Top Stories by Employees Working for the Ultra-Wealthy

Author image for Eleonora Bader
Eleonora Bader
Jun 21, 2023 6:00 PM EDT

When you have a lot of money, the world tends to become your oyster. There isn't a problem that money can't fix… said almost nobody, ever. It's not that you don't get problems when you're super rich, but rather that at least you can cry in your mansion and go on a million-dollar shopping spree. You don't like the items you bought? Pay someone to return them. Or don't, because what's a couple of grand?

We can't imagine what it's like to have that kind of cash at hand or to look at your bank account and not cry. Inflation is at an all-time high, and when we see celebrities buying a purse for over 70 grand seems like a waste of money. All this made us wonder… what is it like to work for the elite? Below you'll find an interesting Reddit thread with a bunch of gobsmacking replies to this question. Cleaners, construction workers, nannies, and more tell all in r/askreddit.

For more, here are some top slip-ups by servers that made them wish they were six feet underground.

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  • 01
    Font - Posted by u/AMGBOI69420 1 day ago 4 People who work for the super wealthy, what stuff have you seen?
    via u/AMGBOI69420
  • 02
    Font - wjescott 17 hr. ago The CEO of the company I worked for was the founder's son. Not an unintelligent guy 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. Managerial staff was ordered, upon penalty of termination, not to treat him any differently than a new hire.
    via u/wjescott
  • 03
    Font - So when he became CEO he wasn't a bad guy to with for. Now, this is a company of over 10,000. One night, I'm working overtime on the late shift and we get this call. "Hey! You guys... Got... 'Lectrician?" The guy is clearly drunk, we have no idea who it is or why he's calling our maintenance/engineering group. We ask who he is and he informs us, light heartedly.
    via u/wjescott
  • 04
    Font - He wants someone to take a ride to his house and figure out why the internet isn't working. This is an hour drive away. I volunteer, I was bored off my nu't anyway. I get to the house, entry gate is smashed, section of the white horse fencing is gone, Jaguar is stuck in the field.
    via u/wjescott
  • 05
    Font - Here in the house is dude, completely blasted. He's got a huge cut on his hairline. "Are you ok, (boss)?" "I'm fine! Why?" He asks, blood literally caked on his face. I accompany him to the bathroom and help him clean himself up, wash off the gash and put some bandaging on it.
    via u/wjescott
  • 06
    Font - Then I corrected the Internet. Unplug-plug. As I'm walking out, he asks me to do a shot with him. I comment, worried about my job, that it might be a bad idea. He agrees and hands me the bottle, "Take it home and do a shot later. Keep it."
    via u/wjescott
  • 07
    Font - When I get back to work I look the stuff up... Never heard of it. It's a $1500 bottle of scotch. The next day I'm at work early. About eleven in the morning he comes walking up. "Uh... We're not going to be... Talking about last night?" I tell him it's all good, "Awesome."
    via u/wjescott
  • 08
    Font - A little bit later I get an envelope. There's a check attached for 'Emergency Tech Support' $5,000. 19.8k Reply Share
    via u/wjescott
  • 09
    Font - Blackhawk-388 · 18 hr. ago 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
    via u/Blackhawk-388
  • 10
    Font - 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."
    via u/Blackhawk-388
  • 11
    Font - 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. 5.7k Reply Share
    via u/Blackhawk-388
  • 12
    Font - sooofarms 16 hr. ago 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
    via u/sooofarms
  • 13
    Font - 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
    via u/sooofarms
  • 14
    Font - piled with dried food that smelled, dirty clothes thrown everywhere, piles of cr p 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 tar pons on top of overflowing trash so she had to
    via u/sooofarms
  • 15
    Font - pick up their used women's products thrown on the floor not even wrapped in paper. So these fancy bies 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
    via u/sooofarms
  • 16
    Font - 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. 2.7k Reply Share
    via u/sooofarms
  • 17
    Font - woul DrGrizzley 17 hr. ago edited 17 hr. ago I did a Manny (Male Nanny) job for a rich couple who wanted someone to care for thier kids. The wife didn't want a female nanny and I was in college so it helped pay the bills. One day they asked "Do you want to go to Hawaii?" Turns out the company that the husband was the COO of was doing an executive
    via u/DrGrizzley
  • 18
    Font - retreat in Hawaii. Instead of finding daycare in Hawaii for their kids they thought it'd be easier to just 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, had my own hotel room, they paid me for my time and gave me a large
    via u/DrGrizzley
  • 19
    Font - stipend for my own food/entertainment. I ended up with pretty much every evening off so I got to spend it. During the day I brought their kids to the beach, we went hiking, and did some touristy running around. On top of that they gave me $5k in "spending money" in case any of the kids wanted anything. I had to show reciepts,
    via u/DrGrizzley
  • 20
    Font - but when I tried to turn in the receipts the wife just said "Oh don't worry about it, it's only a couple grand" and 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 truely thought the amount was so small it didn't matter.
    via u/DrGrizzley
  • 21
    Font - They were a really nice family, just very well off which made just spending money on any problems the easiest answer. I actually got invited to the oldest daughter's high school graduation because she considered me a friend. 22.4k Reply Share
    via u/DrGrizzley
  • 22
    Font - kingJoffi 18 hr. ago 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. 12.6k Reply Share
    via u/kingJoffi
  • 23
    Font - Interesting-Step-654 · 19 hr. ago 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) 8.1k Reply Share
    via u/Interesting-Step-654
  • 24
    Font - CindeeSlickbooty · 19 hr. ago 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
    via u/CindeeSlickbooty
  • 25
    Font - 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!! This was also the night when I was making an older man a drink and he decided to ask me "so, what are the poor people doing tonight?" ↑ 6.2k ↓ Reply Share
    via u/CindeeSlickbooty
  • 26
    Font - UncleGrako 20 hr. ago 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. 34.3k Reply Share
    via u/UncleGrako
  • 27
    Font - expanding_crystal. 19 hr. ago Galaxy brain right there. Also he had the spare cash to buy a marina I guess. 13.0k Reply Share kjm16216 21 hr. ago Well don't we all. I think I looked at that marina, but seemed like a lot of maintenance so I bought groceries instead. 7.8k Reply Share
    via u/expanding_crystal, u/kjm16216
  • 28
    Font - ShakyTheBear - 20 hr. ago 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. 1.5k Reply Share
    via u/ShakyTheBear
  • 29
    Font - kl_dudey 21 hr. ago 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.
    via u/kl_dudley
  • 30
    Font - Client buys the apartment below, approves the column, jacuzzi is installed, then privately sells the apartment below. Voila problem solved. 36.7k Reply Share
    via u/kl_dudley
  • 31
    Font - TheNoisyNomad - 22 hr. ago "Never work for millionaires. They're just trying to prove something. Work for billionaires. They know what they want and will just pay what it costs to get it right." - a caretaker getting paid six American figures for keeping up a multimillion dollar house that gets used two weeks a year. Reply Share 9.8k
    via u/TheNoisyNomad
  • 32
    Font - watson_exe 22 hr. ago edited 16 hr. ago 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.
    via u/watson_exe
  • 33
    Font - EDIT: We redid the glass to her shower when I was at a glass shop. How the actual plumbing and stuff worked is beyond me. My job was to bring in giant panes of glass, attach them to the wall/floors, waterproof the seals, and dip. With how large her house was and the other 2 'smaller' houses that were attached I'm sure she had enough money to throw at someone to solve those plumbing problems. 12.2k ↓ Reply Share
    via u/watson_exe
  • 34
    Font - djauralsects 1 day ago Radiant heated driveways to melt snow. A turntable to rotate their car so they didn't have to back out of their driveway. Lifts in the garage so they can park cars underneath eachother. 2.2k Reply Share
    via u/djauralsects
  • 35
    Font - Duranis 23 hr. ago edited 14 hr. ago Worked in recruitment finding crew for super yachts many years ago. Put forward a candidate for a chief engineer on a very well known yacht owned by a very well known individual. Was the perfect fit of knowledge and experience and the guy was super friendly and nice as well. They turned him down because "he wears glasses and the owner doesn't want anyone with disabilities working on board".
    via u/Duranis

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