The Shocking Lives Of The Super Rich

August 24, 2023 | Nia Williams

The Shocking Lives Of The Super Rich

Ever wonder what it’s like to work for the super-elite? These Redditors share their eye-opening best and worst experiences of working for the top one percent of society. From donating a $10,000 guitar to buying live rabbits to be used as lawn decorations, here are some of the most fascinating and absurd stories of how the rich live and what they do with their money.

1. Pricey Change Of Heart

I worked as one of four full-time groundskeepers at a large estate. There were 46 acres of lawn to mow twice a week. They owned two clay tennis courts and three pools (one for the main house and one for each of the two guest houses), a 100+ acre private lake with a boat house.

I’ve no clue how big the whole estate was, including the woods. My personal favorite was the three-mile personal racetrack. But that's not what really blew my mind—it was that the owner hosted his niece's wedding one summer at the estate. 

He paid $350k to have this massive willow tree trucked in and planted by the lake for wedding photos. In the end, he ended up paying another $50k just to have it removed and the landscaping returned to its original state after the wedding. 

Apparently, he did not like the look of it.

Happy couple are standing under the willow tree.Marina Abrosimova ,Pexels

2. Filthy Rich And Totally Disgusting

I used to work at a member-only golf and country club. Some members had been actors, athletes, race car drivers, former CEOs of Google, etc. We’re talking about a lot of money and egos going on.

There was one family who had three teenage kids: two 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 that their multi-million-dollar home was a disaster filth zone. 

They did no housework in between having the cleaning lady there. They had dishes dried with food on them, piled high that smelled, dirty clothes thrown everywhere, piles of garbage all over, sticky floors, dog poop left on the floor—it was disgusting!

The nastiest part of the house was the bathrooms. She said they wouldn't empty their bathroom trash. The ladies of the house would throw their used feminine products on top of overflowing trash, so she had to pick up their used women's products thrown on the floor. 

They weren’t even wrapped in paper.

So, this fancy entitled women would walk around the club like they were superior to everyone else. They’d look down on people then would go home and act like wild apes—throwing their trash and feminine products on the floor.

The thought of being so out of touch that you believe it is beneath you to even be sanitary just because you can pay someone to pick up your trash, is beyond insane.

cottonbro studio, Pexels

3. Don’t Mention It

The CEO of the company I worked for was the founder's son. This company has over 10,000 employees.

Now the guy wasn’t unintelligent, for the most part. His dad made him start with the most basic jobs in the company and work his way through the different departments. 

The managerial staff were told not to treat him any differently than a new hire. So, when he eventually became the CEO, he wasn’t a bad guy to work for.

One night, I was working overtime on the late shift, and we got this call:

"Hey! You guys—Got 'Lectrician?" The guy was clearly intoxicated. We had no idea who it was or why he was calling the maintenance/engineering group. We asked who he was, and he informed us—light heartedly that he was the boss.

He wanted someone to come to his house and figure out why the internet wasn't working. The house was an hour drive away.

I volunteered. When I arrived, I saw that the entry gate was smashed, a section of the white horse fencing was gone, and a Jaguar was stuck in the field.

Standing in the house was a dude who was completely plastered. He had a huge cut on his hairline. When I asked, "Are you ok, (boss)?"

"I'm fine! Why?" he asked. Blood was literally caked on his face.

I accompanied him to the bathroom and helped him clean himself up, wash off the gash and put some bandaging on it. Then I corrected the internet by unplugging and plugging the unit.

As I was walking out, he asked me to take a swig with him. I was worried about my job and said that it might be a bad idea. He agreed but handed me the bottle. He said, “Take it home and do it later. Keep it".

When I got back to work, I looked up the brand. I never heard of it. Apparently, it was a $1500 bottle of scotch.

The next day, I arrived at work early. About eleven in the morning, the CEO came in, walked up to me, and said, "Uh—we're not going to be talking about last night?"

I told him that it was all good.

A while later, I got an envelope which contained a check for $5000 for 'Emergency Tech Support'.

Two man in suits are talking and shaking hands in office.Pavel Danilyuk, Pexels

4. Life’s A Vacation

My dad was a mechanic for private jet owners. At the time, he would fly exclusively with his employer and would supervise any of the crews working on their planes. 

He has seen some ridiculous things, but he said that the ultra-rich people are generally nice because they have so much money that they don't need to be mean. He said that they usually treat their staff and crew like humans. Here was the bigger revelation—the guests they would bring were the terrible ones.

He said the richest of the rich do not pack. Most would just travel somewhere that they own and already have what they need, or they will have their private assistants procure what they need ahead of time.

He worked for a person who was so wealthy that he had over 30 residences. This man continuously traveled, and he said that ever since he was a young boy, he has never stayed in one location for very long.

My dad spoke highly of him and said he was his best employer because he treated everyone with respect. I guess you can do that when your life is like a vacation.

RDNE Stock project, Pexels

5. Mothers Know Best

When I was in college, I helped some rich people move out. They decided that they didn’t want to take the love seat and offered it to me.

I brought it to my parents’ house to see if they wanted it, seeing that I was living in a dorm at the time. My mom instantly recognized that it was a real suede, handmade, love seat worth roughly $4,000. She told me under no circumstances could I have it while I was in college and that I would thank her later.

A few years later when I was moving abroad, I sold the coach on consignment for about $3,000. My mom was right.

RDNE Stock project

6. What A Truck Load

My brother-in-law builds custom homes in the redneck riviera belt of Florida.

One day, he called me to come over to this $15 million beach house he was completely remodeling. He was the original builder. He asked me to bring my truck and trailer.

When I arrived, he walked me through all four floors of the home and said, "The owners have taken all the stuff they want to keep. I was told to dispose of everything as I see fit. So, take what you want".

The left 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.

I only got one trailer load because I simply couldn't fit anything else in my house. I likely had over $20,000 worth of furniture and appliances on that trailer.

Two men are carrying boxes inside of the house.RDNE Stock project

7. It Just Doesn’t Fit

I worked as a greeter for a high-end limo service.

A family came in with their triplets and an au pair—so six people in total. They should have ordered a minibus or two vehicles for six people. Plus, they had a lot of luggage, three car seats and a giant Italian triple stroller.

Money was not an issue for them. They had a large suite at the Peninsula.

It was my fault. The Ford SUV they requested wasn't big enough. They went into town while I waited for a second vehicle to come take all their stuff that didn't fit. No tip of course.

People are putting their luggage in back of a car.Zeynep G. Icoz, Shutterstock

8. Stunning Admission

I used to work in a private school. A few dozen of the students were children of the local super-rich from Bay Street.

One mother started coming into the school every day to visit the uniform shop and to buy new uniform items for her child. This went on for a week straight before the shop attendant finally asked if everything was okay with her child’s clothes, etc.

The mom responded with, "Oh, we're fine. It's just that our nanny is on vacation for two weeks, and I have no idea how to use the laundry machines at home".

I was stunned into silence when the shop attendant passed that one along to me.

Young woman is standing and looking at clothes in the store.cottonbro studio, Pexels

9. Comply They Did

Years ago, I used to do carpentry. One of my clients was a brain surgeon who happened to be married to a lawyer. They had a massive house on a large property. 

Their son was also some type of neuroscientist and with his parents' permission, had yet another massive house built on the same property. The problem was that the city ordinances prohibited two separate, livable dwellings on the same property.

Mind you these houses were about a quarter mile away from each other. So, to comply with the ordinances, THEY BUILT A FREAKING WALL BETWEEN THE HOUSES.

Now this wasn't just some dinky picket fence-type of wall. It was a massive medieval-style wall that had round towers with merlons and crenels, a gym midway through AND a massive $750k+ all-glass sunroom. It was wide enough to have room for a walking path and a road for golf carts—all inside the wall.

Man with the plan of construction and helmet.Iurii Davydov, Shutterstock

10. Put A Lei Around That

I was a manny (male nanny) for a rich couple who looked after their kids. The wife didn't want a female nanny so being in college, this helped pay my bills.

One day, they asked if I wanted to go to Hawaii. It turns out the company the husband was the COO of was having an executive retreat there.

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

So, I went to Hawaii on their dime. I had my own hotel room, they paid me for my time and gave me a large stipend for my own food and entertainment. I ended up with pretty much every evening off, which was marvelous.

During the day, I brought their kids to the beach, we went hiking, and did some touristy stuff. On top of that, they gave me $5000 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 grand". So, I never verified how I'd spent some of that money. I couldn't tell if she just trusted me implicitly by that point or if she truly thought the amount was so small, it didn't matter.

They were a nice family, just very well off. They used money as the answer to any problem they had as the easiest answer to everything. I got invited to the oldest daughter's high school graduation because she considered me a friend.

Father is standing on the beach with two kids.NadyaEugene, Shutterstock

11. Banned For Life

I was the bodyguard for someone who was filthy rich but had next to no class whatsoever. After buying a very sought after, rare classic car from a renowned Italian carmaker, he proceeded to have the roof taken off. 

He then 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. I presume it was because they were absolutely disgusted with what he’d done to the car and didn’t want the abomination to go any further. They probably felt continued exposure would damage their brand even more.

He sold it to them and was then banned from ever purchasing any factory new models, globally, from that brand ever again.

Black woman in a car salon is taking the car keys from man.prostooleh, Freepik

12. What A Bunny Sight

I was bartending at a fancy party. The owners were a couple of wealthy older folks who had art on display they had bought from museums. The room I worked in had three walls made of glass. You could see out into their beautiful, manicured garden which contained all sorts of 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. Apparently, the owners bought the bunnies as a garden feature.The rabbits were decorations!! 

But that's not even the worst part—occasionally, they had to cull the rabbit population. 

Cute rabbit on the green grass with a blurred background.wirestock, Freepik

13. I’ll Take Everything

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 information transferred to his name and saw how much it cost to store the yacht there, he bought the marina.

ot.sun, Shutterstock

14. Aye, Aye, Captain

After graduating from university in 2012, I moved to southern France to work on mega yachts for the super wealthy and famous. After my visa in Europe expired, I came back to the States and worked on two other private yachts for families with a net worth in the hundreds of millions and billions.

What was fascinating was how money wasn't an object for some things, but they freaked out over other little expenses.

I worked as the chief officer on this family’s 120-foot-long motor yacht that had six guest suites and four crew cabins. The funny thing is, they only used their yacht one day a week for lunch on Sundays. 

Every Sunday, they would show up with their entourage of butlers, maids, and private chefs to do a three-hour lunch cruise.

The best part of the job was that I had six days off a week. I was paid a full salary with benefits, lived on the yacht so I had free room and board and had one of the private chefs making us all our meals.

They also consumed exclusively Fiji bottled water. Everything from their lemonade to the water the pasta was boiled in all came from those darn square Fiji bottles. The biggest time I ever got chewed out on the job was when I filled their dog’s water bowl with tap water.

I was promptly and forcefully told that if I ever gave the dog anything other than Fiji bottled water again, I would need to find another job.

Anna Gawlik, Shutterstock

15. Despicable Shows Of Wealth

I do high-end florals in a very rich area and see tons of obscene shows of wealth all the time. The amount of money some of these people spend on flowers alone is unfathomable.

The one that sticks in my mind is a client who we were decorating their house for Christmas. As I was hanging garland around their six-car garage, I looked in to see that each of the six spots has a car elevator and is three cars deep. There were 18 of the same exact $350k+ car.

Why would anyone need 18 of the same exact cars, let alone one that expensive?!

Young bearded man is looking surprised with hands up.Cookie Studio, Shutterstock16. Problem Solved

I had a client who purchased a newly built penthouse apartment and wanted a jacuzzi on the balcony. This would’ve required a structural column put in the middle of the balcony below. 

The contractor who built the apartment block wouldn’t go for it as he believed that installing it would impact selling that apartment. 

Well, my client just scoffed—the client buys the apartment below, approves the column and installs the jacuzzi. He then privately sells the apartment below. Voila, problem solved.

vilnis Izotovs ,Pexels

17. Joke’s On You

A few years ago, a rich French guy opened a school. A bit before the grand opening, the staff were having a small party on the roof when the rich guy came in. He asked them if they had everything they needed. Someone said, jokingly, that it was missing a jacuzzi.

A few days later, a jacuzzi was delivered on the roof.

Jacuzzi on wooden floor in a housevwalakte, Freepik18. All Is Secure

Years ago, I did a catering job for John Paul DeJoria, Patron Teq. and Paul Mitchell. This house was awesome. It was a stunning place.

At the end of the night, as we were packing up, the security guard came by and told us to stay away from the windows as they locked up. We said ok and about five minutes later, these metals drop down armor plates came out what seemed like the roof. 

They covered each window and door—thick metal plating armor.

Security guard stopping waiter man from entering at luxury establishment.SeventyFour, Shutterstock

19. Never To Be Seen Again

I used to work for a composer who is worth around $100 million. He was generally a nice guy and was hilarious. There were times when he was in a bad mood and would lash out at people, specifically when it came to preparing food for him.

One specific incident that sticks out was when an intern went to get a whole lobster for his dinner and set it out on the table. Our boss hadn't come out to eat it for hours. It was probably around midnight at this point, so the kid just sat down and started eating it.

Well, wouldn’t you know it? The big boss finally comes down to eat his lobster dinner only to find the intern had already sat down at the table wearing a bib and eating his super-expensive—now cold, lobster dinner.

That kid didn't come into work anymore.

Waiter holding seafood platter with lobster king.KamranAydinov ,Freepik

20. Time Over Money

I used to do some financial work for someone who became very wealthy through their very popular chain of surf gear.

I had run through their tax position and had found a way for them to save a little over $2 million in taxes a year by reshuffling some of their entities. 

It would have taken him around an hour to sit down and change some things around, a lot of paperwork, signatures and then maybe an hour extra of his time a year to administer.

What was his response?

"Nah, I don't want to waste that much time with paperwork. That's what I pay you guys for".

I can't even imagine what it would be like to be in a position where a bit of paperwork wasn't worth that much money. Heck, offer me $20 and I will gladly fill out an hour’s worth of paperwork for you!

Business man is looking at lap top and talking with senior man standing next to him.LinkedIn Sales Navigator, Pexels

21. Not Worth The Stress

I worked for some guys who were probably worth between $5-15 million. They paid me to do ridiculous things.

One guy paid me $150 cash to put lights on his Christmas tree since he and his wife always fought over how to do it. The dang tree was 12 feet tall, and it took me a while.

Another one paid me to be his designated driver for holiday parties because he was running for governor. So basically, I chauffeured him around in his Range Rover and hung out at his multimillion-dollar home while he was boozing it up with other socialites.

These guys seemed to live in a world that was completely different from mine. However, the stress and responsibilities they put up with were also more strenuous.

Personal driver is talking with passenger seating in the back.freepik, Freepik

22. What A Waste

I briefly cleaned houses for the wealthy one summer. These houses were INSANE. Some had elevators, some had STALLS in their master bathroom. 

One even had a cave manufactured in the bathroom, with shower heads all throughout it—you could walk from one end and come out the other side of the bathroom (split by a massive hot tub).

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

The weirdest house I cleaned though, wasn’t huge and it wasn’t gorgeous. It looked average on the outside. But inside, the entire house was FILLED with piles of clothes—everywhere.

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, 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. 

There were smaller piles in every corner which prevented you from fully opening or closing doors around them. The kids’ bathroom didn’t even have a shower curtain.

My best guess after “cleaning” that house as best we could, is that they don’t wash any of their clothes. I think they just buy more and discard the dirty clothes into the piles.

I think about that house a lot and wonder if they ever got their life together.

Clothes in piles stacked over.Vyacheslav Svetlichnyy ,Shutterstock

23. Generous Invite

I used to work at a Relais & Chateau property and served a bunch of rich people.

One lovely couple I served and got to know, asked what I was doing on my days off. I replied by saying that I was going to the mainland to visit. They happened to be leaving the same day, so they offered me and my co-worker dinner and a helicopter ride back.

So, we all flew out and they took us out to one of the nicest restaurants in Vancouver and paid for it all. This was after spending about $15,000 a night at the resort.

It was such a lovely time. I keep in contact every now and then!

Pilot holding hand of a woman getting off the helicopter.Jacob Lund, Shutterstock

24. Shower In Wealth

I once worked on re-doing a lady’s shower during the middle of a nasty divorce. The shower was 6'x10' with the entire ceiling covered in shower heads.

I thought she'd be snobby, but she totally surprised me—she tipped us so well. She gave everyone who worked on that bathroom a $500 tip because it was her ex's money.

Woman is giving a money to young man wearing yellowjacket and grey hat.Antoni Shkraba, Pexels

25. Every Penny Saved

My dad worked for an extremely wealthy, yet super old man as his personal accountant.

One day, my dad was driving him to a meeting. The man asked to swing through McDonald's. After ordering a coffee for $1.06, they began pulling forward. 

The man asked my dad to reverse his car back to the speaker. He wanted the cashier to know that he had a senior’s discount card.

A man worth well over $20 million, had a massive and nice luxury car, was not about to miss out on saving four cents at McDonald's.

Smiling senior man is seating inside a car.Andrea Piacquadio ,Pexels

26. For The Love Of Cars

My friend is a mechanic. A wealthy, fat, famous and all-round unlikable entrepreneur came into his workplace one day and took a liking to his co-worker. 

He asked my friend's co-worker if he wanted to come and work for him to maintain his car collection. It was 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. Every now and again he'd get sent to Europe or the United States to check out cars the entrepreneur was interested in buying. 

He'd also get sent to auctions all the time and bid on the cars on his behalf.

Mechanic is working next to a black car in workshop.cottonbro studio, Pexels

27. Whatever Tickles Your Fancy

I was a personal shopper for a pop star for about seven months before they moved out of my area.

The main thing I witnessed about working for them was inconsistency. The first day, they asked me to go find them this exact rug and to find some picture frames that would complement their room. 

No problem. I even put in a little extra foot work and found that same rug at a discounted price. Well, they didn't want it discounted when they could afford full price.

The next day, while they were out for the day, they saw this fantastic sculpture at a home goods store. They asked if I could find it and get it for them. 

No problem—but wait. I found that discounted rug yesterday, which didn’t please them. Now they’re asking me to put in time to find this sculpture at a discounted price. Huh?

Despite their inconsistency, they were a joy to work with. It was just not ever knowing what would strike their fancy—whether I should go the extra mile to save money or find a newer model, or just get paid for a full day's work for walking about a mile to Bed, Bath, and Beyond.

Young woman is holding a white head statue in hands.Tima Miroshnichenko, Pexels

28. An Unforgettable Experience

I was the project manager for a mansion being built for one of the founders of a major health insurance company here in the US. This guy was one of (if not the) best billionaires I’ve ever worked for. He showed up nearly every day in shorts and flip flops and would treat all of us like equals.

This was around the time that President Obama was about to put out Obamacare. While I was in a meeting with the owner, the craziest moment happened—President Obama called him, on his cell, to discuss the plan.

He (the owner) told us to hold on, that the president was calling. Someone jokingly made a comment about it (thinking he was joking). So, the owner asked Obama to say “hi” to the team—and he did!

It was surreal to be at the table with him when the call came through—an experience I will never forget.

Senior man is having a meeting with other people in office.Andrea Piacquadio, Pexels

29. Eating It All

I worked on a school project with a girl whose family’s net worth is more than $9 billion. They have a consumer product, family-run company that is a household name everyone would recognize.

At dinner one night, she made an offhand comment. She said, “Growing up, my parents would tell me to eat all the food on my plate”. And I thought, ‘yeah, me too, until she continued, “because when I’m running the family business, it would offend our overseas suppliers if we didn’t eat all the food they served”.

Young girl is seating and smiling at dinner table ,looking at food.freepik, Freepik

30. That’s Insane

I was a trainee sailing on a container ship going from Dubai to Tokyo and back (via all the big ports).

One day, the route was changed. We were now going from Singapore to Los Angeles. Since this change wasn't planned, we (the two trainees) didn't have visas for the US— meaning we couldn't leave the boat once we docked. 

For us, this was not a problem. We would only be there for two or three days at most.

The company decided that we should get the visas. They flew us from Hong Kong to our home countries. They got us a 10-year work permit for the US in a matter of days, and then flew us back to Dubai to join the ship. I've never seen money thrown around like that for little to no reason. It was insane.

Young woman is looking up to shipping containers and smiling.JU.STOCKER ,Shutterstock

31. The Best Day Of My Life

I am a dentist and used to own a dental office in an extremely wealthy area. I feel like rich people come in two flavors: very humble and generous or just 100% idiot. Unfortunately, most were jerks. Not many were in the middle.

True wealthy people care a lot about time, not money. If there was any hiccup in a procedure or something wasn’t correct, they would FLIP out.

Most of the issues that they would flip out about I could fix but that meant they had to make another dentist appointment which “wasted” their time. I HATED working on rich people.

When I sold that dental office, it was the best day of my life.

ArthurHidden, Freepik

32. Hey, That’s My Dinner

I did carpentry for a summer to save up money for school. We would go to huge mansions and amazing houses that needed work done. Most of the work was easy and didn’t take more than one or two days to complete. Usually, the family would be home while we worked but it wasn’t a problem.

One time, we worked for a family with kids. They watched a TikTok video about what poor people ate. It showed them how to cook things like 10 cent ramen noodles and bread with sausages to make hot dogs. This is when I realized we were living two different lives.

They laughed and thought it would be fun to try and make that food in their kitchen. Well, they hated it all. This was the food I grew up eating my whole life. That packet of ramen was the same one I was having for dinner and waiting for me at home.

Young man wearing white shirt is eating a noodles outside.Taryn Elliott ,Pexels

33. Good Catch

The owner I work for lives on a lake, but his booze cellar is in a building across the lake. So, he takes his boat to the booze cellar in a building also on the lake. He wanted a bigger cellar, so he paid to have them expand the building to accommodate for his vino.

Once said and done, he created a code specifically for the drinks cellar. Being it’s across the lake, he takes multiple boxes at a time. While he’s there, he scans them with a little 3D scanner that automatically orders the booze from various places. 

He then would email his assistant to order certain drinks. He once threw me a bottle of vino and said, “Good thing you caught it. That bottle is $10,000”.

Rana M ,Pexels

34. Expensive Memory Lapse

I interned for this wealthy CEO in Houston. He was traveling to Mexico and had forgotten his laptop which had all his stuff that he needed on it. He called the company and asked to have it sent to him. They told him that it would take three days to ship it even with priority service.

So, he paid me $500, plus a plane ticket, and for a hotel for me to stay the night to fly his laptop down there so he could have it within 12 hours. ,Freepik

35. Kindness Never Forgotten

I worked for a very rich man who owned a string of retail stores. I was a college student at the time.

One day, I went to work but was quite ill. The owner insisted that I visit an Urgent Care center. When I returned, he asked what had transpired. I replied that I had a sinus infection, etc. but that I didn't fill my prescriptions because they were too expensive.

He quickly pulled out his wallet and peeled off a $100 bill and insisted that I go straight to the pharmacy. I repaid every penny but have never forgotten how much it meant to me that he cared enough to send a lowly part-time college student, retail worker to Urgent Care. 

He then took the time to follow-up to see if I was okay.

Senior man wearing pink shirt and white hat is giving a money to other man.RDNE Stock project, Pexels

36. Sad Reality

My friend’s wife was a nanny for a family where both parents were VPs of a pharmaceutical company who already came from wealthy families.

They paid her $1,000/week in cash to basically be a full-time parent. When she left around 5 pm, they had a second nighttime nanny that would come and take over.

The kids were not allowed to go to their grandparent’s house because the grandparents had a lot of nice antiques and were afraid the kids would break something.

When she quit, the kids were never the same. They had to be put in grief counseling because they felt like they lost a parent. The parents would regularly have to ask her what their favorite food was, what they enjoy doing, what clothes they like and what sizes they wear.

She loved the money but said it just became too depressing to keep doing it because of how little they cared about interacting with their children.

Woman seating with two kids on the sofa and having a video call on laptop.freepik, Freepik

37. Leftover Mania

My wife worked as the personal assistant for a wealthy, self-made, humble but incredibly powerful man. He was uncomfortable in small social gatherings but was a lion in a business setting.

What I found most interesting is the guy would think nothing of dropping five figures on jewelry or other luxury items, but come the end of the work on Fridays, he was in the office kitchen taking home all the leftover bagels from the morning.

Birch Photographer, Shutterstock

38. At Your Service

I used to work for a real estate development company. The boss was the richest guy in town. The second biggest office was given to his wife, who did nothing. Her office was entirely bright pink. They put in a private bathroom just for her. Her parking space was double wide because she couldn't park straight, and she used employees to run all her personal errands.

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

Senior woman is seating on desk and working at pink office.Ivan Samkov, Pexels

39. Just Wanna Be Normal

I grew up with the children of a very famous musician. Their house had four stories and three elevators. The kids’ room (for their identical twins) was two stories itself and bigger than my family's two-story home with a pool.

They had every toy you could imagine including a dirt bike track and baseball field.

One of the twins was very kind and I really liked him. The other had a bit of a chip on his shoulder and his personality would change a lot. He wasn’t a bad guy, at least when I knew him. I believe the "nice" one joined the army for a short time. When he got out, he helped with supporting the family business. I’m not sure what happened to the other twin.

His parents were very kind too. After my dad had a heart attack, the musician showed up at our house to drop me off one day. My dad recognized him immediately.

Funny enough, they just wanted to be normal. We all wanted to go to their house, but they just wanted to come hangs out with us and not be treated differently. I didn't understand it at the time, but I do now. I hope they are all doing alright.

Askar Abayev, Pexels

40. Music To My Ears

A friend of mine was doing some work in the house that belonged to a wealthy family. When he passed one of the rooms, he saw a Gibson Les Paul leaned up in the corner. He casually mentioned it to the owner of the home and just said, "Hey, I saw that Les Paul up there. Do you play?"

The owner basically said that they had purchased the guitar for their son when he was in high school. He had since gone off to college and the guitar probably hadn't been touched by anyone except their maid in over five years.

My buddy was like, "Cool. Well, that's a nice guitar. It's a shame it doesn't get played more often" and then went back to working. That was it, end of the conversation—or so he thought.

After he had finished the job and was walking out, the owner came down with the guitar in his hand and asked my buddy if he wanted it. My friend tried to say “no” but the person wouldn't hear of it.

That is how my buddy got a $10,000 Gibson Les Paul for free.

2006 Gibson Les Paul Standard DesertburstFreebird, Flickr

41. How The Wealthy Treat Money

My father was the private chef for a famous billionaire. My father would travel with him on his private jet, make him anything he wanted and so on. He was a very genuine billionaire and was very good to my father and us as his family.

One time, he wanted a smoothie. They had just arrived at his house in a beautiful location. My dad hadn’t been in that kitchen in quite a while and couldn’t find the blender. So, he was told to just go out and buy another one (high end of course) and make a smoothie. My dad does this, makes his smoothie and the boss is happy.

Later, when my dad started cleaning the kitchen, he found ten blenders in obscure spots likely put there by the cleaning crew.

Chef is making a green smoothie in the kitchen.Racool_studio, Freepik

42. Last Minute Errand

A wealthy client dispatched his pilot to fly the private jet from Pittsburgh to DC to pick up a Rolex at a jeweler in Tysons Corner. It was a gift for this wealthy man’s wife. Apparently, it was her birthday and he'd waited until the last day to begin looking for the $22,500 diamond encrusted watch she wanted.

Young man is seating on private plane with hand up.RDNE Stock project, Pexels

43. Man’s Best Friend—Just Not Mine

Worked for a dog walking, doggy daycare company that had three employees. I ended up getting some VERY wealthy clients. These people traveled for fun so often, my boss and I had their dog for more days out of the year than they did.

It was to the point that people at my favorite dog-park thought he was my dog!! As you can imagine, the dog misbehaved a fair amount, but he was also sweet.

Young black man wearing blue hoodie is walking with dog in the park.Zen Chung, Pexels

44. My Thing Is Flying

I worked for an upscale condo complex that started at $500,000 and up, so most of these people were wealthy. Most people were nice. I received all kinds of Christmas gifts and even leftover stuff that I didn't care about like clothes and food.

One time, I was talking to a guy about why he drove a beat-up car compared to everyone else. It was like a 1998 Yukon. He simply told me that his thing was jets. He then proceeded to take me to his private hanger after work. 

He showed me his three private jets and offered to fly me anywhere, anytime I needed, to just ask. Unfortunately, I never took him up on the offer.

Light white plane is parked in a hangar.John Booth, Pexels

45. It’s Not That Funny

I used to work at a vet clinic. One of our clients was extremely rich. They owned a publicly listed company that was valued at over $10 billion.

After one of their dogs stayed with us for a month, they asked if we could take it back to their house. We were to leave it in their backyard until they returned home later that evening.

That wasn’t a problem but unfortunately, they didn’t say which house to return it to. I ended up taking their dog to the wrong house.

Soon after, the dude called my boss and asked where his dog was. When my boss called me, I read out the address I was given. He called the guy back and apparently, he just started laughing. He said that I dropped the dog off at the wrong house and he must’ve forgotten to tell us which house to go to.

The dude thought it was hilarious. I, on the other hand, had to go back, wrangle this dog into the truck, and take him across town. He was super cool when I dropped the dog off. It just seemed odd to have three huge houses 20 minutes apart.

Woman is playing with her white dog in a park.Elizaveta Mitenkova, Pexels

46. Cool But Odd

I worked for a guy who had some major stakes in the oil business. He was cool, but very weird about his money. He wanted these odd projects done but he always hired local kids to work for him. I was his landscaper but only had a two-year landscape degree at the time and didn't make all that much money.

His wife owned about 100+ sheep, just because she found it fun. His entire basement was full of survival supplies for “when the world ends”.

He once asked me to price out installing a helicopter landing pad in his backyard in case anyone ever has a heart attack at one of his dinner parties. He had a second house on site, which he used to house his German Shepherds.

Senior business man is talking on the phone outside.senivpetro, Freepik

47. Kind And Generous

My sister-in-law worked on the maid staff for a mega-wealthy guy for several years. She was pregnant at the time, then gave birth two months early. As you can imagine, this was time consuming and expensive.

The rich family gave her all the time she needed and paid for the entire process. It wound up costing over $100,000.

My niece is now 33 years old.

Maid is preparing a room wearing black and white uniform.freepik, Freepik

48. Drowning In Money

I was hired to install a custom pool for a billionaire which included custom iridescent tiles. The entire pool cost $440,000 for material alone and another $400,000 to install it.

We informed him that because it was a special order, it couldn't be changed once ordered. He approved so we installed it—but just when we thought it was over, it wasn't.

Once installed, everyone who worked on it thought it looked amazing. He didn’t like it. He ordered us to tear it out and replace it. He blew about $2.4 million on the pool tile before he even got anything done. The guy didn’t even bat an eye.

Worker is installing pool ladder in an empty swimming pool.M Dorta ,Shutterstock

49. This Man’s Junk Is My Dad’s Treasure

My dad is currently working as a landscaper for an obscenely rich man.

One day, he struck up a conversation with my dad. He mentioned that he had just moved to the area and was saving up for some new basic appliances like a washing machine, etc.

It was weird that someone so rich would need to "save up" for anything. Then, the truth came out—Mr. Richy Pants is the type who threw out perfectly good and functional stuff whenever a new model came out. 

Perfectly good furniture would get dumped because his wife saw a dining room set, couch etc, that she liked better. So, my dad could just take home any of the discarded stuff the rich guy had in his shed—a washer and dryer, a new fridge, a dining room table, a BBQ...

He basically outfitted his whole place with fancy things he never thought he'd have. From the rich guy’s perspective, he was basically letting the staff pick through his trash.

Most of the stuff wasn't even used! All the appliances but the fridge still had the plastic film on it! Such wasteful people.

Hadrian, Shutterstock

50. Princess Feline

My sister is a butler for a super wealthy family. The family once got this super expensive rare breed cat.

A few months later, the wife tells my sister that she thinks the cat isn’t quite happy in their house. The solution she came to was just outrageous—she asked my sister 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.

Grey cat is sitting in a brown luggage case and looking at side.freepik, Freepik

Sources:  Reddit

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