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If you’re not someone who was born or married into the world of the uber-rich, there’s a good chance you don’t really know what it’s like to live on the inside.
Most of us never will, but these 17 people work jobs that give them clearance, if only for a little while – and luckily, they’re willing to dish on the things they’ve seen.
17. That’s a lot of booze.
Worked at a restaurant where a few of the regulars were the children of billionaires. “I told my parents that my tuition costs $500,000” – a student (from china, in America) i overheard after being asked how she has so much money.
Another time i was serving a table i was asked to bring a tray of sixty patron shots ($600, for a 19 year old student) i must have had an incredulous look on my face because his only response to assuage my concern was “my father owns diamond mines in Africa”
16. Organs on hand.
I briefly worked with one of the top Saudi Arabian crown princes. He would buy out the top three floors of the best hotels.
Two floors were for maids/help/security, top floor was for the Royal family… once it was only the prince and his three wives.
My brother dealt with many of their jets. One had a full on surgery room and there was a guy who traveled with him at all times to be his organ donor.
I wish I was making this up.
15. A whole computer.
I had a classmate whom’s father or mother was filthy rich from family money cant remember.
But they and he were amazing people. In uni this girl in class who was really nice but also came from a poor family dropped her macbook she worked 60 hours a week for 3 months in the summer.He just came up, gave her his macbook, and said he would just get a new one after school and his parents wouldn’t care. Pure generosity there was no tiktok movie or karma whoring going on.
He was a stellar dude spending his parents money but only on stuff for other people and in a nice helpful way.
He also gave all the guys in class a suit for graduation. lots of the people where talking about renting one and stuff and he told everybody he knew a place to rent real nice suits, we all went there and we all rented a suit for 100 euros or so everything included and when you went to return it we found out they were all payed for by this dude.
He was like renting a suit is stupid, but buying a suit is expensive now you got best of both worlds.
last thing I heard he bought like 10 ps5 from scalpers and sold them for retail to kids in the neighbourhood
14. Saves on the commute.
I used to work for a billionaire Russian family as a tutor for their daughter. One day we’re in her room studying and suddenly she yells “daddy’s home!” and runs to the window.
She’d heard a helicopter and knew is was about to land on the lawn.
13. Awkward.
I heard an interview on the radio from a guy who was from my hometown in the UK who was Stallone’s personal chef in the 90s. He said Stallone was a nice guy, he had something in his house where he could watch the amount of tickets his films was selling in live time so knew almost immediately whether it was a flop or not.
He was married to Bridget Neilson at the time and this chef said she was walking about topless or naked all the time which he thought was strange until she walked up to him one time when Stallone was out and offered it to him on a plate. He politely declined because he liked Stallone and they were divorced a few years later so there may have been other things going on.
12. I cannot imagine.
My dad’s client bought a whole block of houses to build theirs.
It is so wide that they installed a moving walkway like the ones at airports.
11. Friends you’d like to have.
I went to a New England prep school for high school on a full ride sports scholarship.
There were a decent amount of foreign national students – mainly from Asia, that came from EXTREMELY wealthy families. One of those students parents bought him a brand new BMW 5 series – fully loaded, when he got his license our Junior year.
When we graduated a year later, he was going back to Korea and obviously couldn’t take the car, so he gave it to his best friend…kid got an $80k car at 17 years old, just for being good friends with the right guy! I’ll never forget that.
10. I’m thinking about a career change.
A friend from high school worked a few years as a deck hand on yachts in the Mediterranean and he said he once jumped in to get a customer’s bag and got tipped €4000.
He also observed actual bricks of coke brought onto P Diddy’s yacht.
9. A quick collection.
This was ages ago, I worked in a DVD store a woman came in with five A4 pages (double sided) of movie titles and just asked me to fetch what we had. I ran about and collected DVDs and Blu-rays close to 1k worth.
I asked what they were for – she was a PA for a billionaire and getting then for his yacht.
8. Surreal, for sure.
I am an art student working as a gardener. We work in one of the wealthiest areas in my country. Some customers are really eager to show me their collection of artworks that they have hanging on their walls once they find out that I study it.
I remember one time standing in a bathroom, with my dirty gardening clothes and there was a Picasso above the toilet.
7. Hand-me-downs.
My dad used to work for a private air field. They had a ton of people fly in but most of the more richer clients always flew in at night. I remember one time in high school, I had to do a “job shadow” thing and went to work with my dad. They had the owner of a California air port fly in for the weekend. My job was to stand outside with an umbrella.
So I stood outside with the umbrella. His wife tipped me 20 dollars and said “the sandwich trays are real silver, have at it kid.” After they got in their car, I asked my dad what she meant. Apparently, when some richer folks fly, they let the people who detail their planes have the platters and other serving items. I always wondered how we got so many weird serving trays.
Another time when I visited him at work I got to hold an albino kangaroo. Most adorable and softest animal I’ve ever touched.
6. A total waste.
My dad works in shipping and has a lot of friends who have worked on super yachts. In the 90s one of his mates got a call up to bring the yacht of a particular Australian media tycoon billionaire (not that one) from Sydney to New York, with instructions to be anchored in a particular bay at an exact time with a lunch spread for 50 people ready.
So they got there and set up the food.
The guy never showed up. Turns out he was having a rich dude party in a building overlooking the harbour and wanted to be able to point down and say “that’s my boat”. He wanted the lunch just in case he decided to take his rich friends down to his yacht, but he didn’t feel like it that day, so all the food got wasted and they sailed back to Aus without seeing him.
5. A lucky pooch. Maybe.
A woman who owned a small private jet business told me one time someone paid them to fly their dog (by itself) to NY for about $45,000 for some training.
No other passengers.
4. Nothing new.
Worked graveyards as a valet at an ultra luxury boutique hotel. It’s quite shocking how some of these people live and you’d never have a clue by just looking at them on the street.
One weekday night I was asked at 2am by a guest to bring around his Bentley. Regular looking dude came out with a backpack, got in and left. Not 30 min later the same dude pulls up in a Ferrari and now has a briefcase instead of backpack. Skip ahead an hour and the same guy orders 5 shot glasses to his room. I go up and it’s 2 guys in robes and 2 naked ladies on the couch. They have lines of coke and booze on the coffee table.
They tip me 50 for the shot glasses and I leave. 2 hours later, just as the sun was rising, the two guys come out together in suits looking like they were heading to the office. The ladies left shortly after.
Obviously drugs and escorts were nothing new but the car swap middle of the night was a bit strange.
3. It’s not all perks.
I tutored a wealthy 5 year old. I got paid good money to spend an hour drawing and coloring and playing with this kindergartener but all in French. He had been to more places in the world by 5 than I’ll ever go to in my whole lifetime probably. The best part of the job were the perks, though. They would take me and my SO out to dinner at fancy restaurants and pay the bill no matter what it was. They would invite us over to eat some delicacy they prepared (wife was Chinese/Vietnamese, husband was Indian) and they’d always have some house guest staying with some crazy resume, for example, one time they had a diplomat for the Netherlands there to do business. They had houses in my city and in San Francisco and would fly there all the time. They invited me on several occasions but I never had time to go.
I also befriended and stayed with the daughter of Russian oligarchs who lived in Paris. The mom was a famous writer and the dad did something in business. Their grandfather was a famous Soviet writer and so in general they lived a very cultured life. They lived in the richest part of Paris called Neuilly-sur-Seine and had houses in the Alps, Crimea and Moscow. The crazy part, or rather sad part, was that she only had a few options for a career. She could be a doctor, a lawyer, or a businesswoman.
Their son was lucky enough to study at the Geneva conservatory but that was only because he was really talented. In this family, if you didn’t have a natural artistic talent you only had those three career prospects to chose from. I had the impression that she was rather depressed about how limited her options were and how much pressure was put on her to succeed.
2. They never use it.
I used to do pool and spa maintenance in my 20s. I worked on one property with a mountainside, 10 bedroom/14 bath mansion, with a saltwater pool, tennis courts, guest mansion, and a servants house that was 4 bedroom 5 bath. The property had so much more stuff, but that isn’t the crazy thing.
I worked on this property for 2 years, year round, 5 days a week, and not a single person was ever there. The middle aged, single woman that owned it lived in a city about 4 hours away and just didn’t come to the property, because she was so busy with work. A multi-multi-multi-million dollar compound, just empty. All the time.
Finally, after 2 years, I got a call from my boss on my day off. He asked if I could go to the house to put some pool floats away. He apologized, because it was my day off, but said the owner would pay me $500 to go put them away. I was confused as to why there were even pool floats out anyway, because nobody was ever there, but I figured fuck it; $500 for 10 minutes. I show up to the house and the woman’s adult children were staying at the house with about 10+ kids between them all, and they were having a massive pool party/cookout. I awkwardly walked up and said to one of the parents, “Sorry, it must have been a mistake, but I was told to come put pool floats away, but you’re obviously here so I’ll leave.” Presumably the woman’s adult son said, “Oh, no, we’re getting ready to leave. You can take them.” Then he instructed the kids to push them towards me. I literally grabbed one inner tube float and 4 pool noodles, brought them 10 feet into the pool house, and put them away. I, confusedly, said they were all set and went to leave. The son thanked me and handed me a folded mass of $20 bills. It was $400. I was expecting $500 from my boss for payment, but I figured $400 cash was still overpayment, so I didn’t mention it. The next day at work, my boss gave me $1,000. I told him the son had already paid me $400, which was fine. He said the son told the woman how great a job I did, so she wanted to pay me $1000 instead of $500 and the $400 was a tip from her son.
For 10 minutes of work…. She actually called my boss the next day to ask if she should reimburse me for gas, since it was 15 minutes from my house. I told him that I was all set.
1. Silk. Carpet.
I used to work for a company that modified aircraft for really rich people. I’m talking 747s, not gulfstreams.
This company had made several aircraft for this one customer, who I was told had purchased a new one solely because his spiritual advisor had told him that one of his current planes was bad luck. He still let his wife use it for her personal travel.
To me, one of the most exquisite features of these planes wasn’t the gold plated everything, or rare wood veneers, it was the silk carpet. That stuff cost over $1,000 per square foot and feels like walking on a bed of angel feathers harvested in the most inhumane way possible.
Granted, these guys don’t deck out the whole plane, just their personal areas (the aft third is usually reserved for staff and such and is more like a fancy economy class), but yeah… silk carpet.
I’m flabbergasted, though I don’t really know why.
If you’re in a position that allows you to see some stuff, drop your stories in the comments!
