There are rich people, and then there are people that are so exorbitantly wealthy—their lifestyles seem straight out of a dreamland. These Redditors have stood on the sidelines, watching millionaires in their natural habitats, and their stories are so outrageous—they're unforgettable. Buckle up: Here are the secret lives of the world's most affluent citizens.
1. 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.
2. 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.
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3. 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.
4. 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.
5. 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.
6. 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.
7. 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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8. 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."
9. 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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10. 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.
11. 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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12. 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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13. 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.
14. 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.
15. 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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16. 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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17. 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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18. 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.
19. 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.
20. 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."
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. 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.
27. 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.
28. 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.
29. 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.
30. 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.
31. 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.
32. 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.
33. 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.
34. 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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35. 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.
36. 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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37. 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."
38. 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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39. 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.
40. 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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41. 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.
42. 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.
43. 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.
44. 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.
45. 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.
46. 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!
47. 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."
48. 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?
49. 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.
50. 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.
51. 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.
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