“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.”

“I briefly worked with one of the top Saudi Arabian crown princes in the 80’s. He would buy out the top three floors of the best hotels (Four Seasons etc); two floors were for maids/help/security, top floor was for the Royal family… once it was only the prince and his three wives. Crazy stuff.

“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.”

“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.” - eggtasticness

“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.”

“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.”

“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.”

“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.”

“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.”

“Worked at a resruraunt 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."

“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.”

“A friend did some work on Sylvester Stallone's home. Apparently there's a ton of statues and art of himself, some of which are naked and very well endowed”

“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 them for his yacht.”

“Russian guy I sometimes work for, bought a nice house in a pretty nice area of the French Riviera (Mougins). He didn't even visit it before buying, and just judged he liked it on pictures. He paid 11 million Euros for it. But when he arrived, he though the view wasn't perfect because of another house that was in the way. To me honestly it was barely there and didn't even mask the sea. So he sent his lawyer there to make an offer to the owners (4 million Euros). But they declined... so he doubled the offer, and they declined again... So he doubled again, and this time they accepted to sell. He had that house destroyed the very day he got the keys, and had an underground parking lot built instead, for the cars he "won't be using much here". So basically the guy paid for that distant house more than the one he's planning to spend his summers in, just to have it disappear because it kinda annoyed him. And when he told me the story, he was laughing the whole time.” - captain_obvious_here

“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.” - viktor72

“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.”

“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.” - Prune_the_hedges

“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.”

“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.” - rayrayrayray

“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- you money and there's "it's not even a thought money."