Contrary to what the media portrays, working for the rich isn't all bad. It's quite interesting and insane. These former employees of very wealthy people share the most mind-boggling thing they’ve witnessed on the job. Content has been edited for clarity purposes.
"I used to do pool and spa maintenance in my 20s. I worked on one property with a mountainside, 10 bedrooms, and 14 bath mansion, with a saltwater pool, tennis courts, guest mansion, and a servant's house that had four bedrooms and five baths. The property had so much more stuff, but that wasn't the crazy thing.
I worked on this property for two years, year-round, five days a week, and not a single person was ever there. The middle-aged, single woman that owned it, lived in a city about four hours away and just didn't come to the property, because she was so busy with work. A multi-multi-multi-million dollar compound, just empty. All the time.
Finally, after two years, I got a call from my boss on my day off. He asked if I could go to the house to put some pool floats away. He apologized, because it was my day off, but said the owner would pay me 500 bucks to go put them away. I was confused as to why there were even pool floats out anyway because nobody was ever there, but I figured why not. It was five hundred bucks for 10 minutes.
I showed up at the house and the woman's adult children were staying at the house with about 10 plus kids between them all. They were having a massive pool party/cookout.
I awkwardly walked up and said to one of the parents, 'Sorry, it must have been a mistake. I was told to come put pool floats away, but you're obviously here so I'll leave.'
Presumably, the woman's adult son said, 'Oh, no. We're getting ready to leave. You can take them.'
Then he instructed the kids to push them towards me. I literally grabbed one inner tube float and four pool noodles, brought them 10 feet into the pool house, and put them away. I, confusedly, said they were all set and went to leave. The son thanked me and handed me a folded mass of 20 dollar bills. It was 400 bucks.
I was expecting 500 bucks from my boss for payment, but I figured 400 cash was still overpayment, so I didn't mention it. The next day at work, my boss gave me 1,000 bucks. I told him the son had already paid me 400 bucks, which was fine. He said the son told the woman how great a job I did, so she wanted to pay me 1,000 bucks instead of 500 bucks and the 400 bucks was a tip from her son.
All for 10 minutes of work. She actually called my boss the next day to ask if she should reimburse me for gas since it was 15 minutes from my house. I told him that I was all set."
"I worked for some of the richest people in Maryland and the one thing that stood out more than others was this doctor I worked for in Montgomery County. It's one of the most affluent zip codes in America.
Anyway, this guy owned a ton of offices around the Washington DC area, tons of employees, and associate doctors. The guy was seriously loaded. His huge garage was full of super expensive cars like multiple Ferraris, art collection, cellar, and the works. I used to do IT work for his medical practice and manage all the servers and stuff, and occasionally went to their house because I was the lead admin.
I once was working in his house and was walking around upstairs where the bedrooms were. I kid you not, this guy was laying in bed being fed by an assistant. Like he was literally laying in bed while someone hand fed him, and not like grapes but a regular meal. It was so weird. Imagine someone feeding you a full meal like a steak and spoons of soup and salad and you never used your hands. It was like an adult being fed like a baby. I've never seen anything like that before and that was what popped into my mind, like a dictator or something who demands to be treated like a literal king. There was nothing intimate about it.
Keep in mind this was a man in his 50s who was in fine physical shape and didn't need a caregiver. It was just pure opulence.
Then one time I was working in the kitchen area and his young son, probably late teens/early 20's came walking past me and stunk to high heaven of pot (which I'm totally cool with and we joked about), he went to the kitchen and poured himself an adult beverage and went back to his room. It was only nine am. I thought it was hysterical. He was a cool kid from my interactions with him, probably just figured 'my dad is rich, so I don't have to worry about anything.'"
"I worked for UPS for a hot minute as a driver helper and got to see some interesting things. The one driver had the rich of the rich route where the mansions were worth tens of millions around the Ann Arbor, Michigan area, like the Ford Mansion, Lloyd Carr, and Dave Brandon.
Anyway, I got to see Dave Brandon's mansion. It was gated, deep in the woods, and absolutely huge. The driver who was a 33-year-old UPS veteran, told me these guys with these huge mansions like this, don't live there by themselves. Sometimes they don't live there at all. They move their entire extended families in there like their parents, sisters, brothers, aunts, uncles, and cousins. And they all live off the rich guy's dime, ordering whatever they want and whenever they feel like it. I think we delivered 30 or 40 packages there that one day.
We delivered to a smaller but still huge house with an extremely long and wooded driveway. The driver was cursing about how much he hated these people because they always parked this huge boat in the only possible turnaround point in the driveway. So he went in backwards and floored it. Maybe 40 miles per hour backward, about 250 yards of bends, straights, and he drove it absolutely perfectly, never driving off or missing the driveway.
We got to the house and he needed a signature. He handed me the package and said he'd get the signature, hand them the package, and we'd go. Well, we got to the door, and this late 40s or early 50s man, kind of a Rick Moranis/George Costanza type of built, short, extremely thick glasses, balding, but very skinny man was standing in the front door with a lab looking dog on a leash.
The driver said, 'Good evening! We just need a signature and we'll be on our way.'
The guy said, 'No. I can't I have to take my dog out first.'
This guy was fully prepared to make us stand there and wait for his dog to do whatever business before just signing his name and letting us drop the package by his door.
The driver said, 'No, we just need your signature. And then we'll be on our way and you can walk your dog.'
The guy said, 'Fine'
He took the two seconds it takes to sign your name and we dropped off his package and left.
That left an impression on me. That guy valued our time so little it was worth less than his dog's turd. Like he was in his own world, while we weren't delivering 300 stops just before Christmas."
"I started working for this couple's company and managed to be accepted by their two Irish Wolfhound dogs, which the owner said had never happened before with anyone but him and his partner. As a result, they hired me to come over after work to brush, walk, medicate, and feed the dogs as well as come over, and take one of their high-end 'spare' cars to pick up bulk orders of diced mutton (we're talking 100 kilograms plus at a time) from a butcher they liked on the other side of town.
They gave me the keys to their Heritage listed home in a posh area while they were away, so I could take care of the dogs and sleepover if I wanted. They were both absolutely lovely people, filthy rich, and always treated me with great respect and friendliness.
They bought a brand new Toyota Troop Carrier for the dogs to travel in, as two Wolfhounds would not fit in his Porsche or her Mercedes. I'd load the dogs into the Troopy, and we'd go to a fairly local beach so the dogs could run and play to their heart's content once a month, splashing around in the sea. Then I'd bring them home, happy and tired, wash them, feed them, tuck them in for the night, and return to my own home. The dogs slept on a huge, fantastically expensive leather sofa on the back deck, that had been replaced with a newer smaller version inside the house.
They were always renovating, and would ask me to dispose of the old furnishings. I asked if I could use some of them for myself, and was always told 'Oh yes, take what you want, and dump the rest.'
They only wanted the stuff gone, and I had their blessings to sell off and keep the proceeds. For someone earning less than 50K a year, this was a Godsend, and my tatty old house benefited from their cast-off rugs and furnishings so much."
"My cousin worked at a higher-end, worldwide known hotel chain, and he worked at one in a large United States city. A couple of years back, a random guy came up to him and asked him for a dinner suggestion and said the price wasn't a concern.
My cousin kept up with what was trendy in the city and gave the guy a suggestion. The next day the guy asked for him by name, gave him 100 dollars, and said the dinner was amazing.
Then he asked, 'Now where should we eat tonight?'
My cousin gave another suggestion and the next day, he got another 100 dollars from the man. Only this time, his manager saw this go down.
Then a few minutes later, his manager asked, 'Do you know who that is?'
My cousin replied, 'Nope.' Then the manager told him.
I won't say the name, but let's just say old money and probably in the 100's of millions net worth. Cool story, huh? Well, a couple of months later my cousin went to work one day and was told this person would be calling at six pm, and only wanted to speak to my cousin.
The conversation was short, basically, a 'We're in town next month for four nights, book the six of us for four wonderful dinners. We trust your opinion.'
He was given an email for basically their family assistant, and to let that person know the plans. The family arrived, said 'Hi' to him as they checked in, and said they were looking forward to their dinners. Four days later upon checking out, the man handed him 1,000 dollars 'for his wonderful local knowledge.'"
"A colleague of mine, who used to be a bouncer at this club that were the place for rich kids to hang out at.
Now he saw a lot of the typical 'Look at me! I’m so rich!' shenanigans, like buying the most expensive drinks in the club and telling the bartender to pour it down the drain, wearing several Rolex watches and handing them out like candy to strangers, or tipping the staff thousands of dollars. Occasionally after telling them to do something embarrassing like barking like a dog but the thing that stuck with him the most was just how far removed these kids were from reality.
Case in point. One night he had door duty and didn’t let a kid, who was clearly under the influence of something into the club. So what did the kid do? He decided that it was a good idea to take a swing at him.
Turns out that it wasn’t a good idea, something he quickly found out after he was lying facedown on the ground, handcuffed with his hands behind his back.
But even then the kid didn’t seem to be too worried, he just kept saying, 'It’s alright. Just call my dad, he’ll sort this out,' over and over again.
He seemed incapable of realizing that he was actually getting arrested for attempted assault. Not even when the police finally arrived and put him in the back of their car did he seem to fully grasp the fact that he was actually in trouble and that his dad wouldn’t show up, wave a wand, and make this all go away."
"I used to install DirecTV in wealthy areas of an east coast city in the United States. While I tried to give customers options on where I could install the satellite dish, I had to get a good line of sight for it to work properly, so sometimes the location options were limited. One rich lady’s house (gorgeous house right on the beach) I only found two good spots for the dish.
It could either be on a pole in the middle of her backyard or on the corner of the roof. She definitely did not want it in the middle of her yard, however, the only problem was that she had a metal roof and we used specific mounting hardware for that. And we happened to be back-ordered on that hardware for a few weeks out. When I informed her of this, she got visibly upset that she’d have to wait that long to get her cable up and going. I apologized many times and told her she’d need to reschedule a few weeks later and I left.
Three days later, I was looking over my work orders for the day and I noticed her name and address.
I was like, 'Wow' and bet she thought she was getting a different installer who she could try to convince to give her a different answer.
I was wrong. I pulled up to the house and it had a brand new shingle roof. I did the install on the roof."
"When rich people want to buy a Jaguar in the United Kingdom, 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 Chris'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 Arabian prince wanted to buy this new Jaguar that had been released, so they met up and spent a full day inspecting the Jaguar out. I believe the final price was something like 125k for the vehicle. Then came the decision for color. At the time the factory had 16 different color choices for this model. The Prince asked if he could sleep on it as it was getting late and almost time for dinner/prayer.
My friend Chris said, 'Of course.' And they set a time to meet the next morning.
The next morning the Saudi Arabian prince said, 'I figured out an acceptable solution to my color dilemma.'
Chris asked, 'And what would that be?'
The Saudi Arabian prince replied, 'I'll order one of each color.'
And my friend Chris was like, 'Oh, well of course.'
They quoted delivery time and the Saudi Arabian prince was fine with it and asked for his options.
Chris presented with ocean travel options to which the Prince said, 'What about air cargo?'
Chris thought maybe they'd do one or two by air cargo and the rest by boat, but the Prince was like, 'No I want all 16 vehicles loaded on a plane, and flown to Saudi Arabia.'
So that's the story on how 16 of the same Jaguar with different colors ended up being flown to Saudi Arabia all in the total cost was around two point five million pounds.'
"A Russian guy who I sometimes worked for, bought a nice house in a pretty nice area of the French Riviera (Mougins). He didn't even visit it before buying, and just judged he liked it on pictures. He paid 11 million euros for it. But when he arrived, he thought the view wasn't perfect because of another house that was in the way of the sea.
To me, honestly, it was barely there and didn't even mask the sea. So he sent his lawyer there to make a four million euro offer to the owners. But they declined so he doubled the offer, and they declined again. So he doubled again, and this time they accepted to sell.
He had that house destroyed the very day he got the keys and had an underground parking lot built instead, for the cars he wouldn't be using much.
So basically the guy paid that distant house more than the one he was planning to spend his summers in, just to have it disappear because it kinda annoyed him. And when he told me the story, he was laughing the whole time."
"Some kids have whole plans and strategies they practice to prevent being kidnapped or harmed by crazy stalkers. One kid I worked with was the kid of a big Hollywood player. And people would stalk the kid in an attempt to get to the parent.
So this nutjob wielding a screenplay broke in and cornered the kid. Here I was thinking I was going to have to throw myself physically between them but the kid dove into a nearby dog kennel first and locked himself in. He couldn't get out but the nutjob couldn't get in either. So the nutjob just threw the screenplay at him into the kennel, meanwhile, I had called the cops.
I was so impressed by the kid's quick thinking and asked how he got the idea. He said that he always kept an eye out for a way to escape, so when he saw someone he didn't know approach, he would get ready to run.
I felt awful that this kid had to live like that. If I hadn't seen it happen myself, I would have thought it was just paranoia."
"My cousin was a caretaker for one of those Beverly Hills' rich ladies. While the lady was alive, my cousin didn't know how to cook. So she flew a chef from Paris first class and have him set up in a hotel. All the chef did was come to the lady's place every day and teach my cousin to cook.
While they were watching tv, my cousin remarked that the newest Benz on the commercial was nice. When he came to work the next day, she bought it for him top of the line with all the bells and whistles. Ever since that day my cousin had to be careful about what he said to her. They returned the car.
Also, my cousin has a daughter. His daughter has a trust by the lady and could go to any school from elementary to university fully paid.
Sadly the old lady died a couple of years ago. She left them about 20 million dollars. I think they were fighting the grandkids at court because of it."
"I did IT work for a tiny little private company with the owner, his brother, and me. A guy called because his new personal computer wouldn't turn on and since it was like three pm, he was 100 percent willing to pay for me to drive five hours one way to get it working because he wanted to play games that day.
Fine, I went on the five-hour road trip (one way) and the address was this huge mansion. At first, I 100 percent thought I was in the wrong place. I used the intercom at the gate and nope that was the right place.
The guy and his wife were really cool and the dude had built his own gaming rig. It was absolutely over the top, I had never even laid eyes on hardware that expensive before.
Found out, he never turned the power switch on his PSU (power supply unit). Basically, he paid the base rate of 1,400 bucks for me to come out there to flip a switch. I also installed his graphic drivers but that was technically free, and then gave me 5,000 dollars in cash as a tip all because he was excited to play league of legends on his new personal computer."
"I worked at a low-end retail store and had a rich woman spend 1,500 dollars on clothes. She didn't try any of them on, and she filled two shopping carts. As I was ringing her up we had a long time to chat because the transaction took so long, and she told me that she hated clothes shopping. She would occasionally just buy a bunch of random stuff and put it in her closet, and anything she didn't like as she was getting dressed, she would simply throw away.
I also just want to add that this customer was extremely unpleasant and rude to us lowly cashiers. She bragged about the limit on her credit card and how much money she had. This made me think she was newly rich, or maybe only moderately rich."
"I worked for a rich Chinese lady who told me and her CFO (chief financial officer) to hire 30 English teachers and start an NGO (non-governmental organization). We all flew out to a poor part of China and helped hundreds of gifted kids learn English so they could pass the foreign language portion of the gaokao (their SAT). We gave each of the students' thousands of dollars to pay for college tuition.
Why did she do all this?
To help her daughter study in the United States, being the nominal head of the charity with her college application. The organization was dissolved when she was accepted into Yale."