (sold company) | Lexus |
| $15M+ (tech VP) | Tesla Model 3 |
| $10M+ (hedge fund) | Three-year-old Range Rover |
| Undisclosed (VC) | Mini Cooper, stick shift |
| Undisclosed (VC) | Agonises over Nespresso pods, you think he bought a nice car? |
| Undisclosed (Executive) | Toyota Prius he plans to drive into the ground |
| $8M (fintech founder) | Six-year-old Honda |
| $8M+ (foundation) | Subaru |
| $5.2M (dentist) | Four-year-old Toyota |
| $6.0M (engineer) | Aging Prius/Tesla Model 3 |
| $5.3M (corporate executive) | Camry |
Now there were many exceptions, as some people had lots of cars and many luxury cars but this was not the norm.
One person's dream car is a 20-year-old Lexus LX470, specifically because it has no computerisation and therefore no remote kill switch. "If you had to pick a doomsday car, it's definitely going to be up there."
Part V: Luxury Is Time, Not Things
Not a single person we spoke to defined luxury as a thing. When asked "what does luxury mean to you?", the answers were remarkably consistent:
"Time off without guilt."
"A weekend with no work. Sounds sad but that's the truth."
"Having time to spend with my kids."
"Coffee on the porch in the morning with no schedule."
"Space and time."
"Not having to think about logistics."
"Not having to check my bank balance before buying something."
The closest anyone got to a material luxury was the Manhattan lawyer who spent $100 on chocolate in a single visit: "No sane person does that. That's luxury. Really, really good chocolate." And another who defines luxury as "nice bedding" because her mother always invested in quality sheets.
The $68 million manufacturing exit who still flies commercial: "I still can't bring myself to fly private. Everyone at my level flies private but it seems ridiculous to me. Business class is plenty comfortable."
Part VI: What Money Actually Means to Them
If you strip away the surface-level answers, the wealthy define money in basically four ways, and none of them are about buying things.
Freedom to Walk Away
"Always have the ability to say, fuck off. I'm not doing this anymore. You need to make sure you have enough money that your brain doesn't take you to dumb places."
"Never having to depend on anyone else. Never being in a position where someone has power over me because of money."
"I don't like to wait in line, and I don't have to be told what to do. So what it represents to me is autonomy."
Security Against Chaos
"In Russia you grow up... your grandparents talk about World War II. And when you hear your grandmother telling you about how people are eating paper to survive. And how one time they found a piece of bread that fell behind a dresser and it was like the best day of the year. You kind of look at your problems and say, I can handle it."
"If anybody ever did the marshmallow experiment with me, they'd be waiting. I'd earn a lot of marshmallows."
A Multiplier of Character
"Money is a tool that allows you to write your will upon the world. It's leverage. Pun intended. And that's why it's so dangerous, because it exacerbates all of your negative tendencies and also your positive ones. But in some ways, I think it exacerbates your negative ones more."
"You can never be safe. Like there is no safety. No amount of money makes you safe. I mean, look at all the oligarchs in Russia. They all thought they were safe. And then Vladimir Putin showed up and said 50%."
A Scorecard (Acknowledged With Slight Embarrassment)
"Honestly? Scorecard. I know that sounds bad but in my industry, the money you make is how you're measured. I've never been motivated by consumption, but I am motivated by excellence, and money is one indicator of excellence."
Part VII: Made It, Lost It, Made It Again
About a third of the people we spoke to had, at some point, lost everything or close to it, and rebuilt.
One interviewee went from a "really nice house to a pretty regular apartment" after a financial downturn and messy divorce, then rebuilt his wealth entirely. His reflection: "The second time it's easier because you understand what. First time you get lucky and you don't appreciate how lucky you got."
A $68 million exit lost $2 million to a Ponzi scheme, classic affinity fraud, the guy was from his own industry, seemed trustworthy, had returns that were "too great." He's now permanently conservative with his investments. "Old habits."
A woman who'd been a successful banker was simultaneously abandoned by her husband, had her youngest child diagnosed with cancer, and lost her clients, all at the same time. "Of those three things, the no money became the worst." She rebuilt through real estate and is now comfortably wealthy, but carried what she calls "the bag lady fear" until her 60s. (Personal note: this was one the most impressive people we interviewed in my opinion, the other being a 50 year old entrepreneur who was homeless in his early 30's)
Part VIII: Fun Anecdotes
Some stories from the interviews that are just great:
The Man Who Didn't Know He Was Rich
One interviewee, an IT services business owner in LA, was paying himself $100K a year and taking distributions but never tracked his actual income. When he wanted to buy a house and asked his accountant if he had enough for the $1 million down payment, "she was like, yeah." When they later converted his accounting from cash to accrual, they discovered $4 million in unreported (but legitimate) income. His accountants were terrified to tell him: "They slid the thing across the table. No one would tell me what was going on." He was actually pleased: "I didn't realize I was so successful."
The WNBA Dildo Bet
One interviewee is a self-described "fucking degenerate" on prediction markets. He once bet on when the next dildo would be thrown at a WNBA game. He loves Polymarket because "it makes it feel like it's not absolute gambling, but it is."
The Doomsday Prepper Banker
An investment banker whose dream car is a 20-year-old Lexus because it has no computerisation and therefore "no remote kill switches." He lives in "a series of Airbnbs" despite being successful because he values not being tied to a property. And his biggest financial regret: "I got too frustrated in high school and never really went through on setting up an early bitcoin miner and instead played more World of Warcraft. It was a very expensive rating session."
Part IX: The Calvinism Problem
One interviewee identified what he calls "a cancer in America":
"There is a cancer in America. The cancer is Calvinism. Calvinism holds that if you're rich, you're supposed to be rich. The biggest way in which money fucks with people's heads is they feel that they owe it entirely to their hard work and not to getting fucking lucky."
The role of luck in wealth creation was a real dividing line in our interviews. The more self-aware ones framed their success as "single digit modifiers to dice rolls that compound over time, everything is Dungeons and Dragons." The less self-aware ones genuinely believed they'd earned every penny through hard work alone.
"I finally sort of clogged my way up the ranks when I realized how freaking easy it was. Corporate America is just so easy. I mean, my God. Because everybody's making it up. It is karaoke out there. So, you know, it turns out that no one's an imposter. We're just brilliant con men."
Part X: Women and Money
Three women in our interviews, completely unprompted and independently of each other, gave the exact same advice to their younger selves: negotiate harder.
"Don't be afraid to negotiate. Early in my career I took whatever comp was offered because I was grateful to have a job. Men in the same roles were asking for more and getting it. I probably left millions on the table."
"Negotiate harder. I was so grateful for every job offer that I never pushed back on compensation."
"Negotiate harder. I accepted too many offers without pushing back."
This was the single most common piece of advice from women to their younger selves, and not one man said it.
Part XI: The Quiet Philanthropy
The people in our sample who give the most money away are the ones who talk about it the least.
One interviewee secretly paid for a friend's surgery to prevent him from committing suicide. He never told the friend. He also housed another friend rent-free in New York for a year.
One woman stopped giving to big charities entirely and now only gives to GoFundMes for people she knows: a family whose toddler fell out a window, a babysitter with mental health issues, a neighbour in a motorcycle accident. "Helping people who are like real people who are struggling I think is like the most important cause for me."
Another gives $400K a year to his university, the historical society, and legal aid, but would never put his name on a building. His grandmother's voice in his head: "Pride goeth before a fall."
And my favourite: one interviewee sends his broker a box of donuts from his hometown "every time they make me $50,000."
Part XII: The Wisdom
I'll close with some things our interviewees said that stuck with me:
On spending as politics: "You can't control a lot in your life, but you can control what goes in your mouth, how you use your body, and how you spend your money. Those are the three things we all have the ability to do, and the ability to spend our money is the most powerful political statement a person can make."
On habit: "Motivation is bullshit. Discipline is bullshit. Habit is everything. Motivation triggers discipline, discipline triggers habit, and habit makes the man."
On career planning: "Security for my family and the ability to live on my own terms. I don't need more money. I need time. Which is ironic because I spent decades trading time for money."
On mortality: "I will be forgotten. Someone, when I'm dead, someone else will live in my house. My things will be in a landfill. And no one will remember my name in a hundred years. But hopefully some of those ideas carry on."
On money and safety: "Money is really useful and money is really limited. It can buy comfort, security, experiences, time. It can't buy health, love, or meaning. Took me 40 years to really understand that balance."
Thank you for reading this far. More to come.