30+ Workers Share Bizarre and Fascinating Insights from Serving the Wealthy

Have you ever wondered what goes on behind the fancy curtains of the wealthy elite? Some people online opened up about their experiences while working for the rich. They revealed jaw-dropping truths about the wealthy and certain habits they had never witnessed before.

While some individuals navigate the everyday grind, working tirelessly for a living, there exists a unique segment of society untouched by financial concerns. This privileged group encompasses those with generational wealth and those who earned millions through hard work.

Because of the financial difference, these two groups lead entirely different lives. The difference is so stark that it leaves people shocked. Brace yourself for this journey into the world of the riches as we delve into the first-hand experiences shared by Redditors who worked for the wealthy.

Comments have been edited for grammar and clarity.

1. Renting Hotel Floors

u/Elysian-Visions: I briefly worked with one of the top Saudi Arabian crown princes in the 80s. He would buy out the top three floors of the best hotels like Four Seasons.

Two floors were for maids/help/security, and the top floor was for the family. Once, it was only the prince and his three wives. That was unbelievable!

2. The Huge Estate

u/Rarnah: I worked as one of four full-time groundskeepers at a large estate with 46 acres of lawn to mow twice a week.

The estate had two clay tennis courts and three pools: one for the main house and one for each guest house. There was also a 100+ acre private lake with a boat house. I had no clue how big the whole estate was, including the woods.

My personal favorite was the 3-mile private racetrack. But what really blew my mind was that the owner hosted his niece's wedding one summer and paid $350k to have this massive willow tree trucked in and planted by the lake for wedding photos.

He did this 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.

3. The Backseat Traveler

u/LanceFree: Years ago, my friend's father was trying to sell his start-up company and picked up an investor at the airport.

He was impressed by the investor's classic Rolls-Royce but noticed him looking around, playing with the air vents.

Curious, my friend's father asked, "Is this your first time in a Rolls-Royce?" The guy said no, but it was his first time in the front seat.

4. The 'Fancy' Women

u/sooofarms: I used to work at a members-only golf/country club, where some members were former actors, athletes, and race car drivers. One of them was even a former CEO of Google. Some major money and egos were going on.

One of the families who visited the club had three teenage kids: two girls and a boy. The mom and the girls were beautiful, and they knew it. They always looked great and had overly entitled attitudes to match. They were "fancy."

The lady who washed the county club's linens also cleaned some members' houses. This family was one of them. She said their multi-million-dollar home was a disaster filth zone.

They did no housework while the cleaning lady was there. There were dishes piled with dried food that smelled, dirty clothes thrown everywhere, sticky floors, and dog feces left on the floor.

The nastiest part of the house was the bathrooms.

She said they didn't empty their bathroom trashcans, and the ladies of the house would throw their used sanitary products on top of overflowing trash, so she had to pick them up, and they were not even wrapped in paper.

These women would walk around the club like they were superior, looking down on everyone, while they didn't care about cleanliness at home.

5. 'Daddy's Home!'

u/DiscombobulatedBabu: I used to work for a billionaire Russian family as a tutor for their daughter.

One day, we were studying in her room when she suddenly yelled, "Daddy's home!" and ran to the window. She had heard a helicopter and knew it was about to land on the lawn.

6. The Brand-New MacBook

u/kingJoffi: I spent one summer working for a well-off family. One day, I went inside to get a drink and saw the kids' mother cleaning the kitchen and putting things away.

At that point, she picked up a MacBook and said, "Hey, do you want this? No one uses it." That's how I got a brand-new MacBook for college.

7. The Huge House

u/atot806: My father's client bought a whole block of houses to build theirs. The total area of their home was so vast that they installed a moving walkway like the ones at airports.

8. The Rich Family

u/Inequitom: My sister is a butler for a wealthy family, and she told me some hilarious stories. The family once got this super expensive rare breed cat, and a few months later, the wife told my sister she could feel the cat wasn't entirely happy in their house.

So, she asked her to take their private jet to drop the cat off in their mansion on Lake Como, Italy, so that it could spend a holiday in the sun.

That same woman sometimes scolded my sister for buying soap in plastic dispensers instead of just soap bars because it was not good for the planet.

Besides that, they bought this extremely huge, super-luxurious cabin in one of Switzerland's most expensive ski stations. When they realized the cabin next to theirs was for sale, they bought it so they wouldn't have close neighbors.

9. Artwork in the Bathroom

u/useroftheinternet999: I am an art student working as a gardener. We work in one of the wealthiest areas in my country.

After working for some time, I noticed my clients usually want to show me their collection of artwork hanging on their walls once they learn I am an art student.

Once, I was standing in their bathroom with my dirty gardening clothes when I realized a Picasso artwork was hanging right above the toilet.

10. A Trip to Hawaii

u/DrGrizzley: I once worked as a male nanny for a wealthy couple who wanted someone to look after their kids. The wife didn't want a female nanny, and I was in college, so it helped pay my bills.

One day, they asked, "Do you want to go to Hawaii?" It turns out the company where the husband worked as the COO was doing an executive retreat in Hawaii.

Instead of finding daycare in Hawaii for their kids, they thought it'd be easier to pay for me to fly to Hawaii, care for the kids during the day, and then have my evenings or their "family time" free.

So, I went to Hawaii on their dime, where I got a separate hotel room, payment for my services, and a significant stipend for my food/entertainment expenses.

I got almost every evening off, so I spent it my way. During the day, I used to bring their kids to the beach, go hiking, and do touristy things running around.

On top of that, they gave me $5,000 in "spending money" in case any of the kids wanted anything. I had to show receipts, but when I tried to turn them in, the wife just said, "Oh, don't worry about it, it's only a couple of thousand dollars," and never verified how I had spent it.

I couldn't tell if she trusted me implicitly by that point or if she genuinely thought the amount was so small it didn't matter.

The family was lovely but very wealthy, which explains why they spent so much money to solve their problems. Moreover, I was invited to the oldest daughter's high school graduation because she considered me a friend.

11. The Unexpected Payment

u/TheApprenticeLife: I used to do pool and spa maintenance in my twenties. During that time, I visited one mountainside property.

It was a 10-bedroom/14-bath mansion with a saltwater pool, tennis courts, guest mansion, and a 4-bedroom, 5-bath servants' house. The property had so much more stuff, but that isn't the crazy thing.

I worked on this property for two years, year-round, five days a week, and I never saw a single person there.

The middle-aged, single woman who owned it lived in a city about four hours away and 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 two years, I got a call from my boss on my day off. He asked if I could go to the house to remove some pool floats.

He apologized because it was my day off but said the owner would pay me $500 to put them away. I wondered why there were even pool floats out anyway because nobody was ever there.

However, I showed up at the house once I realized I would get $500 for working ten minutes. Over there, 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 since you're here, 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 grabbed one inner tube float and four pool noodles, brought them ten feet into the pool house, and put them away. Confused, I 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. I got paid this much for 10 minutes of work.

The woman also called my boss the next day to ask if she should reimburse me for gas since their place was 15 minutes from my house. I told him that I was all set.

12. They Banned the Wealthy Man

u/grexbear: I 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 presumably offered to buy the car because they were disgusted with what he had done to the vehicle.

They wanted to avoid the abomination getting further exposure as they felt it would damage their brand tremendously. The man sold it to them. Then, he was banned from purchasing factory-new models from that brand ever again globally.

13. The Wealthy but Generous Guy

u/Priest_Soranis: I had a classmate in university, and one of his parents had a lot of generational wealth, but they were good people.

One day, this girl in our class, who belonged to an underprivileged family, dropped her MacBook that she had bought after working 60 hours a week for three months during summer.

When my classmate learned about it, he just gave her his MacBook, saying he would get a new one after school and his parents wouldn't care. He gave it out of pure generosity.

He was a stellar guy 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. When they were talking about renting one, he told them he knew a place to rent nice suits.

We all went there on his recommendation and rented a suit for 100 euros or so, everything included, and when we went to return it, we found out this guy had already paid for it.

14. The Custom Pool

u/Lousyfer: I worked on a billionaire's home installing his custom pool. He ordered a custom iridescent tile.

The whole pool cost $440,000 for the materials and $400,000 for the installation. After calculating the cost, we informed him that we couldn't change his order once it was finalized because it was special. He approved.

When we installed it, he walked out but said he didn't like it. Meanwhile, all the people working on it thought it looked amazing. He asked us to replace it. Eventually, he blew about $2.4 million on his pool tile before he got done.

15. He Became Friends with the Right Guy

u/JAG23: I went to a New England prep school for high school on a full-ride sports scholarship, where there was a decent number of foreign national students, mainly from Asia. These kids belonged to EXTREMELY wealthy families.

One of those students' parents had bought him a new BMW 5 series—fully loaded. They bought it when he got his license during 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.

The kid got an $80k car at 17 years old, just for being good friends with the right guy! I'll never forget that.

16. Too Many Piles of Clothes

u/HarleyQueen90: I briefly cleaned houses one summer, and these houses were INSANE. Some had elevators, while some had bathroom STALLS in their main bathroom.

One had a literal cave manufactured in the bathroom, with showerheads throughout it—you could walk from one end and exit from the other side of the bathroom (a massive hot tub split it).

The sense of disuse struck me as odd in almost every house. They had grand pianos covered in dust, expensive lamps and throw pillows with the tags still on them, and sprawling playrooms with every toy any child could want, devoid of playing children.

The weirdest house I cleaned wasn't huge, and it wasn't gorgeous. It looked like a typical house on the outside, but the inside had piles of clothes everywhere.

One day, I pulled aside my fellow cleaner and asked, with all sincerity, how to clean this house. She told me to "go around the piles as best you can."

They had a mountain of clothes in the living room, and it looked like something out of a cartoon. Every couch had stacks of brand-new clothes with tags on them. They were the only folded clothes anywhere.

In the bedroom, it was the same. It had small piles in every corner, and we couldn't fully open or close the doors around those piles. Moreover, the kids' bathroom didn't even have a shower curtain.

After "cleaning" that house as best we could, our best guess was that they don't wash clothes. I think they just buy more and discard the dirty clothes into the piles. I often think about that house and wonder if they ever changed their habits.

17. Buying Airplanes

u/Prune_the_hedges: I worked for a company that modified aircraft for rich people. I'm talking about 747s, not gulfstreams.

This company had made several aircraft for this one customer, who had purchased a new one solely because his spiritual advisor had told him that one of his current planes brought him bad luck. He still let his wife use it for her personal travel.

One of the most exquisite features of these planes wasn't the gold plating or the rare wood veneers but the silk carpet. That stuff was for over $1,000 per square foot and felt like walking on a bed of angel feathers.

18. Everything Should Be New

u/TheMysticalPlatypus: I worked with a wealthy man, and we weren't allowed to hand him or his family things that had already been opened or used. Not even the bottle of sunscreen that was used only once. Don't even think about it.

Everything had to be new. There was a desk filled with bottles of sunscreen that they had only used once and never again. The interesting thing was this guy owned an eco-resort.

19. The Wealthiest Man in Town

u/handsthefram: I used to work for a real estate development company where the boss was the wealthiest guy in town. His wife had the second biggest office, and she did nothing there.

Her office was entirely bright pink and had a private bathroom. Her parking space was twice as wide as the regular parking spaces because she couldn't park straight. Besides that, she used employees to run her errands.

It was very annoying, but we were told we had to do everything she said. I remember she once asked me to print out a website for her.

20. Thirty Birthday Cakes

u/circleinsidecircle: I used to 'work' for an Arab billionaire's son. He lived on his father's money and was a terrible human being.

Once, I saw him spend $16,000 on a wallet. It was a fancy one with little gold spikes on it. He also had shoes with gold on them.

I remember one year, for his birthday, he received over 30 big, fancy cakes and 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 instructions. Two weeks later, we were told to throw them away.

21. That's Too Heavy!

u/C_Beeftank: My mother's cousin worked for a billionaire in China, building a hospital as his general contractor.

One day, he returned home and found out he had a package waiting for him that weighed over 700lbs. It turned out the billionaire bought him a statue he remarked on. It was a recreation of a terra cotta warrior statue.

22. Buying Sixteen Cars at Once

u/luther_williams: When rich people want to buy a Jaguar in the UK, they get assigned an incredibly knowledgeable salesperson. They meet in a fancy office, and special arrangements can be made.

This was my friend Chris' job. He had access to things that a regular Jaguar salesperson wouldn't have. For example, he could call the factory manager for special access requests.

Once, a wealthy and influential man from Saudi Arabia wanted to buy this new Jaguar, so they met up and spent an entire day together. The final price was something like £125,000 for the vehicle.

Then came the decision for color. At the time, the factory had 16 different color choices for this model. The man asked if he could sleep on it as it was getting late and almost time for dinner/prayer. Chris agreed and set a time to meet the next morning.

The following day, the man said, "I figured out an acceptable solution to my color dilemma," to which Chris asked, "And what would that be?" the man replied, "I'll order one of each color."

They quoted the delivery time, and he agreed. Then, he asked for his options and was presented with ocean travel options, to which he asked, "What about air cargo?"

Chris thought he might do one or two cars by air cargo and the rest by boat, but the man said, "No, I want all 16 vehicles loaded on a plane and flown to Saudi Arabia."

So that's the story of how 16 of the same Jaguars with different colors were flown to Saudi Arabia, and the total cost was around £2.5 million.

23. The Jacuzzi Problem

u/kl_dudey: I had a client who had purchased a newly built penthouse apartment and wanted a jacuzzi on the balcony.

Doing so involved installing a structural column in the middle of the balcony, which would impact the apartment below and lower its value in the market. The contractor wasn't ready to do that.

Upon learning about the problem, the client bought the apartment below, approved the column, had the jacuzzi installed, and then privately sold the apartment below. Voila! Problem solved.

24. The Cat Bathroom

u/Kpop_TWD: I used to work as a pet sitter. I remember a rich person asking me to look after their cat. There were a lot of TVs, one in almost every room.

The weirdest was the bathroom. Sorry, the cat bathroom. There was a TV playing cat cartoons, an overly fancy litter box, and paintings of cats.

25. Too Many Showerheads

u/watson_exe: I redid a lady's shower once during a nasty divorce. The shower area was six feet long and ten feet wide, with the entire ceiling covered in shower heads.

She explained, "Since he was off with half of the office, I figured I'd get the other half all in here." The lady was wealthy and lived a lavish lifestyle. She gave $500 tips to everyone who worked on that bathroom's plumbing because it was her ex's money.

26. Money Can Solve Your Problem

u/waterloograd: My family friends were having marital issues, and their marriage counselor figured out that many of their problems were overcooking meals.

The counselor reminded them that they were rich and could just cater all their meals, and it would be cheaper than getting a divorce. They listened to the counselor and are now happily married again.

27. Leftover Bagels

u/PapaChoff: My wife is PA for a wealthy and incredibly powerful man. The guy is self-made and humble. He is uncomfortable in small social gatherings but a lion in a business setting. What I found most interesting is the guy would think nothing of spending five figures on jewelry or other luxury items, but leftover food bothered him.

On Fridays, that guy is in the office kitchen at the end of the day, taking home all the leftover bagels from the morning.

28. The New Millionaires

u/Feedmelotsofcake: I worked as a nanny for a millionaire family. It was new money, and the couple had grown up in blue-collar families. They were very down-to-earth, giving, and kind.

However, their children had no rules, structure, or expectations inside the house. Their previous nanny gave them whatever they wanted. That changed when I stepped in.

I firmly believe kids need to know how to clean a bathroom, wash dishes, sweep the floor, and clean their rooms. It took about a year to get to that point, but I can rest easy knowing they're both in college and know how to clean a toilet.

29. The Car Collection

u/Spade18: I do high-end florals in a wealthy part of the town. Over here, I have seen tons of obscene shows of wealth. The amount of money some people spend on flowers alone is unfathomable.

Once, we were decorating a client's house for Christmas. As I hung a garland around their six-car garage (a separate garage from the one connected to the house), I noticed each spot had a car elevator and was three cars deep.

So, there were 18 of the same $350k+ car. Why would anyone need 18 of the same car models? And that too so expensive?

30. The Unexpected Reward

u/SuvenPan: I once told my super-wealthy boss that we had completed the work well before time. He removed his expensive watch, gave it to me, and said, "Good job!"

31. What Do You Mean I Can't Have It?

u/ShakyTheBear: I often do work for the wives of wealthy professionals. What has always stood out is that if I tell them 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 what they want that it's as if they don't understand what is happening when they are told they can't have it.

32. He Was Aware of Every Transaction

u/[deleted]: We do IT support for a company owned by a guy who casually bought a $16 million yacht. He walks to the office in standard office attire with his backpack on and beelines to his office, where a personal assistant shields him.

He'll come out frequently and just chat with folks at their desks. I even saw the guy walk down a hallway, bouncing a tennis ball off the wall as he walked along. You'd never guess he was the owner. I never did until it was pointed out to me.

But he isn't casual with people he does business with. They're out if they try to take advantage of him or don't give him what he thinks he should be getting based on what he's paying.

That's how we got the account. The old IT got the boot because they weren't giving them the right value.

Although he has a CFO and an entire accounting department, he's still very involved in what gets bought. If we send a quote to our contact (CFO), the response is always, "Well, let me get this over to [the rich guy]." He knows what gets spent.

33. The Two Types of Rich People

u/notbritishtay: I worked as a nanny for eight years in a very affluent neighborhood, and I learned that there are different types of "rich" people, the main two being "new money" vs. "old money." "New money" is the absolute worst.

The wealthiest family I worked for was an "old money" family. They RARELY talked about money, looked like average people, drove decent but not crazy expensive cars, and treated everyone equally.

There was subtle snobbery, but it was never in your face. They taught me not to get attached to material possessions and to never live beyond my means.

One thing that left me amazed was how much they respected me and supported my decision to pursue a law degree.

On the other hand, the "new money" family I worked for always talked about money. They always judged others based on cars, houses, and where their kids went to private school. Besides that, they never introduced me by my name. I was always just "the nanny."

They also brushed off my law school plans as a pipe dream. I could go on, but I'm sure I conveyed my point. They taught me how tacky it looks to talk about money and be obsessed with their image and material things.

34. The Rich Wives

u/[deleted]: I currently work for rich people, and I can say that New Yorkers with money are terrible. They are loud and don't let you get a word in. They're not bad people; they're just very hard to deal with and communicate with.

Those who bring all the money in don't annoy me when it comes to wealthy people. You know who annoys me? Their wives.

You show me the wife of a multi-millionaire, and I will show you an entitled, conniving woman. The husband will be the most polite, endearing person you have ever met. But his wife, who didn't earn a cent, would be terrible.

These women aren't mean to other men but are like this to women. I have to be stern with these women because they walk around with an attitude.

They have this perpetual belief that they have been disrespected or wronged somehow. Everything would be fine, but they'll find a reason for everything to be a problem.

35. They Did Not Care

u/VelocityMax: My bosses (husband and wife) are not billionaires, but they are very small-town rich. The man comes from the biggest farm family in the area, and he and his wife started up an oil trucking company over ten years ago, seeded with his father's money.

They own about ten semi-trucks and about 50 trailers, with owner-operators pulling most of them. They both mostly only care about money and don't care at all about their drivers.

For example, one of the drivers suddenly started feeling very unwell and had to go to the hospital. At that point, the couple only cared about the oil load and how it would get delivered. They showed zero compassion for that driver.

Eventually, the driver resigned over it, so they decided not to pay him. He had to go through the labor board to get paid.

Before this happened, they paid all company drivers as contractors instead of employees. We all had to maintain our own companies to get paid, so they didn't have to pay us overtime, and the risk of spill clean-up costs was shifted from them to the employees.

36. Different Kinds of Rich People

u/Rustywoodpecker: I've worked for several wealthy people and still work for two whenever they need me. Some couples are like everyone else, while some are messy and don't care because they pay you to clean up after them.

Some are very clean and need help with other things. Some hoard, some give you stuff all the time. Some couples are real penny-pinchers, while others spend like crazy.

The people I've worked for have worked hard their whole lives to get rich. They are very nice, interesting individuals who pay well for a well-done job. Sadly, I see their kids and grandkids are not like them.

As we wind up this journey through the lifestyle of the rich, we learn that there are certain things that only the wealthy can experience. People living ordinary lives may never experience what goes on behind the scenes in a rich person's house.

Have you ever experienced something similar about rich people that shocked you? We would love to know about it. Share your story in the comments section.