People Who Worked For The Elite 1% Are Sharing What They Saw Behind The Scenes, And Some Of These Stories Are Shocking

Let's talk about the extremely wealthy, the strata of society who basically live on a separate planet from the rest of humanity. Redditor u/AMGBOI69420 asked, "People who work for the super-wealthy, what stuff have you seen?" Here are the real-life Succession moments that employees to the ultra-rich have actually witnessed.

Roman from "Succession" raising his eyebrows.
Roman from "Succession" raising his eyebrows.

HBO

1."I was a male nanny for a rich couple while I was in school. One day the parents asked if I wanted to go to Hawaii. The husband was the COO of a company that was doing an executive retreat there. Instead of finding daycare in Hawaii, they thought it would be easier to pay for me to fly out with them. I would care for the kids during the day and then have my evenings 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 and entertainment. During the days I brought the kids to the beach, took them hiking, and saw some touristy sites. They gave me $5K in 'spending money' in case any of the kids wanted anything. They were a really nice family. They were just very well off, which made spending money on any problem the easiest solution."

Tropical beach with palm trees at sunset in Hawaii.

2."I was working for a well-off family for a summer. The mother was cleaning the kitchen, putting things away and such. She picks up a perfectly good Macbook and says to me 'hey, do you want this? No one uses it.' I got a brand new laptop just in time for college."

—u/kingJoffi

3."My wife is a veterinarian and she went to an estate where you could not see the main house from the stables. You could, however, catch a glimpse of the eight car garage, the swimming pool, the helicopter pad, and the guest house. Oh, and this was their second home."

Horses in a stable.

4."One night, I'm working overtime on the late shift and I get this call. Turns out it's the CEO, who is clearly drunk. He wants someone to drive to his house an hour away and figure out why the internet isn't working. I get there and this guy is clearly completely blasted. I quickly corrected the Internet, and as I'm walking out, he asks me to do a shot with him. I respond, worried about my job, that it might be a bad idea. He agrees and hands me the bottle, tells me to take it home. When I get back to work I look the stuff up... It's a $1,500 bottle of scotch. The next day at work and I get an envelope containing a check for 'emergency tech support' containing $5,000."

Pouring a glass of whiskey on ice.

5."My mom was a maid when I was growing up, and got so much free stuff because of this family. I'd receive clothing with the tags still on, boxes of VHS tapes (I'm old), Gameboys, computers whenever they upgraded, and more. These people were very nice and generous."

u/cenasmgame

6."I worked for a family that spent $40K per year on sports coaching and travel, each, for two kids. They thought was a better option than allowing them to get into drugs or blow money in other destructive ways."

A young boy hitting a baseball.

7."Years ago I worked 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. They built two massive homes on their land, but the problem was that city ordinances prohibited two separate livable dwellings on the same property. Mind you, these houses were a significant distance apart from each other. To comply, they built a freaking wall between the houses, and not some dinky picket fence type of wall — it's a massive medieval-style wall that has a path large enough for golf carts, round towers with merlons and crenels, a gym halfway through, and a massive, all-glass sunroom. They basically just made one massive hallway between the two houses as a solution."

u/Bombxing

8."I worked as one of four full-time groundskeepers at a large estate. We had 46 acres of lawn to mow twice a week in addition to two clay tennis courts, three pools (one for the main house and one for each of the two guest houses), and a 100+ acre private lake with a boat house to maintain. The owner hosted his niece's wedding one summer and paid $350k to have this massive willow tree trucked in and planted by the lake for wedding photos. He then paid 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."

Wedding arch decorated with flowers and greenery.

9."I had a client come into our 3D printing office. A large, industrial 3D printer in the showroom immediately caught his attention. He pulled out a credit card and bought the $250K machine on the spot."

u/robertcboe

10."I had a client who purchased a newly-built penthouse apartment and wanted a jacuzzi on the balcony. To install the jacuzzi meant he would need a structural column in the middle of the balcony. The contractor who built the apartment unit wouldn’t go for it. So this guy just buys the apartment below, approves the column, and installs the jacuzzi. Then he privately sells the apartment below. Problem solved."

Rooftop oceanfront hot tub.

11."My wife is an assistant for a wealthy and powerful man. He's self-made, humble, and uncomfortable in small social gatherings, but he's a lion in a business setting. What I found most interesting is that this guy thinks nothing of dropping five figures on jewelry and other luxury items, but come Friday afternoon you'll find him in the office kitchen taking home all the leftover bagels from the morning."

u/PapaChoff

12."They bought a $300 dollar cashmere sweater for their baby that will fit for 6 months max and likely get thrown up on."

Baby clothes hanging in nursery closet.

13."I was bartending at a fancy party hosted by a very wealthy older couple. Their house had museum-quality art on display. 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 about the rabbits. Turns out, the owners bought them as a garden feature and the rabbits were just decorations."

u/CindeeSlickbooty

14."My mom worked as a house cleaner for a really rich family. The homeowner was a TV and movie producer for a couple of well-known shows and movies. On my mom’s first day of work, the woman was showing her how she liked her laundry done and insisted all of her dirty underwear be thrown away instead of washed. My mom reconfirmed with her a few times to make sure that she understood her correctly. She only wore a pair of underwear once before tossing them."

A full bin of laundry.
Robert Reader / Getty Images

15."I worked as a caretaker and got paid six figures for keeping up a multimillion-dollar house that gets used for just two lousy weeks a year."

u/TheNoisyNomad

16."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 decided to just buy the whole marina."

A yacht parked in a marina.

17."You weren’t allowed to hand my boss or his family anything that had already been opened or used. That bottle of sunscreen that was only used once — don’t even think about it. Everything had to be brand new, so many things around the home were only used once and never again."

u/TheMysticalPlatypus

18."I installed a custom pool in a billionaire's home. He ordered a custom iridescent tile, which cost $440K in material alone, plus another $400K to install it. I informed him that it was a special order and couldn't be changed once placed. He approved it on the spot and I installed it. In the end, he didn't like the look so he tore it out and replaced it. When all was said and done he had spent about $2.5 million dollars on his pool tile and he didn't bat an eye."

A pool in a modern home.

19."I work as a private chef in the New York, New Jersey, and Connecticut areas for high net-worth families. I've seen a room dedicated only to silverware and another just for serving platters. I've seen a dining room table that cost $250K and a $20K+ range in a private home. Many of these families give me all-expenses-paid trips to Aspen, Cabo, the Hamptons, Jackson Hole, etc... just so they don’t have to worry about cooking their own meals while they're away."

A man preparing gourmet food.

20."I have a client who buys all his neighbor's homes when the opportunity arises just to knock them down. The homes that are being leveled are all $2+ million, 2+ acre, 4+ bed, 3+ bath houses that the majority of people would give their left arm to live in."

u/Duh_Dernals

21."I did carpentry for a summer and worked in huge mansions and amazing houses. I was once working in a house where the kids were watching a TikTok video about what poor people eat. It was all about how to cook things like 10-cent ramen, hot dogs, etc. The kids laughed and thought it would be fun to try to make all the meals in their kitchen. They hated it all. Meanwhile, this was the food I grew up eating my whole life. That same packet of ramen was the same as the dinner waiting for me at home."

Instant ramen in a pot.

22."I work in luxury retail and had a client who would buy three of the same item — one for his wife, the other two for his side pieces. He said he'd buy the same things so he didn't forget who he gave which item or get confused and blow his cover."

—Anonymous

23."The guy I work for lives on a lake and his wine cellar is in a different building across the lake. He takes his boat across the lake to access his wine cellar. He once threw me a bottle of wine and said 'good thing you caught it because the bottle is worth $10,000.'"

Wood boat at dock.

So, what's the wildest thing you've seen or experienced while working for or interacting with the super wealthy? Tell us in the comments.