People Who Have Worked For Billionaires Are Sharing Their Stories, And I'm Convinced The .1% Live In A Different World Than We Do

Buzz Feed

12-02-2025

The wealth disparity in the US is huge right now, and the culture gap feels even bigger. It's hard to relate to people in the .1%, especially because so few of us ever interact with them. It often feels like they live in an entirely different world than we do. So when someone on Quora asked what it was like to work for a billionaire, I was super curious about the answers. Here's what people on the thread — and similar threads about working for billionaires and high-level millionaires — had to say.
1. "I know a private chef who works for one. He and his wife enjoy going out to eat but hate crowds. So, they built seven restaurants on their compound, each with a different theme — e.g., Italian, steakhouse, diner, etc. Each day, he lets her know what 'restaurant' they will go to, and she shops, prepares the menu, greets them, announces the specials, and takes their order. They are the only ones in the restaurant. The rich are eccentric because they can afford to be."
— Jake H, Quora
2. "I did consulting work for two multi-millionaires who had been rich all their lives. They did not think like normal people and could not relate to them. One was a woman. We got to know each other quite well. Over lunch one day, she spilled some wine on her dress. She said she had another dress in her office but no extra underwear. I suggested she get them at the store on the first floor of the building we were in, where there were several exclusive, expensive clothing shops. She looked at me like I was out of my mind. She said, '…and buy that K-Mart crap? I pay $400 per pair for my panties and can't stand to wear that cheap crap.' I was looking for a sign she was just kidding, but she wasn't."
"The other was a guy. He came from a rich family and got much richer. He was in his sixties and lived like a king — only the best cars, houses, restaurants, clothes, etc. Here is the gist of a conversation he had on the phone while I was in his office. I could, of course, only hear one side. It went something like this:
Hello.
How's it coming along?
I know it's an uphill battle, but I'm counting on you to stop it.
OK, how much do they want?
I can do that, but I need your guarantee you can stop this or dilute the hell out of it.
All right, I'll send over half tomorrow.
NO! I don't want any records or paper trail. I'll have a courier deliver it to your office.
OK, but keep in mind if this bill passes your committee, there will be hell to pay.
Have a good day, Senator."
— Tom W, Quora
3. "Back in my 20s, a friend worked for a millionaire directly; he ran his house in the UK and played chauffeur when needed. The guy only spent about half his time in the UK, so my friend got to use most of his things; sometimes I did, too. The guy owned about 90 cars, and my friend was allowed to drive most of them and use the yacht. Over half of those cars were Ferraris, by the way. It's not bad driving around in one in your twenties. My friend's job was really running the house and staff and making sure the billionaire did not get ripped off. I have no idea what he earned, but he was soon buying a house every year. When I lost contact with him, I thought he owned nine. He was lucky; I doubt most are as generous. But yes, working for one can be great, though he was never allowed to borrow the plane."
— John P, Quora
4. "Working for the very rich reinforced my desire that I don't ever want to be rich. The security they have to live with boggles my mind. The entire family is surrounded by security 24/7, 365. When the children attend school, an armed nanny is there. When mom or dad drives somewhere (if they actually drive themselves), a security guard is in the front passenger seat, a security guard drives a car in front, and another follows behind. They are prisoners of their own wealth. I'm happy if I have enough to pay my bills and a little extra for gifts to give."
— Fran I, Quora
5. "I did work for wealthy people, and it was kind of a good job, but it sucked too. I had to follow them around and do whatever they told me to do. I mean, their kids would call me 'the help' and not hang out with me outside of work. But during work sometimes they bought me burgers and hot black coffee so that was good. But I had to do things like wash windows, sweep floors, and fix a broken tree, and they loved to tell me to clean the toilet. When I protested, they said, 'What? You think you are too good to clean a toilet just because you have a college degree?' You know? I knew they were disrespecting me, but it's hard to say no to fifty-dollar bills."
— Andy M, Quora
6. "Way back in 1980, I had a cabinet-making business in Los Angeles. We did a huge job for a very wealthy person in Bel Air. The kitchen cabinets alone were $108K (that's $411k in today's dollars). When the house was almost completed, I was told that this person was suing all the tradespeople for conspiracy to commit fraud (not sure of the actual legal complaint). According to this person, all the tradespeople were involved in an illegal act. She even sued the Mexican workers who did the roof on the house."
"The lawyer I hired spoke with her lawyer. It turned out that my insurance company (and many others) won't defend against fraud. Her lawyer told my lawyer, 'Tell your client to walk away. He can't win.' He was right, and I (and I'm guessing many others) had to walk away while getting stiffed.
Did it change my opinion of the rich? Well, it made me less likely to think that rich people got their money through hard work and creativity, but I avoided the temptation to think all rich people are heartless."
— Hal H, Quora
7. In a word? Surreal. I used to work for an EXTREMELY reclusive billionaire (he will be called Greg) as a personal aide. Only one or two pictures of him have ever been publicly published, and he has never given a personal statement. He maintained a zero social media presence and would always grumble about the dependency of modern society on rapidly changing technology. He and his family always maintained a low profile."
"But don't for a moment underestimate the man. He always maintained a composure of calmness throughout even the most trying situations. There was a time when a client agreement between his firm and the client had fallen through, and they only had a few hours to rehash all the details. Unfortunately, he had given the lead architect of the deal a few days off earlier in the week. Greg knew that the architect was out deep in the countryside, helping with the after-party of his sister's wedding. Within one hour, a helicopter from a local tour agency (that always had one on standby) was chartered, sent out to the architect, and brought him back so they could work on the deal. The deal eventually fell through (it was beyond saving if you asked me), and Greg felt extremely guilty for the inconvenience he caused the architect. As a form of thank you, he paid for the sister's wedding and gave the architect another month off.
He always attempted to remain frugal. He never owned any form of private transport (jet, helicopter, yacht, etc), though he had a small car collection. He always donated money or reinvested it into the market. His neighbor's son had been involved in an extremely gruesome accident when his car was slammed by a truck. Knowing that financing the operation and hospital stress for the son would be too much for the mother, he quietly paid for the entire operation and set up a trust that would cover the living and medical treatment costs for that young man for the rest of his life. Greg was a fantastic individual. It gave me great pleasure to work for him, and I definitely miss him."
— Anonymous, Quora
8. "I worked in a family-managed, private firm's money management/payments department. We'd often have the billionaire and his son call us directly (bypassing the family office in case of emergencies). We were asked to draw up plans one evening to finance a new personal jet and a new yacht. The plans were drawn up overnight, and funds were made available within a week. We were once asked to draw out around $4 million in cash from banks within two hours (most banks have rules against such huge cash drawdowns) and just hand it over to the secretary of the billionaire, no questions asked. My American CFO got all red-faced and threw fits, but he had to do as told."
"We'd regularly get calls from the son to arrange for the equivalent of $100k in cash in odd currencies. Sudden travel plans would develop, and he hated being without some petty cash.
Our billionaire told his Chief HR Officer to keep a list of 10 top/senior-level executives ready for him to fire every quarter. 'Keeps everyone on their toes,' he used to say.
The billionaire started living almost exclusively on his yacht, usually in international waters. The yacht was known to be a magnet for young people (the billionaire himself was rather old), and one can imagine why.
The billionaire usually usurped all the company's profit as loans to related parties using some rather dodgy accounting. Auditors were given vague explanations and, to my utter surprise, were actually willing to buy them.
They never seemed happy to me. They were always a bit hyper — always pushing, always mistrustful of everyone, always rushing off to vacations (from god knows what; the senior team/ C-suite guys managed everything for them).
One incident: while in NY, the billionaire all of a sudden ordered his pilot to start the chopper as he wanted to go somewhere. The pilot went into a tizzy (there are approvals, maintenance logs, etc., to be taken care of) but had the chopper started soon enough. Then the billionaire canceled the trip and told his friends (looking at the befuddled pilot from afar), 'Good, that should help his blood circulation.'
Their lives seemed unnecessarily complicated. Though both father and son paid a lot to charity, the daily misery they tended to make their staff endure by being exacting and demanding was intense."
— Anonymous, Quora
9. "I have worked briefly for two billionaires who were very different people. One of them would always travel with his family, and they talked almost incessantly about the things they were buying. New jackets or new shoes. They were always taking pictures of each other and looking at pictures on their phones of themselves, their new jacket or new shoes, etc. They had hosts of very expensive cars, and they hopped on private jets to other parts of the world as casually as most of us drive to the grocery store. Very nice people gave a lot of money to charity, but in my surface opinion, wrapped up in the material things of the world."
"The other billionaire was just a smart businessperson. I never would have suspected it if I didn't know he was a billionaire. He just seemed like a successful CEO or president of a company. He was soft-spoken, asked smart questions, and demonstrated excellent knowledge of international business. A very low-key individual. He was private with an enormous home up in the mountains surrounded by trees and snow. Instead of speaking of things in the world, he mostly spoke about flying family members out to stay with him for extended periods of time, skiing with them, and enjoying their company."
— Jason C, Quora
10. "When I was hired for him, I hardly knew anything about him. His assistant was my contact. After a few visits to his office and two last-minute calls to see him at his home on a holiday weekend pissed me off, I guess he read my body language. As I was leaving, he asked how upset I was. I told him all the money in the world can never buy lost time. He laughed and said he agreed with that fact. He offered to double my rate and have his driver take me to any restaurant I liked; dinner was on him. I thanked him but declined, as that day was my girlfriend's birthday, and I knew she had already gone out with her girlfriends, as I had to cancel at the last minute with her. The next day, he sent me a 5-star hotel credit for a suite stay for two, with all in-house meals/drinks inclusive; I only had to choose my dates, book ahead, and enjoy."
"The next weekend, my now ex-girlfriend and I had a great weekend. She thought I had done everything; I was a tired but happy man after that great weekend.
Work-wise, he could be an asshole; he was very driven to get his projects done. But after that's over and he's happy, he at least tried to be a better boss. I moved on after learning some useful trade insights; his style and mine were not meant to last. There was no work-life balance, but still, no regrets."
— Allen G, Quora
11. "It was tough in the beginning until I learned just what he required from me. There is so much variety to what a billionaire is involved in. The work varies from locating more lands for him to buy (even though he is the largest landowner in the country); selling vast tracts of land that he no longer needs or uses for his business activities; driving his vehicles over great distances to have them serviced or repaired (he doesn't trust the local vehicle agents to do a good job); shopping for goods that he's unable to find locally (like binoculars, special quality sunglasses, different types of food — like an imported meat sauce that is not available in his 50 local supermarkets — as he's forgotten to import it); selling his Rolls Royce as he's bored with driving it..."
"...Piloting him from his home airport to another city where hospital care is more efficient; hiring a car and taking him to wherever he wants to go; doing the same work for his wife and two adult children; supervising the building of a new shopping mall (plus finding tenants for the numerous spaces available)...I could go on for ages, but he is a delightful man to work for, and I've known him for about 40 years, so he is now in his mid-seventies, and his requirements are increasing on a weekly basis."
— Suzanne S, Quora
12. "I got my big break as a lawyer when my father-in-law introduced me to his billionaire network. Not long after, I was considered the go-to guy. I never considered myself a friend, but I was an insider. I was in their home at six in the morning, listening to potential deals. I went on vacation with them, and I saw things I wouldn't tell people about, and I did things that, at this age, I wouldn't do again. When they gave instructions, it was always vague and could be interpreted in many ways. What was always clear and explicit was: don't lose money. I often felt like a pet more than anything else, and it was an interesting few years."
"It was also different because I was not an executive; I was an outsourced lawyer. A lot of the time, they just want to be heard as they go on and on about something they think they are experts on. I was also once given a Mercedes for my 36 birthday. A few years later, I reached a philosophical moment where I contemplated making more of myself instead of being the guy in the background. I learned a lot and still keep in touch, but people like myself are expendable and easily replaced. There are probably three of me by now."
— Donny W, Quora
13. "My father has worked for multiple billionaires. His main client made his money from a major tech company and is among the wealthiest of even the billionaire class. He and his wife have a full-time team of maids and security. There are, on occasion, very high profile guests, from other billionaires to former presidents, and maybe a personal delivery of their Teslas from Elon himself. My father doesn't really have anything to say about these clients in particular. They know their staff by name and generally treat them pretty well. They send out Christmas cards and other gifts throughout the years, sometimes in the tens of thousands of dollars range."
"Another client my father has worked for is even more well-known than the last. Yeah, 99.9% if you're on the internet, you've heard of him. Apparently, this client refuses to allow most of his staff to even step foot near him, relegating them to working from a distance. His teams of housekeepers and security are many times larger than my father's other client, and that's probably due to his somewhat infamous status. He's known for continuous cost-cutting measures and trying to hire the cheapest labor possible for his personal protection.
My father has never said anything good about this client, and the mainstream American population has a disdain for this billionaire as well. He believes that he's above not only the law but above the normal person as well."
— Anonymous, Quora
14. "I owned a general contractor company that built custom homes in and around Memphis and Nashville from 1999 to 2014. In 2001, I was contacted by a billionaire who owned several businesses. Quite likely, he was the richest man in Tennessee. I went to his office, and we talked about building him a home. He already had a house and site plan, and we reviewed it together. After reviewing the plan, I told him he was probably looking at $3.5 million to $4 million. He stuck his hand out, and we shook. He said to prepare the contracts and wanted to know how soon we could get started. This began one of the strangest relationships I've ever had."
"The home took 29 months to complete. It was a beautiful home. During the construction, he showed me what a billionaire lives like. On one occasion, he came to the job site and told me he wanted to take me to lunch and introduce me to his wife. I said okay and got into his Rolls Royce Corniche Convertible. We drove out of town, and I wondered where we were going. He drove to a small private airport just south of Memphis and pulled up next to a Citation jet. I asked where we were going. He said New York. I was shocked and asked why we were going to New York. He said he wanted me to meet his wife, and she was in New York. We flew to New York, met his lovely wife, and had a wonderful lunch. It was not the lifestyle I was used to, even though I did very well building homes.
There were other incidents over the time I was building his home. He had me go with him to Atlanta, and we were going to drive because his jet was being serviced. When I started to get in the car, he said here and tossed me the keys. He said I was going to be driving it back, so I might as well get used to it. Then he told me we were going to Atlanta to pick up his new Rolls Royce. So I drove his $300,000 car to Atlanta and back."
— Jim W., Quora
15. "My last boss was a very high millionaire, with assets in the mid-9 figures. The guy drove a Prius that he wrecked every month. There was a body shop on our street, and they got a LOT of work from this guy. The Prius was red, and all the body panels were eventually just slightly different tones. He thought he was always right. Always. On subjects he didn't have any knowledge of. This was a guy who still had an AOL account, but he thought he was an expert on embedded systems and position control. He would take us to lunch, but if we went somewhere where you get your soft drinks, he would ask for water, then fill the cup half full of water and add lemonade, looking around like he was getting away with something."
"But he was generous and gracious to our families. He charmed everyone he met. He was married for over 60 years to the sweetest woman you ever saw. She was awesome. We all went to her funeral. We went to his, too. People from all over the country came to it. There were admirals, congress members, high city and state officials, Cleveland business owners, and entrepreneurs he helped get started. He knew everyone in the business community. He knew presidents of other countries and got a personally hosted tour of the Panama Canal lock system. Hosted by the president of Panama. He was a fascinating, gracious, intelligent, pompous, obnoxious, awesome pain in the ass. I miss him."
— Michael L, Quora
16. "I arrived for some contract work at an airport in the south of France. I was met by a down-to-earth, friendly guy who dressed like a casual middle-class guy in his early fifties. He asked if I'd like something to eat before he dropped me at my hotel. I said I could just grab something at the hotel later. He gently insisted that it was no problem and that his wife would like to meet me before he dropped me off. He called home as we drove and asked what kind of food I liked. I said anything would be fine. He asked, 'Do you like chicken?' I said, 'Sure, but please ask your wife not to go to any trouble.' He said, 'It's no trouble.' We drove for twenty minutes and had a nice conversation. Then we arrived at his home. It was walled and gated."
"The automatic gate swung open, and we drove inside. His home was a beautiful mansion with views over the Mediterranean. There was a pool. And lots and lots of marble.
His wife came out to greet us. She reminded me of Lara Croft. He looked like a normal guy; she looked like someone who had just walked out of a movie screen. She smiled and welcomed me to their home. I sat at the table on the veranda with the pool, a long rolling green lawn, and the Mediterranean as the backdrop. A number of servants had set up the table and were bringing food.
I never would have guessed in a million years that the guy who picked me up was a billionaire. And the best thing was, he was one of the nicest and humblest guys I've ever met."
— Sean M, Quora
17. "Back when I was in college in Chicago, I worked temp jobs occasionally for some extra cash. One day, the agency called about a possible job, driving a woman's kid to a rehab medical appointment one afternoon a week. My first indication that I might not be in Kansas anymore was when the elevator opened on a decorated foyer that contained a single large residential door at which a maid was waiting. She ushered me into a large formal living room, asked if I would like some water or lemonade, and told me that Mrs. C would be with me shortly. While she went to get the water, I noted that the furniture and artwork in that room looked like the sort of stuff one would see in an art museum."
"Mrs. C turned out to be an impeccably dressed thirty-something-year-old woman who spent a half hour or so talking to me about my studies and plans, my driving history, and the nature of what she needed done.
And so it began. For the next couple of years, I would take their son to the Rehab center, have lunch in the cafeteria while he did an hour of rehab, and then I would drive him home. Generally, I would then drive Mrs. C to a department store, leave her for an hour or so, and return to load the back of the car with a half dozen small purchases. The next time I worked, I would take those purchases, now gift-wrapped and securely packaged, to the post office. I would mail them all over the world, often to names I would recognize from reading them in news magazines. On some days, the cook and I would make the rounds of food outlets and load the station wagon with enough food and wine to entertain dozens of guests.
There were, it turned out, two maids, a cook, and a nanny in regular residence with Mr. and Mrs. C. And there were three other servants out at the country home to which I drove Mrs C a couple of times. Mr. C was the president and major shareholder of one of the country's then-largest banks. Beyond merely being his wife, Mrs. C was managing a household that included more than half a dozen full-time servants and me, and she was functioning as a social secretary, maintaining relationships with movers and shakers all over the world. They controlled a fortune that ran to several hundred million dollars in the 1960s — much more than a current day billion.
Their paternalistic feelings toward 'their people,' i.e., the servants, were right out of an English novel. But I observed them for a couple of years and never saw them behave badly toward anyone."
18. "I have known four billionaires, and worked for only one. The one I worked for was an evil, megalomaniacal tyrant (when he was off his meds, which was MOST of the time). Seriously, he'd fire staff for looking at him funny, or schedule a 3 a.m. meeting, then fire you if you were late to the 8 a.m. meeting the very next day — even if you didn't know there was a meeting."
"But man, he knew EVERY SINGLE ASPECT OF HIS BUSINESS. He knew his job, and he knew YOUR job (because at some point while building that thing, he'd had to do it and figure it out all on his own — this was a truly self-made man). I respected him for that."
— Anonymous, Quora
19. And finally, this story is about a rich coworker, but it's too ridiculous not to share: "I once worked with this young woman called N. She was very sweet, soft-spoken, and loved to wear nothing but designer clothes and accessories. Her background was Iranian, and from what she told me, her family was quite wealthy back home — think, 10+ bedroom manor, butlers and maids, and a father with very high expectations. One brother was a high-ranking investment banker lawyer of some sort, and the other was a heart surgeon. Her wedding was lavish, and her dress was handmade in Dubai (where she frequently traveled from Australia for fittings). She married a nice man but wanted a humble, domestic kind of life. She was also learning to cook after revealing that she and her husband ate out every single night."
"Anyway, a group of us were sitting around the office chatting and lamenting about chores around the house. She then joined in with, 'Oh yes, vacuuming can be quite expensive!' We all paused for a moment and looked at her, and after a moment, I asked her why. She then goes on to tell us that every time the vacuum was full, she'd have to go out and buy a new one. I asked her what she meant - did it break? Was it faulty? Nope.
Bless her heart; every time she filled the dust compartment of her very expensive Dyson stick vacuum, she was throwing it away and buying a brand new one. We all burst out into laughter, and I had to explain to her very gently that you could, in fact, empty the dust compartment. She was a little embarrassed but happy to never have to buy another vacuum again."