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“Still Can’t Get Over It”: 66 People Who Worked For The Rich Share The Wildest Moments That Left Them Speechless
According to statistics, only a small percentage of people will reach “filthy rich” status in their lifetime. For context. Altrata’s 2026 Ultra Wealth report reveals that roughly 556,850 people worldwide (out of 8.3 billion) had $30 million or more in their names.
That means most people may only get to experience a life of luxury by working for wealthy individuals. And as you might expect, these employees will have colorful, juicy stories to tell.
In a recent Reddit thread, they spilled the beans about what it’s like to work in “rich people environments.” And no, they did not disappoint.
This post may include affiliate links.
#1
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.
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#2
Heard a woman [complaining] to her friend cuz her maid was always late due to bus etc. so they bought her a car.
#3
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.
#4
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.
#5
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.
#6
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.
#7
Huge industrial ship just off the coast of Seychelles that we could see from our hotel balcony. Our tour guide showed us all these red roof houses, said Saudi royal family owns that whole block. We asked him about the ship; it's sole purpose is private/personal WiFi for the royal fam. It's stationed there year-long, is manned 24/7 (iirc), and the royal fam will just randomly travel to Seychelles maybe once year...
#8
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.
#9
People who will call to have their empty toilet paper changed in their home: Aspen.
#10
I worked at a rich kid's summer camp as a maintenance guy. One time I get a maintenance ticket for a leaking shower in a cabin.
I go to check it out and the councilor says, "When the get out of the shower, the floor gets wet!"
I was only 17 at the time but still had the common sense to let them know it's not a leaky shower.
#11
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...".
#12
Worked on a private owned yacht and the owners wife had this special ordered tootbrushes that was enameled with real gold.
#13
Years ago, when I was 7 or 8 years old, I was introduced to a woman at a restaraunt in Sun Valley Idaho. She was a friend of my great aunt. 50-ish years later, I don't remember who she was, but a comment my great aunt said about her has stuck with me ever since - "She has 9 houses around the world. Each of them is identical, including identical beds, furniture, bedding, photos on the wall, china, silverware and clothing, and two identical cars in each garage. The only differences are the activity things for each house. She just calls the full time staff from the plane on her way to her next location to stock the refrigerator and make sure the cars have full tanks of gas."
#14
People who own multiple estates (not just big houses) in different high end vacation areas who have year round full time housekeepers/staff. For places they visit a week or two a year.
#15
I heard of a guy, confirmed later..who bought 2 houses side by side in Turks and Cacos. Tore them down and built 1 big mansion. Then he didn't like the ocean front beach sand so he had a few barges of new sand brought in.
#16
Had a guy buy a new BMW because he didn’t want to wait for an oil change. He ubered back 3 hours later to get the first car. We did have loaner cars.
#17
Teacher to extremely wealthy families. The kindergarten end of the year party was on a yacht/ yacht club, each student had their nanny there and own lifeguard.
#18
Not as crazy as some of these comments, but the owner of the company I work for regularly takes his private jet to lunch, and it’s about a 30-minute drive away.
#19
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…
#20
I know a guy who builds superyachts. His worst story was about a Saudi royal. This royal had a massive ship built, over 300 feet. My friend was doing the finishing work in the master bedroom. They were applying a stingray-skin wallpaper all over the entire room. Skin by skin, trying to make the entire thing seamless. They spent $50K on skins alone — I don't even want to know what the labor cost was. They spent over four weeks on it with several people. Mr. Saudi flies into the local airport by private jet. Takes three steps on the tarmac to a private helicopter. Lands the helicopter on the deck of the ship. Spends 30 minutes aboard. Spends three minutes in the master bedroom. 'I don’t like this color, rip it all off and start over, see you in three weeks.' And just [went] back to Saudi Arabia.
#21
I'm a helicopter mechanic and inspector; my employer maintains helicopters for, among others, ultra-high-net-worth individuals. Billionaire helicopter owner didn’t like the iPad-based infotainment system controls in their new $16 million helicopter…despite being personally involved in the selection/specification process. 'There are too many icons to tap to get my music to play.' Proceeds to spend another $1 million to have a one-off audio control interface designed to play nice with the existing interface, so two taps would get their Spotify playlist running when they got in the helicopter, and their phone would auto-connect to the helicopter’s Wi-Fi.
#22
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.
#23
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.
#24
Two ladies talking about new cars. One said I settle for the Jaguar because I only 50k to spend that day.
A guy would bring his wife to the country club on certain days and his mistress on other days.
#25
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.
#26
I was in villefranche once and they literally used a helicopter off of a yacht to ferry them to the shore, maybe a 4 mile trip by boat.
#27
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.
#28
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.
#29
I work at a very high end club in florida which has an annual $2400 minimum to spend on food and beverage, plus the $200k initiation AND annual dues of around $100k.
We hold a wine sale at the end of the year so members can fulfill their $2400 who NEVER come to the club but pay those fees every year just to be a member!.
Member walks up to check out with $2400 in wine and gives me a wrong member # to which I reply, "that's incorrect" he replies "oops, thats my other club member # from.... I need to spend my minimum there too.
I help him to his Lamborghini with the 2 cases of wine.
He says...no room in the frunk, his golf clubs are there. Tells me he will be back. Arrives 10min later in a Pagani.
#30
Someone came in and paid for their new speed boat engines in cash. Counted out around a quarter million in cash.
#31
Former mega yacht carpenter. I was 19 and sanding the teak decks ( punch work). The vessel had finished the refit and was now at a luxury marina awaiting departure. Smaller vessel like 116 foot. As I'm sanding around this polished anchor equipment, a speed boat pulls up and tethers to the vessel I'm working on. The mom comes out with several kids. The kids in thick British accents ask mum for candy money. The lady proceeds to give each of the 4-6 year old kids a couple hundred each for candy! They had also chartered a speed boat to keep the kids occupied while we finished the days work.
I know this doesnt sound like much but literally the day before I was giving my buddies little sister a couple bucks for candy. It was mind blowing. Literally kindergarten kids got my weeks pay for candy.
#32
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.
#33
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.
#34
I attended Billie Lourd's third birthday party at Carrie Fisher's house. There was a monkey and organ grinder, an African elephant, and Warren Beatty pushing a stroller. At one point, Ellen Barkin cut in line for the elephant because "Romy needs to ride the elephant right now." Somehow, the craziest thing there was Warren Beatty with a stroller.
#35
I have a thousand stories. Let's start with the owner of a major fashion brand having a full on stompy feet toddler tantrum because a slice of tomato in his caprese salad was too soft. Dude was in his seventies.
#36
The best ridiculous story I can remember from people who work onboard yachts was the female half of a couple who owned a yacht and had a long list of demands for when they were onboard. She would come back to her cabin plastered and the stewardess was expected to remove her contact lenses for her. She also didn't like it when her champagne glass got condensation on it, so the stewardess would remove it when it got sweaty and replace it with a new one.
#37
My first job was on a farm in New Zealand, the owner of the farm was the richest man in the country at one point. On this farm were exotic animals and a lot of expensive massive pieces of art work and sculptures, one day we come into work and the owner had taken his tank through the farm and destroyed a bunch of art and sculptures. Come to find out they were the ones his now ex wife had made or ordered, this guy used a tank to destroy millions of dollars worth of art while drunk on his farm.
Side note he created the first car that turns into a boat, one day at work he pulls up in one and proceeds to drive it into the huge pond in front of all of us and it turns into a boat and he’s speeding around the man made lake with his car haha I was 16 years old at the time, it blew my mind.
#38
I worked at a private bank in a very upscale neighborhood in So Cal. We would have these old rich guys come in with these barley 18 yr old Asian women ( we called them MOBs as in mail order brides) . They'd open them like a $25k CD and a $1000 checking account with an allowance. The poor women always looked so miserable. It was gross.
#39
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.
#41
A friend of mine worked as a high school teacher in Kuwait. All the students were Oil Kids, or Royal Kids. Her students would regularly have their fashion designer fly in to measure them, go over next season's designs, then fly back to wherever they came from. A month or so later, they would return with the next season's custom-completed wardrobe and a tailor to make any needed adjustments on the spot. A custom-made, hand-delivered wardrobe for each season for each high school girl.
#42
A billionaire taking calls from his mid 30s daughter bc she wanted to buy a $10k handbag. She makes no money on her own and is completely supported by parents, which includes multiple gifts a year costing $50k+.
#43
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.
#44
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.
#45
Private jet (and limo) sent to pick up their little dog, private jet sent to pick up their bed (different rich person) and had to load it into the limo, it was the only bed they could sleep right in.
#47
The brother of my client casually offering anyone going to LA a ride with him on his private jet.
I’m never going to LA but I almost wanted to take a detour just for a ride.
#48
Venture Capitalist flying kid to east coast college in the 10m business jet burning $25k in fuel for trip, loading a $600 washer dryer in the back for the new apartment. Co-pilot hurt back when loading.
#49
A woman in a £10k wedding dress (loudly spoken about by her father) with beaded straps. One of the straps snapped so she took it off, bundled it into a bin bag and left it behind the kitchen.
#50
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.
#51
1. Flew a Sovereign empty to Jackson Hole to get one board member and brought her to the meeting. Upon exiting she handed me her lunch catering packaging and asked me to place it in recycling. It was crazy because we just laid down the carbon footprint of a small US city.
2.Had a charter to take a couple to a gambling state and the request was to place a very expensive diamond engagement ring in a DRINK while serving the female passenger. I just knew she would swallow it and it was going to be my fault. She didn’t and no, I don’t know if they are still married.
#52
Hamptons construction/property management for about 19 years. I’ve seen 3 AMG G wagons pull up full of staff members to deliver someone their dog and a coffee. I have seen a woman in the super market out there load a box truck to the brim with bottled Fiji water… to fill her hot tub. Full staff loading the truck. The craziest thing is their disconnection from reality and general uselessness.
#53
Talking to a qatari heir, he told me he loves driving his car so much he always take it when he travels.
Which includes going back home from London every 3 months.
No it's not shipped by boat. It's by plane. And it costs 30k pounds each way.
Also Qatar airlines also has some planes that only have first class, the rest is just for people's cars.
I felt poor.
#54
I threw away 50 bucks in a casino, got some 20 more at the counter to waste (or win haha).
The guy in front of me got himself 10k in chips.
#55
They’re really mean to their personal assistants, one time my friend was talking to one of them and he said he had to stop talking to her because his boss would get pissed, he wasn’t allowed to talk to anyone else.
#56
One of the craziest things I saw without giving away their identity was the family casually talking about how they were donating addition to a state university. Like I cannot even fathom having that much extra money.
#57
Worked at a super exclusive golf club for a bit. Had to ask the concierge a question and the person in front of me asked her to order the helicopter to pick him up and wrote a $68k check for the next months pro shop/restaurant minimum because he wouldn’t be in the country. Another member was #4 in line to buy a Lamborghini anytime they released a new model, and finally got to watch Michael Bloomberg watch his security detail try to find all his errant shots on Sundays.
#58
A wealthy lady in the suburbs of Philadelphia wanted her swimming pool to be 10’ further from her house so she bought two adjacent mansions, tore them down, then tore out her pool and rebuilt it where she wanted it.
#59
Used to work at Nordstrom. Our location had just opened up, and I sold shoes. We had a very strict policy on how we helped people: one person (or group) at a time, in the order they arrive. There was a waiting list for help, so that we sales people could give you the best experience possible, rather than how it was done at other shoe stores where you're running around trying to get everyone their boxes of shoes and not actually selling them or helping them. Anyway, this old lady comes up to me, shoves a $300 shoe in my hand and tells me she wants it.
I have to tell her that I'm sorry, I'm helping someone else right now, but if she will go to this person here we'll get you on the wait list. OH she goes into an unholy rant about how she's here to spend money and she has to *wait* because she is spending more money than anyone else. I just. Ma'am. Ma'am. You will wait your turn like everyone else because a customer is a customer and we (allegedly) don't care how much you're spending we give everyone the exact same treatment.
I highly doubt she would have been happy with someone tossing a box at her and running off to the next customer. But hey, that's high-end retail for ya.
#61
Woman at the country club I worked at putting her old shoes on the counter after buying new ones and telling me to throw them away for her. When I didn’t jump and do it immediately, she had to remind me to pick up her used smelly shoes and throw them away for her. She was passing by the trash cans on her way out. Horrible entitled woman who lived to show off her husband’s wealth.
#62
I was part of a custom home build for a very wealthy old fart, (85) and was building a 26000 square foot mansion, approximately $50,000,000.
He couldn't visualize anything, he needed to see it with his own eyes, so anywhere the contractor needed his opinion they would have to build 3 or 4 "mock ups" on skids. For example they needed a choice made on window trim so they built 4 mock walls with the stone finish, 4 windows and roof sections, they then trimmed out the windows with 4 options and he'd come to site for 2 minutes and say "that one" then leave. The contractor would then disassemble the mock up, save the windows and throw the rest in the trash.
This was with everything, flooring, trim, tile, plumbing fixtures, electrical fixtures, railings, millwork etc. The amount of wasted time and material was astonishing.
#63
A home I was working on had a $30k carpet installed. In a guest room - a guest room of their guest house. That is all I know/asked, the info came from a fellow contractor working on the project with me (in case anyone was curious about what was so special about it).
#64
I worked for boss that was a lowly multimillionaire. He we went to lunch with us one day. Took a couple of bites of food he had ordered. Didn't like it, so he ordered another meal. Didn't ask for a refund, just bought another meal.
#65
I am one of the “poorest” people in an exclusive community where several celebrities live, including a household name international mega-celebrity. I was recently chatting with a woman at our dog park who lives a few streets over. She was in town for the 4th of July… Her second home is a $4M home. They’re here less than half the year.
I overheard another woman at the country club complaining to her friend that she decided didn’t like color interior she chose for her Urus, so it’s “stuck at the dealership” while they replace it.
#66
Saw a drunk dude fall and knock over a bar of top shelf liquor in a luxury boxand just laughed it off and paid for it.
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