7. 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.
8. Blastoff
Neil Armstrong's nephew or grandson or whatever was attending Space Camp the same week I was. There were many rumors of him being a little brat. It was confirmed true that almost every day he was at risk of getting kicked out. The last day of camp Neil actually spoke to a huge crowd of space nerds. Minutes before the speech, that little brat got kicked out, publicly, in front of mostly everyone at the camp. Neil must have been so embarrassed.
9. 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.
10. Non-Consumable Conspicuous Consumption
There’s a thing in Stockholm‘s rich kid district called “vaska.” Basically, you order an expensive bottle of champagne, pay for it, and watch the waiter pouring the bottle’s contents down the drain. Some places even let you do it yourself. Sadly, it’s an established thing in these kinds of circles. Like it’s on the menus and all that. Honestly the dumbest way of flexing I’ve ever witnessed.
11. 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.
12. Don’t Enable Rich Jerks
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 handpick his steaks from a local butcher. The steaks were massive. It was always specially prepared just for him. Every single time this person would take two or three bites and complain to everyone in earshot that his steak was terrible. Every. Single. Time.
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 annoyingly picky, just buy your own darn bottle of wine. Oh, and one last thing. He parked in the handicapped spot out front, even though he was not handicapped. But because he spent so much darn money at the hotel, the managers refused to make him move his car or have it towed.
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13. 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.
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14. Direct This
Over the summer one year, I signed up to be an extra for a film by a man who had won a fancy award for directing a particular film because I liked theater. When I got there, I actually ran into the director almost immediately, who proceeded to tell me that I would no longer be an extra (even though I said twice 'No, sir, I'm supposed to be in these three scenes'). Why?
Well, instead I would be his wife's assistant for the day. She wasn't in the movie. She was just observing all day. But she still had a change of clothes for when she left that needed to go in a dressing room (again, even though she wasn't acting in the movie). The guy, from what I can tell, is just the egotistical kind of wealthy, and not actually SUPER rich, but the award went to his head and he used it as an excuse to treat everyone on set like trash.
15. 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."
16. To the Batcave!
I knew someone who traded in his Porsche and bought a new one every year. His parents were wealthy, died when he was in his teens and left him a multi-million-dollar trust fund. What was sad was that he felt that he couldn't pick up women without flashing his cash and expensive sports car, but he would dump them all in a couple of weeks because "they were only into me for my money." Loneliest guy I ever met. He is not Batman, by the way. His parents died in a car accident and his butler's name is Davin, not Alfred.
17. 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.
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18. We all Need to Call out Crummy Behavior
I saw an American woman who seemed to be a model out for breakfast at a nice hotel in Barcelona. She demanded the waiter walk the butter over to her table. It was 4 feet away at the breakfast buffet. I actually stood up, grabbed it, and handed it to her, as she was demanding this in English to the Catalonian staff. She actually said, “No, I want them to do it.” I said she was an embarrassment, to which she stormed out. Doing my part!
19. 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.
20. Proxy Parenting
He wasn't super rich and powerful, but I used to work for a pretty reputable set of attorneys a few years ago. I started off file clerk and went up to receptionist. Anyways, one of the attorneys specifically just did not got a darn about his kids whatsoever. He didn't know their ages or their birthdays. He would have the office manager mark down all these things on her own personal calendar so that she could prepare gifts and whatnot for their birthdays.
He even had her paying all their bills and rents (some were in college) with his checks. One of his stepdaughters worked there for many years and he would sometimes forget about her and leave her in the office alone. She would have to call just to get picked up. The attorney was a pretty crummy guy but his complete lack of interest or care in his children's lives always disturbed me.
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21. 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.
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22. I Only Love My Bed…I’m Sorry
I work at a luxury property in California and we once had the co-founder of a large payment processing company stay with us. 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!
23. 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.
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24. Whining About Wine Prices
My son-in-law was working as a waiter in a fancy restaurant in Dubai. A very tipsy customer ordered a bottle of a 1960 Pomerol Bordeaux valued at $15,000. He was trying to impress his lady friend. My son-in-law confirmed the price with him and asked him if he's sure that he wants to open their most expensive wine in the house. He replied yes. The following day when the customer sobered up phoned in to say he made a mistake and wanted his money back. Naturally, it was too late for the restaurant to do anything. They also found out that his lady friend was, in fact, a call girl.
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25. 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.
26. Why Are People So Terrible?
When I was a waiter, I once had a woman and her friends at one of my tables. The woman asked for a can of Coca-Cola. When I brought their drinks and gave the woman her Coke, she looked at me, and, in that typical rich person voice, 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.
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 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, 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 darn 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.
27. 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.
28. Making Amends
A girl at my high school constantly whined and complained because her parents refused to move out of the master suite of their mansion. She felt that she deserved it, because the attached walk-in closet and bathroom were bigger than hers. To reconcile this, she had her parents pay to redecorate her room every single year.
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29. 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.’
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30. Side Gigs
Leader of company, that's a subsidiary of another company, puts pressure on employees to work on his own side business that's not affiliated with the company. Basically, he's ripping off the parent company.
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31. 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.
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32. Some People Are Not Totally Corrupted by Money
One of my best friend’s fathers is very successful in the tech industry and she has what we call “the magic credit card.” Her dad’s financial manager pays the bill, and who knows if there’s a limit. They weren’t always this rich, and she really is a down to earth person who doesn’t spend extravagantly except when it comes to traveling or eating at fancy restaurants.
When I visit her, she often likes to take me to the nicest restaurants in whatever city she lives in. She likes to order almost everything on the menu because she can’t decide what she wants, including all the cocktails. Sometimes for the more expensive items or things that are priced by weight, the staff remind us of the cost to make sure we can pay.
She usually (sincerely) says, “Wow that is kind of expensive... but let’s treat ourselves!” The kicker is at the end when we obviously have all this food we can’t finish she asks for boxes to take it home. They usually try to tell her that it won’t taste as good reheated, but she just tells them that it was so good the first time and she knows she will love it again. She’s very sweet and a huge tipper, but it cracks me up because I know people are thinking what is up with this chick.
33. 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!"
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34. Spoiled and I Know It
I have a billionaire customer with four kids, and all of them are pretty spoiled. However, the worst case is the youngest one, who once said to me spitefully "We're going on Tiger next week and you're not allowed to come!" Tiger is the name of their yacht in southern Italy. It's not just that he's spoiled that gets to me, it's the fact he knows it and rubs it in purposely.
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35. 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.
36. Where Did the Dollar Go?
I used to work at a luxury car dealership as a mechanic. When the market tanked in '07-'08 we were all convinced to take a dollar per hour pay reduction. That year...THAT YEAR the owner bought a Maserati and we all got watches for Christmas for hitting some goal.
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37. 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.
38. Later Years Steinbrenner Was Never Afraid to Spend
I was at a restaurant in Houston in 2004 during the MLB All-Star Week. Yankees owner George Steinbrenner rented out a large area of the restaurant and brought players, coaches, and staff to eat brunch. We got there and were seated as all the MLB folks were leaving. I’m a huge baseball nut, so seeing all of the players was really cool.
Anyhow, our waiter came to our table to welcome us and get our drink orders, and just had the happiest look on his face. I said, “Man, must be cool to be on schedule when these guys come in.” He proceeded to tell us that he and his wife were the two servers for the baseball group, and that Mr. Steinbrenner left them a $50k tip. I’m not a Yankee fan, but looked at Mr. Steinbrenner a little differently from then on.
39. 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."
40. Rich and Judgmental—A Terrible Mix
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 button for the top floor, which was the same as ours.
After about 30 seconds of silence and glares, the woman turns to me and condescendingly says, “You need to press the button for your floor.” I told her our floor was already selected and she had the audacity to ask, “You have a suite on the top floor!?”
41. 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.
42. Typical Karen
When I was a server I would always record my tables' orders. Even though my memory is good, my handwriting is bad so I didn’t want to take the risk of getting something wrong. My manager said it was ok and he even put a sign up stating that some of the staff may record your order for accuracy purposes. Seems normal, right?
At the beginning, I ask each person for their name before I take any drinks or food orders. One of the people at the table orders a steak well done, which is gross but whatever. Food comes and she said her steak was not medium rare like she wanted and I apologized and told her that she did order it well done. Here we go...
This sparked a big rant, lots of cussing, a call for the manager, etc. Again, I apologize and say let’s go to the tape. The look on her face when I played back the recording of “And Karen how would you like your steak?” was priceless. She tried to play off that it wasn’t her but nobody else ordered a steak at her table. Her friends just laughed at her.
43. 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.
44. A Step in the Wrong Direction
I went to high school with the son of the owner of a large TV company. He thought he should be allowed to sit alone in the classroom surrounded by unfilled desks. I had the "privilege" of sitting in front of him and was constantly harassed with attacks from his ruler and pens if he thought I was even remotely leaning back.
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45. 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.
46. Rich People Can Buy Things You Didn’t Even Know Were for Sale
I worked at a 5-star hotel. A pretty normal looking guy came in one day and inquired about the price of a piece of art on our wall. It cost $200, 000 and he bought it on the spot, all within 20 minutes.
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47. 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.
48. Always a Bonus When Your Manager Has Your Back
My wife used to work at a high-end clothing store in Manhattan—the kind with really expensive pieces of clothing you had to make an appointment to just see. She said 90% of people there would return all kinds of clothes. Saying rich people are the cheapest or would get it just for show. One guy got in a huge argument and rudely called her fat, because she wouldn’t accept 6-month-old satin socks that he wanted to return. My wife was clearly pregnant at the time, the manager was a sassy dude that wouldn’t tolerate that and cursed him out into the street.
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49. 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.
50. Aunt Covert Burn
My rich aunt doesn't let us park in front of her house because it makes her mansion look bad.
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51. 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.
52. All That for a Table?
The one story that comes to mind was when I had this awful encounter with this guest who didn't have a reservation and wanted the best seat in the house, which was already reserved for another guest, a regular who was coming within the hour. She was probably in her 80s, smelled wealthy, and was drenched in diamonds.
She pointed her crooked finger to the table in the corner and said, “I want to be seated there now.” I apologized and offered her another table that was just as desirable to my VIPs. She slammed her hand on the podium and croaked, “I dine here all of the time—I live here on the island! I know the chef and that table isn't taken, so I will sit there!”
My years working in fine dining taught me that I had to be confident, assertive, yet gracious. If the clientele sniffed weakness from you, then you were done for. So I explained to the guest that the person who reserved the table, reserved more than two weeks prior and that perhaps next time she visits, she can reserve that table, and in the meantime, I had a number of exclusive tables for her to choose from.
I knew she was lying about being a regular, and many clones of her say they know the owner just to save face in front of their elite friends. So I wasn't impressionable at that point. But when I told her that, she responded by glaring at me and sneering “You're treating me like a black woman!” Fuming, I uttered, “Excuse me?” Before I totally lost it, my manager came to the rescue. I had to go to the break room and regroup from her audacity—all over a table! Palm Beach is something else.
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53. 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.
54. Car Trouble
On my friend’s 16th birthday, her step-dad gave her his one-year-old hummer. She full on cried when he tried to give her the keys, because it was both used and “the wrong color.” Naturally, they went out and bought her a brand new one in the color she liked that same day.
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55. 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.
56. The Nanny Dairies
I'm a nanny for a rich family. When I get paid (in cash) my boss says, "Man now I'm gonna have to go all the way to the bank to get more cash." Not wanting to go to the bank isn't the annoying rich thing. It was an annoying rich thing because he had $500 still in his wallet, and he was complaining it wasn't enough money to have in his wallet. But wait, there's more.
Also, when they travel they prefer two-bedroom suites, one time they could only get a one bedroom and he said, "well that just ruins the whole trip. Finally, My car got broken into and I mentioned it felt so awful to drive it knowing someone was in it. His idea of empathizing? "That happened to me. I HAD to buy a new one."
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57. 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.
58. Rich People Quirks
I worked as a busboy at a restaurant in a hotel that was at the end of its life. The owner, a reputed mob boss, and his eccentric wife lived in a top floor suite that was two stories tall and lined with white marble, Italian statues, a red carpet, etc. The wife would do her grocery shopping from the restaurant’s kitchen, and it would be us busboys who took it up.
However, she made very specific demands on how the food should be prepared. Once, she asked for seven pieces of American cheese, and it needed to be on a plate in a star pattern. Another time, she wanted five raw eggs, each wrapped in a napkin and then wrapped in plastic, placed inside a large Styrofoam cup. Failure to prepare the food to her exact specifications meant being fired.
On top of all that, she never once met us when we brought the food—she would buzz us in and instruct us to put the tray in their private elevator, and send it up to her. I was once berated because I put a plate of bread on the left side of a tray instead of the right. After the husband died, they closed the hotel. For a couple years after, she lived in that penthouse alone, and it was creepy to drive past at nights and see this 14-story hotel completely dark except for her couple lights on the top floor.
59. One Man’s Castle Is Another Assistant’s Prison
I'm a personal assistant for a doctor. He asked me to clean his apartment which is one of the nicest places in town. As he's showing me through all the doors to actually get to the apartment (place is like a fortress), he slams each and every one in my face.
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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. The “Fun” in Family Funds
A cousin of mine is on his third Porsche 911 after he wrecked the first two. He told me that his parents said if he destroyed it again, they'd just buy him some other car. He wrecked the first one while drunk, and thankfully, he somehow didn't injure anyone. I don't even think he got charged with a DUI. But that's just my cousin: there's also my horrible family.
My family usually charters our own plane whenever we go on vacation. It costs something like $6,000 per hour or something. One year the company overcharged my dad for a miniscule amount, I think it was like a grand. And he was considering disputing the charge or something, ignoring the fact that $1,000 is nothing to us, and he already paid $36 thousand for a flight. Oh, and my parents hate tipping the pizza guy for some reason. They have no problem tipping a waiter 50% or even 100% at a fancy restaurant, but the pizza delivery man? Nope.
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. Museum of Woe
Old Masters oil paintings, and modernist masterpieces—recognizable ones you studied in school—leaning up against the wall, stacked against each other. Also, the wife's $40,000 per place setting china from which she ate her boxed Mac & Cheese. I should add that there were a dozen or more of these museum-quality paintings strewn carelessly about the nondescript den of their freaking beach house—with windows open to the sand and corrosive salt air.
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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. We Can Afford to Try Them All
I used to work as a private chef for a billionaire, living in Paris. He is actually a very nice and down to earth guy, treated everybody very well and was just a normal guy that had a lot of money. One time we were at his private villa in southern France with three of his (also very rich) buddies. Let me tell you: rich people are not just like us.
They flew in by helicopter some 10-12 smoking hot Russian models that stayed at the house and partied for five days. Lots of partying with good and expensive food and drinks, etc. At the end of the week, he had slept with every one of the Russian girls. I've worked for a lot of really rich of people and would say that this is nothing unusual.
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66. Friendship
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. 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.
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68. You Can’t Put a Price on Leg Room
I was an assistant to a rich guy who routinely had me buy two first class plane tickets, so nobody could sit next to him on the flight.
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69. 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.
70. As High as the Money Stacks
I was a concierge. I seen lots of things, but the one that made me the most mad was two very well-off families in the building (lawyers and consultants...they were neighbors and best friends). Extremely conservative and active in trying to deny any kind of social services in the city and state. 4 pm was "cocktail hour," as they called it.
They would load up on all sorts of prescriptions and sit in the lobby bragging about how high they were. They had no shame about hiding it. Sometimes if the husband/lawyer was really far gone he would loudly discuss his clients' cases in front of everyone. Then their prep school kids would arrive home and everyone would head out to the most expensive restaurant in the neighborhood. Other than that there was a lot of general entitlement, shacking up with people who aren't their spouses in the building's swimming pool, etc.
71. 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.
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72. Personal Piggy Bank
The director of my former company was a nice enough woman, but she used her position to get employees to do everything for her. The head of Human Resources & Finance was required to help manage her personal bank accounts, enrol her children in school, book her holidays, EVERYTHING. She also had a nanny for her younger kids who was somehow being paid through the company for tax purposes (and so she wouldn't have to outlay the money).
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73. 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."
74. The Price of Love
My neighbor is this really down-to-earth guy who managed to work his way from nothing to being quite wealthy (he has his own company and pulls in north of $200,000 USD per year). A few years ago, he married this beautiful brunette who can safely be said to be on the upper scale of maintenance cost. Worse than that, she was given way too much freedom.
When they redecorated their mansion, they ordered custom-made stairs that cost about $100,000 USD, which were made of glass/steel. Once she had them installed though, she noticed that they didn't really match her choice in furniture, so she had a virtually identical set of stairs made that only differed from the last set by a few shades of white. How this guy puts up with her is beyond me.
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75. 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.
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76. Dishing It out
Someone once ordered the dessert on special—it was tiramisu that day—and sent it back, saying that “Mascarpone cream doesn't go along well with coffee and your recipe should be changed.” That is literally the original and classic recipe. Then get this. She asked for tiramisu with Victoria sponge. Are you kidding me?
First, we had no Victoria sponge, second, just because someone asks for it we are not going to make something we won't end up selling, and third, I think the chef would've rather carved his own eyes out with a fork. Just because you have the money to pay for a 200€ meal doesn't mean you are entitled to whatever you want. We are workers who want to turn a profit at the end of the darn day, not your personal staff of cooks and waiters.
77. 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.
78. Time Is Money, or So They Say…
I work for a very wealthy family in the commercial real estate market, and the one thing I have noticed is how much they lack a sense of time. They have had people doing everything for them for so long they no longer realize how long it takes to complete a task. One example: "Hey take this deposit to Bank A it HAS to be deposited today!" Sir, it's 4:50, they close at 5:00, and it is a 25-minute trip one way.
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79. 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.
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80. Nay Is For Horses (Which I Own)
My dad is a self-made millionaire. He accomplished it through hard work, and he raised me just as toughly as he was (he didn't want me to depend on money). I have some experience with people of my "status." One girl I know convinced her parents to move so she could be closer to the horse stables she liked to ride at.
She upped her dad's drive to work, and her mom's, and her little brother had to change schools in eighth grade, the worst time to pull a kid out. Get this though, she made her mom BUY her favorite horse. She also would try and make ME buy her a horse, because "I was rich, and I didn't need my money like she did."
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81. 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.
82. You Probably Know What Evian Is Spelled Backwards
I worked at a private villa in Bali. One guest stood out because she only drank and bathed in Evian. So one day I spent almost an hour filling a large tub with tons of Evian bottles. The same young woman complained that the path from her villa gate to her room wasn't well lit. This was probably because she wore sunglasses at night.
83. 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.
84. Outbid by the Law
I had a pro golfer hire me solely to list 90% of his belongings on eBay. Everything from huge TVs to golf club head covers. The odd part was he wanted EVERYTHING listed for $0.99 and shipped as fast as possible when it inevitably sold. I lost that job when he went to jail for procuring said items with illegally gained funds from his invalid sister's inheritance.
I was questioned, but since I had no idea how he got rich, no charges were ever brought up on me. I just thought he was a weird eccentric rich guy who wanted new toys, and I assumed he had invested his pro-golf earnings over the years (he was sponsored by Nike after all).
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85. 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.
86. Poor in Practice
I worked for a non-profit that helped extremely low-income women start their own businesses. These women would give up food to scrape together enough money to join our program. One of our E.D.s said she "wished she could relate to our clients more, but she has never been poor." She owned two homes in one of the most expensive zip codes in the US. Also, another woman, whom I really did respect but didn't always agree with, believed people chose to be in poverty. We would debate for days about that statement.
87. 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.
88. Hey, Big Spender
This one girl only ever wore designer clothes and would constantly make fun of people who couldn't afford to wear the same. When we went to the mall, I would often buy nothing. Meanwhile, her parents would give her not one, but two credit cards to go buy whatever she wanted.
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89. 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.
90. A True Diamond in the Rough
I operated a premium chain restaurant in Canada. One day, a very generous gentleman we’ll call Mr. S started coming in. On the first day, he spent $200 on wine and tipped $1,000. The next day he did the same. When he came in for the third time, I had servers fighting over him. Anyway, one evening he got drunk on wine and Brad the busboy made the mistake of complimenting him on his watch. Mr. S. takes off his Tag Heuer 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 then says, “Brad I'm really sorry I got drunk last night and gave you my watch.” Brad is chuckling as he is removing the watch and says it's no problem, and he was just holding the watch until Mr. S returned. But he was dead wrong.
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.
91. 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!
92. Poor as Porsche
The CTO of an IT company I worked for was born into a rich family and didn't know how to talk with his "inferiors." He was so bad at human interaction, our CEO forced him to go to some kind of class to learn how to interact with humans. This douchebag loved Porsches. He drove a couple to work, and he had one he would race at amateur races occasionally. But that wasn't the worst of it.
One day, one our coworkers failed to meet us for lunch because he was broadsided on the way to the restaurant. For some reason, after the accident he came back to work. We were standing around his cube and he's telling us about his car getting totaled when the CTO walked up. After hearing the story, the CTO says (and I'm not embellishing) "At least it wasn't a Porsche." Then he laughed and walked off.
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93. 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."
94. Disrespecting Your Elders
This one girl whose mother I used to know would spit in her Granny's face if she didn't give her money every time she saw her. She also told her dementia-ridden Grandpa that she couldn't wait for him to die so she could buy herself gifts with the inheritance money.
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95. 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?
96. Was His Boss a Bull?
My former boss was insanely wealthy. He used to stay in presidential suites at hotels and would order the staff to have any and all red removed. He was a high roller at several casinos and they made special chips just for him, as a substitute to red chips. He hated the color red because when you’re losing money, you’re “in the red.”
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97. 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.
98. She Doesn’t Sound That Nice…
I was good friends (and still am) with this kid whose mother was an executive for a big gaming company. Basically, she would attend Pax East (pretty big gaming convention) every year and would give her kids tickets for themselves and their friends. I wasn't one of those friends that year, but I got tickets for Christmas and we still went together and oh my god, what his mother did literally sent shivers down my spine.
We went to the booth where she was at (that year she was advertising a new game, I don't think it ever hit off, if it did I don't remember the name of the game then). When she saw me and her son get to the little show floor, she pushed every kid out of the way so that we could be first in line, and actually got a kid kicked out for throwing a fuss about it.
I wanted to say something, but my parents had paid $50 for me to get to the convention and I wasn't looking to get kicked out before even being there for an hour. She was a nice lady though, she was able to get basically a few of everything that the popular exhibits were handing out (hats, shirts, wristbands, coupon codes).
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99. Aren’t They Precious
Young girl about five years of age, getting ready to go into New York City to visit her Grandmother. She was at her Aunt's house and did not have a pair of shoes that she liked. She called her chauffeur, told him which pair of shoes she wanted—the dude got the shoes and drove some 20 miles to deliver them, and she told him he got the wrong ones and he was an idiot. No one in the family thought this was inappropriate.
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100. One For The Road
My dad works in shipping and has a lot of friends who have worked on superyachts. 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.
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