Worked as one of four full time groundskeepers at a large estate. 46 acres of lawn to mow twice a week. 2 clay tennis courts, 3 pools, one for the main house and one for each of the two guest houses. 100+ acre private lake with boat house. No clue how big the whole estate was including the woods. Personal favorite was the 3 mile personal race track. But what really blew my mind was that he hosted his niece's wedding one summer, paid $350k to have this massive willow tree trucked in and planted by the lake for wedding photos. Only to pay another $50k to have it removed and the landscaping returned to its original state after the wedding because he did not like the look of it. u/Rarnah

My brother in law builds custom homes in the redneck riviera belt of Florida.One day, he called me to come over to this $15m beach house he was doing a complete remodel of. He was the original builder. He asked me to bring my truck and trailer. I show up, and he walks me through all four floors. He then says, "The owners have removed all the stuff they want to keep. She has told me to dispose of everything as I see fit. Get what you want." Furniture, appliances, outdoor furniture, rugs, lamps, artwork, you name it. I don't know the value of everything I took home with me that day, but it was the highest end stuff I've ever seen. FOUR floors of it, and I only got one trailer load because I simply couldn't fit anything else in my house. I likely had over $20k worth of furniture and appliances on that trailer. u/Blackhawk-388

I used to work at a member's only golf/country club. There were members who had been actors, athletes, race car drivers, former CEO of Google, some major money and egos going on. There was one family that had 3 teenage kids, 2 girls and a boy. The mom and the girls were very attractive and knew it. They always looked amazing and had overly entitled attitudes to match. They were "fancy." Well, the lady who washed the linens for the county club also did house cleaning for some members. This family was one of them. She said their multi-million dollar home was a disaster filth zone. They basically did no house work in between having the cleaning lady there. Dishes piled with dried food that smelled, dirty clothes thrown everywhere, piles of crap all over, sticky floors, dog poop left on the floor. But the nastiest part was the bathrooms. She said they wouldn't empty their bathroom trashes and the ladies of the house would throw their used tampons on top of overflowing trash so she had to pick up their used women's products thrown on the floor not even wrapped in paper. So these fancy bitches would walk around the club like they were so superior and look down on everyone then would go home and act like wild apes throwing their trash and period products on the ground. The thought of being so out of touch that you decide it is beneath you to even be sanitary bc you can just pay someone to do that for you is just beyond insanity. u/sooofarms

Getting a charted jet stocked with lobster and other expensive food only to show up late with McDonald's. u/Self_Mythology

I often do work for the wives of wealthy professionals. The thing that has always stood out to me is that if I tell them that something they want isn't doable, they respond with literal confusion. It isn't anger. It's confusion. They are so unaccustomed to not being given exactly what they want that it's as if they don't understand what is happening when they are told they can't have something. u/ShakyTheBear

Not the craziest thing but wild to me. I was working for a kind of well off family during a summer. I went inside to get a drink and the mom was cleaning the kitchen putting things away and such. She picks up a macbook and says to me "hey, do you want this? No one uses it " Got a brand new mac book for college. u/kingJoffi

My sister is a butler for a super wealthy family she told me a couple crazy stories :- The family once got this super expensive rare breed cat and a few months later the wife tells my sister she can feel the cat isn't quite happy in their house so she asks her to take their private jet to drop the cat off in their mansion on Lake Como, Italy so it could spend a holiday in the sun. That same woman would then sometimes berate my sister for buying soap in plastic dispensers instead of just soap bars because it's bad for our planet- They bought this insanely huge super luxurious cabin in one the most expensive ski stations in Switzerland. They realized the cabin ( more like a mansion really ) right next to theirs was for sale and then bought that one as well just so they wouldn't have close neighbors. u/Inequitom

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 which the contractor who built the apartment block wouldn’t go for 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. u/kl_dudey

The owner of my company had a customer pay off a giant debt by signing over a yacht to him. When he went to the marina to get the storage info transferred to his name and saw how much it cost to store the yacht there, he bought the marina. u/UncleGrako

Did appliance repair. One lady had a 10x12 walk in wine cooler. Floor to ceiling stocked with wine. In her living room. Another person's house was made of imported stone and had a library the size of two car garage. My favorite was an old lady who just had nice stuff. She took care of what she had. Everytime I went she gave me 40 bucks for " a nice beer with your lady" I would always refuse but she insisted and was basically the typical granny everyone would want. u/kograkthestrong

Re-did a ladies shower one time during the middle of a nasty divorce. The shower was 6'x10' with the entire ceiling covered in shower heads. "Since he was off with half the office I figured I'd get the other half all in here". Lady was a baller- $500 tip for everyone who worked on that bathroom because it was her ex's money. u/watson_exe

Had a client come into our 3d printing office. His attention was immediately caught by a large industrial 3d printer in our showroom. Pulled out a credit card and bought a $250k machine on the spot. Best part was when we installed the machine at his facility. First thing he wanted to print was a meter tall penis. Few weeks after the install we got a photo of him standing next to the meter penis. u/robertcboe

I moved the guy that created ebay. He had Aretha Franklin's grand piano (played it) and Elvis Presley's coat (didn't wear it). u/Interesting-Step-654

My friend is a mechanic. A wealthy, fat, famous and all round unlikable entrepreneur came into his work one day and took a liking to his co-worker. He asked my friends co-worker to come and work for him maintaining his car collection. It was really good pay and he got to work on some cool cars so he thought why not. His days were spent working on old, rare sports cars on his sprawling property but every now and again he'd get sent to Europe or the United States to check out cars said entrepreneur was interested buying. He'd get sent to auctions all the time and ring up said entrepreneur while it was happening so he could bid on the car on his behalf. u/insane_knight

Bartending at a fancy party in a very wealthy older couple's house where these people had art on display they had bought from museums. I was working in a room where three walls were glass and you could see this beautiful manicured garden with sculptures. When the sun started to set these big floppy eared white bunnies started to appear and frolic around the yard. I asked someone who worked in the house about the rabbits. The rich people bought them as a garden feature. Every once in a while they had to cull the rabbit population. The rabbits were decorations!! u/CindeeSlickbooty

As a house keeper. Sex dungeon, weird art, lots of casual nudity. Imagine you have infinite money in Sims and are building a house. Also, you have already traveled a bunch and been to every theme park and fancy restaurant and spa. You start really having fetish stuff at home. There is so much sex stuff that it's not even weird to me anymore. u/Responsibilityjuice

I worked on a billionaires home installing his custom pool. He ordered a custom iridescent tile. For the whole pool it cost $440KUSD for material alone and another $400K to install it. We informed him that it was a special order and couldn't be changed once ordered. He approved. We installed it. Walks out, it looks amazing (all the people working on it thought so) says he doesn't like it tear it out and replace it. All told he blew like 2.4 million dollars on his pool tile before he got done. u/Lousyfer

Bodyguarded someone filthy rich with next to no class whatsoever. He bought a very sought after rare classic car from a renowned Italian carmaker, had the roof taken off, painted it a ridiculous pink sparkle color and put it on the roof of one of his most central buildings in the middle of a large European city. The Italian carmaker offered to buy the car presumably because they were absolutely disgusted with what he’d done to the car and didn’t want the abomination to get further exposure as they felt it damaged their brand tremendously. He sold it to them. Was then banned from ever purchasing factory new models from that brand ever again globally. u/grexbear

You’re weren’t allowed to hand him or his family things that have already been opened or used. That bottle of sunscreen that was only used once. Don’t even think about it. Everything has to be new. There was a desk that had bottles and bottles of just sunscreen that they only used once and never again. u/TheMysticalPlatypus

I did a catering job years ago for John Paul Dejoria, Patron Tequila and Paul Mitchell, and his house was awesome. River side texas hill country. Beautiful place. We were packing up at the end of the night and the security guard came by and said stay away from the windows we are locking up. We said ok and about 5 minutes later these metal drop down armor plates came out of the roof it seemed and covered each window and door. Thick metal plating armor. u/mtrash