"I've Worked For A Few Billionaires...": 29 Secrets And Stories From People Who Work For The Super-Rich
As a non-rich person, I'm always fascinated (and horrified) when I catch a glimpse of how the other half lives. Recently, u/coco_deez_nuts asked people on Reddit who've worked for the super-wealthy to share some of the things they've seen, and people did not hold back. Here are some of the most jaw-dropping replies:
1."An acquaintance of mine works as a senior engineer on huge mega yachts. The husband is barely there, but the trophy wife (number five), ten years younger than his youngest daughter, lives in it most of the time. All of the staff know to stay clear of the sun deck between 11 and 12 every morning. She comes up from her cabin, three stiff gins in, and cries for an hour before lunch to herself. Every fucking morning. The added kicker, the yacht is named after his first wife."
2."I know a lady who bought her kid a horse; then they bought the horse a horse for company. Then they decided they may as well build a stable. They now have about eight horses and run an equestrian school. Imagine having the money to turn a child's whim into a business."
3."He pumped a bunch of money into the Malibu City counsel in order to change a few seats. This would allow him to have the local ordinance changed so his front doors could be taller than 20 feet."
4."When I lived in New York, I worked at a highly regarded hotel, the kind where you would see celebrities every other day. The one that stood out to me was when a guest rented out a honeymoon suite just for their cat. I know it sounds made up, but rich people are weird, and so is New York."
5."The wife of an acquaintance told us a story of how she used to work for a wealthy businessman on his private yacht, but he was never on it. She worked in the kitchen as one of the chefs, and basically, he would have his family or his friends use it when they were in town to save on having to have a hotel; they’d just stay on his yacht. She said in the 18 months she worked there, she only knew of him using it himself once. I mean, can you just imagine having the kind of crazy money to buy a yacht in the first place, then just not fucking using it?!"
6."I worked at a summer boarding school in France for rich English kids. Parents would send the kids to us and jet off for the season. One kid bounced wrong on a bed messing about, and flew through a window, lacerating his liver and almost bleeding to death. He was in hospital for two months with various complications before being moved home. The parents never came to visit, never even spoke to him. After two weeks, his au pair or something came for about three hours. Some of those kids were little bastards, but it was very clear why."
7."We were sitting down at the table about to sign a contract, and his assistant forgot 'the' pen. Apparently, this pen has signed all the deals that were successful in his early career and made him who he is, so he doesn't sign any deals without it. So he legit tells her to get on the jet, and bring it him immediately. He apologized for the inconvenience by adding 20% to the deal. Money isn't an actual thing to wealthy people. It's all a made-up concept of unlimited 1s and 0s."
8."My friend was a security guard for an elderly widow of a Dallas oil baron who lived on White Rock Lake. She had a full-time private chef and kitchen staff, although she lived there alone. He said the chef would cook huge beef roasts, turkeys, brisket, and all kinds of food every day just to have it available in case the old lady wanted something, which she rarely did. They weren’t allowed to give the leftover food away to the staff or anyone else but had to throw it out every single day. And when the old lady requested ice water or iced tea or lemonade, if even one ice cube had cracks in it, she would make them throw it all out and make it again."
9."The CEO of a company I used to work for offered to take me wine tasting. She said it'd be free; apparently, she spends so much money on wine from this vineyard that they get her a limo and free access/tasting whenever she feels like it."
10."Lots of pill popping to handle stress — especially before speaking engagements. People always viewed them as friendly, engaging, and fun. Little did they know that was a public persona thanks to copious amounts of Ativan. In real life, they were picky, obstinate, difficult, and a nightmare for all of us employees to deal with. We had to remember all of these particular preferences and abide by them always."
11."Custom cabinets made and installed only to be taken down and tossed in the trash because they decided the color they picked out wasn't the right vibe."
12."Saw a Prince of Saudi Arabia in the early '90s throw money in a way beyond all imagination. Dropped about $100k for a single dinner for him, his wife, and his two children. Shutting down the fine-dining restaurant in our hotel costs $30k for one night. He flew in his favorite chef from New York to Florida (where the hotel is), made enough food for our entire restaurant staff, his family, and the security staff from state, local, and federal forces he had with him, and tipped us a ridiculous amount, too. He stayed at our hotel every year for several years and rented the top four floors of the hotel for a month. He had one 747 for himself and another for his staff, which numbered around 400 people."
13."My boss has a wooden covering to what once encased an ancient Egyptian mummy. He is elderly, and we were preparing items to be shipped to his daughter, who lives overseas. We didn't send it because it is a known stolen artifact and will be confiscated at customs."
14."My dad was friends with a Spanish rich dude because they shared a love for old cars. My dad had one, and the rich dude had many. The thing is, these people had a maid who worked for them since before this rich dude was born. His parents were never around so she was the one to actually raise him. She fed him, took him to school when he was a child — everything your parents would do for you, this maid did. She had been working in that comically large house for over 30 years. Other staff, such as cooks, cleaners, etc., would come and go, but she was almost part of the family, we thought. One day, the rich dude decides he wants to move to the US and sells the house. What does he do with the maid? He just fired her over the phone. He never even said goodbye to the woman that basically raised him. And so I learned that rich people don't consider the poors to be the same kind of human being as them."
15."Had a client who purchased a newly built penthouse apartment and wanted a jacuzzi on the balcony. It would’ve meant a structural column was needed in the middle of the balcony below. The contractor who built the apartment block wouldn’t go for it as it would impact selling that apartment. Client buys the apartment below, approves the column, jacuzzi is installed, then privately sells the apartment below. Voila, problem solved."
16."I used to work for a grocery delivery service; customers sent their lists through an app, and I would shop and deliver their orders. My most out-of-touch rich person story is the lady who ordered $300 worth of filet mignon from Whole Foods (when it was still good before Amazon bought them out) and wanted it cut into stir-fry strips. The butcher made me show him the order notes because he was also incredulous at the sheer audacity of hacking up $40/pound steaks. The address ended up being the most expensive single-family home in the city at that time. I also delivered laundry soap to Joe Montana."
17."I've worked in private banking, and I can't say too many things, but the weirdest example by far was a billionaire client who employed a private detective or intelligence officer to create a file on me, complete with photographs they took of me going home from work. I think it's safe to say that I'm talking about the kind of billionaire who is linked to a head of state; your average new money tech billionaire doesn't have this kind of security operation. He said that his security team produced a file on everyone before they walked through his door, and he advised me to tighten up my online security."
18."My boss was kicked out of his house and staying at an exclusive Laguna Beach hotel and wanted to leave. He had been drinking, and the valets wouldn't give him the keys to his Range Rover when he wanted to leave. So, he called the dealership (he bought one every year or so and was a good customer), had a new one sent over, and drove off in his new Range Rover after it arrived."
19."Did building maintenance for a wealthy family who had a Lego room for their grandkids. This room was huge and had cupboards full of Lego and building tables everywhere. There were huge Star Wars ships and castles, etc., all over the place. One day, the kids were deemed too old for Lego, and I was asked to dispose of it all. I carefully packed them all into bags and gave them to friends' children. Many thousands of dollars worth. Man, I was popular."
20."I was a waitress when younger. I had a super wealthy guy who wanted to date me but I wasn’t having it. Said no, even after his $500 tips. One day, I came to work, and he was there with a lawyer, and he bought the entire steakhouse and bar I worked in. Then he said, 'Now I own this place, we WILL hang out.' He always told me, 'Money talks and bullshit walks,' and every single person or thing has a price. He took me on trips and bought me a Benz and a small apartment. He would do WILD shit. He was a very impatient person and sometimes would buy the line up of groceries for people just to skip the line. Just unforgettable insane things; I can list many! But when it ended, it got bad; he paid people to follow me, and it wasn’t good."
21."I work at a private social country club. Our members are billionaires and triple-digit millionaires. They 'playfully' discuss their jets like poor people discuss streaming services. Apparently one member had $60 million plane bragging over one member with only a $45 million dollar jet. When we have weddings at the country club, the tents we usually use cost more than $200,000. I feel so poor there sometimes. But I am also more content with my life and have true self-awareness."
22."I got stiffed by the super wealthy. They didn’t feel like paying me, so they didn’t. And they got away with it because I was poor and powerless and scared shitless to take on someone who could whoop my ass in court or even socially."
23."I was a nanny for landed gentry (the title of Sir and Lady get handed down to the eldest child, along with the manor house and lands). Kids were packed off to boarding school at 8. It was heartbreaking. The middle child was dreading it — tears every night, literally sobbing himself to sleep in my arms. Parents' attitude was, 'We were like that too, so he has to do it.' The youngest was two at the time and would always prefer me to his actual mum. He fell over once and came to me for cuddles and kisses, didn't even glance at his mum, who was standing right next to me. She didn't seem bothered. The thing is, the parents were actually pretty nice people, just not bothered about childraising in any way. At least they didn't insist I use their titles, like some of their friends did with their staff."
24."I’ve worked for a few billionaires. One owned a box at the local concert venue. He would give seats to us sometimes. His crew was backstage with all the best bands. Another one started his company and brought in his friends and family on the ground floor. He would pit them against each other in board meetings. He was bored. One founder would have an HR watcher assigned to him at the (amazing) company parties and steer him away from the pretty ladies. Wife one, two, and three were all former employees."
25."I’m a graphic designer. I was designing an annual report for a very wealthy owner of a private equity firm, and he wanted me to match the colors of the book to the interior of his private jet."
26."A colleague made an offhand comment about her kids needing red T-shirts for an art project at school. She said she was going to Run into Lord & Taylor or Bergdoff's to get a 'cheapy' shirt. Me in my head: 'normal people go to Wal-Mart for 'cheapy' shirts.'"
27."The CEO of our company routinely orders catered lunches or has his chef cook food for contractors and various vendors that work within his home. His big thing is cheeseburgers. At any given moment, he's sending one of his staff to buy cheeseburgers, or he's having his chef cook them. Everyone thinks he's so nice for offering them lunch while on the job, but from his own mouth, he says he only feeds them because 'I get pleasure watching these people crowd into my kitchen always looking for handouts of food like dogs.'"
28."I tutored a kid once in math. The kid was a genius, but the other moms got their kids tutors, so I guess I was in fashion. One day, she asked me to drive her downtown to 'shop.' She blew about $24K on diamonds, pearls, and costume jewelry. This was a monthly thing. I was charging $30 an hour and felt like an idiot."
29.And finally, "I worked in the mail room at one of the BIG 10 and got to see a super wealthy person's tax return; it was two entire file boxes, and this person was getting somewhere around $10 million back on his tax return. He’s already super wealthy, and he’s getting a lifetime's worth of wealth back on one tax return."
Have you ever been close to extreme wealth? Share your experiences and observations in the comments!
