66 Crazy Stories About Working In “Rich People Environments,” As Told By The Employees Themselves

This was my ex’s father- we are all hanging out eating breakfast when the housekeeper who also raised my ex from the time his mother passed away told us her aunt had passed away in Italy.

I admit me and my ex did shoot looks at each other because this woman was in her mid-70s, we were young and dumb and didn’t think she would have an aunt still alive.

Anyway, his father immediately asked is she had booked her tickets? He offered to take her to the airport etc. She was like no sir I cannot go. His dad looked at her and said I will pay for the ticket. She still said no.

His dad asked her why? Her reason was there was a dinner scheduled Friday and she didn’t want to risk a flight delay keeping her from getting back in time to supervise the catering company.

His dad looked a bit puzzled, grabbed his phone and made a quick call. He then told her to pack and he would drive her to the airport and she wouldn’t have to worry about any delays.

His father arranged for her to fly to Italy on a private jet that same afternoon. His father also arranged for the jet and crew to be on standby until she was ready to come home.

I learned a few lessons about class, loyalty, dedication and family that day, and that I had no business dating someone that was that wealthy.

JD Vance calling a military helicopter to take his 9 year old to golf lessons.

I didn’t work this.

But we should all be mad.

I was at a very expensive resort I won't name. Everyone coming off their mid sized yachts dressed in designer brands. A lot of logos everywhere. A guy trying to buy a Mercedes while in line (unsuccessfully). Then a black limo rolls in, a very average family gets out, no brands, just whatever clothes. All of the staff trip over each other to greet them by name. They know all the staff too. They keep a suite year round in this place while all these logo people haggle taxi drivers. You know when the real money comes into room.

Heard a woman [complaining] to her friend cuz her maid was always late due to bus etc. so they bought her a car.

Work in the Yacht industry.

Customer of ours is billionaire class rich.

Guy is demanding when it comes to yacht repairs.

Turns out when he was having his 80ft custom boat built, the company building it wasn't getting it done fast enough.

So, he bought the entire boatyard and boat manufacturer out to prioritize his boats completion.

Once it was done, he sold the company. It went [banckrupt] up after that. Probably 100 people lost their livelihoods because some weirdo rich jerk wanted his toy sooner.

Guy dresses like he is near homeless and acts like he has a substance problem, but very smart dude. Just a very strong 'not from this planet' vibe all around.

Many years ago, back when BurningMan was much smaller and even more hands-on / DIY, a friend agreed to work for one of the very, very first "Playa tourism" camps, where stupidly rich people flew in to have this ultra-curated, ultra-indulgent experience with air conditioning and jacuzzis in their RVs, out in the middle of the Nevada desert.

My friend still quotes the spoiled "guest" who refused her crystal dish of chilled berries, pushing it away saying "These berries are ... mixed...".

There was a relatively wealthy woman in the community I live in who was quite elderly but remained social and donated quite a bit to local artistic groups, the ballet, etc. She liked to dress a little flamboyantly at galas and other events, usually with a large hat as part of her outfit. She said that, when she would buy new clothing or dresses, she would buy two and have the second item made into the hat so it matched. She accumulated quite a bit of clothing over the years and eventually cleared out some rooms in the top floor of her home to install one of those drycleaner’s sized revolving machines that held it all.

I worked at a high-end country club. One member lived at the course and was always blasted. So he decided to buy a high schooler in his neighborhood a new Lincoln. The only catch was the kid had to pick up the member at the golf course each day when he was done playing 18 holes.

Work in professional auto racing, with many rich “gentlemen drivers.” One family had their kid racing Porsche’s the same weekend as his little brother racing karts. Same state, but ~200mi apart. Whole family would commute by helicopter back and forth so they could watch each others sessions on track. So 3-4 trips a day by helicopter to watch each other drive their race cars.

Had a different client crash their older racecar. No parts on hand at the track. So fired up their private jet, flew halfway across the country that evening to pick up parts to bring back to the track so they could make the next days sessions. Same client had an old cannon on display in one of his houses. A guest asked if it was real, he said for sure, and proceeded to fire it off out of his front door. The shockwave blew out all of the windows in the house.

Highest luxury brand. Closed for the VIPs visit. He walks through the store, pointing at a few items and asks them to put it in the middle (suggesting he wanted to buy those items). He finally says, I’ll take everything else, wrap it up.

I’ve vacationed in areas where wealthy and wealth adjacent people mingle and what strikes me is how hard the wealth-adjacent people spend money to look like wealth, while the truly wealthy are often like the old guy who stopped caring and just wears flip flops and some beat up tee shirt.

Edit: this is in the US, wealth in EU tends to look differently due to a third tier: Nobility.

Ok I have a wild one…

I was a PA and piano tuner in my early 20’s (don’t ask… just is what it is). I would visit a house and do some basic stuff … pick up groceries and drop them off … pick up laundry and drop it off … carry the trash bags to the trash can etc. at the time I had only ever met the husband …. Then on that fateful morning as I am putting groceries away in walks one of the most beautiful women I have ever seen (think Gal Gadot but with more meat in her bones) wearing a poor excuse for shorts and a top that probably belonged to a child … totally shocked (it was the norm)…. I try and behave and not look and she’s oblivious to everything … happened a few more times and finally I asked what the deal was … she said “her husband paid for everything so she didn’t mind showing it off … I must be someone her husband trust otherwise I wouldn’t have a key”

So I’m thinking this is too good to be true so I keep my distance.

I come in another off day and the husband is sitting in the kitchen… asking about how much I would charge for a piano tuning. I’m going over prices when in she walks wearing the same or similar outfit … nothing is said other than a kiss.

As I’m going over he just gets frustrated when I tell him there’s some warping in the wood that probably happened when someone spilled something. The guy just asks me if I want the piano… he’s just going to buy another grand piano … 3 days later there’s a moving company dropping off the piano at my parents house at no charge and I was tasked with purchasing a piano on his behalf … the guy didn’t even play piano he just liked the aesthetic of it with an Xmas tree behind it.

Long story short… got to check out a hot wife, husband gifted me a grand piano, was paid a stupid amount of money for doing little to no work and while not part of this story I got a free car out of it … nothing like driving around in a Lexus 5+ years old just because the wife didn’t want it anymore.

This is going to sound crazy, and it is, but it happened. I know a case where an extremely wealthy family had a kid who was a picky eater. Finally grandma asked this little boy what he wanted to eat. The kid said he wanted an egg salad sandwich from a particular deli in a city 175 miles away from their home. Grandma called the airport and hired a pilot to fly to the other city, take a cab to the deli, return to the airport, fly home and then deliver the egg salad sandwich to their house. The pilot did all of this and the kid ate the sandwiches.
This was at least 40 or more years ago, but even then it would have had to cost several hundred dollars or more.

Amex many years ago: cardholder wanted a "special" bottle of sand from some island that they and their partner got married on years ago as a gift for their anniversary...

They didn't want to just buy a bottle of any old sand, so we needed someone to go to the island, "scoop it up" into the bottle and cap it, then package and deliver as a well presented gift. Total cost was like ~$400k after all logistics etc was accounted for.... all of that for a literal jar of sand (insert johnny Depp meme)

This one ALWAYS bemused me so much that it's definitely a recurring thought whenever I think I may have splurged too much on a takeaway coffee or something.

Eta: $ is AUD. Also, if they use reddit and ever see this I hope you had/still have many happy years together. If anything, your anniversary is regularly remembered by someone in this world.

I'm a veterinarian and for a long time i was working in mobile service. So, first really crazy thing I witnessed in my early professional years - in a penthouse with size of the entire floor, their cat has their personal room. To me it was just mind-blowing at the time. I was 24 and lived with mother in small apartment, basically with zero personal space - just a place to sleep in between work shifts. And then I went in closed elite village outside the city. Their single dog has 3 people for daily care. Still can't get over it kinda.

There’s a store in Phoenix that sells mattresses. One of the lines they sell are Hastens Vividus. One of them costs $316,000 and another one costs $657,000.

You ain’t getting those at Mattress King.

I work with a lot of wealthy people. I had a multi billionaire let us host a dinner in his very very large house. For reference, the room we used was 10,000 sq ft. He forgot we even using that section of his house until later that night when we ran into him in a hallway.

Imagine a house so large you didn’t realize 50 people were there. I’m not talking about a spread out property in different structures on acreage, but a single, continuous home.

That was wild.

Used to work line service on the corporate aviation side. There was a group of ladies who chartered a jet to take their small dogs to Miami because they’d never been to the beaches there.

I’m a climbing arborist who often works for the super-rich in towns like Telluride, Aspen, Vail, and Boulder. I’ve met people who make $56 million a week. I’ve met people who, when they like a couch, buy one for every house they own. I’ve had a guy forget he paid me $10,000 TWICE, same guy! I’ve had someone ask if I can remove every rock, stick, and leaf from five acres of forest because they didn’t like how it looks…

Worked in high end luxury retail. A regular billionaire would buy the exact same Cartier bracelet twice every Christmas. One for his wife, one for his mistress. Our store database literally had a massive red warning flag on his profile to never mention duplicate receipts if either woman came in.