July 22, 2023 at 5:44 am

Here Are The Weirdest Things People Have Seen Who Work For The Wealthiest People In the World

by Matthew Gilligan

SuperWealthyWeirdAR Here Are The Weirdest Things People Have Seen Who Work For The Wealthiest People In the World

You never really know what it’s like to be around incredibly wealthy people unless you spend a good deal of time with them.

And those of us who have never been around the elite for long periods of time are in for a big treat today!

Because these AskReddit users shared the weird and interesting things they’ve seen while working for wealthy folks.

Take a look!

Big money.

“I 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.”

The butler.

“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.”

That’s a big house.

“Years ago I used to work carpentry mainly doing sunrooms. One of our clients was a brain surgeon who was married to a lawyer and they subsequently 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 this same property. Problem is, city ordinances prohibit 2 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 BUILD A F**KING WALL BETWEEN THE HOUSES. And this isn’t just some dinky picket fence type of wall, it’s a massive medieval style wall that has round towers with merlons and crenels, a gym midway through, AND a massive $750k+ all-glass sunroom all the while being wide enough to have room for a walking path and a road for golf carts…. inside the wall.

The city ordinance said only one livable dwelling can be on their property, so they just made a massive hallway between their houses…..”


“I did a Manny (Male Nanny) job for a rich couple who wanted someone to care for their 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 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 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 receipts, 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 truly thought the amount was so small it didn’t matter.

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.”

That’s wild.

“I set up a party for a family out in the hamptons that bought the house next door just to level it and set up a giant temporary party tent on the plot.

Wild s**t.”

No class whatsoever.

“Bodyguarded someone filthy rich with 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.”

Rich people are weird.

“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!!

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?””

I’ll take it.

“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.”

Didn’t need to see that.

“Their kids (all young 20s) never shut the door when using the bathroom.

Plenty times while cleaning the house I’d walk past the bathroom and see one of their daughters on the can, they’d often wave or say hi.

Fu**ing odd.”

Took care of that problem.

“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. Problem solved.”

More money, more weirdness.