People Are Revealing The Wildest Things They Saw Working For The Super Rich, And Truly It Is Wild

I read a Reddit thread a while back about how the redditor's mother had been a housekeeper to a very rich family. Occasionally, they would join their mother at work but were told they could never go down into the basement. Of course, one day, they did open the basement door and saw piles upon piles of panties everywhere. Turns out that the woman their mother worked for never wore the same underwear twice, but she also didn't give them away or throw them out. Instead, they would just throw them into the basement.

a pile of women's underwear
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The story made me really curious about other just bizarre things very rich people do because...well they can. I recently came across three old Reddit posts (one from eight years ago, one from a year ago, and one from three years ago) where people shared the wildest things they have seen working for the super wealthy.

Screenshot from "Succession"
Graeme Hunter/ Courtesy Warner Bros. Discovery

The threads had all sorts of responses, from stories about pampered pets to moving a super yacht across the world just so the owner could point at it from a building. Below are the top and best comments:

1."A woman who owned a small private jet business told me one time someone paid them to fly their dog (by itself) to NY for about $45,000 for some training. No other passengers."

a dog on a private plane
Olga Ovcharenko / Getty Images

2."My dad's client bought a whole block of houses to build theirs. It is so wide that they installed a moving walkway like the ones at airports."

a person on a moving walkway at an airport
Ge Jiajun / Getty Images

3."My brother dealt with many jets that belonged to Middle Eastern princes. One had a full-on surgery room, and there was a guy who traveled with him at all times to be his organ donor. I wish I was making this up."

a private luxury plane
Pinkypills / Getty Images/iStockphoto

4."I was a chef for one back in the early 2000s. He asked me if we could have abalone for dinner. I told him I wouldn't be able to get it to the house in time. He's like, 'Don't worry...I'll get you some.' One hour later, a helicopter from San Fransisco lands on the lawn with the abalone."

abalone on a platter
Plan Shooting 2 / Getty Images/ImaZinS RF

5."I used to work for a billionaire Russian family as a tutor for their daughter. One day we’re in her room studying, and suddenly she yells, 'Daddy's home!' and runs to the window. She’d heard a helicopter and knew is was about to land on the lawn."

a helicopter
Artyom_anikeev / Getty Images

6."Hired someone to take his credit card and create for him (and pay for) a whole fake and very expensive trip to Europe so he could go to Mexico with his mistress during that same time. He was in the middle of a divorce, and he didn’t want any evidence of his affair affecting the proceedings, so he had someone create a whole alibi."

A man who's traveling and using his phone
Golero / Getty Images

7."When rich people want to buy a Jaguar in the UK, they get assigned a special salesperson who is incredibly knowledgeable, they meet in a special fancy office, and special arrangements can be made. This was my friend's job; he had access to things that a normal Jaguar salesperson wouldn't have. Like, he could ring up the manager of the factory for special requests level of access. Well, a Saudi prince wanted to buy this new Jaguar that had been released, so they met up and spent a full day checking the Jaguar out. I believe the final price was something like 125k for the vehicle."

Closeup of a jaguar

8."I used to petsit. I remember a rich person asking me to petsit their cat. There were a lot of TVs, in almost every room. The weirdest was the bathroom. Sorry, cat bathroom. There was a TV playing cat cartoons, an overly fancy litter box, and paintings of cats."

A cat sitting on a pillow
Yelizaveta Tomashevska / Getty Images/iStockphoto

9."I used to work in a private school, and a few dozen of the students were children of the local super-rich from Bay St. One mother started coming into the school every day to visit the uniform shop and buy new uniform items for her child. This went on for a week straight before the shop attendant asked her if everything was okay, the child keeping track of their clothes, etc."

a children's school uniform

10."My cousin was a caretaker for one of those Beverly Hills rich ladies. My cousin didn't know how to cook, so her boss flew a chef from Paris first class and put him up in a hotel. All the chef did was come to her place every day and teach my cousin to cook."

A chief unveiling a dish
Gerenme / Getty Images

11."I worked as the chief officer on their 120-foot-long motor yacht that had six guest suites and four crew cabins. The funny thing is, the owners 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. Best part of the job was I had six days off a week, paid a full salary with benefits, lived on the yacht — so had free room/board with one of the private chefs making us every meal."

Fiji water

12."My dad works in shipping and has a lot of friends who have worked on super yachts. In the '90s, one of his mates got a call up to bring the yacht of a particular Australian billionaire from Sydney to New York, with instructions for it to be anchored in a particular bay at an exact time with a lunch spread for 50 people ready. So they got there and set up the food."

Closeup of a yacht

13."Was a boyfriend of a girl from an obscenely rich family. The sister used to have the nanny (who was sleeping with the husband, but that's another story) fly to Paris in their Gulfstream G550 to buy the newest Hermès bag so she could show it off a few days before it went on sale in the US."

An Hermes storefront
Francois Guillot / AFP via Getty Images

14."I worked for a guy who had some pretty major stakes in the oil business, he was pretty cool, but very weird about his money. His wife owned, like, 100-plus sheep, just because she found it fun. Their entire basement was full of survival supplies for when the world ends. And they had a second house on site, which he used to house his German Shepherds."

Closeup of a dog


Mariya Borisova / Getty Images

15."Four rooms filled floor to ceiling with TiVo boxes. This was 2004, so TiVo was pretty much brand new. I was installing light fixtures in an eight-room, six-bath house in a gated community. The house was...strange. Went in one room and was shocked to see it literally filled with TiVo boxes, but they were all empty. Went in another room, and same thing, at least 600-plus TiVo boxes, all empty. This one hallway had four rooms and two baths, and all four rooms were so filled with TiVo boxes you could barely open the door. Must have been over 4,000 empty TiVo boxes."

TiVo boxes

16."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 Center. It was a gift for a wealthy guy's wife — it was her birthday, and he'd waited till the last day to begin looking for the $22,500 diamond encrusted watch she wanted."

Closeup of a Rolex
Pidjoe / Getty Images

17."I have a good one. I interned for this wealthy CEO in Houston. He was traveling to Mexico and had forgotten his laptop which had all of his stuff that he needed on it. He called the company and asked to have it sent to him; they said it would take three days to ship it even with priority. He paid me $500, plus a plane ticket, and for a hotel for me to stay in for the night to fly his laptop down there so he could have it within 12 hours."

A man on a plane smiling
Izusek / Getty Images

18."I currently work for a multi-millionaire. My boss offered to pay my child support to my ex-wife. He said I am too important to be distracted by my ex-wife. The $1,000 a month comes out his pocket to help me."

Money next to a gavel
Zimmytws / Getty Images/iStockphoto

19."A friend from high school worked a few years as a deckhand on yachts in the Mediterranean, and he said he once jumped in [the water] to get a customer's bag and got tipped €4,000."

A seaside town
Neirfy / Getty Images/iStockphoto

20."I worked as a personal assistant for this millionaire, and let me tell you, the wildest thing I saw was when he made me go out and buy him a new pair of underwear because he said his were 'unlucky.' Like bro, just do your laundry. But hey, when you're a millionaire, I guess you can just buy yourself a new pair of undies instead of dealing with your own laundry. And honestly, that's just the tip of the iceberg. The amount of entitlement and lack of basic life skills these people have is also wild. But hey, they're paying my bills so I can't complain too much."

Calvin Klein underwear

21."A coworker used to be a housekeeper for an ultra-wealthy natural gas tycoon ($100,000,000 net worth), and she said it was the easiest money she ever made. His daughter, who worked for him, frequently flew around the country for business, and this guy would pay my coworker between $5,000 and $15,000 simply to accompany the daughter and keep her company on business trips that lasted a few days. Everything was top of the line luxury and all expenses paid. Private jet, 5-star hotels (she had her own room every time), 5-star restaurants, etc."

Cipriani sign


Smith Collection / Getty Images

22."I'm a driving instructor, and one group rented the track to drive their supercars for the day. At the end of the day, they all partnered up and got into the cars to leave. After they were gone, we realized that they had forgotten their Lamborghini Aventador at the track."

Lamborghini Aventador
Sue Thatcher / Getty Images

23."I used to work for a company that modified aircraft for really rich people. I’m talking 747s, not Gulfstreams. This company had made several aircraft for this one customer, who I was told had purchased a new one solely because his spiritual advisor had told him that one of his current planes was bad luck. He still let his wife use it for her personal travel."

a plane in the sky
Andrew Holt / Getty Images

24."I am an art student working as a gardener. We work in one of the wealthiest areas in my country. Some customers are really eager to show me their collection of artworks that they have hanging on their walls once they find out that I study it. I remember one time standing in a bathroom, in my dirty gardening clothes, and there was a Picasso above the toilet."

a Picasso painting
Vickie Flores / In Pictures via Getty Images

25.And lastly, "A good friend worked for an elite GOP political family. This family actually hired a high-end catering service to cater a food fight for a 7-year-old's birthday party. The staff set up a big tent outside, and then had the nannies lay out special painter's coveralls for the 25 kids at the party. Then, the kids destroyed $6K worth of food. My friend and the catering staff were horrified. The kid's parents all stood around watching and cracking up. The kids and families all got gift baskets worth $2K–$3K each as well. Vulgar, to say the least."

Kids having a food fight


Sean Murphy / Getty Images

You can read the original Reddit threads here, here, and here.

Note: Some responses have been edited for length and/or clarity.