More money, more problems—or rather, less information. Wealth cam insulate people from the everyday problems that force us to be aware of this complicated world. These Redditors were asked to talk about their strangest interactions with people of wealth, who could afford to be clueless. From the confused shoppers to helpless self-caretakers, what happens to the humans who can pay away their need to know? Open a wallet to these outrageous stories about the most out-of-touch rich people.
1. You Can’t Bargain With the Skies
Upgraded to 1st class recently on a flight that ended up delayed on the ground for an hour. I wasn’t even mad. A woman in front of me turned to her husband at one point and said, “Why don’t you go have a word with the captain and see if you can get him to hurry up? Tell him who you are.” There was just one problem.
I had no clue who he was and I don’t think anyone else would have either. But at least the guy understood that that wouldn’t work even if the woman he was with didn’t. He refused.
2. I Got a Golden Ticket
My classmate got three traffic tickets in two consecutive days. About $700 total, including fees and whatever. His response was disturbing. He just paid the fines without batting an eye and then cheerfully said it was a good lesson to learn. Pretty sure I was more appalled and upset about the whole thing than he was.
3. Two Hundred Reasons Why
I once asked one of the directors of my company to spot me for lunch because I had forgotten my wallet. He handed me two $100 bills and was legitimately concerned it might not be enough.
4. The Grass Is Only Slightly Greener on the Other Side
I used to go to middle school in one of the wealthiest neighborhoods in Staten Island. The local kids who lived right next to old mobster mansions thought they were lowly “middle class” people. One of the teachers had to kindly explain to them the difference, diplomatically calling them “lower upper class.” They were sill upset about it.
5. The Cost of Opportunity Is Steep
My uncle who is really rich told me that if I wanted to change careers, I should just take an unpaid internship or beg to work for free. Well, I need to pay the rent, so I don’t really have that option.
6. On a High (Income) Note
I have some very wealthy extended family. One of them recently purchased an $80,000 violin for their teenage son. I remarked that it seemed pretty excessive, especially because he had exactly zero plans on playing it after he was through with high school. Her only response was, “Well what else was I going to spend it on?”
7. She Nailed It
I work at a veterinary hospital in a fairly wealthy area. Once had a client hand me a $50 for a $9 nail trim on her dog. I told her the price and she just shrugged, told me to keep the change and said that would be my lunch money for the week. Sad thing is, it was.
8. Let Him Eat Bread
I was flying a private jet, and the caterers forgot the owner’s sandwich. He graciously said, “No big deal” and I replied that I’d call when we landed because they charged us $100 for it. He said “Is that a lot? How much does a sandwich normally cost?”
9. Wage Wars
The president of my company asked me if I thought I could live on $100 per day. I told him I did every single day. I was probably making $13-$14 an hour at the time.
10. The Smell of Success
I grew up in a very well-to-do suburb, and there was a family who had an extremely bizarre habit. They would buy cedar clothes hangers for their closets, but then once the cedar smell “wore off” after a month or so, they’d buy new ones and take the old ones to Goodwill. Apparently just lightly sanding them to refresh the scent was too much trouble.
11. Here’s a Tip: Don’t Be a Jerk
My dad and I worked for the owner of a big beverage company. The owner’s wife was yelling at my dad for tipping the garbage man $20 while I was carrying a $20,000-dollar lamp she just purchased.
12. My Entourage Should Burn Carbs Too
I live in Hong Kong. Back in the early 2000s, a local gym/fitness club changed their regulations so that only people with paid up membership could enter the premises. Why? Because tai tais (a colloquial term in Hong Kong for a wealthy married woman who doesn’t work) were bringing their maids to the gym to help them undress and dress.
The (mainly) Filipino maids would sit in the changing rooms for an hour or more while their employer did a class, then help them dress (dry hair, etc.) when they came back. The gym basically wanted to get rid of the Filipinos sitting around in the change rooms, but the tai tais simply bought them memberships!
13. Friends With BIG Benefits
My sister and I, both Latin American, befriended a Chinese girl in college. We always helped her in studying and with her English. Turns out her dad was some billionaire in China who owned a Chemical producing company. She drove an expensive Audi and for the longest, up until 2 years ago, I was freeloading off the Chegg account she opened up for me.
That account was paid for about 3 years. Whenever she’d invite us to go eat, the bills were super expensive, like $300+ for just 3 people, but she played it off like they were nothing. I had never once eaten a single meal over $40 per plate until we ate with her. She’d always take us Starbucks, food, and on a couple of occasions, she bought us books for school.
At one point, we went shopping with her. She wanted a laptop; she was gonna buy me one too, but I felt too guilty to accept it. The laptop was $3,000. I felt like it was too much. She was really cool and treated my sister like her sister. She was living alone and didn’t know many people. We were always friendly with classmates and that’s how she got to know us.
My sister and I are from low-income families. The money that was spent around her was ridiculous! Like $300-$400+ per lunch almost every day, that was around my weekly pay back then. Really miss her though, she was fun to be around with and always wanted to learn more about the US, always insisted we go out with her to movies, shopping or dining and teach her about our culture. Have not heard from her in 3 years. She went back to China and we never saw her on campus again.
14. Her Ego Puts Her Over Carrying Capacity
There was this incident I heard about a couple of years back about a local socialite, who married into one of the richest and most powerful families here. The story goes that she was at a bank’s main office to meet with the CEO. Instead of taking the elevator like a regular person, she had her bodyguards remove all the people inside the elevator so that she could go up alone without people bothering her.
She said something along the lines of, “Get out of my elevator.” Funny thing is, one of the people she had forced out the elevator was the bank owner’s wife, who decided to take another elevator with the rest of the people who were forced out. The owner’s wife got her sweet revenge. Once the socialite got to the office, the bank owner’s wife was already there and promptly told her to “get out of her building.”
15. The Sweet Taste of Financial Security
When I was a supervisor for Starbucks, we had a regular who ordered the same (extra modified) Frappuccino every day, three times a day. She had to have it all the time and only liked getting them from a few stores. When she would go on road trips to her cabin, she would come in the night before and we would pre make a whole bunch of Frappuccino’s and not add ice or blend them.
This would be so she could blend them in her car on the way there and back. Did the math, she spent over $8,000 per year on this stuff. For the record, she was an heiress and only stayed home all day watching soap operas.
16. A Touchy Statement
I work in auto parts and a really flustered woman came in last winter. All she said was that she couldn’t see clearly anymore cause the things weren’t cleaning the glass. I go out to look at her wiper blades. It’s a newish Mercedes, and the rubber is torn clear off the frame. So, I go back inside and while I’m getting her replacements, I’m explaining to her how you need to free the blades from ice before you turn them on, or they’ll tear like that.
She gives me the most puzzled look I’ve ever seen on a person: think puppy hearing a weird noise for the first time, head cocked and all. She asks me what I mean… I said before you get in and turn them on, just give them a gentle pull so they’re not attached to the ice anymore. Her response made my blood run cold. She gives me that look again and says, “It’s cold, you can’t expect me to seriously touch it.”
Now it was my turn to be a little puzzled. She says, “I thought the car took care of that nonsense, you can’t expect a regular person to work on it like that.” I said ma’am, the only way to prevent this happening again is to ensure the blades aren’t stuck in ice…that’s it. She huffs out loud and says, Fine! I guess ill have to talk to the help about being on top of that from now on.
Then she pays and leaves before I can process and say anything else.
17. Too Rich to Use Your Noodle
Last year, I lived in university accommodations with a boy whose father was a high-ranking member of the Chinese government. Perhaps due to the fact that I was also Chinese, or as the result of the excess privileges lavished upon him from an early age, he immediately established me as his “best friend.” Then it got really disturbing. He started to stalk me to and from lectures, to the extent where I had to vary my routes every few days. I’m a girl.
Anyway, this chap was intelligent, however, had difficulties using common household appliances. He did not know how to use a microwave or a toaster. One day, at 10 pm, I heard a rapid knock on my door, which of course, was this guy. He had microwaved a bowl of ramen in a ceramic bowl and did not know how to get the bowl out because the ceramic was far too hot.
Sarcastically, I replied that he had better let it cool. Half an hour later, he knocked on my door again, and started whining, in the most piteous of voices, that now the bowl was cool enough to handle, his ramen had also turned cold.
18. Jet Set for Misunderstanding
I was working in a fine dining restaurant and in one of our private rooms was the birthday party of a very well-known local rich guy. His wife was greeting people at the door, and my job was to stand next to her with a tray full of cocktails for her to offer people as they arrived. When there was a lull between arrivals, she started telling me a story that she thought was hilarious about the trials and tribulations of decorating their private jet.
I responded politely of course, but all the while I really just wanted to ask her if she honestly believed I could relate to anything that just came out of her mouth.
19. She Could Do the Time, So She Did the Crime
On the hill from Hampstead tube station, some Joan Collins 1980s clone of a woman parked her Range Rover outside a shop on a double yellow line (no parking on that road) with her hazard lights flashing. She was coming out of the shop carrying her frou-frou little paper bags as a traffic warden was fixing the parking ticket to her window. Her reaction was priceless.
She snatched it from the windscreen and said in a posh but aggressive voice, “I don’t care. I can freaking afford it.” Threw the flapping paperwork into the vehicle and roared off down the hill. To most of us, parking meters and Do Not Park signs and road paint are parts of society with a financial penalty to keep the system going.
For this woman, it was like having a park-where-you-like system that occasionally had a fee that made her whiny and wasted the time it took to write out the cheque and post it for the fine.
20. The Toughest Customers Cost the Most
There is this lady that comes into my store who is so awful, just seeing her makes my blood boil. As far as I know, she has let her kids destroy the store. Literally throwing merchandise all over the place. She’s asked for someone to get a key for the perfume case—then whenever someone got there, she decided that she wanted to shop more.
She brings an entire cart full of stuff to check out and then halfway through the transaction, she goes to get more stuff, sometimes more than once in a transaction. She REFUSES to read stuff on the packages. I seriously had to read the differences of two items to her. She once had me figure out what kind of batteries an item needed, get them for her, and then put them into said item.
She frequently had us check the back for an item we told her we no longer carry. She insisted that we check regardless. She left her child throwing a tantrum right in front of the register so that no one behind her could check out. And, as if that weren’t enough, she asked me to go get items for her while I was checking her out.
Keep in mind that this lady isn’t old, maybe mid to late 30s. My manager said that we would honestly tell her to never come back if it weren’t for the fact that she spends so much money at our store.
21. The Not-So-Magnificent Seven
My dad, who is very wealthy and very stingy, once offered to get me out of a tough situation financially. I didn’t have a car and was really struggling to make ends meet. I was telling him about what was going on in my life, and he opens up his wallet and hands me all of it’ contents. It was seven dollars. He kept saying how “He’ll give me everything he has,” and hands me the $7.
He felt really proud doing it too.
22. I Prefer to See the Wallet as Half Full
Somebody told me about a guy bragging about spending $100 on a bottle of wine, and she told me “Everyone knows good wine is $100 a glass, not a bottle.”
23. Way to Throw a Dog a Bone
I once got asked to watch my buddy’s mom’s dog. Cute Pomeranian, super well behaved. I was stoked to watch the little dude. She messaged me and told me where the garage key was and that she left a couple of hundred dollars on the table for me. I did a double take. A couple hundred!? I showed up at noon and took the money and the dog and went into town.
Took him to the dog park, then the beach, and then we kicked it and napped for a couple of hours. Dropped him off around 6 pm. It was the easiest $200 I’ve ever made.
24. Hand-Me-Down Drivers?
I kind of have one. I work in estate management as a side gig, and most of my clients are wealthy. It’s usually the kids who are out of touch. I once spent 10 minutes trying to explain the concept of “used cars” to the college-aged daughter of one of my clients. She just could not grasp that some people buy cars that are not brand new.
She seemed to think that after a car get used for a while, it gets returned to the dealer and shipped off to a poor country. It was really bizarre; she was pre-med too.
25. It Should Be Illegal to Be This Rich
I used to intern at a law firm that dealt in tax and estate management for “high net worth individuals.” Given the worm’s eye view of the place that I had, I could only ever catch glimpses of our clients’ crazy; but suffice it to say, their stories are absolutely insane.We had a respected spinal surgeon who became convinced that he no longer needed to sleep or eat to survive. Oh, it gets worse.
Instead of sleeping, he would meditate for two hours a day and would eat vitamin pills instead of food—except for when he came to town for a meeting and made the firm take him out for a steak dinner. He was performing two or three operations a day in this state. We also had a powerful CEO, who became convinced that her rivals were trying to cast black magic curses on her and her family.
She paid our $600-an-hour attorneys to investigate shamanism for her to get to the bottom of it. We had another client, who owns a major restaurant chain and who shot his neighbor’s dogs for coming onto his property. The neighbor was also wealthy, and they both owned several hundred acres of land with no fence between them—and there was no livestock on the property, so he wasn’t exactly trying to protect his chickens either.
Not a client per se, but the wife of one of our clients ordered a hit on her husband. The hitmen she hired were so laughably incompetent that they didn’t even come close to killing him. On the first attempt, they shot out the windows of their house on a weekday afternoon when he was at work; the second attempt, they tailed him for a few miles but never did anything.
She got so frustrated with their incompetence that she fired them and hired another hitman, who turned out to be an FBI informant. The reason for the hit? They had just started divorce proceedings, and he was already seeing another woman who she feared was going to get her divorce settlement, which isn’t even a thing.
I wish I had more but as an intern there I had very little client interaction and got most of this through hearsay and digging through client files for our attorneys.
26. No Back-Up Plan?
Had a roommate in college who was pretty well off. I was pretty much putting myself through school and was almost always broke. One day we went by the ATM that dispensed in $5 increments (yeah, I made darn sure I knew where those were!) Anyway, turns out I had less than $5 in the bank, so looked at my buddy and said, “Well, looks like no beer for me tonight.”
He literally looked at me and said: “Well, just take it out of your other account.” I just stared at him and asked what he meant. Turns out he legit thought that everybody had a second account their parents kept filled with “emergency” money! He did buy beer that night though, so he was a good guy. Just kinda clueless.
27. Too Big to See a Difference
I have an aunt and uncle who are both experienced aerospace engineers (retired military officers, now higher-ups at private contractors), so they make an obscene amount of money. You can always tell how much they’ve lost touch with the value of a dollar when you look at presents that they’ve bought. One time, years ago at Christmas, they made a huge, offensive mistake.
They bought my aunt a $600 iPod and my mom a $20 t-shirt. Still, they didn’t mean any insult; they just thought my mom would like a shirt better and that my aunt would like an iPod better, and they didn’t even look at the prices of them.
28. His Jokes—Like His Tab—Are Rich
Kinda the opposite, but I once went out with the ultra-wealthy parents of this girl I was dating, and they made a big deal of me ordering whatever I wanted and getting appetizers and dessert and drinks and everything. Once I put in like a $75 single-person order; her dad just ordered 2 hot dogs and laughed at how expensive my meal was.
It was the most expensive lunch I had ever had at that point, and I really respect that man’s trollery. He had a much better sense of humor than his daughter.
29. You Can Take Home with You
I should preface this saying I was born to a very wealthy family, though one who put a great emphasis on a strong work ethic and that eschews attention or special treatment. That being said, having grown up around people of great wealth my whole life, I can honestly say their entire reality is different from most peoples. They are accustomed to a certain lifestyle that most people can’t fathom.
Take my best friend, for example, he has been in South Carolina all summer at his 15,000 square foot “beach cottage”. When he shows up to his house in June, he wants no transition period. That means no spending the first few days getting the summer house ready, unpacking, going to the grocery. He wants his life no different when he boards his Citation X in TX than when he lands in SC.
To achieve this, he has a handful of employees go a week ahead to SC and get everything ready. Deep clean the house, polish silver, manicure the grounds and on and on. They go to the store and buy food, drinks and all the sundries one would need for a summer vacation (sunscreen, toothpaste, etc.). They start unpacking the packages from Neiman Marcus containing his wife and kids’ new summer wardrobes that they have never even seen because they were purchased by their private shopper/stylist.
They train any new summer help and those who are staying with them, like the chef and a personal assistant, or two, move into their small house a few miles away. Cars are readied, boats are docked activities are planned all so that he and his family do not have to waste time enjoying their vacation. For a summer spent at this lavish estate and having a rotating cast of family and friends come and visit, I imagine it costs about one million dollars, not including private jet airtime or normal house maintenance.
I was just there last month and asked to use a car to go play some golf, five minutes later there was a Chevy Suburban parked out front with our clubs already loaded. I go to put the car in drive and notice it only has 87 miles on it. It had just been purchased the day before in anticipation of a large group coming to visit. His time is valuable, and he chooses to spend it a certain way.
His “disconnect” from reality can be seen in how there is this massive effort behind the scenes so that he is not inconvenienced with things that most people would find mundane. Yes, it costs him millions of dollars to never have to go to the grocery or fill up with gas, but he will tell you it is worth every penny.
30. The Minimum Effort
Several years ago, a job of mine led me to encounter a person who had come from a wealthy background, had a cushy job with a successful company, and rarely interacted with those below his socio-economic level. He decided to weigh in on a conversation about the economy I was having with some people. His opinions sounded so stereotypical that I was waiting for him to use the term “bootstraps” in a serious manner.
The reason I share this is that he went on to say that with minimum wage what it was, anyone could support themselves. He then revealed that he thought the minimum wage in the United States was $19.63 an hour. It took quite a bit of effort to convince him how wrong he was with that amount, and I respect him for accepting his mistake, but it blew the minds of everyone there that he could be so out-of-touch.
31. Work to Live, Live to Complain
Had a friend tell me that he was “done dealing with [mutual friend] because they had given up on themselves”.
What they had actually done was worked for a year before starting grad school because their father isn’t a millionaire, who has paid all their bills into their thirties while they played around and had fun with hobby-jobs without having to worry about financial security.
They didn’t understand how much life actually costs when you pay your own bills and thought less of people for working to pay their bills.
32. The Smoking Cash Stash
I sold hash to a business partner of my dad’s when I was in college. I had a variety, and it was the only drug he enjoyed. He obliquely asked me to bring it over to him—no discussion of what or how much. I biked over to his (very nice) place, and he had a coffee and a chat, and I simply handed it to him and was getting ready to leave, thinking maybe he’d have my dad pay me??
Nope, as I left there was an envelope on next to the rear entrance. It contained $500. For like $80 of hash. He would repeat this several times. He just needed a source he could trust and not raise eyebrows. When my dad passed, he helped manage the estate and we had an implicit mutual trust that made things go much easier.
33. One Man’s River is Another Person’s Bathtub
I repair bathtubs and showers. I’ve been in poor homes, middle-class homes, wealthy homes, and super mansions. So, we were at this mansion, the kind where there’s a tennis court and pool in the back yard. The kind where the foyer and first room of the house had 16×16 black granite tile with subfloor heating. Just this magnificent house with its three-car garage; but in the garage, there were three lifts to literally stack their vehicles. These guys were loaded.
They are “updating” the house to sell so they can move back to North Jersey. They replaced the soaking unit in the master. The granite in that bathroom was absolutely breathtaking. It was blue, and under a certain light sparkled like there were lights built into it. The deck was cracked at the caulk line. So, we’re in there fixing it, being as anal and meticulous as possible because we know we’re in probably the most expensive house ever.
The wife comes in to chat with us and basically states that they just got the same kind of soaker as before because it’s the only thing that fit in the spot. Eventually, she says something like, “It’s okay though, it was only $8,000.” If I was drinking something, I’d have choked on it. She said it like the tub was a piece of trash that she settled for because it was cheap. $8,000 was a drop in the bucket.
34. Shop ‘Til You Drop (Your Innocence)
In college, as I was making dinner one night, my wealthy roommate expressed surprise that you could get vegetables in a can—like totally in shock at the idea of canned vegetables. It turns out that in his house the cook simply went down to the market every afternoon to pick up fresh veggies, and he’d never known it could be done any other way.
This was not a post about the virtues of canned vegetables, but about the idea of someone so isolated by money that they had never been in a grocery store.
35. Would’ve Been Loaf to Deny Her
I worked at a very expensive and exclusive country club, the type you’d see the Bluths at. One of the members drove her golf cart over from her house. She said the help had forgotten to buy a loaf of bread, and she wanted to buy one from our kitchen. I told her that we couldn’t sell her a loaf of bread, so she asked how many sandwiches a loaf of bread can make.
I ended up selling her 10 sandwiches with nothing on it at $7/piece.
36. That’s a Wrap!
I’m wicked late to this but back when I was a cashier at Chipotle, I had a woman misunderstand the price of a burrito. She heard me say “that’ll be seven-twenty-eight” and without any hesitation, counted out eight $100 bills from a wad of cash that must have been several thousand dollars. We had a good laugh when she realized her mistake. She was carrying a suitcase and had a thick accent, so I think it may have been her first cash transaction in the US.
She was just so rich that it didn’t occur to her that $800 was a load of money to spend on a burrito.
37. The Widow’s Windfall from Grace
My Pops (grandfather) handled all the finances for him and my Nana (grandmother), so she never did the shopping or paid any bills. Her net worth now as a widow isn’t shy of £1m. When Pops died, she bought herself a brand-new car that was tailored to her disabilities, because again, Pops always did the driving. Her car was around £16k.
This was her first experience of buying a vehicle and thus thought this was the standard price for ANY CAR. I bought myself a new car a few months later. It was the same model as hers but a few years older and had previous owners. All my other cars had come in under £600, and this new car was £5k and I took it out on finance, which was a huge deal for me.
When she asked how much my car was, she was terrified that I’d bought a rundown POS car, and that there must be something horrendously wrong with it. We had to explain the value of cars to her and why mine was £10k less than hers. Flash forward to this year, my broke brother’s deathtrap car pretty much exploded, so she took him to buy a new one.
He’d seen a pretty good car for just under £1k and figured that’s what he could afford to pay back. Before he mentions it, she drags him to the dealership and buys an approved used car (same model and year as mine) at £3k and can’t believe her luck at how cheap it was, and gifts it to him because it was so cheap. Brother is speechless and very grateful.
This is the same woman who had an absolute meltdown because her Ambrosia custard pots had risen in price by 20p, and she was now (very seriously) concerned that her continued purchase of them would bankrupt her.
38. Swipe Your Fears Away
A friend of mine was dating a super-wealthy girl in college. Not sure how they got together, it was some internship thing or something. He grew up pretty poor, and he told me a story about how they were at Wal-Mart and he was considering buying a pair of flip-flops, but they were like $10 and he wasn’t so sure it was something he could afford at the time.
Apparently, she said to him “What do you mean, you don’t know if you should get them? Whenever I want new clothes, I just ask my daddy for the money card.” She literally used the phrase “The Money Card,” as if it was some weird artifact that magically made all clothes free for her (which, I guess it kinda did). He also told me she felt the need to take a full shower every time she pooped, which… I mean, that’s a different thing, but still funny.
39. Some Heroes Use Credit
I worked at the concessions stand at a movie theatre, and it was opening weekend for a large Marvel movie; the line was super long to get popcorn. This rich millionaire dude from India walked up to me and handed me his AMEX black card and waved a hand over the entire line of customers and said, “WHATEVER THEY WANT, MY FRIEND,” and plopped it down hard on the glass counter.
I’m just like “…Are you sure?” Him: “WHAT UH EVA THEY UH WANT!” with a huge smile on his face. He waited as the entire line ordered tons of food, entire combos, large everything, extra candy. I was like “You total is uh… $10,718.62” and I swiped the card and it said, “Transaction complete,” and he said, “Thank you my friend” and he went to watch his movie having fed everybody in line.
Absolutely unreal moment. And no, I didn’t get a tip or anything but now I have a cool story to tell. Complete strangers with just an unlimited budget to spend on movie snacks and drinks thanks to this man they didn’t even know.
40. Born to Spend
I had a classmate in college who was apparently some wealthy diva. Marries a guy whose parents were millionaires as well. Both eventually flunk out and tour the world on mommy and daddy’s account, soon getting married and have a child. They lived with his parents in a mansion at the time. It seemed like a dream, but it was actually a nightmare.
She gets tired of living with them and blackmails her mother-in-law to buy them a house or she will never see her grandchild again. His family refuses. Weeks of tantrums, Facebook and Twitter rants, eventually she moves out…to her own parents’ vacation home…oh, but it turns out she was actually just getting started.
A few years go by, and she is about to get cut off. So she has a brilliant solution: She gets pregnant again then goes back on social media to complain about how her family would abandon a pregnant woman and her child. Her parents crack and continue pouring money in. Husband’s family cracks and buys the home.
Now years down the line, I still see regular social media updates from her about overcoming adversity, triumphing over hardship, beating the odds, chasing your dream etc. etc. The married couple to this day has never worked or gotten a paycheck.
41. You Can’t Buy This Kind of Friendship
“Why would you take the train?” This a sentence that led me to believe that a lot of rich people have lost touch with reality. Though they can still be good people, as I learned over the week. Several years ago, I was a contractor in Afghanistan. I was in my early 20s and making a bunch of money. I decided I’d go to the Monaco Grand Prix. I flew from Dubai to Paris then to Nice.
On my flight to Nice, I sat next to a Jordanian guy in his mid-30s. I could tell he had money because of his Patek Phillipe watch that probably cost around $50k. We got to talking, and I jokingly said, “Nice watch. Private jet in the shop?” He laughed and said, “Actually my father is using it, so I have to fly commercial.” We chat for the rest of our flight about attending the Grand Prix and movies and whatnot.
When we go to get our bags and I say my goodbyes. I tell him I gotta catch the train to Monaco that’s leaving soon so I can get to the cheap apartment I rented on the edge of town. He looks at me and just says “Why would you take the train?” I tell him I can’t afford a taxi, so I have to take the train in. What he said next blew my mind. He just says to take the helicopter with him.
I put up a half protest (who wouldn’t want to take a helicopter into the city?!) and eventually go with him. It ruled. He had his driver, who drove a freaking Rolls Royce, drop me off at the apartment. We exchanged numbers, even though I never expected to hear from him. The next day he invites me to the docks to attend a private party on a yacht. Lewis Hamilton was there!
What was originally supposed to be a few days of me hanging out and watching the races from the stands turned to me attending parties with celebrities and Formula 1 drivers and the richest of the rich. Hanging out in the pits and all sorts of cool stuff. On one drunken night, he confessed his secret. He said that he invited me because it’s the first time in years someone treated him like a person.
Not kissing his butt or being fake. I sort of felt bad for him. He didn’t seem like he had any real friends. I’d be lying if I wasn’t envious. But little things he said made it seem like he was completely oblivious to how everyone else lived. But I don’t think I can really blame him.
42. Helicopter Parents Never Fly Coach
I worked as a nanny for a 1% family. The stuff I saw haunts me. I remember having one parent complain how rude it was a friend hadn’t offered to fly them to Miami on a private jet for a weekend getaway, and they were “forced” to go first-class. Had the other parent tell me they thought it was really “sweet” I was happy to help others and never be wealthy.
They would also spring last-minute trips on me and their kid all the time, so I’d stay in the main house with their child while the parents were country-hopping. Poor kid never had any sense of who was going to be where. There were business-related videos of the parents on YouTube, so it got to the point where I’d play them on an iPad so the kid had some sense of consistency.
Just to be clear, the kid was absolutely adorable and very sweet (which made it really hard to leave, I felt terrible), but it was pretty disheartening to think they’d probably turn out like their parents in a few years. The best part about the parent complaining over the first-class flight was when they asked me if I thought they were overreacting.
Literally asked me “Wouldn’t you be upset? Don’t you think that’s rude? They’ve been doing better [financially] now that they have Company X money they could have sent a plane etc.” and I’m thinking, well I’m pretty sure my entire year’s salary couldn’t pay for one chartered flight, so you know I’m probably not the best person to ask.
43. Small Business, Big Problems
Small business. 20 employees +/-. Boss made a big speech about austerity measures and no raises this year. A week and a half later he drives up in a brand new Silverado with all the bells and whistles. Expensed to the business of course. He would hate to have to pay taxes on those profits.
One of the less subtle members of the staff took a literal dump in front of his office door.
44. Sometimes It’s Best to Keep Your Mouth Shut
Company consisted of something like 1,200 employees at the time, and rented out a big conference center for a Christmas party. At the opening of the party, the CFO was giving opening remarks, and asked—expecting cheers—if everyone liked their Christmas bonuses. He got booed. See, of that 1,200 people, a bit over a thousand were in customer service. No one in customer service got bonuses, only people in the “corporate” departments got them.
And our awesome CFO decided to rub everyone’s noses in it, because clearly the Chief Financial Officer of a company would have no idea that 80%+ of his company didn’t get bonuses. At the same party, the CEO made an announcement that the company would be closed on Friday (Christmas that year was on a Thursday), and everyone got a day off.
Now, he had literally just finished making a speech about how everyone was important, and everyone was part of the company, no matter the department. He had shoveled crap hard, trying to make CS happier. The next day, we all got a memo that Customer Service still had to work on that Friday. We apparently didn’t count as “everyone” and the CEO just hadn’t realized that the announcement wouldn’t apply to anyone.
January saw a 60% attrition rate.
45. 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.