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If you weren’t 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 in that exclusive world.
Most of us never will, but these 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.
1. Just for a few days.
Was a boyfriend of a girl from an obscenely rich family.
The sister used to have the nanny (who was sleeping with the husband, but that’s another story) fly to Paris in their G550 to buy the newest Hermès bag so she could show it off a few days before it went on sale in the US.
2. Like a movie.
Was invited to a Christmas Dinner while i lived in Seoul by an extremely wealthy Korean family. Very nice family but I think in hindsight they wanted to show their friends that they had foreign friends like me. Wife had everything catered and the home professionally decorated – it felt like we were in a department store. Multiple Christmas trees, a working train set, staff handing out appetizers on plates etc. It looked like she studied Christmas movies from the USA and copied everything.
Dinner is served on a comically long table with 2 huge oven roasted Turkeys and all of the trimmings – they looked perfect. I was later told that Koreans don’t like turkey & were just for decoration – they would be thrown out later. We ate Korean food.
The family said I could take a turkey home and that the caterer would drop it off with anything else I wanted.
3. Bummer.
Keith Urban tipped me $7 on a $4 shake and left the keys to his Bentley at the store but he came back and got them.
Keith also bought a couple of guitar pedals for a local kid here in one of the guitar shops. Kid had a budget and was struggling to pick one, so Keith just bought them both for the kid by quietly paying the shop owner on the way out the door, before the kid even knew what he’d done.
By all reports he’s a genuine decent, down to earth bloke.
4. What is money?
Have been working for the super rich for sometime.
Craziest thing I’ve seen – brand new 90 metre multimillion pound (GBP) yacht was built in Netherlands. Maiden voyage to Antibes in France. Owner came onboard and left after a few hours. Next week we get sent to Genoa Italy, where all the bathrooms onboard were ripped out and upgraded.
That doesn’t sound like a big deal but I’m talking about brand new marble sinks, showers, floors and lobbies all crowbarred out chucked in skips. Tonnes of brand new polished marble binned.
New marble colours and patterns arrived in the weeks following.
There’s feed me money, there’s f**k you money and there’s “it’s not even a thought money.”
5. The dog goes first.
I worked for UPS for a hot minute as a driver helper and got to see some interesting things. The one driver had the rich of the rich route- the mansions worth tens of millions around the Ann Arbor, MI area. The Ford mansion, Lloyd Carr, the one recent guy for Michigan football that I’m forgetting that also worked for Little ceasers. Edit: the name I was forgetting was Dave Brandon
Anyway I got to see Dave Brandon’s mansion- it was gated, deep in the woods, and absolutely HUGE. The driver (a 33 year UPS veteran) told me these guys with these huge mansions like this, they don’t live there by themselves. Sometimes don’t live there at all. They move their entire extended families in there. Parents, sisters, brothers, aunts, uncles, cousins, etc. And they all live off the rich guys dime, ordering whatever they want whenever they feel like it. I think we delivered 30 or 40 packages there that one day.
2nd story from the same day and with the same driver, we delivered to a smaller (but still huge) house with an extremely long and wooded driveway. The driver was cursing about how much he hated these people because they always parked this huge-ass boat in the only possible turn around point in the driveway. So he goes in backwards- and FLOORS IT. Maybe 40 mph BACKWARDS, about 250 yards of bends, straights, and he drove it absolutely perfectly, never driving off or missing the driveway. We get to the house and he needed a signature. He handed me the package and said he’ll get the signature and just hand them the package and we’ll go. Well, we get to the door, and this maybe late 40s or early 50s man, kind of a rick moranis/George costanza type of build. Short, extremely thick glasses, balding, but very skinny build. He’s standing in the front door with a lab looking dog on a leash. The driver says, good evening we just need a signature and we’ll be on our way.
The guy says… No. I can’t I have to take my dog out first. This guy was fully prepared to make us stand there and wait for his dog to do whatever business before just signing his name and letting us drop the package by his door. The Driver said, no we just need your signature, and we’ll be on our way and you can walk your dog. The guy said fine and took the 2 seconds it takes to sign your name and we dropped off his package and left.
That left an impression on me. That guy valued our time so little it was worth less than his dog’s poop. Like he was in his own world, and we weren’t delivering 300 stops just before christmas
6. Royalty.
Used to be a housekeeper for some of the wealthier people in my city.
The best thing I have ever seen is the wife of a rich guy had custom suits of armor made for her cats.
She had them displayed along with tiny suits of armour for mice.”
*Edited because ? This dude just has some sort of gaming company. I just remember his wife telling me he made some pretty neat games. They are far richer than I’ll ever be so to me that’s rich enough. Also thank you for the awards you wonderful people.
7. Oopsie.
I’m a driving instructor and one group rented the track to drive their supercars for the day. At the end of the day they all partnered up and got into the cars to leave.
After they were gone we realized that they had forgotten their Lamborghini Aventador at the track.
8. Some of them aren’t so bad.
My grandfather died with a 20 million dollar portfolio. He lived in a 1 bedroom condo that was build in the 50s, drove a rusted out honda, and his entire wardrobe came from Walmart and was 10 years old. At his will reading, a bunch of distant relatives showed up hoping to get a piece.
In his will, he made fun of all of them, then spent 10 pages detailing how and where he wanted all of his money donated to specific charities and foundations.
Some of it was even really surprising, as nobody besides him was aware that he casually owned 160 acres of land in Vermont that was just forest. The land was donated to a land trust, and turned into hiking trails.
9. A lack of patience.
Some extremely wealthy people I have been around have a more acute sense of their own time and mortality, leading to impatience. Like they understand how awesome their lives are and therefore how short they feel.
I knew a guy whose vintage yacht broke down before summer so he bought another one strictly for that upcoming Summer. His reasoning was he likely had 20 full health summers left in his life and didn’t want to spend one of them without a boat considering he had the means to.
Honestly can’t argue with that logic.
10. For two weeks?!
I used to ‘work’ for an Arab billionaire’s son, a Daddy’s money guy, terrible garbage human being.
Once saw him spend $16 000 on a wallet, was a fancy one with little gold spikes on it and stuff. He had shoes with gold on them.
I remember one year for his birthday he received like 30+ cakes, big fancy cakes and he told us to leave them on the floor in the hallway outside his room.
We walked by those cakes every day for two weeks waiting for instruction, after the two weeks we were told to throw them away.
11. The gulf is substantial.
My college roommate was from a pretty wealthy family in Thailand, but his friend was from “the 8th richest family in Thailand.”
One day I was sitting on the couch exhausted after working a 14 hour shift when they came in giggling about how the guy just bought a $9000 jacket.
I’ll never forget that feeling.
That was pretty much exactly how much money I was killing myself to make to pay my tuition that semester.
12. Her love language.
I became personal friends with my boss and his wife; super nice people.
The wife turned out to be an heiress and would buy me whatever I mentioned, like in passing during a conversation.
I learned gifts were how she was raised to show love.
I’ve trained myself to only talk about things I already own, unless I find something useful she might like and suggest it for her.
13. Sure, sure whatever you want.
When rich people want to buy a Jaguar in the UK they get assigned a special sales person who is incredibly knowledgeable, they meet in a special fancy office, and special arrangements can be made. This was my friend Chris job, he had access to things that a normal Jaguar sales person wouldn’t have. Like he could ring up the manager of the factory for special requests level of access.
Well a Saudi Price wanted to buy this new Jaguar that had been released, so they met up and spent a full day specing the Jaguar out. I believe the final price was something like 125k for the vehicle.
Then came the decision for color, at the time the factory had 16 different color choices for this model. The Prince asked if he could sleep on it as it was getting late and almost time for dinner/prayer my friend Chris says of course and they set a time to meet the new morning.
The next morning the Saudi price is like “I figured out an acceptable solution to my color dilemma” to which Chris goes “And what would that be?” the Saudi Prince goes “i’ll order one of each color”
And my friend Chris is like O well of course. They quote delivery time, Saudi prince was fine and asked for his options and was presented with ocean travel options to which the Prince said “what about air cargo?” Chris thinking maybe they’d do 1 or 2 by air cargo and the rest by boat, the Prince was like “No I want all 16 vehicles loaded on a plane, and flown to Saudi Arabia”
So thats the story on how 16 of the same Jaguar with different colors ended up being flown to Saudi Arabia all in the total cost was around 2.5 million.
Please note the prices should be £ not $
14. They don’t do inconveniences.
I did IT work for a tiny little private company like the owner, his brother, and me. guy called because his new pc wouldn’t turn on and it’s like 3pm he was 100% willing to pay for me to drive 5 hours one way to get it working today because he wanted to play games today.
Ok so 5 hour road trip one way and the address is this huge mansion 100% thought I was in the wrong place. Use the intercom at the gate and nope this is the place, guy and his wife are really cool and the dude had built his own gaming rig… it was absolutely over the top, I had never even laid eyes on hardware that expensive before… he never turned the power switch on his PSU on… he payed the base rate of $1400 for me to come out there to flip a switch I also installed his graphic drivers but that was technically free, and then gave me $5000 cash as a tip all because he was excited to play league of legends on his new pc.11.
15. 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.
17. 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
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. 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.
27. 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.
28. 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.
29. 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.
30. 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.
31. 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!
