Rich People Horror Stories
There are some rich people out there who genuinely think their wealth makes them better than everyone else. They act as if their net worth is a personality trait. Unfortunately, it’s the good, hardworking people who often end up on the receiving end of their arrogance. The following horror stories prove that having enough money can really change you, and not for the better, either…
1. Free Drinks
I watched a customer order the most expensive wine in the house, pour two and a half glasses, take a sip, and send it back—knowing full well they are paying for it. To those folks, I say thank you! Nothing makes employees happier than free (expensive) booze.
2. One Color Too Many
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 Chris’ job. He had access to things that a normal Jaguar salesperson wouldn’t have, like ringing 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 customizing the Jaguar. The final price was something around 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 it was almost time for dinner.
Chris, of course, said yes and they set a time to meet the next morning. The next morning the Saudi prince said something like, “I figured out an acceptable solution to my color dilemma.” To this, Chris asked, “And what would that be?” The Saudi prince’s response was so outrageous—it’s unforgettable. He said, “I’ll order one of each color,” and Chris responded, “Oh, well, of course.”
They quoted the delivery time which was okay with the prince who then asked for his delivery options. On being told about ocean travel options, he asked about air cargo. Chris thought that they could do one or two by air and rest by boat. But the prince said, “No, I want all 16 vehicles loaded on a plane and flown to Saudi Arabia.”
So that’s the story of how 16 of the same Jaguar, in different colors, ended up being flown to Saudi Arabia. The total cost was around 2.5 million pounds.
3. Send it Back
In this case, I was the weird rich person. I ordered the Waygu at Cut in LA a few years ago. I want to say the steak was $200-300. They asked me how I liked it and I said it was okay, which apparently wasn’t an enthusiastic enough response. They practically insisted I send it back and order a different steak.
4. Hark, The Sound Of Their Arrival
I used to work for a billionaire Russian family as a tutor for their daughter. One day we were in her room studying when suddenly she yelled, “Daddy’s home!” and ran to the window. Did she hear him pull his car into the driveway? Not even close. Nope, she’d heard a helicopter and knew that it was about to land on the lawn. That’s how she knew that her daddy was home.
5. Remove the Red
My former boss, who was insanely wealthy, used to stay in presidential suites and would have any and all forms of the color red removed. He was a high roller at several casinos and they made special chips just for him as a substitute to red chips—all for a bizarre reason. He hated the color red because when you’re losing money, you’re “in the red.”
6. A Job Well Done
I used to do pool and spa maintenance in my 20s. During this time, I worked on one property with a mountainside, 10-bedroom, 14-bath mansion, with a saltwater pool, tennis courts, guest mansion, and a servants’ house that had four bedrooms and five baths. The property had so much more than this, but that wasn’t the craziest part.
For about two years, 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 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 who cares; $500 for 10 minutes.
I showed up at the house and the woman’s adult children were staying at the house with over 10 kids between them all, and 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, but I was told to come put pool floats away, but you’re obviously here so I’ll leave.”
But, instead, I got the weirdest response ever. 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 bills. It was $400. I was expecting $500 from my boss for payment, but I figured that $400 cash was still overpayment for what I had done, so I didn’t mention it. The next day at work, my boss gave me another $1,000. I told him the son had already paid me $400, which was fine.
He said that the son told the woman what a great job I did, so she wanted to pay me $1000 instead of $500, and the $400 from yesterday was a tip from her son. 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.
7. You’re on This Floor?
During our honeymoon, my husband and I came back to our (very nice) hotel from a day full of hiking looking like homeless people. We were waiting for the elevator with another couple who were both giving us the side-eye. Once on the elevator, the couple pressed the bottom for the top floor, which was the same as ours.
After about 30 seconds of silence and side-eyes, the woman turns to me and says, “You need to press the button for your floor” in a condescending tone. I told her our floor was already selected—but then it got worse. She actually had the audacity to say, “You have a suite on the top floor!?”
8. Artful Contemplation
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, with my dirty gardening clothes and, lo and behold, there was a Picasso hanging above the toilet.
9. Get in Line
I had a lady yell at me a few times that I was standing in the line for business passengers only and that I needed to get into the correct line because I obviously couldn’t afford business class with Emirates. People are so prejudicial and rude it blows my mind.
10. A Lifetime Supply
Back in the nineties, I was friends with a very wealthy international student. We were out drinking as a group, under the influence enough to get kebabs on the way home. We each got our kebab, and the international student was the last one to be served. He was chatting away to the store owner while the rest of us waited outside.
They kept chatting and chatting, and by now, we all had finished our kebabs and we were still waiting for him. He finally shook hands with the store owner and walked out with a really big smile. We asked, “What was all of that about?” His response floored us: “I liked the food, so I bought it.” Turns out that he bought the whole restaurant because he liked the kebab he just ate.
11. We’re Miners
I work in mining and I fly to and from work. One of the company’s perks is membership to the business class lounge. On one of my breaks, I was going skiing with a group of friends. A guy and I were queuing for drinks and chatting. A bunch of miners entered the lounge and we began very sarcastically joking about how awful it was they let smelly people “like them” into our lounge.
The woman in front of us turned around to agree and ranted about horrible miners for a good few minutes before asking us what we did for a living. We both happily replied, “We’re miners.” She stopped speaking to us after that.
12. Hitting The Bar
Through past work, I met a guy who asked if I would be interested in some extra bar work at his house occasionally. I said that I absolutely was, happy for the extra cash and change of scenery. So, for the next about four years, I would turn up at about eight, along with a few tools of the trade that I favored, and head through the beautifully disguised secret door.
This led down to what amounted to a self-contained underground house with a fully stocked bar, ice machine, etc., where I would make cocktails for the participants of these periodic “special parties.” From about nine, couples, some in little masquerade masks and little else, would arrive and mingle and then vanish and reappear, with a different thirst to quench.
I worked for barely five hours; it was hardly even work. It was an insight into a world I would never know. Afterwards, he came over, fully dressed, thanked me and gave me an envelope with cash. He also mentioned that I may have recognized a few people and that they would appreciate it if that fact remained undisclosed.
I assured him that I hadn’t saw a thing, like I was in some terrible movie. My five hours of work made me more than I make in a week. Next day, I got a call, asking if I could come over, just for a few minutes. I was off, so I headed over. He greeted me at the door, brought me into the hall, and said that the guests wanted me to have that, and hoped they would be seeing me again.
It was another envelope with the same amount as before. Every few months for the next four years this was repeated. Until I couldn’t do it anymore. I can’t describe why, but I would dread the call. I think being part of something that was so throwaway to them while I was living off a bag of change was, at times, just depressing.
13. Economy’s That Way
My parents have been pretty successful in the last decade or so. However, they’re very humble and hardworking people. My dad has dark skin and wears cheap sweatpants 90% of the time. He and my mom treated themselves to an upgrade to first class on a vacation. When my dad was taking his seat, another passenger tapped him on the shoulder and told him “economy was further down the plane.”
I reckon she was lucky mom didn’t slap her.
14. A Potty Decision
A client went on vacation to France and saw a small one-bedroom one-bath cottage with an earthen roof in the mountains of some village they stayed in. They thought it was “cute and quaint” and bought the cottage off the owner in France. They then proceeded to turn around and have it completely disassembled, loaded into sea containers, and shipped to America.
Upon arriving here, it was completely reassembled. It looked exactly like it did in France. Sadly, they now use it as a “potting shed.” The walls were made out of stone and were, basically, the rocks the farmer had picked out of the field who knows when. Every stone had to be numbered and reassembled exactly like how was in France.
If that’s not the absolutely “no thoughts given about money,” I really don’t know what is.
15. Who Are You?
I worked at a nice restaurant in downtown Portland, and one day a lady called to make a dinner reservation for a large group. But first, she starts asking all these questions about “security” (we had none) and how I thought the staff and patrons would handle a “celebrity” dining there. Is there enough space to be private? They like to be private. Would it be okay if they brought their own security, to stop people from taking pictures and such? But of course, she couldn’t name names.
I rolled my eyes, told her whatever they need to do, and booked the date and time. Yes, I was super curious who it would be, and stayed past my shift to see who walked through the doors when the big night came. The group arrived, and it was…no one. Not one of us who worked there recognized a single member of their party. They sure acted like they were someone, but all we saw was a loud group of 20-somethings.
They actually did bring a “bodyguard” who stood in the corner with sunglasses on the whole time. The only attention they got from other diners was the occasional side-eye because they were being rude and obnoxious. Shock of shocks, they treated our staff horribly and tipped even worse. Will never know who that person thought they were.
16. A Meal To Remember
A cousin works at a branch of a higher-end, world-renowned hotel chain, in a large US city. A couple of years ago, a guy came up to him and asked him for a dinner suggestion and said the price wasn’t a concern. My cousin keeps up with what’s trendy in the city, knows some owners and such, and gave the guy a suggestion.
The next day the guy asked for him by name, gave him $100, and said that the dinner was amazing. He went on to ask where they should eat that night. Another suggestion and the next day, another $100. Only this time, his manager saw this go down and, a few minutes later, asked my cousin, “Do you know who that is?” He didn’t.
It turned out that he was a well-known old money guy. But that was just the beginning. A couple of months later, my cousin went to work one day and was told that this person would be calling at 6 pm, and only wanted to speak to my cousin. The conversation was short, basically along the lines of “we’re in town next month for four nights, book the six of us four wonderful dinners, we trust your opinion.”
He was given an email for 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, while checking out, they handed him $1000 “for his wonderful local knowledge.”
17. Silver Spoon
I don’t even work at that nice of a restaurant, but last month I got chewed out over the phone because some lady left her baby’s actual silver spoon on the table. We didn’t know where it was, so obviously one of us had stolen it.
18. What’s Mine Is Yours
I had a classmate whose father or mother was extremely rich from family money. But they were all amazing people. There was another girl in our class who was really nice but came from a poor family and worked 6o hours a week for three months in the summer. One day, he dropped her MacBook, and my rich classmate came to her rescue.
He just came up, gave her his MacBook, and said he would just get a new one after school and his parents wouldn’t care. Pure generosity. There was no social media chest-thumping going on. He was a stellar dude spending his parents’ money, but only on stuff for other people and in a nice helpful way. He also gave all the guys in class a suit for graduation.
Many of the people were talking about renting and he told everybody he knew a place to rent real nice suits. We all went there and rented a suit each for 100 euros or so, everything included. When we went to return it, we found out they were all paid for by this dude. His thought was that renting a suit is stupid, but buying a suit is expensive and now we had the best of both worlds.
The last thing I heard, he bought about 10 PS5 from scalpers and sold them for retail to kids in the neighborhood.
19. Got You Covered
I’m a soldier. We held an annual ball at a local marina hotel restaurant and had it reserved for the evening. The host grabs our commander a few hours into the event and says, “There’s a guy, he’s a daily regular for the past 15 years. He wants to grab his usual nightcap. Do you mind?” The commander agrees and the gentleman comes in, sits at his spot, and proceeds to enjoy the show while “occasionally” covering costs for those of us grabbing drinks.
He did this in exchange for a little small talk about what we do. After about three hours, he grabs his coat and heads out. He then returns about an hour later, and proceeds to shut down the joint with us, still covering drinks “here and there.” The next day when I came in as part of the clean-up crew, the host gave me the breakdown after I asked how long their charges normally take to process, as I hadn’t seen my tab hit my account yet. Then they told me something that knocked me off my feet.
Turns out the regular owned a chunk of the marina and covered a combined $12,000 tab as “thanks to the servicemen and women.” I had a tab of over $450 waiting on my card, completely covered that night. It was glorious.
20. Suiting Up
I used to be a housekeeper for some of the wealthier people in my city. The best thing that I have ever seen is the wife of a wealthy man who had custom suits of armor made for her cats. That was not all though. She had them displayed along with tiny suits of armor for mice. Yes, she had those custom made too along with the armor for cats.
21. Two Different Worlds
I got back from a four-day trip to Hawaii. The first two days, we stayed in a modest hotel near Waikiki and last two days, we splurged on a fancy resort hotel because we thought it would give us a nice break. At the first hotel, every time we got in the elevator, other guests made small talk, wished us a happy new year, etc. In the fancy hotel, so many guests did the “rich snarl” where they would stare at us in disgust.
We saw so much bad micro behavior. But the staff were super nice and I felt for all the nonsense they must deal with.
22. Hitting The Roof
I used to install DIRECTV in wealthy areas of an east coast city in the US. While I tried to give customers options on where I installed the satellite dish, I had to get a good line of sight for it to work properly, so sometimes the location options were limited. At one rich lady’s house—a 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. The only problem was that she had a metal roof and we use specific mounting hardware for that. We happened to be back-ordered on that particular 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 that she’d need to reschedule a few weeks later, and then I left. Three days later, I was looking over my work orders for the day and I noticed her name and address again.
I thought, “Wow. I bet she thinks that she’s getting a different installer who she can try to convince to give her a different answer.” I was wrong. When I pulled up to the house, I couldn’t believe my eyes: She’d completely re-shingled the roof. This lady must have been desperate for some cable. Luckily for her, because of the new roof, I was able to install the satellite dish.
23. A Gift for You
I operated a premium chain restaurant in Canada. One day, this Indian gentleman started coming in, at first by himself. On the first day, he spent $200 on wine and tipped $1,000. The next day, he did the same again. When we saw him the third time, I had servers fighting over him. One evening, he had too much wine and the busboy made the mistake complementing his watch. Mr. S. takes off his Tag and gives it to Brad.
The next morning, Mr. S comes back to get his car and asks if Brad is there, I say yes and go get him. Brad knows what’s up and is removing the watch as he walks over to Mr. S. Mr. S says, “Brad I’m really sorry about last night and for giving you my watch.” Brad is chuckling as he removed the watch and says it’s no problem. He also reassured him that he was just holding the watch until Mr. S returned.
The next thing Mr. S. said, I could not believe. “Brad you don’t understand. I’m sorry because it was very rude of me to give you a used gift.” And at that moment, Mr. S pulled out a box with a brand-new Tag Heuer inside and handed it to Brad.
24. A Silken Flight
I used to work for a company that modified aircraft for really rich people. I’m talking about 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.
To me, one of the most exquisite features of these planes wasn’t the gold-plated everything or the rare wood veneers, it was the silk carpet. That stuff cost over $1,000 per square foot and felt like walking on a bed of angel feathers harvested in the most inhumane way possible. Granted, these guys didn’t deck out the whole plane, just their personal areas, but yeah…silk carpet.
25. Take Your Pick
Back when I was a waiter, there was a woman and her friends at one of my tables. The woman asked for a can of Coke. When I brought their drinks and gave the woman her Coke, she looked at me and said “Excuse me, honey? I asked for Fanta, not Coke”. So, I apologized, wrote it onto my notepad, and went back to get her a can of Fanta.
I brought it to her, and again, she turned to me and said, “I didn’t ask for Fanta, I asked for cream soda.” By this time, I was getting a bit annoyed. But, I went back and got her a cream soda anyway. And surely, when I returned to her table, she did the same thing again. “I asked for Sprite. Should I call the manager?” So, for the last time, I smiled and I went back to the kitchen and packed one can of each: Coke, cream soda, Fanta, Sprite, Pepsi and Sparberry soda.
I put them into a small plastic box and took it all to her and said, “Here you go, miss. Take your pick.” She looked offended and almost made a scene. She started lecturing me about how I’m incapable of getting the simplest order right and that she wants to talk to the restaurant’s manager. I told her that I can call him and that I’ll show him all the soda types I wrote on my notepad that she asked for, and we can get his opinion on the matter.
She turned and took her Sprite out of the plastic box and said, “Just leave it.” Her friends were silent throughout the whole ordeal and none of them gave me any issues further on. I didn’t receive a tip, as expected, but I shrugged it off.
26. Game On
I did IT work for a tiny little private company which was basically the owner, his brother, and me. The guy called because his new PC wouldn’t turn on. It was about 3 pm and he was fully willing to pay for me to drive 5 hours one way to get it working that day because he wanted to play games that day. So, a 5-hour road trip later and I pull up to this sprawling mansion.
I thought that I was in the wrong place. Still, I used the intercom at the gate and found that this was, in fact, the place. The guy and his wife were really cool and the dude had built his own gaming rig, which was absolutely over the top, I had never even laid eyes on hardware that expensive before. Turns out that he had never even turned the power switch on his PSU on.
He still gladly paid me the base rate of $1400 for me to come out there to flip a switch. I also installed his graphic drivers but that was technically free. And the most mind-boggling part of all? He also gave me $5,000 in cash as a tip all because he was excited to play League of Legends on his new PC.
27. Brand New Bag
I worked at a grocery store in uppity Gold Coast Chicago when I was a teen. We sold soup for lunch and when bagging them, we put it in a paper bag followed by a plastic bag to make sure it was secure. This one lady buys soup and I proceed to bag it. She then says, “No, I’ll just put it in my bag.” I asked if she was sure. Mind you, she has a Louis Vuitton bag that looks brand spanking new.
She took it on its own anyway. 15 minutes later, she comes in raging that she has minestrone all over her Louis Vuitton and demands to speak to a manager.
28. Christmas Spirit
I was invited to a Christmas Dinner by an extremely wealthy Korean family while I lived in Seoul. They were a very nice family but I think, in hindsight, that they wanted to show their friends that they had foreign friends like me. The wife had everything catered and the home professionally decorated. It felt like we were in a department store.
There were multiple Christmas trees, a working train set, staff handing out appetizers on plates, etc. It looked like she had studied Christmas movies from the USA and copied everything. The dinner was served on an absurdly long table with two huge, perfect-looking oven-roasted Turkeys and all of the trimmings. I was later told that Koreans don’t like turkey.
These ones were just for decoration and would be thrown out later. We ate Korean food. The family said that I could take a turkey home and that the caterer would drop it off with anything else I wanted.
29. To Each Their Own
I work at a luxury property in California, and we had the co-founder of a large payment processing company stay with us a while back. He only liked to sleep on his own bed, so when he woke up that morning, he paid a team to load his bed into a truck and have it delivered to our property. We then removed the bed in his luxury suite and set up his bed that his team had brought us.
He only stayed with us one night and the process was done to send the bed back home the following day. It kind of blew my mind that he went through all that trouble, just so he could always sleep on his own bed. To each their own, I guess!
30. Just Redecorating
I have been working for the super-rich for some time and the craziest thing I’ve seen was a brand new 90-meter multi-million-pound yacht built in the Netherlands. Its maiden voyage was to Antibes in France. The owner came on board and left after a few hours. The next week we were sent to Genoa, Italy, where all the bathrooms on board were ripped out and upgraded.
I’m talking about brand new marble sinks, showers, floors, and lobbies all crowbarred out. I’m talking about tons of brand-new polished marble just chucked to the wayside. The new marble colors and patterns arrived in the weeks following. There’s ‘feed me money,’ there’s ‘in your face money,’ and there’s ‘it’s not even a thought money.’
31. Good Service
I worked in a fancy lobster restaurant on the water with a lot of outdoor seating. These very wealthy people come to eat and demand a table outside for dinner. Now, it’s just before sundown in the middle of summer in Maine and we’re on the water, so mosquitoes are definitely not scarce. These people sit down and order a $200 bottle of wine, a massive lobster each, and some appetizers.
They seem to enjoy the meal up until the sun sets and the bugs come out. These people were not happy and started complaining about it. They also complained about the “stupid restaurant not paying for mosquito spraying.” The waitress gets a couple of candles to light and asks if they need anything else. Those fools actually asked her to stand next to them with a flyswatter.
She laughed, thinking they were joking. The man said, “Whatever happened to good service?” They also didn’t leave a tip on a $350 bill.
32. Cooking Up A Storm
A friend of mine used to work in a private Caribbean resort, the type that has individual lodges on their own bit of land, beach etc. The butler came to the main headquarters building to request two bottles of excellent French vintage Bordeaux, something in the region of $10,000 a bottle—nothing too extraordinary by the standards of the resort. But what happened to that fine wine hurts my heart.
He returned an hour later in tears to report that the contents of the said bottles hadn’t been tasted and savored, but rather, the owners had used the wine for cooking, dumping it into the pot as they tried their hand at making coq au vin.
33. All on Black
I play poker for a living and every now and then, some rich guy will sit down and start going all in every hand for $300-500 without looking at his cards. One day, I was in a game where a guy was betting $1,000-$3,000 dollars without looking at his cards. It was insane to me, but for him, I guess it wasn’t that much money.
34. For A Friend
I once worked at one of the largest private clubs in the world, in one of its little boutiques. In addition to clothes, we also had a small selection of things you’d find at a convenience store, like snacks, magazines, and newspapers. For some reason, these mega-rich, high society people loved buying the magazines, like People, Cosmopolitan, etc.
They were somewhat fixated on them but they all acted like it was below them and like it was trashy and frowned upon to look at them. The men would come in and grab their newspapers, buy a magazine and hide it inside the newspaper so no one else at the club knew they had bought it. The women would come in and buy multiple, asking if we had newest editions yet, and then hide them in their purses.
One of them, who was a Golden Globe awarded actress, got a magazine with something about The Bachelor on the cover. I said to her that I loved that show too and asked her if she watched it too. This was before I knew it was taboo to ask that there. She got very weird and embarrassed. She looked around paranoidly, making sure no one had heard me say it.
She had been pretty friendly with me up until that point and afterward wouldn’t really make small talk with me anymore. I wish I could have said to all those people, “Don’t you realize you all buy these magazines? That’s why we keep them in stock! Just admit you all buy them and stop acting like prudes!”
35. Open the Kitchen
My dad used to work as a valet for Lawry’s in downtown Chicago. Some pretty well-known football player came in about 15 minutes before closing with a group of friends. He made them re-open the kitchen, so they could all have steaks. Then they stayed for almost two hours after close being really loud and obnoxious and rude to most of the staff.
He also tipped everyone horribly, especially considering everyone had to stay later because of him.
36. Just A Regular Guy
I was a mailman, and when I was first starting out, I filled in for carriers who went on vacation. One of these shifts led me to a rather memorable encounter. I live in the middle of the country and had no idea that some of the wealthiest people in the country live here. And of course, those people still get mail, but it’s almost always to a PO box or to a business box.
But packages still have to go to the front door. I tried leaving packages with the security guys at the front gate, but they just waved me in my mail truck through and said to leave it at the side door around the back of the house. Once, I delivered an insured package to a “house” that required a signature from the recipient, and it had to be by the person on the mail.
The assistant or butler was annoyed about it, but one of the richest people in the country truly surprised me. He signed happily after I waited a few minutes. He was also happy as a clam about whatever was in the box and wasn’t fazed at all about showing me his driver’s license and having to sign my scanner. It was truly bizarre that even this man, with his immeasurable wealth, had to jump through the hoops of the USPS, and he seemed to have no problem with it whatsoever.
37. That One Guy
I worked at a restaurant in the lobby of a rather nice hotel. There was a rich dude that basically lived there. He would eat in our restaurant every night. Our chef had to hand-pick his steaks from a local butcher. The steaks were massive. It was always specially prepared just for him. Every time this guy would take two or three bites and complain to everyone in earshot that his steak was terrible.
This dude was odd. He would only drink the cheap wine that we served by the glass. However, he would request that you open a fresh bottle just for him. He couldn’t possibly drink a glass of wine out of a bottle that was first opened for someone else. Even if I just opened the wine and poured a glass to the person next to him. That bottle was considered “tainted” to him.
If you are that picky, just buy your own bottle of wine. Oh, but that wasn’t the worst part. He also parked in the handicapped spot out front, even though he is not handicapped. But because he spent so much money at the hotel, the managers refused to make him move his car or have it towed.
38. Keeping It Real
I worked for a member of a Forbes 40 richest Families. The wealth went back generations. He was a truly great human being. He’d spent his career running a Fortune 500 company then spent his retirement in public service. He worked harder than anyone I’ve ever known and didn’t care at all, ever, about impressing anyone.
He served his guests cheddar cheese Goldfish as a cocktail snack and had an elderly housekeeper who cooked the most basic things imaginable—hot dog casserole, creamed chicken over rice, liver and onions, etc.—for whomever came to dinner. I once sat between a Secretary of the Treasury and the President of a foreign country as they happily wolfed down the basic country food provided by the housekeeper.
You could see how grateful they were not to get another overly complicated fancy dinner. My boss, as a rule, also wore old hats, carried a briefcase he’d had for 30 years and, every winter, helped people push their cars out of the snow. He drank Old Taylor bourbon, smoked Cuban smokes, and drove around in a Mercury Tracer wagon for years after I crashed his BMW.
He also never let dignity get in the way of having fun. We were once leaving a congressional office building, which required taking an elevator down to the basement, then making our way past huge stacks of materials fresh from the printer’s office. So, several stories up, we waited for the elevator and two of them arrived at the same time. I tried to brace myself, knowing what’s coming…
I got shoved back as he leapt into an elevator yelling, “Race you!” and hammered on the close door button. He was 65 years old. I jumped into the other elevator just as its doors were closing and miraculously got a small head start. My advantage disappeared, however, when my elevator stopped on a lower floor to take on another passenger—a very high-ranking and famous member of Congress.
Silently, we rode together to the basement and, when the doors opened, my boss was nowhere to be seen, even though he definitely beat me. I followed the famous congressman toward the exit, and as we reached the first towering pile of boxes, my old boss came leaping out from behind it with a cry of victory, landing right in front of the now very freaked out congressman I’d been following.
It was glorious to watch my old boss try to explain just what he was doing, especially since he kept breaking up in laughter the whole time! That sort of thing happened a lot. He just lived his life and made his choices without worrying about what people would think. He was wonderful to his staff and literally became my godfather, since his example and encouragement led me to a career as a minister, despite my family’s strong objections.
When he was in his 90s, and a year before he left this earth, I visited him and introduced him to my spouse. He took her hand and said, “I’ve loved MDAccount for a very long time; I hope you’ll let me love you, too.” Now and again, someone who is very, very rich still understands what’s of true value.
39. Special Guests
I interviewed at a large hotel attached to a casino and while I was being shown around the front desk, a woman walked up, said nothing, and got room keys after being greeted by the front desk agent. She immediately turned and walked away. Then the manager who was interviewing turned to me and said, “That’s Mrs. Rich Lady. You never ask her for her name, her ID, or god forbid a credit card.”
He continued: “She stays here comped once or twice a week because her husband spends so much in the casino. If you upset her, she will yell at you and then hand the person working next to you a $100 bill just to spite you.” I ended up turning down a job there, thankfully so, because apparently, she wasn’t the only guest of her type there.
40. Pocket Change
I worked at a restaurant where a few of the regulars were the children of billionaires. One time I was serving a table and was asked to bring a tray of sixty patron shots—that’s $600, for a 19-year-old student. I must have had an incredulous look on my face because the only response from the said student to assuage my concern was “my father owns diamond mines in Africa.”
41. Here’s Your Tip
I’m loosely acquainted with someone who is obscenely rich. He dated my best friend for a while back when we were in college. As you can imagine, he bought her fancy things all the time, took her on expensive family vacations with his folks, etc. He was a stereotypical rich kid, but he was also kind and still very down to earth. They dated about a year and in the spring, we went spring breaking in his family’s condo at a famous spring break beach location.
There was just me, my best friend, him and a couple of his friends. The group decided we wanted good old-fashioned Waffle House breakfast after a night of revelry. After eating, I noticed he was lingering behind the group. He’d said he had to take a leak, but he stopped back by the table on his way out to the car. Curious, I ran back to the restrooms just so I could pass by the table to see what he’d done.
He left the waitress a small pile of Benjamins as a tip. There had to be four or five hundred dollars. I couldn’t quite tell because they were folded and rumpled from being in his wallet. My mouth fell open when I saw it and I forgot I was even heading to the restroom. I looked out by the car and he was watching me through the glass windows. He held up his finger to his lips and beckoned me back out to the car.
I didn’t tell, but my eyes were glued to the table as we pulled away. The waitress collapsed into the seat of the table when she saw it. I’m pretty sure she was crying. Letting that guy get away was the dumbest thing my best friend ever did in her life.
42. Let Them Not Eat Cake
I used to work for an Arab billionaire’s son, a Daddy’s money guy, who was not the nicest human being. Among other things, one thing that stands out was a birthday. One year, for his birthday, he received more than 30 cakes, big fancy cakes and he told us to leave them on the floor in the hallway outside his room. We walked by those cakes every day for two weeks waiting for instruction, and after the two weeks we were told to throw them away.
43. Smart Choices
Dog walker here. One of my clients only lets her dog drink smart water.
44. Tables Turned
I had a friend who is from a wealthy Saudi family. He is the eldest son of the family, so he comes to Canada for his university degree and the expectation is that he’ll work a few years in banking before returning home to manage the family’s businesses. That all goes according to plan except that, after his business degree, he’s working the same entry-level banking job that I am.
That’s a pretty solid job for 22-year-olds, but about 16 levels below what his privileged family would expect someone of their social rank to get, since Canada doesn’t quite work like that. Note, he wasn’t obscenely rich, or else it would work like that here too of course! So, after a year or two, his family decides he should just come home.
But he was never really the ‘wealthy-heir’ type and quite enjoys Canada and the low-pressure career he has embarked on and is good at, and has even met a lovely woman. So, he wants to stay, and secretly applies for permanent residency. A few months go by, and time is running out for his application. He then finds out that his family has been applying pressure to hold it up.
After a fight with them, he gives in and agrees to come home. As far as he’s concerned, he is leaving Canada forever. So, what does he do? He applies for as much credit as he can and runs it to the max! And he gets a decent amount, since he has been in Canada for years, has regular income, etc. Then he made a rash decision he’d come to regret: He maxes out all of his credit cards.
He mostly buys clothes and rents fancy cars but also donates a bunch to our team’s social fund and a friend’s charity drive, and spends over $1,000 helping our coworker buy their schoolbooks for the year. He puts in his resignation; we have a goodbye party, and it’s all a bit somber and sad. The day before he flies out, he has another argument with his parents.
Apparently, his younger brother is also turning away from the family, and this has given the parents a softer approach. They agree to let him stay! He gets a visa extension. His family calls the local embassy and his permanent residency magically gets pushed up and approved. It’s honestly a really moving situation, to see a conservative religious family really take a step back and evaluate things, and to allow their eldest son to go against their plans and pursue his own happiness.
Our company allows him to rescind his resignation, we have another party to welcome him back, and he proposes to his girlfriend. As of now, they have been married for eight years. So, everything is amazing, except for one thing: The joker now has credit card debt that’s twice his annual salary! Apparently, he was too ashamed of it to even tell his parents what he did, so it was all on him.
So, for the next three years, he had the most amazing suits and ties, lots of fancy customized stuff. At the same time, he was also eating ramen or canned tuna for every meal. To his credit though, he worked hard, lived frugally and paid it all off. Now he has a senior banking job, a happy marriage, and a strong relationship with his family.
45. It’s an Emergency
My sister is a nanny for an NBA player and his wife. The wife called my sister at 9:00 pm to come to their house for an “urgent” matter. When my sister gets to their house, the wife tells her to take the trash out. That’s it. My sister drove an hour round trip to take out the trash. She has so many ridiculous stories about this family, but that one is my go-to.
46. A Dog’s Life
I started working for a 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, meditate and feed the dogs regularly. Additionally, I was to come over and take one of their high-end ‘spare’ cars to pick up bulk orders of diced mutton.
We’re talking over 100kgs (220lbs) 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, money rich, but time-poor, and always treated me with great respect and friendliness.
They also 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 Troop, 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.
Then I’d 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.
47. I’m Just Frugal
I know a lady who’s discreetly rich. For example, she would wear designer jewelry sets to the gym. Anyway, her quirk was she liked Costa coffee, so she’d get one once a day, drink half of it, let it cool and then put the rest of it in the fridge. Then she’d reheat and drink the other half the next day. When she told us that she does this, and we asked her why, she laughed and said, “I’m just frugal.”
48. The Personal Bubble
I briefly worked with one of the top Saudi Arabian crown princes in the 80s. He would buy out the top three floors of the best hotels, such as Four Seasons, etc. Two floors were for maids/help/security while the top floor was for the Royal family. On one such occasion, it was only the prince and his three wives and their entourage.
49. The Little Things
Where I work, I’ve seen some crazy things. The wife was driving through the home improvement part of the city and saw a sale on bathtubs. So, she popped in and bought three. As she was leaving, she saw another tub she liked and simply had to get that one too. She wasn’t renovating a house at the time. They also refuse to throw away food. Used by and best before dates are completely ignored, to the point where I found a tin of seafood marinara which was 15 years out of date.
They have a holiday home in the South Pacific and have a housekeeper clean it three times a week. Yet, they only visit three or four times a year. When they’re not visiting, no one lives there. When the family go out for dinner, the father will happily pay for the expensive meals but not the drinks. The kids (who are all teens or older) have to pay him back for the drinks and he will send reminder messages about the amount.
Yet, when any of the kids offer to pay for the meal, he won’t accept. The wife is a hoarder and will often take way more samples than any normal person. She always makes sure to take all the toiletries from hotel rooms. If she passes the housekeeping trolley, she’ll grab as many as she can from there. Yet she never uses them.
They have a whole bathroom cupboard dedicated to samples!
50. Cat Time
I used to pet sit and was once asked by a rich person to pet sit their cat. Their home was lavish and there were also a lot of TVs—one in almost every room. The weirdest room of all, however, was the bathroom…Or should I say—the cat bathroom. In the said bathroom, there was a TV playing cat cartoons, an overly fancy litter box, and paintings of cats. Clearly a cat bathroom.
51. Drawers Upon Drawers
I nannied for a New York City power couple in 2014. Both were corporate lawyers for national banks. The husband owned more socks than I had ever seen at one time in my life. Drawers upon drawers of them, all navy blue, black, and grey. The horror.
52. Backup Plan
Some extremely wealthy people I have been around have a more acute sense of their own time and mortality, leading to impatience. It’s like they understand how awesome their lives are and, therefore, how short they feel. I knew a guy whose vintage yacht broke down before summer so he bought another one strictly for that upcoming Summer.
His reasoning was that he likely had 20 full healthy summers left in his life and didn’t want to spend one of them without a boat considering that he had the means to ensure that did not happen. Honestly, can’t argue with that logic.
53. Eating Habits
I used to be a live-in nanny for the CEO of a major German investment bank in Berlin. They were a lovely couple with a sweet baby girl and they made me feel like part of the family from day one. They paid me well, had a separate car for me and weren’t concerned about what I did in my spare time. They were very generous, lovely people. My only gripe is that they had strange eating habits.
Some days, they would have three enormous meals, and other days they would “forget” to eat all day. I was often too shy to say that I was hungry.
54. Special Delivery
I worked for UPS as a driver helper and got to see some interesting things. One driver had the rich of the rich route—the mansions worth tens of millions around the Ann Arbor, MI area. The Ford mansion, Lloyd Carr, Dave Brandon to name a few. Once, the driver—a 33-year-old UPS veteran—and I 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 goes in backward and floors it. It was about 250 yards of bends, straights, and he drove it absolutely perfectly, never driving off or missing the driveway.
Then, we got to the house and he needed a signature. He handed me the package and said he’d get the signature just hand them the package and we’d go. Well, we got to the door, and this man in his late 40s or early 50s was standing in the front door with a dog on a leash. The driver wished him a good evening and said that we just needed a signature and we’d be on our way.
The guy says, “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 his business before just signing his name and letting us drop the package by his door. The driver replied, “No, we just need your signature, and we’ll be on our way and you can walk your dog.”
The guy relented, 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 like he was in his own world where we weren’t delivering 300 stops just before Christmas.
55. What’s in the Bag?
Once when I was a nanny, I was housesitting while the family was out of the country. The refrigerator in my apartment broke, so I packed up some perishables and brought them to the family’s house to store them until the landlord could fix it. When I brought my groceries back to my place, I realized I had accidentally grabbed something that wasn’t mine from the cheese drawer.
It was a gallon Ziploc bag. Inside that was a smaller Ziploc bag. Inside that was a bundle of wax paper. Inside that was a bundle of plastic wrap. Inside that was another bundle of plastic wrap. Inside that was a bundle of tinfoil. Seven layers deep, I found an old lump of fruitcake.
56. Always Alert
Some kids have whole plans and strategies they practice to prevent being kidnapped or harmed by stalkers. One kid whom I worked with was the child 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 into the house 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 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 authorities. I was so impressed by the kid’s quick thinking.
I asked him how he got the idea to do what he did. He merely said that he always keeps an eye out for a way to escape and when he sees someone he doesn’t know approaching, he gets 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.
57. Would Fly Again
I treated myself to first class on a vacation many years ago. I’m a large guy who doesn’t do dress up just for a leisure flight. I had on a t-shirt, cargo shorts, Vans, a typical outfit for me. Priority boarding gets called to line up at the gate and of course, I’m there. So much side-eyeing and people praying they don’t sit next to me during the flight. Some guy says, “Um, I think this is just for priority boarding.”
I said, “Yeah it is, thanks”. I had a smug look on my face when the guy saw me relaxing in first-class (he was sitting in economy plus). 10/10 would fly first again.
58. A House With A View
A Russian guy I sometimes work for bought a nice house in a pretty nice area of the French Riviera. He didn’t even visit it before buying, and just judged that 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 view.
Mind you, this was only to him. To me, honestly, it was barely there and didn’t even mask the sea. So, he sent his lawyer there to make an offer of four million euros to the owners. But they declined. So, he doubled the offer, and they declined again. So, he doubled again, and this time they accepted it. He had that house destroyed the very day he got the keys.
Then he had an underground parking lot built instead, for the cars he, in his words, “won’t be using much here.” So, basically, the guy paid that distant house more attention than the one he’s planning to spend his summers in, just to have it disappear because it kind of annoyed him. When he told me the story, he was laughing the whole time.
59. All These Holes
I was a nanny for an affluent family. They had a beautiful home and nice vehicles and the kids all had lots of toys and new clothes. But, while doing laundry one day, I had to take a load of mom’s clothes out of the dryer. Every single pair of her panties had multiple holes in them. They were worn out and the most tattered panties I’ve ever seen.
I got curious and looked in her undergarment drawer. This was par for the course. She was like a major high up in a huge company and her panties looked worse than I would imagine a homeless person wearing.
60. No Match
My partner once helped build a $350,000 pergola. It was built from something like mahogany imported from Fiji because, apparently, they couldn’t source solid beams from anywhere else even though we’re in the middle of the Midwest. It was then painted because the color didn’t suit the homeowner. I still sometimes think about the fact that our beautiful historic home that we’re lucky enough to own was still over $100k cheaper than this person’s glorified outside stick fort.
61. Someone Fix This
My friend works for a tax lawyer for the obscenely wealthy. Their firm is one of those go-to places when you want to take advantage of tax havens. Think Panama-Luxembourg. He tells me he one of their clients had an issue and called the people he always turns to for help. His lawyers. The problem? He bought a new jet and only just realized its entertainment system doesn’t have a Blu-ray player. Find someone that can fix it. Today.
He had lawyers at three different firms searching for a solution that afternoon, and they all billed him for it.
62. Leaving A Legacy
My grandfather left this earth, leaving a 20-million-dollar portfolio behind. He lived in a one-bedroom condo that was built in the 50s, drove a rusted-out Honda, and his entire wardrobe came from Walmart and was 10 years old. At his will reading, a bunch of distant relatives showed up hoping to get a piece. However, no such luck for them. In fact, the contents of the will were hilariously brutal.
In his will, he made fun of all of them, then spent 10 pages detailing how and where he wanted all of his money donated to specific charities and foundations. Some of it was really surprising, as nobody besides him was aware that he casually owned 160 acres of land in Vermont that was just forest. The land was donated to a land trust, and turned into hiking trails.
63. It Shouldn’t Decline
I work at a ski school office at a fancy ski resort in Colorado. I’ve had guests come in and get a private instructor just for them for three weeks straight at a grand a day and then throw the biggest hissy fit when their credit card declines a $20,000 charge. I tried to explain that their card company might think it’s fraud, and they lose their minds.
“I have a $200,000 limit, it shouldn’t decline!”
64. Airy Thoughts
My dad used to work for a private airfield. They had a ton of people fly in but most of the richer clients always flew in at night. I remember one time in high school, I had to do a “job shadowing” and went to work with my dad. They had the owner of a California airport fly in for the weekend. My job was to stand outside with an umbrella.
So, I stood outside with the umbrella. His wife tipped me 20 dollars and said, “The sandwich trays are real silver. Have at it, kid.” After they got in their car, I asked my dad what she had meant. Apparently, when some richer folks fly, they let the people who detail their planes have the platters and other serving items. I had always wondered how we got so many weird serving trays. Mystery solved.
65. Paying Too Much
I work at a Marriot, one that is more expensive than your typical hotel. But, by no means is it a place that millionaires or celebrities would come to, especially because of our suburban location. However, that doesn’t mean I don’t often get people who think that because they’re paying 150 bucks a night, that they can be just rude and entitled. My favorite little story is the guy who was shooting hoops at our sports court too early in the morning.
When I asked him to stop, he just looked at me and threw the ball as far as he could into the parking lot. He then said, “I’m paying too much to be treated this way. I’m talking to your manager.”
I went to a New England prep school for high school on a full-ride sports scholarship. There was a decent amount of foreign national students—mainly from Asia—that came from extremely wealthy families. One of those students’ parents bought him a brand new, fully loaded BMW 5 series when he got his license in our junior year.
When we graduated a year later, he was going back to Korea and obviously couldn’t take the car, so he gave it to his best friend. The kid got an $80k car at 17 years old, just for being good friends with the right guy! I’ll never forget that.
67. Great Pleasure
I once saw a Wolf of Wall Street-type character trying to impress his flock of sheep in an expensive place. He approached the server and abruptly ordered a round of expensive drinks. He then pulled a wad of $100 bills out and extended his arm to her saying, “Take some, peasant.” The whole time, he refused to look at her, instead looking at his friends for approval—but he messed with the wrong woman.
She swiftly smashed the entire wad out of his hand and I took great pleasure in his angry reaction while he scrambled to pick up the cash in a crowded place.
68. Movie Night
I worked in a DVD store where once a woman came in with five, double-sided A4 pages of movie titles and just asked me to fetch whatever we had from the list. So, I ran about and collected DVDs and Blu-rays close to 1k worth. I asked her what they were for—she was a PA for a billionaire and was getting them for his yacht.
69. Only the Finest
I worked at a private villa in Bali. One guest stood out. She only drinks and bathes in Evian, so one day I spent almost an hour filling a large tub from tons of Evian bottles. The same young woman complained that the path from her villa gate to her room wasn’t well lit. She wore sunglasses at night.
70. Dance Like Everyone’s Watching
I was catering a wedding for a very wealthy Nigerian businessman’s daughter who was living in the US. She was marrying a white American whose family looked like that stereotypical mid-west family. During the wedding, the dance floor opens up and it’s time for the father/daughter dance, and it turns into the bride dancing as the dad starts throwing cash around, probably like $10k in total, as the Nigerian guests start to collect the fallen money.
Imagine that all of the Nigerian guests who had been flown in are going wild and this mid-west extended family are just standing there with a look that can only be described as, “What are we even watching?” Just that look is one of the funniest things that I have ever seen. All the catering staff had been told beforehand about this part of the ceremony by the event planner.
It was apparently customary for the bride’s culture, but clearly the in-laws hadn’t been told about it. It was just a surreal experience.
71. We Own These Floors
I once stayed in a hotel an NFL team had rented for an away game. It was a really nice hotel and the only reason I was there was for a family member’s wedding and I was sleeping on a couch in a room. The whole place was filled with very wealthy people and to separate them from the other guests, they rented the three top floors. They also had security to stop anyone from getting to the floors.
The best part about the trip was seeing a guy valet park a rented muscle car by just stepping out and handing the keys to the nearest person.
72. My Treat
I tutored a wealthy 5-year-old. I got paid good money to spend an hour drawing and coloring and playing with this kindergartener but all in French. He had been to more places in the world by 5 than I’ll ever go to in my whole life. The best part of the job was the perks, though. They would take me and my SO out to dinner at fancy restaurants and pay the bill no matter what it was.
They would also invite us over to eat some delicacy they’d prepared—the wife was Chinese/Vietnamese and the husband was Indian—a distinguished guest staying over or not. They also had houses in my city and in San Francisco and would fly there all the time. They invited me on several occasions but I never had time to go.
73. Just a Taste
This was not stereotypical, but ridiculous it was. I had a customer come in in the most basic cheap clothes. But, he then pulled out a bundle of $2,000 in cash. He bought a glass of our most expensive wine and sat by himself for about an hour, not doing anything. He then wound up leaving after having taken only one or two sips.
74. Hamming It
Until recently, I was working on the bread and pastry team at a very high-end restaurant in LA. Aside from the bread that was served before the meal, we would also have to make burger buns. We didn’t have burgers on the menu, but we had to have some buns stocked in the freezer just in case some VIP decided they wanted a burger instead.
Now, there was also one particular regular who would order burgers but only liked to eat them as sliders. So, of course, we also had to make slider buns just in case he came in. God forbid we were to tell a rich person, “I’m sorry. We don’t have hamburgers here.”
75. You Can Have This
I used to work as a chef at a restaurant in this massive five-star resort. Our restaurant is usually quiet during lunchtime, as it is more of a fine dining restaurant and people would go to the less fancy places for lunch. This guy comes in once, casually dressed, and orders a salad and the five most expensive main courses on the menu.
Two other colleagues and I are on shift, so we prepare everything and send it out. 20 minutes later, the waitress serving the guy says he requested five clean knives. The guy had tried a bit of everything, then proceeded to cut a layer off the part where he’d eaten with a clean knife (hence the knives), so the rest is not contaminated by him trying it.
He said he was full and insisted the food not be wasted, so he gave it to the staff on shift so “they can also taste the great food they make.” When leaving, he came to the kitchen and shook everyone’s hand. We later found out the guy owned over half the resort, apparently.
76. Doggone It
A few years back I worked at a dog hotel/training center in Beverly Hills. We had a lot of celebrity dogs and clients with way too much money to spend. We had a raw food bar and a full bakery for dogs. The setup was like a restaurant. There were fancy little tasting tables. For dogs. We served wild venison, raw wild rabbit, lamb, pheasant, duck, and bottled beverages for dogs and cats.
These drinks were literally broth in fancy wine bottles. We also had a grooming spa where you could get your dog a mud bath with a seaweed wrap and a professional massage. It was the best job I’ve ever had. The tips were incredible. My first job there when I started was to sleep in a bed with all of the overnight dogs. A literal human bed with sleepover-style dog beds all around the room, and my job was to sleep in a pile of rich people’s dogs so they wouldn’t get lonely at night.
77. Toss ‘Em Down
I helped my mother-in-law, who was a maid once, with a very large mansion in NC. Beautiful house, amazing architecture. They traveled the world all the time. But the kitchen had old appliances from the ‘70s, the wife’s bathroom had a broken toilet seat that was duct-taped together. The wife did not re-wear her underwear. We were not to go in the basement.
I peeked down there once, though, and my blood ran cold. There were clothes three-foot-deep in the basement where she took off her clothes and just threw them down there. There were thousands of pairs of underwear. They were very weird people.
78. Comfort Food
A friend of mine comes from a family that owns the largest group of car dealerships in Southeast Asia. She’s been stranded in my country due to the present global situation, and whenever she’s feeling homesick, she’ll call up the bakery in her home country to place orders. Then the said orders get flown in on a private plane the next day.
79. Running Around Vegas
I was a nanny for a rich family in Vegas. The amount of food they wasted was crazy. One instance I can remember is the woman buying Monster energy drinks for her nephew who only visited her house maybe twice a year. The garage was stocked with cases of the stuff for the kid. When it went bad, they threw it out and bought more.
There was also the time they had me buy $25-dollar gift certificates for their annual company Christmas party, from 25 different places in Las Vegas two days before Christmas. That was fun.
80. Briefly Good
I worked for a rich Chinese lady who told me and her CFO to hire 30 English teachers and start an NGO. 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. We also gave each of them thousands of dollars to pay for college tuition.
Why did she do all this? To help her daughter—the nominal head of the charity— studying in the US with her college application. The organization was dissolved when she was accepted into Yale.
81. Not That Coffee
My dad is an electrician and has worked in some very rich houses. He did a job in one where the couple only drank very posh fresh coffee. Fair enough, who wouldn’t? But they had a cleaner who was permitted one cup of coffee each day, but not their coffee. She had her own separate coffee, but it wasn’t even a decent, if cheaper, brand.
It was the cheapest possible sort to buy.
82. Having Your Cake And Eating It Too
When I was in high school, I used to face paint for kids’ birthday parties for some extra pocket money. I face painted for this one kid’s party—his parents being rich enough to be in the top 5% of the country. The mom was very nice. She sent her driver to pick me up from my house and shuttle me to their mansion so I didn’t have to worry about transportation since they lived on the other side of town.
A bunch of other rich families were there—both the kids and their parents. The party started around 3 pm and lasted until late evening. I was done painting all the kids after one to two hours and when I finished, the mom insisted that I join the party, i.e., watch the other entertainment and eat the food and cake. At the end, she tipped me $100 and had her driver drop me home.
I was essentially tipped for eating cake and having a good time.
83. Can You Cook This?
The first guy I dated was worth $30 million while his parents were worth $300 million. He didn’t know how to cook. There was a list of phone numbers on the refrigerator that you called when you wanted food, a guy would show up and cook it for you. He wouldn’t step foot in my car because the check engine light was on and was convinced that the car was going to hurt me.
He used his money to open a yoga studio, that’s all he wanted in life.
84. Put A Sock In It
I had a client tell me that he never reuses a pair of socks. He hates unfurling them to put in the wash, finding the two halves and folding them, and dealing with stretched out socks. Oddly, he didn’t have a preference for types of socks. Mostly basic black and some random funky ones that randomly caught his eye. He, apparently, had purchased enough socks to fill the sock drawer, which was about 40 pairs.
85. Bleach Them
Growing up, my mother would clean houses for wealthy individuals. There was an elderly widowed woman with large, all-white poodles. She insisted that my mother clean them with bleach. She would provide two gallons of bleach each week. My mother never did bleach them, she just poured out the bleach in the tub.
86. Dangling The Carrot
I worked for Comcast for a few months and had a person, who was the coach for a college football team, want 11 DVRs. He wanted one for every room of the house plus the detached pool house—which in itself was literally another house that I could comfortably live in for life—just for the pool. When I first knocked on his door, he gave me a $300 tip before I had even done anything.
I told him to hold it, and he said, “This is just an incentive to do the job. Another $700 will come once the job is complete.” He, apparently, had had four techs try to get it working and everyone had failed. I spent all day working on it but I, eventually, got every DVR working, all on his account. I absolutely circumvented the system just for this guy. But I did get it all working and did get a $1000 tip from it.
87. Off the Grid
My husband used to work for a landscaping company. There was one lady he would always come home with crazy stories like they paid a pilot year-round just to be on standby in case they wanted to fly somewhere. Also, they apparently paid Google a fee every year to keep their property off of Google Maps?
If this is the same woman and I’m remembering correctly, she also had two solid platinum reindeer for Christmas decorations.
88. Just A Little Rain
I briefly worked as a consultant with a family office set up by an individual with a low nine-figure USD net worth, living in India. Everyone in the said family would travel by their own car to meetings, even if they traveled to and from the same place. They also employed separate concierges for each of the family members.
They even had a closet in the family office ‘for emergencies’ and it was bigger than our living room. And the most flabbergasting thing of all? The patriarch of the family didn’t like monsoons, so they flew to the US to their other home during the monsoons in India. Considering everything else, they were surprisingly sensible about their cars and houses.
They never bought new cars every year and the ones that they had were not extravagant cars, either. Instead, they were just sensible mid-range Beemers or Mercedeses.
89. Jungle Gym
My sister used to be a nanny for a very famous former F1 driver. I’m pretty sure the kids’ outdoor playset (jungle gym, castle-like playhouse, etc.) cost more than my sister’s apartment. On the plus side, he and his wife are apparently the most down-to-earth, sweet people.
90. Working Example
I was doing a shoot at a winery, and as we worked, I got talking to one of the winery workers, as you do. The guy was doing barrel work/assembly line work. As we talked, it turned out that he was, in fact, the owner of about six wineries and was a millionaire, but there he was working right alongside his employees and doing his fair bit.
91. Washing Bags
I was a nanny for a pretty affluent family for a summer. On the whole, they were really nice and great parents. Two things stood out to me, though. On one occasion, they had family friends visiting with their three children, so I worked a full day taking care of the five kids while the four adults just hung out in the house. I understand occasionally having the nanny come while you’re there, so you can work well from home, but nannying five children whose parents were ten feet away was a little absurd.
The second thing is that they reused Ziploc bags. I probably spent at least 45 minutes a day washing, drying, and organizing their Ziploc bags.
92. Drinks On Me
A friend of mine just got his law-related qualifications and is presently practicing law. He has started at 50k annually—not exactly a fortune but unimaginable for the work I do. He always gets a lot of drinks for people when we’re out in London. If he’s just met you, he’ll ask if you want a drink. If the bar is crowded and he can’t be bothered to wait he’ll just see who at the bar wants in. Not spectacular and not a morally epic thing, but he’s a good bloke and, I guess, keen to keep the party going!
93. Cleaning 101
I lived with a girl from an insanely wealthy family in college. What amazed me the most was how completely clueless she was when it came to cleaning. I mean, she grew up with maids her entire life and college was the first time she didn’t have someone cleaning up after her, so I figured she might be untidy, but I wasn’t prepared.
I asked her to clean the kitchen once and she came home with a box of powdered bleach from the Dollar Store and sprinkled it around the counters, then rubbed it around with a wet paper towel.
94. The Burden Of Things
My grandfather was one of the wealthiest men in the state. When he received a call, he demanded the phone be brought to him on a serving tray, because he thought it beneath him to get up and answer a phone call. But that’s not the craziest stunt he pulled. He also legally disowned his daughter because she was seen carrying her own luggage, and the event so traumatized his third wife that she sought therapy for the “disgrace.”
95. Special Tag
I used to work security for a high rise building in Uptown Dallas. There was a VIP parking garage underneath the building. Entry required a special toll tag to be in the window of your car. The wife of a couple that owns a large part of Home Depot, had it mounted on the bumper of her Bentley and then had the entire bumper repainted to hide the tag.
Long story short, the tag was now at the wrong angle to transmit to the reader. Thousands wasted when she could have just asked first. Of course, she couldn’t ask personally, she always had her PA do it. I think he was also her lawyer.
96. Déjà Vu
This unfathomably rich woman tried to buy a multi-million-pound property in London purely because she liked how it looked from the outside. But there was just one problem: She couldn’t buy it though because she already owned it. Yeah. She had bought it on a similar whim during her trip the year before and totally forgotten about it.
How much money must you have that dropping eight figures doesn’t even register as memorable?
97. More Appetizers
My brother was an apprentice cook in one of the most prestigious hotels on the French Riviera. That week, he was assigned to prepare the free tapas and amuse-bouche they were giving at the hotel for customers. This super famous French actor came in. He played a lot of comic roles, so there was this good aura attached to him. But all day long, he requested to have more of the free appetizers.
He was getting mad at my brother when he didn’t prepare them fast enough because he was hungry. It changed our view of the guy in his movies.
98. Missing Fairy Godparent
A colleague of mine used to be a bouncer at a club that was the place for rich kids to hang out. He saw a lot of the typical “look at me I’m so rich!” behavior. Things like buying the most expensive champagne 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 were not uncommon.
The thing that stuck with him the most was just how far removed these kids were from reality. In particular, one disturbing incident stood out to him. One night he had door duty and didn’t let a kid under the influence into the club. So, what did the kid do? He decided that it was a good idea to take a swing at him. It turns out that it wasn’t a good idea.
The kid found this out quickly after he was lying face down on the ground, handcuffed with his hands behind his back. But even now the kid didn’t seem to be too worried, he just kept saying, “It’s all right, just call my dad and 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 authorities 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.
99. A Month’s Wages
When I brought the bill after lunch, this rich dude fumbled with the unknown currency, walked off then walked back, and threw about half my month’s wages on the table. He then said, “Oh yeah, here’s a tip.” I’m not complaining, though.
100. One For The Road
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 media tycoon billionaire from Sydney to New York, with instructions 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. The guy never showed up. And the reason is so ridiculous—it makes me sick. Turns out that he was having a rich people party in a building overlooking the harbor and wanted to be able to point down and say, “That’s my boat.” He wanted the lunch prepared just in case he decided to take his rich friends down to his yacht, but he didn’t feel like it that day.
So, all the food got wasted and they sailed back to Australia without seeing the tycoon.
101. Feeding Time
I have worked for some of the richest people in Maryland and the one thing that stands out more than others is this doctor I worked for in Montgomery County, one of the most affluent zip codes in America.
This guy owned a lot of offices around the DC area, employing tons of employees and associate doctors, etc. He was really wealthy. He had a place with a huge garage full of exorbitantly expensive cars like Ferraris, an art collection, a wine cellar—the works. I used to do IT work for his medical practice and managed all the servers, etc., and occasionally went to their house because I was the lead admin.
Once, I was working in his house and was walking around upstairs where the bedrooms were when I came across the most off-putting sight. What I see is that this guy was lying in bed being fed by an assistant. I mean, he was literally lying in the bed while someone, completely platonically, hand-fed him, and not something like grapes but a regular meal. It was strange, to say the least.
Imagine someone feeding you a full meal with things like a steak and spoons of soup, salad, etc. and you never use 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. 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.
102. More Income, More Intergenerational Problems
My mom works in a family-owned business, and while the owners aren’t excessively rich they’re definitely upper class. I think the most messed up thing that I know about them is just how they treat members of their own families, let alone strangers. For example, the founder of the company fell and broke his hip when he was around 80.
Since he could barely walk around on his own anymore, let alone run a company, he finally retired and gave the company to his daughter. This was a huge mistake. She put him in a home, never visited him again for his entire life (He passed away at age 92, just to give some perspective on how long that was), and almost immediately began to drive the company into the ground.
Around three years after the daughter became the owner of the company, her grandson is hired into basically the same sort of secretary job my mother has. Now it’s a bit of a long story, but he lives with his aunt who also works for the company, basically in the same job his grandmother had before she became the company owner.
So, things are going fine for a while, then eventually he comes out as gay, and is immediately fired for some BS reason by his own grandmother. On top of that, she demands that her daughter kick him out of her house or she’ll fire her too, but thankfully she wasn’t taking any of that, and said she’d sue her mother if she fired her over it. Her mother backs down, and thankfully the kid isn’t kicked out onto the streets, but he’s sure as heck not getting his job back. Then of course since he was fired, all of the work he was doing is piled onto my mother’s desk.
103. Helicopter Parents Never Fly Coach
I worked as a nanny for a 1% family. The stuff I saw haunts me. I remember having one parent complain how rude it was a friend hadn’t offered to fly them to Miami on a private jet for a weekend getaway, and they were “forced” to go first-class. Had the other parent tell me they thought it was really “sweet” I was happy to help others and never be wealthy.
They would also spring last-minute trips on me and their kid all the time, so I’d stay in the main house with their child while the parents were country-hopping. Poor kid never had any sense of who was going to be where. There were business-related videos of the parents on YouTube, so it got to the point where I’d play them on an iPad so the kid had some sense of consistency.
Just to be clear, the kid was absolutely adorable and very sweet (which made it really hard to leave, I felt terrible), but it was pretty disheartening to think they’d probably turn out like their parents in a few years. The best part about the parent complaining over the first-class flight was when they asked me if I thought they were overreacting.
Literally asked me “Wouldn’t you be upset? Don’t you think that’s rude? They’ve been doing better [financially] now that they have Company X money they could have sent a plane etc.” and I’m thinking, well I’m pretty sure my entire year’s salary couldn’t pay for one chartered flight, so you know I’m probably not the best person to ask.
104. Side Chicks
When I was a poor college student my wealthy cousin and his wife went on vacation and offered to let me house sit to give me a break from my three slovenly roommates. They live a few towns over in a very nice house with a huge front lawn and a fancy, tall iron fence with double gates. The fence and gates are about 11 feet high. You have to have a remote to open the gates.
That first night I slept so well! I breakfasted like a king and then drove to school. I got back around five, made a supper fit for a king, and settled down to write an Econ paper. My cousin has a warning system for when someone driving turns off the road and comes up to the gate. There’s a chiming sound and you can look at screens in a couple of different rooms to see who it is so that you can buzz them in.
I was deep into my paper when I heard the chime. I was confused at first and check my phone before I realized what it was. I looked from the sofa and could see a movement on the security screen. I stood up and got closer and had a clear view of two women getting out of a white car. One tried to squeeze between two bars of the gate—impossible—and then the other woman tried to boost her over the top of the gate—hilarious.
The top one fell and even from the house I could hear swearing. I was about to press the intercom button and ask WTF was their problem but I was chuckling at their antics and just watched silently. They peered at the house intently from between the bars like a couple of jailbirds for a while. The skinnier one actually stripped down to her bra and panties and tried to squeeze through the bars again. No dice. Butt and boobs were not allowing that to happen. More swearing.
Then, as the skinny one got dressed again, the bigger one went back to her trunk and got out a tire iron. As soon as she started with the hinges of the gate I was calling 911. The cops took too long and the women left. I showed the cops the video but they couldn’t get a license plate number. When my cousin and his wife returned the next week I told them what happened and we watched the tape. He said that he had no idea who the women were but his wife looked pissed. I packed up, thanked them for my “vacation” and left.
She divorced him that summer.
105. Too Little, Too Late
I was working as a General Manager at a struggling restaurant—struggling despite excellent business, because the owners would do stupid things like take trips to Italy on the company dime to source the “perfect” panini press. They also wouldn’t staff properly; I was the only waiter ever there, open to close, six days a week, on top of handling phone orders, inventory, and other managerial duties. I was wildly overworked, but I sucked it up because the base pay was good, plus tips.
However, to fund their lavish “business” trips, costs had to be cut at the store. They decided to do this by bumping me down to minimum wage for tipped employees—effectively cutting my salary to 1/10 of its previous level. They were also too chicken to tell me until I got my new teeny paycheck and questioned the mistake. “Oh yeah haha, forgot to mention that blah blah cost-cutting blah valued team member please work with us through this difficult time.”
I had worked for two weeks at this new lower rate without my knowledge. Pretty sure that’s illegal, but hey, a lot of illegal things go on in the restaurant industry. That’s not when I rage quit, though….a couple of hours later, I’m fuming and have decided that I can’t work for the lower rate, so now I’m just waiting for the perfect chance to give my notice.
They called in a delivery guy who was fired a few weeks before, and they talk about hiring him to start doing our Facebook posts and handing out flyers around town. Whatever. Then I hear them offer him close to my old salary as “Promotions Manager”! What??? I was basically running the place for $2.13/hr and you’re offering this dude almost $20/hr to walk up and down the street saying “Eat at (Name)”?
And yet, it gets worse.
They bring up our negative Yelp reviews and this guy suggests asking friends to post positive ones. The boss starts laughing and says “Better not ask our waitress to post one, it’ll be all boohoo don’t eat there, I can’t pay my rent this month because they cut my pay without telling wahhhh!” I don’t think I was supposed to hear that, but I was five feet away, so of course I did.
I RAGED! I quit on the spot, told them to screw their job, and wished them good luck keeping the place open without me. They quickly realized I was right, as neither of them knew how to do more than pick up the takings once a week. They begged me not to quit. They were so desperate that they sat there for half an hour and allowed me to bluntly tell them exactly what kind of huge idiots I thought they were in excruciating detail.
I went on and on as my rage burned, and they just quietly listened, nodding and apologizing. Once I had cursed myself back into calmness, I walked out, 30 minutes before the dinner rush began, leaving them with an unstaffed floor and no clue how to even open the cash register. God, they were morons. I loved that they actually listened to me telling them exactly how stupid they were. No repercussions on my side, as the restaurant industry isn’t known for checking references.
The place closed down about 18 months later, and I was surprised it even made it that long.