The Secret Lives Of The Rich
Rich people tend to be flashy and ostentatious by nature of their status, but what do they get up to behind closed doors? The following stories told by servants expose the real lives and behaviors of the 1%, and after reading them, they’ll make you wonder whether money can actually buy happiness (or not):
1. Reality Check
I work nights right next to a bar. The conversation that’s stuck with me the most was when someone’s baby mama found them and started a one-sided shouting match outside the window. She said something along the lines of, “You’ve got a million dollars in your bank account and still can’t take care of your kids.” Saw her running and screaming at him as he got in his car and drove off.
2. Keys To The Jet
About 25 years ago, I had a summer job at a very posh country club. It had a six-figure joining fee plus five-figure continuing membership dues, and that got you nothing but the privilege of paying top dollar for rounds, food, etc. I was a porter some of the time, as we had cottages on club grounds for members to stay and make a weekend of it.
One of my duties was driving members to and from airports—usually, they were private airports for private jets. One time, I was driving these two guys to the airport and one of them started complaining. It seemed as though he and his wife were always fighting over who got the jet every weekend, and where they wanted to go.
Well, the other one replied, “My third jet is actually just gathering dust right now since my son went to college. Wanna take it off my hands?” They shook on it right there in the van.
3. Good Thing She’s Got Harry
This lady sitting behind me was just tearing her dude apart while on the phone with a friend. The two lines I remember were, “He’s fine, but he’s got no ambition,” and “I don’t even let him touch me. I’ve got Harry for that. God, if he didn’t make good money, I’d leave him.”
4. Easy Money
When we were in high school, my friend used to caddy at a local country club. Some guy really liked him and asked if he would be willing to drive him around while he went out partying. This was in like 2003 and in a pretty rural area. He had no idea what he was getting into. My friend agreed and on his first day, he picked the guy up at like 8 pm. Right off the bat, the guy handed him $200.
He went to a bar for a little bit and my friend sat in the car. The guy came out, handed him another $200, and told him he had to visit his “friend” real quick. He went and got a bunch of illicit substances. They went to another bar and he handed my friend another hundred dollars to look out the window and turn up the radio.
He came out a couple of hours later with a girl, even though he was married with kids. He handed my friend another $200 and they went back to her house. After they did the deed, he came out and asked to be taken to the beach. At this point, it was like 2 to 3 am. My friend said that the guy slowly walked around the beach, went into the water up to his ankles (in his shoes), threw a bunch of rocks into the water, and then sat in the sand for about 45 minutes.
He came back to the car and asked to be driven home. When they got out of the car, he hugged my friend, gave him $500, and asked him to never tell anyone what happened. None of us really believed my friend when this happened—but then, six months later, we learned the disturbing truth about the guy. That guy got detained for assault and possession six months later.
5. I Hope They Have Insurance
I was about 15 and waiting to be seen by my eye doctor. I think I got there early and was in the waiting room. There was no one else in there. However, I heard two doctors behind the wall talking about some patient and whether to offer a surgery. Essentially, they said the patient didn’t need the surgery but they could make a decent sum of money, so they should encourage the patient to go through with it.
6. Bougie Skiing
I used to tutor an oligarch’s daughter in a wealthy suburb outside Moscow. One day, she mentioned that she likes to ski. I asked her which kind of skiing she preferred. Downhill is more popular where I’m from, but cross-country is quite popular in Russia and it’s even part of some schools’ curricula. Her answer? “My favorite kind of skiing is the type where you jump out of a helicopter.”
Silly me, I forgot about that kind…
7. Maybe Walk Down The Street Next Time
My ex thought I was sleeping. She went out on the back patio which was under my master bedroom window that was open. I wasn’t trying to eavesdrop, but overheard her talking to her friend about how they were both seducing an old man for money and pills.
8. Rockstar Antics
I used to drive limousines and taxis. One time, I got the manager of a fairly famous Canadian band in my car asking me where to buy illicit substances. I had no idea where and I told him that, so his next bright idea was to find a woman and hire her for her company. I told him I couldn’t help him do that either. He was disappointed but understood.
He had me drive down a well-known street until he saw someone. He asked me to pull over, got out of the taxi, paid the fare, and then immediately flagged me down again as a new ride. I knew what was up, but whatever. He got back into the car with the stranger and she told him exactly what house to go to for what he was looking for.
I took them there and waited a bit, then they came back out and I drove him back to the venue. He offered me two free tickets to his show which I gladly accepted as I loved his band and had seen them three times. Alas, since I was still working during the show, I gave them away to two friends who had never seen the band. They had a good time and I had a fun story to share with them about how I scored those tickets.
9. Not Something To Brag About
I was on a bus once and I heard two guys sitting on the seat next to me. I was dozing off, but just woke up to hear one of the most messed up things I have ever heard. So, this guy was just telling the other guy how his mother and his brother used his father’s retirement money to build a house and kicked him out later mercilessly.
He was smiling the whole time. He even showed the other guy a video in which his father was being interviewed by a local news channel to request people donate some money. I don’t know how bad his father was to them, but that seemed pretty cruel.
10. That’s Your Ticket
A buddy of mine ended up picking up a Netflix producer while driving an Uber. He said they had a great conversation as he brought him to his hotel. The producer invited him up for a drink and since my friend was a film student, he thought it’d be a good idea to go and try to get some good networking in. They hung out for about an hour when he asked my friend if he knew of any massage places nearby.
He didn’t, but the guy paid him $500 to bring him to the closest massage place which was only a few miles out. Upon dropping him off, he gave my buddy a card and said, “There’s a big party I’m hosting. That’s your ticket in.” All for bringing him to a massage parlor.
11. Always Be Nice To The Staff
I managed a theater for years and we had all types of rich entitled jerks come in. So, one night this guy comes in with a super-hot lady on his arm. Buys popcorn, a drink, and pays $100 because he is rude. And they go inside to get a seat. About 10 minutes later he comes running out and his phone is ringing.
He answers the phone and goes, “Hello? Oh, hey sweetie. Yeah, I’m stuck at the office late with some meetings. Kiss the kids goodnight and I’ll see you when I get home.” One of my employees has the great idea to scream, “SIR YOUR LADY FRIEND FORGOT HER POPCORN!” Right as he is getting off the phone.
12. Next-Level Rich
I drove L.I.M.O. at Marquette University during undergrad and grad school. Some of the students that went there were obscenely wealthy. Limos are the vans that take tipsy students anywhere on campus and a few blocks outside of it. One time, a tipsy guy left his wallet in a van and another driver called it in so I and another supervisor could take it to campus security.
We picked up the wallet from the driver and opened it to get the student ID so they knew who to email. There had to be a few grand in there. When we called the kid to tell him about it, I couldn’t believe his reaction. He told us we could just keep it because it was too far from his dorm for him to bother picking it up. K.
13. 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.”
14. Big Guy Behind The Wheel
I used to know a chauffeur and he ended up driving around some big stars. He was a big dude, like 6’8″ tall and super muscular. His best story was when he was driving around a few WWE stars. Almost all of them would awkwardly ask him to not get out and open the door for them because he’d make them look smaller.
15. A Little Too Casual
My elderly, very well esteemed, uncle once invited my partner and me out to dinner at an exclusive country club. We were careful to ask what the dress code was and was told we’d be in the club’s more casual dining room and to “just wear anything.” So we showed up in jeans and polos. Big. Mistake. We arrived before him, and when we walked in we immediately felt like we were peasants.
The entire staff stared at us. The host, standing behind his little podium in a tux, said nothing for a long time, and then, drawing each word out as though it pained him to even those such as us, he said: “I’m sorry, we don’t serve people in… dungarees.” It was the most insulting and hilarious thing I have ever been told. Every single syllable was shaped with contempt and derision.
We told him whose party we were here for. Suddenly they were falling over to explain that, no, no, the jeans would be no problem at all. We waited until my uncle arrived, told them to get bent, and went for pizza.
16. Out Of Touch
I did have the distinguished privilege of working with a multimillionaire one time for a couple of days and I was just astounded at how out of touch he was with people. In one conversation, he was talking about how he hated all the new homes they were building. He liked old castles so he was having a castle in Scotland disassembled and reassembled here in the US piece by piece.
On another occasion, he asked me why I wasn’t in college yet (the job was after high school and I was working as a plumber) and gave me an “Ohhh right” when I told him I couldn’t afford to go yet and had to save up.
17. Neat Freak
I worked as a valet for about a year at a really classy hotel. We routinely had Mercedes, BMWs, Range Rovers, football players candy-colored cars, Porsches… Think of pretty much any kind of high-end car and I must have driven one at some point. One time, a guy pulled up in a decent Mercedes, not anything super high dollar. He seemed cool at first, but then he did the rudest thing I have ever seen.
After I gave him the valet claim ticket, he casually went to his back seat and retrieved a newspaper. I was still holding the driver’s door open for me and he started disassembling the newspaper. Once he had 4-5 single sheets of newspaper, he began setting the newspaper on his driver’s seat, as if to protect it from my apparently dirty self. He didn’t even have to say anything, and it was still the rudest insult I had ever received
18. A Rich Man’s Disguise
My daughter played soccer for many years and at one practice, a guy drove up in a Ferrari, got out, and started talking to another of the dads on the team. After a few minutes, the guy left and another of the dads went over there and asked him who that guy was. He replied that the guy was his lawyer or something. I came to find out years later that that guy in the Ferrari was a multi-millionaire and had one and only one client: that dad.
His only job was to handle the dad’s charitable donations. So this dude got filthy rich donating millions of dollars of somebody else’s money and taking a percentage off the top. The dad, who was apparently worth several hundred million dollars, never came across as rich at all. He wore sweats and was at every practice and game. He drove a Camry and had been married to his average-looking wife for like 25 years. Stuff like that. He acted like a normal guy like the rest of us.
19. 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.
20. Shady Payday
A small part of my family was the Chicago Mafia. Grandpa told me a story of a family wedding in Chicago they went to in the late 60s. They were picked up at the airport by a limo with some high-ranking family members. On the way to the hotel, they were stopped about eight times by various officers. The officer would walk up to the driver’s window.
The chauffeur would reach into a money bag and pass a bill to the officer. Nothing would be said and they’d take off again. Eventually, my grandpa asked if they were being blackmailed. His cousin laughed and said, “No, it’s Thursday. That’s when we pay our boys.” So I guess that’s how they did it. It’d be at a traffic stop and in the open where it’s not unexpected.
I’d imagine that chauffeur had seen some things.
I was a sous chef at a fancy country club and it was 10 minutes before we opened for the Easter buffet. Needless to say, it was going to be a very busy day. I was walking through the dining room and checking all the final details when suddenly a little girl of about two years old ran into the room. She had escaped from her mom who was at the front desk.
She comes to a stop about six feet in front of us and looks up with her eyes wide. I must have been quite a sight, I was wearing my tall white hat and white apron down to my toes. Her mom appears in a heartbeat, turns her daughter by the shoulder, and whisks her away saying: “Don’t talk to them, that’s the help, dear.”
22. Partners In Business
I was driving for Uber and I picked up two businessmen in an industrial park. They were building developers. The man who was clearly the boss spoke to me as if I was always the driver who picked him up. Although they were clearly from the Middle East, they chose to speak English. Maybe they thought it was rude not to, being in the US.
But if that would have been rude, I’m not sure what the rest of the conversation was. They spoke about the future of business as if it were all so futile and how everyone will be either very wealthy like them, or very poor. They also discussed how their children really won’t be able to get jobs either, but that they wouldn’t need to anyway. I logged more than 4,000 rides between 2015 and 2017 and that was one of the weirdest.
23. Excuse Me!
Once I had a job as a cocktail waitress at a bar in Hollywood. It was very “A-List.” We served movie stars and celebrities there all the time. It was a very busy Thursday night and I was running drinks back and forth from the bar to the tables. One of my tables had about five glammed-up women that looked like they were on a girls’ night out.
They were probably in their late 20s and they obviously had money, I could tell by the purses, shoes, and snotty attitudes. I put their order in for their second round of drinks and I’m rushing by their table holding a tray full of drinks including martinis going to another table. The one girl decides she wants to change her drink order so as I pass by her, she turns and grabs the back of my dress to stop me so she can change her order.
Of course my tray tips over when I’m jerked back and the drinks crash all over me and onto the floor. I turn and give her a withering look but she barely makes eye contact and says: “Instead of a cosmo I want a vodka on ice” and turns back to her friends as if nothing happened. I was very tempted to spill some drinks on their outfits next!
24. Wild Beliefs
I picked up a guy from a dispensary. He was really good-looking and very well dressed, but he was in some kind of mental distress. He wanted to visit more dispensaries, but he had clearly already bought the max. I got his hotel information through conversation and we went there instead. On the way, he told me (in all seriousness) all about how his father was God, which meant he was divine.
“Didn’t you notice how much brighter the sun got when I got in your car?” He was serious. He also followed Guns N’ Roses like they were The Grateful Dead and thought Axl Rose was the smartest man alive. He didn’t really notice when we got to his hotel instead of the dispensary. I did ask him if he had taken any other illicit substances that day, and he insisted he hadn’t.
25. No Class
My ex-husband worked as an artist for really rich people. He had a client who paid him in cash, but good god, the way he paid him was beyond awful. He’d wad up the bills and throw them at my ex one-by-one as he spoke disparagingly to him. The guy’s home won some awards so clearly my husband did a really good job with his work. But this guy still treated him with so much disrespect.
I can’t even imagine what is going on inside that guy’s head.
26. A Governor’s Grace
I used to caddy at a fairly exclusive country club in Massachusetts. It’s the kind of place where, no matter how rich you are, you can’t buy a membership. You’re either born into it or you marry a member. As a result, a lot of the members like to show off their influence by inviting guests who would otherwise be unable to play at the club.
Someone invited Mitt Romney. We were given a heads up that the governor (he wasn’t a senator yet) would be coming and they wanted us to know how to act around him. We were told he wanted to be treated like anyone else but they didn’t want us to gawk. So, I guess to make sure us dumb caddies weren’t gawking, we were instructed to not look at or acknowledge the governor.
Because this is precisely how we would treat other people. I did get to shake his hand and chat a little bit. He was friendly, personable, way nicer than a lot of the members. I still don’t like a lot of his politics but he seemed nice enough in person.
27. View From the Top
I once worked at a super-expensive restaurant in Boulder, CO. It was a beautiful place on top of a mountain that overlooked the town. There was this older couple that visited at least twice a month, sometimes weekly. I once overheard them talking about how they love coming up to the mountains and looking down at all of the “trash” in the town below. They were good tippers though.
28. Realtor Revelations
I work in high-end real estate so I’m in the homes of the affluent a lot. Once, I was in a home selling for over $10 million with two Bentleys in the garage. I overheard the homeowner talking to her friend in the next room. They said: “These new tax laws are destroying us in the middle class. We had to open another trust just to save more money this year.”
It’s insane that this woman really believes that she’s middle class. They continued: “The billionaires are pricing us millionaires out of the neighborhood.” She was referring to her gated community in Park City and I was apparently supposed to feel sorry for her.
29. Bottle Service
I was opening a bottle for this table when I started getting chest pains. I was scared because the last time that happened I had a seizure. The pain hit so quickly that I almost dropped the bottle, so I put the bottle down on the table. One lady said: “Honey are you okay?” because it was clear something was wrong. The man who ordered the bottle said “We aren’t paying $50 a person for you to die here.”
After a couple of seconds—which felt like it lasted forever—the pain gradually went away and I apologized and explained what happened to me the last time. Then the man replied with the cruelest words: “At least you didn’t drop the bottle—it costs more than your life.” Tears started to well up in my eyes as I poured their drinks. I never went back to that table.
The lady who asked if I was okay came up to me later and apologized for the man and gave me a $100 tip. But still, I remember feeling completely worthless at that moment. The bottle cost $300.
30. Party People
I picked up a wedding party: a bride, bridesmaid, and the bride’s boyfriend who was paying for the wedding. They had a magnum of champagne and we drove around for quite some time while they did some illicit substances in the back. They tossed rolled-up $50s and $20s to me in the front seat as tip money. I dutifully brushed off each bill and added them to my wallet, pretending not to know what was going on.
But that’s not the most bizarre part. The “couple” argued on and off about showing up to the wedding because, apparently, she felt weird about getting married and he was trying to convince her it was a good idea. I finally dropped them off at the church and he slipped me a matchbook with his name and number written on it. Yeah, it was the late 80s and I was a young woman, one of the only female limo drivers at the time in that city.
I scored a sweet leather jacket with the tips from that night.
31. Did I Do That?
Somewhat distant relative spent all of his university years and twenties partying hard with the ~$100-120K allowance his rich company-owning father gave him each year. He’d travel the world each year going to Bali, Thailand, Europe, every year Oktoberfest, just rampaging. At 32 or so he decided to settle in an upscale ski resort area of the US and open a business with his hot gold digger fiancé.
When he went to transfer his money to his US bank account, he noticed it only came to a few thousand dollars. He angrily asked the bank worker why she hadn’t transferred the entire amount only to be told that that was the entire amount. His father had cut him off without saying anything and he just hadn’t noticed. Absolute flatline.
32. Cadillac Conversations
Many years ago, I had a security job that included the occasional responsibility of driving our rich clients around. I would typically drive them in my employer’s Cadillac Escalade that we had for those types of requests, so there was no divider between the front and back seat like in a limo. These were mega-rich people who treated me politely but quickly forgot I was present.
I overheard conversations about lots of shady and shady financial stuff. I overheard clients talking about insider trading, embezzlement, price-fixing, and stock pumping. I also heard some speaking openly about extra-marital affairs, intimate exploits, and expressing pretty disturbing attitudes. All of this was done with me sitting a couple of feet away in the driver’s seat like I was a piece of furniture instead of an actual human being with ears.
33. A Little Harsh
I worked as a waitress at a fancy bed-and-breakfast when I was 20. We hosted a date-night special and it was completely packed with couples. There was an older married couple that was in my section and the husband was super nice. He asked how my night was and even postponed his order so that I could clear a nearby table.
His wife had a permanently angry face and glared at everything I did. After their meals were cleared, it was time for dessert and champagne, as per the date night feature. She orders a brand that technically isn’t champagne, it’s a sparkling white wine. I didn’t want them to feel ripped off so I told her: “That’s a great choice but just so you are aware, this is sparkling and not champagne. Is that okay?’
She looked at me for an uncomfortable amount of time. Her husband is looking at her with an expression of mild concern. Well, her brain must have been going into overdrive trying to think of something insulting, because after a long silence she says the meanest thing: “Sweetheart, I see how hard you’re working. Have you considered getting some work done? You wouldn’t have to work so hard if you were a little prettier. Just a thought…”
I could not even process what she said until I got to the kitchen. Her husband’s face was what made me cry. I can take an insult but the mix of embarrassment and shame on his face just made me lose it. I comped his dessert and made her drink with mostly apple juice. I hope that $27 glass of 80% cheap apple juice was good.
34. Fox And Friends
I drove Uber part-time on Saturday nights. I would start the app directly in front of one bar in Hoboken. That was the bar that the Fox News people went to, so I was always in for long rides. I met both on-air and behind-the-scenes talent. One night, I was bringing back one of the on-air talents. It was a woman and there were three guys with her on the ride.
After I dropped her off at her home, the three guys were basically upset that not a single one of them was not being invited in. They were also tipsy and she had been the one who set the destination. They ended up hailing my Uber and I drove them home. So there you go. Not laughing was one of the hardest things I have done in my life.
35. On a High (Income) Note
I have a 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?”
36. Secrets Of A Musician
I had a job as a runner. I would pick up music artists from the airport and drive them to the venue, among other things. I won’t name the artists, but I picked up one duo from the airport in an Escalade. It was raining heavily that day and I had the windshield wipers on next to full. It created a beat. One of the guys has a small, handheld sampler and started making beats in time with the windshield wipers. All of us were driving along, bouncing to the rhythms. It was sweet.
Another time, I was driving a famous songwriter and guitarist back to the airport after the gig with his family in a 15-seater van. His family was telling him how great he was, but the dude was old. All he could say was, “What?” and “Huh?” It dawned on me he couldn’t hear. One of the most legendary musicians of all time, couldn’t hear ANYTHING.
37. 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.
38. It’s All A Fantasy
I once worked at this really exclusive club in Massachusetts, the kind you have to be born into and have generational wealth to be voted into a membership by the board. Drew Barrymore was a frequent guest, and there was always a lot of tension between her and her ex, who always came in with his extremely young new wife.
She wasn’t super friendly (no one was supposed to acknowledge they recognized her) and she seemed constantly stressed. I felt kind of bad for her. It didn’t seem like she had a fun life. Mitt Romney, Morgan Freeman, and a bunch of big-time athletes were also frequent guests.
39. Say My Name!
I used to live in Whistler, BC, so we saw a lot of athletes during the winter and summer, and offseason when they did training camps. I don’t really follow sports. One run-in with a guy, I’m assuming pro snowboarder by the looks of him. I think we accidentally bumped into each other in a club or something. He pulled the, “Do you know who I am” thing at me, and I just responded with, “Do YOU know who I am!?” right back.
He looked shocked. I added, “Half the people in this town are famous, bud. Get over yourself.” The look on his face was priceless. I am essentially a nobody but my facade seemed to work.
40. Business Pitch
I’ve encountered so many wealthy kids with rich kid problems and wildly different upbringings. Parents would constantly talk and quiz their kids on politics, history, science, etc. One group of guys was challenging their teenage sons to come up with a business idea. The boy with the best idea would receive a million for start-up costs.
The kids talked about stocks constantly at the dinner table. Teenagers would come to eat with their friends, drink, and drop a casual $15,000 on their parent’s tab. Just such a stark contrast from the way I was raised, where money was a taboo topic and my weekly $2 allowance for a week’s worth of chores made me feel rich.
41. Spend Like You’re Going Broke
The rich guy I know was completely delusional. He walked around and bought items like he was a prince. Spent $1,000s on clothes in one sitting and would buy drinks for people at the bar. His bills were examples of the “rich and don’t care” attitude. Then one day he asks me to print out his banking info and credit score. Turns out he was $100,000 in debt, despite pulling in a six-figure salary. His spending habits were insane.
42. Wealthy And Wonderful
While looking for a tennis partner, I met this truly lovely couple who basically adopted me. I would bike to their house to play matches on their backyard tennis court every day. They loved to take me out to eat at these incredible restaurants (as a foodie, I was in heaven). They even let me drive their cars on the beach, use their surfboards, and drive their jet ski.
They took me out on their yacht and even flew me out on their private jet to nearby islands to explore in the morning. Then, they’d fly me back in time for my job at the club. They were the kindest and most wonderful people, and they never asked for anything but my company in return. I think they missed their daughters who both lived out of state. I fell out of touch with them, but I think of them often and hope they’re doing well.
43. 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.
44. Screw The Administration
I drove the chancellor for a large university around and was told to actively forget everything I heard in the car. Throughout my undergraduate career, I constantly heard about massive cuts to the Humanities and Fine Arts budgets because we simply didn’t have the money. Multiple buildings worth of people were forced to share a single, outdated building during five-year-long renovations.
Graduate students and university staff were underpaid and underfunded. RAs were screwed out of salaries when the campus closed despite protections in their contracts. All in the name of budget shortages. I overheard the Chancellor and the head of the Athletics department discussing an enormous, multimillion-dollar training facility that was being commissioned on land that we were buying off-campus.
Our current training facilities are fairly new and our sports teams do not draw any crowds. We also bought an entire campus over a hundred miles away. Screw this place, and screw the administration.
45. Anchors Away
This story happened while I was working on a yacht in South America. A lady had helicoptered in a bunch of stuff for a party, and I guess her helicopter violated someone’s air space. The coast guard followed the helicopter to the yacht and boarded the vessel looking to arrest someone. She tossed her checkbook at them and as she walked away she said: “Fill it out, then go die and be forgotten.”
46. Absolutely No Chill
I drove a 180” Super Stretch Cadillac Fleetwood Brougham in the mid-90s. There was this elderly Japanese gentleman who would fly into our city several times a month, on his own Gulf Stream, no less. I believe he was an early video game developer. He was always dressed to the nines, tons of bling, a different Patek Phillippe watch every time.
He also traveled with a young male intern, usually the same one for a few trips, then a new one the next month. He would get in the car, exchange a few pleasantries, and then close the divider for the 45-minute drive into the city. Even with the divider closed, I could usually still hear the muffled conversation. One time, I thought I heard different sounds; though, I noticed the whole car, despite weighing about eight tons, was rocking side to side.
The first thing that came to my mind, silly me back then, was that the old man had a heart attack and the young man was doing CPR. I still can’t believe how naïve I was. I lowered the divider to see if he was OK. Well, he wasn’t having a heart attack and they both had happy looks on their faces. I put the divider back up and kept driving, wondering how much it was going to take to wash that mental image out of my cerebral cortex.
When we got to the hotel, they both acted as if nothing happened; although I noted the intern was walking a bit funny.
47. Geography Lesson
I worked at this fancy event center where a bunch of yuppies host their weddings. My job was so easy; I literally just opened doors or clicked buttons on the elevator. One time, a man who I had previously opened the door for had come back to talk to me. He proceeded to ask me where I am from and what I thought about him adopting a daughter from Korea.
I am an Asian American, born and raised in the United States, so I responded with something along the lines of: “Yeah that’s really cool..good for you.” He kept asking me uncomfortable personal questions about living in Korea and made offensive comments. For example, he said the fact that I could fluently speak English was amazing.
The funniest thing is that I’m not even Korean, I’m Cambodian! I told him this, and that Korea and Cambodia are very different places even though they are both in Asia. I come from a very educated and upper-middle-class family and in times like these, I literally feel like they think I came straight from the slums or something.
48. Well Then…
A guy I used to know back when we were teenagers had a lot of money. We just never knew how much until I was invited to go on holiday with him and some other friends, all expenses paid, of course. Anyway, we took a taxi to an area where this guy wanted to buy an apartment. We ended up spending the whole day walking around the area.
We got tired and eventually wanted to go back to the house, but we were so far away that walking was not an option unless we wanted to walk for about three hours. Neither of us had enough cash to pay for a taxi, and back then, taxis didn’t accept cards (this was around 2000 or 2001). So this guy rang up his dad and asked if he could send a chauffeur to pick us up, but the chauffeur wasn’t available. The solution his dad came up with was truly ridiculous.
Instead, the dad said, “There’s a Mercedes Benz dealer shop near where you are. I know the manager there as I’ve bought several cars from them—just go there and buy a car with my credit card. You can leave it in the house and we’ll figure out how to bring it home later.” So we went to this dealer shop and somehow, the manager did all the paperwork. We ended up driving back to the house in a brand new Mercedes C class, which we used for the rest of the holiday.
49. Well Wishers
I live in Florida so this table I was serving asked me how I fared during Hurricane Irma. I told them that we just had some minor damage to our roof but were lucky that none of the oak trees in our backyard fell on our house. This lady goes on to say something on the lines of “Well, I hope your landlord is taking care of that soon”.
I go on to tell her that my fiancé and I own the house and her mouth dropped. She says, “Wow aren’t you lucky to be with someone who makes enough money to own a house.” I simply replied by saying “I actually make more money than her” and walked away.
50. The Stingy Player
A co-worker of mine was telling me how, during his side gig as an Uber driver, he had picked up one of the receivers for our local NFL team. He complained that he had driven this man for a half hour and didn’t even get a tip or a good rating. “That jerk just signed a six-million-dollar contract and he couldn’t even tip me!” But there was something he left out.
It was only after he got through his whole complaint that he added how he trash-talked the NFL guys’ abilities during the whole ride.
51. Idle Threats
I once told a customer that he would have to wait an extra 10 minutes for his food. He replied: “I have 7,000 followers on Twitter!” I stared at him blankly for a moment and responded: “Did you just threaten me with a tweet?” 7,000 isn’t even that high!
52. A Football Tip
This happened to my roommate years ago while he was living in NY . He worked part-time as a chauffeur. He was always picking up rich people. One night, his boss told him to pick up Lawrence Taylor of the Giants. He was going to a party uptown. When my friend picked him up, he was very nice to him. He had two other guys with him as well.
He took him to this party and there were limousines parked all over. LT got out and said, wait on me. So he waited for like two, maybe three hours. LT came out later and said, “ I’m sorry to keep you waiting, but I’m going to catch a ride with friends. I apologize. He handed him $500 in cash.
53. 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.
54. Unfaithful Scum
One of my first ever jobs was at a driving service in Munich, Germany. I was just out of high school and it basically meant that whenever I was called, I had to pick the people up. Now the people hiring these services are popular football players, musicians, actors, diplomats, and a bunch of high-ranking politicians. One night I was picking up a football player.
He and a girl started making out in the back of the car. Two weeks later, the same thing happened with the same girl. Again another week later. However, this football player was married to another woman and they had two kids. How did I know? I drove him and his family around a couple of times before. From what I get from the news, his affair never came out.
He is so well-known that 99% of the people know his name, even if they have zero interest in football.
I worked in the VIP area of a now-defunct stadium. I was in high school and was working a summer job washing dishes. We served various VIP staff including the stadium owner. The owner was actually okay. He even thanked us one time, which was more than we usually got from our guests. His relatives, however were another story…
One day we hear a shriek coming from one of the guests, it sounds like someone was being attacked. My boss, the head chef, runs out to see what just happened. Turns out there was some dressing on the handle of the label. And one of the owner’s relatives was shrieking as if a rat had just popped out of her food!
56. Wasteful Practices
I worked as a caterer for private jets and the insane folks who owned them. I had a huge order from what I knew to be a smaller jet, so I really wondered about it. When one of the owner’s handlers was training a new flight crew, he ordered $12k of meals for a flight that didn’t exist, just so the new flight attendants could practice the fine points of checking in a catering order.
I listened outside after the food drop as the handler started explaining what to do to six of the most beautiful humans I have ever seen. We provided food for a lesson! The food was wasted. I found it in the dumpster outside one of the hangars the next day.
57. Fresh Air
I once worked at a country club in Texas for four months. I asked a customer, who I should mention was fairly intoxicated, if needed anything else besides his next apple martini. Even though I’d dealt with smug businessmen for ages, his words made my jaw drop: “Some air that lacks the stink of welfare.” I’d never heard that one before!
58. Unexpectedly Boring
I drove a few celebrity athletes to signings and stuff, but the craziest things were what the quiet billionaires who had $10M summer homes in my area would talk about. Nothing depraved or dangerous; quite the opposite, really. The mundanity of life with security that few can fathom. One guy, I would pick up in Manhattan twice a week and drive him to his summer house. It was gigantic.
I live in a 4-bed, 2.5-bath with a finished basement. It would fit in his pool house. On one drive, he was laughing with his business partner about a phone call he had on speaker. A major retailer was trying to back out of a deal because the merch was not making it on time. He talked around it, sending them news articles about slow shipping due to emergency tariffs and politically motivated blockades.
It was like someone trying to sell you the extended warranty, but he kept the deal. The next week, he was stressed out because we were stuck in traffic with nowhere to go and he was going to be late to a fundraiser his wife started for his kid’s school. He made a big box store fold like a cheap suit, but “unhappy wife, unhappy life.”
Another was an older lady who was the community gossip. She was going on and on, telling the stories of these prominent families who all belonged to the same house of worship. One was pretty well known and influential, but, as she would tell it, also flat broke. The rest of their community could not let it seem that way and buoyed them up. They kept living in mansions, driving high-end imports, and getting added to business deals as a tertiary partner to replenish the fortune like rain gathering in a bucket.
But my absolute favorite was a guy who probably wasn’t a billionaire, but he was in the nine-figure range, easy. He always had great cars and tipped well, but explained that all his cars were bought off-lease. Someone else paid too much to drive them for two years and now he pays for a top-end car but at a reasonable price.
Any time he wasn’t headed to his office or to get smashed at his country club, he was in jeans and a polo or a concert T-shirt. When his father-in-law passed, who was a nice old man that we often drove to medical appointments, he texted each of the drivers from the service to thank us for driving him and having conversations with him as he always had a good time and brought our stories back with him (most of us active or retired servicemen or LEOs).
People who could buy a country if they wanted, but really just people in the end.
59. Job Offer
Just a couple of days ago I was serving a very important business meeting, important enough that one of the gentlemen flew in from Hong Kong. I guess they left some documents on the table that got thrown away and they came back in a couple of hours later and was frantically looking for them. He pulled me aside and said the most entitled thing I have ever heard: “Look, I make more in a week than you do in a year. Find me those papers or I’ll have you shining my shoes just to make a little extra.”
60. They Just Love Golf
My collegiate baseball coach was a friend of Toby Keith and got him to visit one of our fundraising golf tournaments. I knew little to nothing about golf or Toby, so I was completely out of my element, but Toby was nice enough to show me how to drive a golf ball. Turns out, the guy is extremely nice. So nice that we lost our coach the following year as Toby financed his baseball career (he never made the show and gave up after years in the minors due to family).
Toby paid for the housing, food, and everything else so this other guy could pursue his childhood dream. I guess that’s somewhat related. Rich people. Golf. So, there you go.
61. 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.
62. A Simple Solution
Several years ago, I did European delivery on a BMW. People would order a car from a dealer in the US and then they would make it in the factory in Europe. Instead of shipping it straight to the US, they would let the customers fly to Europe and drive their cars for a while. They’d then drop them off and then get them shipped to the dealership in the US. They’d receive their cars just like any other order.
While in Europe, I took it to the Nürburgring, which is a racetrack that has tourist days (you can pay about $30 to drive any car on it). Lots of Porsche GT2/3 R/RS which are $150K to 200K cars, high-end supercars, and very expensive dedicated race cars. We took my new BMW around the track and while on it, we came upon an accident where someone totaled their car and the track was shut down.
I went into the bathroom and was at the urinal when one guy with a British accent told another guy “You just need to buy a house and keep your car here. That way, you can just fly over and not have to drive your car here any time you want some track time.”
I used to work in a “high-end” tea room, and we had this regular who was absolutely awful. I was on my knees cleaning up a drink that another customer had spilled and the woman needed to get past me. I said “Sorry, I’m almost done!” and she said, in the most condescending way possible, “That’s quite alright, I like having people at my feet.” It took all my self-control not to trip her.
64. Like It’s Nothing
Back in the late 1970s, I worked as a carpet cleaner for a company whose clientele was exclusively in Beverly Hills and Bel Air, California. I’ve been in the back door of some of the most fabulous mansions in America. One morning, I got sent to a Beverly Hills house owned by a rich guy named Irving Chandler, as in, the Los Angeles opera house, the Dorothy Chandler Pavilion. That family of Chandlers.
So, I was in the kitchen getting my machinery set up when Irving himself came shuffling in, wearing pajamas and slippers, to get a cup of coffee. Indicating me, he asked the cook, “Who’s this?” “Carpet cleaner” he’s told. So, Irving sat down at a little table with a wall telephone, pulled a notepad and pencil from his pocket, and made a phone call.
My ears perked up. He called a Beverly Hills bank and got put right through to some big shot, saying “Hi, Don. It’s Irving. Chandler. Fine, you? Listen, I’m calling about that guy of yours who has been after me to make an early payoff for that loan I made last year. Why is he bothering me about this?” Now, I was really listening.
He went on, “Well, sure I could pay it off right now but what’s the big deal? Heck, it’s only two hundred and eighty thousand dollars?” “Only” two hundred and eighty thousand dollars. I was getting paid $4.50 an hour to suck the dirt out of his rugs.
65. VIP Guest
I was working as a server, and one night I brought water and menus to a table and asked if the guests would like to order drinks right away. The man glared at me and told me that I’d have to do better than that if I expected a tip. He wanted the best service. I was a little befuddled, smiled, and said that I’d do my best to make his visit an enjoyable one.
He said loudly: “Do you know who I am?!” When I admitted that I did not he was really offended. He then informed me that he was a professor at the community college the next town over. Seriously. The community college. His wife was shushing him, turning beet red, and face-palming the entire time. That poor, poor woman.
66. The Truth Behind The Dragons
We had a family limousine company and I drove an SUV for a few years while in university. I picked up a family (a mother, father, and adult son) and they were having an engaging conversation during the trip to the airport. As a driver, you learn how to tune out, so their conversation becomes white noise. Anyway, the adult son was an inventor and appeared on Dragons’ Den and his pitch was accepted by one of the “nicer” dragons.
But during the whole car ride over, the son was complaining that this Dragon was a liar, cheat, and unfair, yadda yadda. He then mentioned how Kevin O’Leary was the only one who was nice to him and gave him good advice (I think Kevin had passed on his pitch). By the time we reached the airport, I recognized the product that they were talking about and realized I had seen the son on Dragons’ Den.
67. Famously rude
We had a famous guest in our private dining room once, he would come to our place every time he was in town. One of my server assistants, who was pretty young, was pushing a cart of bottles when it accidentally fell over right in front of him. He said “Hey you. Why don’t you pour me another drink before you clean up that mess you made.”
His tone was awful and it really irked me. She started crying out of embarrassment and he just turned to me and said: “Well, why don’t you pour me a drink then.”
68. Unknowing Accomplice
My uncle drove limousines for a while some years back. He had regular clients, like General Schwarzkopf. But one night, he took a new client out. The guy asked my uncle to drive him to the bank and then take him home. When the guy called a second, third, fourth, and fifth time, my uncle gladly drove him because he tipped really well. Later, he learned the dark truth.
Then the authorities showed up at my uncle’s house, accusing him of being an accomplice to a bunch of recent local bank thefts. He somehow managed to convince the officers that he had no idea that the guy he was driving was robbing the banks…He just took him there, drove him home, and got a nice tip.
69. Childish Dad
I was working a catering job for a 4th of July party at an exclusive yacht club. I went about my business and was clearing used plates from tables. After stacking as many plates as humanly possible, I turn and start walking back to the kitchen. Next thing I know I feel something hit me in the back of the head. It was a chicken bone.
A grown man had been watching me the entire time, with his four-year-old son at his side. Apparently, he decided he didn’t want to wait the five minutes it would take for someone else to come by and clear his table, so he chucked his garbage at my head. And then he pointed at me and cracked up. I calmly set down my tray and just walked out of the restaurant without saying a word.
My dad has worked for a company for the last 20 years or so, and in his company’s earlier days, they were very rich and would waste money on the most ridiculous things, like private jets, swimming pools in offices, company helicopters, the works. Of course, this carelessness when it came to money eventually led to them going bankrupt, and a much more frugal competitor came and bailed them out in the early 2000s.
This was around the time my dad joined the company, and while he started out as a pretty low-level IT support employee over the years, he has carved himself into a niche providing personal IT support to the VIPs in the company. The office my dad worked in was a remnant from the past. The building was essentially two Victorian mansions joined together by an office block.
It really was a stunning building, but it was a massive cash drain and the company wanted to move everyone out of there and sell the building. For various reasons, they couldn’t sell it, so most of the building was unused, but it was also the company’s UK head office and the VIPs loved it because it was such a nice building.
When I was between the ages of about 9-18 I would frequently go to work with him as he had his own office. His colleagues and bosses also liked me coming along and as I have an interest in IT. I found it really fun, so what this all meant was that I got to meet quite a few rich people. My dad was also pretty good friends with the company’s chauffeurs.
About 10 years ago, the company’s CEO wanted to make a trip to the UK, and that meant visiting the UK head office. Now, this was an insanely big deal, so everyone in the UK did everything possible to make the CEO’s visit as pleasant as possible. It had been a very long time since his last visit to the UK, and after months of preparation, the day came for his arrival.
Everything was in place, and the company’s chauffeur was sent to the airport to pick up the CEO from his private jet. The chauffeur got there as the CEO landed in his jet. It just sat there for about 10 minutes before the jet turned around and took off again. No one was ever told why this happened, but the theory is that he looked out the window and didn’t like the look of the weather.
I can’t even imagine the amount of time and money this wasted, but it is also hilarious.
71. 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 the 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 the 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.
72. Sensitive Information
My mother’s family is all from the Detroit area, this story specifically is from one of her cousins. He was a helicopter rescue pilot in Vietnam, and apparently a dang good one. Once he got out, he and his best friend got a job flying people in and out of Detroit. They were generally very wealthy businessmen having important conversations, so it wasn’t uncommon for him to be told to turn his headset off.
Well, one day, there was a mechanical problem shortly after they took off; nothing catastrophic, but they had to cancel the flight. He turned his headset on and informed his passengers. On the ground, he apologized and started working out an alternate flight for them, but they told him not to worry about it. They set up the flight for the same time the next morning, insisting that he be the pilot.
Not long after midnight, his best friend from the army called him. “Run, get your family and get the heck out.” Now, apparently, when a man who has seen all kinds of horror tells you to run, you freaking run. He packed his family and left within an hour. His friend then took the flight for him, and the chopper exploded before it got 30 feet in the air.
The family’s best guess is that some mob bosses were having a very private conversation, and even the tiny risk of him overhearing anything was unacceptable. That cousin has lived in a remote part of Alaska since then, seemingly far enough gone that whoever was involved never found him.
73. VIPs: Very Irrelevant People
I worked at a nice restaurant in downtown Portland, and one day a lady called to make a dinner reservation for a large group. But first, she starts asking all these questions about “security” (we had none) and how I thought the staff and patrons would handle a “celebrity” dining there. Is there enough space to be private? They like to be private. Would it be okay if they brought their own security, to stop people from taking pictures and such? But of course, she couldn’t name names.
I rolled my eyes, gave her the go-ahead to do whatever they needed to do, and booked the date and time. Yes, I was super curious who it would be, and stayed past my shift to see who walked through the doors when the big night came. The group arrived, and it was…no one. Not one of us who worked there recognized a single member of their party.
They sure acted like they were someone, but all we saw was a loud group of douchey-looking twentysomethings. They actually did bring a “bodyguard,” who stood in the corner with sunglasses on the whole time. The only attention they got from other diners was the occasional side-eye because they were being such rude and obnoxious nitwits. The shock of shocks, they treated our staff horribly and tipped even worse. I will never know who that person thought they were.
74. You Think You Know Someone…
I had a roommate once and my boyfriend at the time always said that his family was well off. It was a joke because “J” was always broke and bumming off people but still drove a nice car. I just assumed they lived in a multi-million dollar home in a nice neighborhood, maybe La Jolla or something like that, and just refused to help him out.
Then, one day, I learned the truth about him. The dude brought home a literal BOOK full of specs and photos of his parents’ compound they were selling. Turns out, his dad was a freaking billionaire. They just don’t help him out because he didn’t want to finish school or start a career. It was wild.
75. 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.” The 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.
76. Breaking In
I worked as a “luxe” Uber driver. I had a fascinating conversation with a gentleman whom I picked up from the airport. His job was to break into casino vaults around the world and help them improve security. He went into extensive detail about how the most recent vault he broke into, the Bellagio vault in Las Vegas. It started with access through a construction entrance, then he climbed through an open window, jimmied a door open, found an unattended security pass, and strolled into the vault.
While it wasn’t exactly a “stroll,” he told me about some of the “old” security measures including false rooms with doors that would seal behind you, the infrared camera, laser tripwires, complex locks, fingerprint scanners, etc. He then took a selfie from the inside of the vault and sent it to the head of security with the caption: “Is this your vault!?” The head of security was promptly let go. He showed me the selfie and everything!
For those curious what the inside of the vault looked like, it was surprisingly similar to the vault in the movie Ocean’s 13.
77. Dish Disaster
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. 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 damn day, not your personal staff of cooks and waiters.
78. Uber Noob
John Boehner, a former Speaker of the US House of Representatives, was so rich he did not know how to use Uber. As the story goes, one of his aides downloaded the app onto his phone and showed him how to use it—but there’s a hilarious twist. Unknown to him, he’d been stuck on the carpooling option, Uber Pool. That’s what he used for years.
There are all sorts of tales of commuters hopping into their carpool and bam, there’s John Boehner stuck in a middle seat asking to get dropped off at the Capitol Building. However you feel about his politics, I think that’s pretty funny.
79. 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 of years after, she lived in that penthouse alone, and it was creepy to drive past at night and see this 14-story hotel completely dark except for her couple of lights on the top floor.
80. Bidding Battles
I grew up in an upper-middle-class family in a suburb of Washington DC. It was comfortable and we had nice things, but we were not millionaires by any stretch of the imagination. Because of the area, my grandparents who were helping to pay for private school were around some crazy rich people. My husband was hired by some of those wealthy nuts who lived in Napa, so we moved to a town in the valley.
They invited us to the annual fundraiser for the hospital, a gala with an auction. We got all dressed up at check-in, they asked if we wanted to go ahead and put a card on file. We declined, knowing already we couldn’t afford anything. They gave us a paddle for the auction and we found our table. We looked through the catalog and EVERY SINGLE ITEM started at $10,000.
Ten. Freaking. Thousand. Dollars. MINIMUM. I went to just move the paddle away from my plate and my husband almost leapt out of his chair. “DO NOT RAISE THAT UP, THEY MIGHT THINK WE’RE BIDDING!!!” At least one item that night went for over $120,000.
81. Spite Trip
I drive a limousine, often for wealthy clients. My least favorite is the children. One of my spoiled trust fund clients once insisted on picking up four friends from different areas of town. He convinces these people to go to the bar with him, but when we get there, he kicks them out and has me drive him to the airport, where he picks up a last-minute flight to Vegas.
82. Laughing To The Bank
A friend of mine is a pilot and was contracted by Justin Bieber when he was touring here a few years back. Apparently, Bieber was arrogant and pretty much threw around $5 bills in the helicopter as an insulting gesture. He also talked down to the pilots and complained about how backward our country is. But there was something he didn’t know.
It turned out that the bills he threw around in the copter wound up to be around $100k in our local currency, which equates to an average starting annual salary. The two pilots were laughing all the way to the bank the next day.
83. Rude Reunion
The father of a friend I grew up with is the department chair in a prestigious field at the nearby university. It’s publicly available that he makes over $400k a year and all of his children went into successful careers straight out of college. One day the friend walks into my restaurant, looks at me, looks around the restaurant, and says, “So…this is your life now?”
84. Sympathy Deposit
When I worked at a hospital, one of our technicians went home after their shift ended but left themselves logged into Amazon on the computer at work. This technician was a huge fan of the Boston Red Sox, like a legit superfan. One of the surgeons thought it’d be funny to order a bunch of NY Yankees stuff on their Amazon account.
I thought it was a funny idea too—at first. It turns out that the surgeon spent over $250 on the Yankee staff. This technician was probably only making $9 an hour, so that’s a massive amount of money to them. When I told the surgeon they definitely went overboard, he smirked and said, “It was only a couple hundred bucks.”
Being a surgeon myself who grew up with no money, I uploaded $500 into the tech’s Amazon account so that we could still enjoy the joke without ruining this guy’s financial life.
85. To My Defense
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 six-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.
86. She’s Beneath Him
I once worked for a guy who took his full-time nanny along on a ski trip with his wife and three under-10 kids. Because of my boss’s job, he was able to get high-end hotel rooms comped for him and his family, but even so, I heard him telling the person arranging it on the phone that they could stick the nanny in any old, tiny, and nasty room because she didn’t need to be treated nicely.
Later, when discussing the trip, he said he didn’t get why the nanny didn’t enjoy herself and take time to ski. I asked if she knew how and she said no, but there were lessons there for something like $200 to $300. Knowing my own budget, I asked if the nanny made more money than I did and my boss said no. I said there was no way his nanny could afford those lessons.
He scoffed and said if that was so it was because she didn’t budget properly. He added that it wasn’t like she had to spend her money on rent because he knew she was still living with her parents. I just marveled at how he never put the pieces together at how much money $200 was to someone in her situation, or that the reason why she was living with her parents was probably that he wasn’t paying her enough.
For a couple of years in high school, I went to this super expensive American private school in Switzerland. The company my dad worked for paid for almost all the tuition, so it was an amazing opportunity for me. Most of the kids in this school were either State Department or from American families living in Saudi Arabia (the Saudi government provided ex-pat kids with school up until 10th grade, so you had to go to a school abroad to finish HS).
There were, however, a few Saudi kids that were there, mostly so that they would be able to speak flawless English to help out their future careers. One of these kids, who I will call The Prince, was somewhere in the line of Saudi succession, but honestly, he was like 1,455th in line for the throne. Not a real contender for King, but his family was rich. Like, rich in a way that most of us can’t even imagine.
This school had some rules like you couldn’t have a car as a student, even if you were old enough to get a license in Switzerland. This rule was a real buzzkill for The Prince, but he made it through the year somehow. Over the summer after his Junior year, he drove back to the school from Geneva in his Lambo, probably just because he could do it outside the school year.
On his way up the mountain (the road is like an endless series of hairpin turns) he managed to flip his Lambo into a vineyard while trying to navigate one of those tuns. I’m guessing a Lambo has a lot of power, and he took it way too hard. His parents, furious at what he had done, decided to punish him by replacing his Lamborghini with a Porsche.
Of course, The Prince was SOOO angry. He complained about it bitterly when the school year started up again. The rest of us kind of just looked at each other in amazement. Same planet, different worlds I guess.
88. Dog Daze
I run a higher-end store that sells lighting and ceiling fans, etc. I once had a customer roll up in her brand new Jaguar F-Pace and get quite upset when we didn’t have multiple of the $2,800 lights in stock that she wanted. A simple web search would have told her that we are a showroom and such items are order-only.
She proceeded to get extremely huffy and asked how her dogs were going to get into bed. She demanded a manager ‘fix this right now.” Trying to keep my composure, I explained I was the manager and asked for a bit more information. It turned out, this lady had a separate house built for her Cavalier King Charles Spaniels on her property complete with televisions, beds and a person to care for them after 8 pm when she was done with spending time with them.
She eventually ordered the lights and brought one of the dogs into the showroom when she came to collect her goods. It was the most unsocialized dog I have ever seen and it yapped loudly the entire time, disrupting my other customers and snapping at a child who tried to pat it. She was gobsmacked when I explained due to the fragile nature of many of our displays, we have a “no dogs” policy.
She still bought her little hounds nearly $6,000 worth of crystal chandeliers for their house. Her story regularly gets retold when we have entitled customers to make ourselves feel better. She is our “It could be worse…” story.
89. 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 backyard. 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.
90. Old Money, New Money
After I graduated high school, my dad’s business really took off. We were middle-class comfortable—I went to public school, was never given a car or an allowance, had to work through high school for money for personal use, etc., but I was never food insecure or anything like that. But once I graduated, about 15 years ago, it was insane.
My parents moved from their three-bedroom house to a six-bedroom with two kitchens, a pool, and a barn with gardens. They suddenly had multiple cars and traveled the world. My little brother who’s 13 years younger than me has only ever known private school and first-class flights to Europe. So sometimes I’ll be with my mom and she’ll say something like “at our other house…” and it’s just wild how nonchalant she is about it.
They now own three homes and a nice condo. They will pay for me to go on vacations with them sometimes if I’m able to go, but otherwise, I work my little job for bad pay and drive my Kia Forte like a normal person.
91. Shop ‘Til You Drop
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.
92. Daddy’s Got It Covered
I had a friend in high school whose parents owned an honest-to-god mansion. Big slate flagstones, plush red rugs that I was informed were from Arabia, eight bedrooms, cabinets lining the hallways full of interesting and expensive-looking items, a kitchen the size of the downstairs of my house…I mean, my parents aren’t struggling—we have a three-bedroom with an extension—but this was something else.
I think her dad was a banker. We were playing hide and seek on a sleepover and also throwing balls around and stuff, and at one point, I told another friend to be careful. “What if we break one of the cabinets???” To which my friend who lived there replied “Oh, it’s okay, I’ve done it before…Dad will just replace it!” Boggled my mind completely.
93. Spoiler Alert Will
Two sons of a really wealthy couple go to the family lawyer to have their recently deceased parents’ will read. The lawyer is super nervous because he has known them both since they were kids. One son gets the entire inheritance, and the other gets nothing. The explanation was that it should be passed through to blood relatives only. So that was the day he found out he was adopted.
94. Nothing Special Here
I walked into this large home and asked if there was anything special about it that we could feature in the sale. The homeowner said, “No, I don’t think so—pretty average.” So later, walking around alone in the basement, I saw a shut door and I opened it. There was a staircase leading further down. That’s when I made an incredible discovery.
I hit the light switch and at the bottom of this narrow staircase, I just saw this blonde-colored wood floor. I walked down the stairs to a full-size regulation basketball court under the basement…Nothing special though. It also had a mezzanine with a set of seats looking over the court and an arcade.
95. Side Chicks
When I was a poor college student my wealthy cousin and his wife went on vacation and offered to let me house sit to give me a break from my three slovenly roommates. They live a few towns over in a very nice house with a huge front lawn and a fancy, tall iron fence with double gates. The fence and gates are about 11 feet high. You have to have a remote to open the gates.
That first night I slept so well! I breakfasted like a king and then drove to school. I got back around five, made a supper fit for a king, and settled down to write an Econ paper. My cousin has a warning system for when someone driving turns off the road and comes up to the gate. There’s a chiming sound and you can look at screens in a couple of different rooms to see who it is so that you can buzz them in.
I was deep into my paper when I heard the chime. I was confused at first and check my phone before I realized what it was. I looked from the sofa and could see a movement on the security screen. I stood up and got closer and had a clear view of two women getting out of a white car. One tried to squeeze between two bars of the gate—impossible—and then the other woman tried to boost her over the top of the gate—hilarious.
The top one fell and even from the house I could hear swearing. I was about to press the intercom button and ask WTF was their problem but I was chuckling at their antics and just watched silently. They peered at the house intently from between the bars like a couple of jailbirds for a while. The skinnier one actually stripped down to her bra and panties and tried to squeeze through the bars again. No dice. Butt and boobs were not allowing that to happen. More swearing.
Then, as the skinny one got dressed again, the bigger one went back to her trunk and got out a tire iron. As soon as she started with the hinges of the gate I was calling 9-1-1. The authorities took too long and the women left. I showed the officers the video but they couldn’t get a license plate number. When my cousin and his wife returned the next week I told them what happened and we watched the tape. He said that he had no idea who the women were but his wife looked pissed. I packed up, thanked them for my “vacation” and left.
She divorced him that summer.
96. Losing The Client
A friend of mine worked for an upscale concierge chauffeur service. His most memorable moment was when he lost Marie Osmond. It was a fairly simple gig: go to the airport and pick up Marie Osmond, who was to be the featured entertainer at a private event. The plane came in and he met her—she had a carry-on bag but her checked suitcase, containing her stage dresses and makeup, was missing.
She was unflappable, though. At some point, she asked to be taken to the nearest upscale mall. He did as he was instructed and when they arrived, she went into a large upscale department store, selected two long sequined cocktail dresses, and tried them on in the fitting room (without him, of course). Unfortunately, there were two entrances and exits to the fitting room.
Marie Osmond exited out through the other side and couldn’t find my chauffeur buddy, who was waiting patiently on the side she’d initially entered. 20 minutes passed and he began to suspect that something had gone wrong, so he grabbed a female manager and asked her to go into the fitting rooms to look for Marie Osmond. The manager thought she was being pranked and declined.
My chauffeur buddy was in panic mode, running wildly around the store asking random customers: “Have you seen Marie Osmond? Have you seen Marie Osmond?” The store security was summoned and he was asked to leave the premises. He called his employer and told them he had lost Marie Osmond. The employer didn’t have her cell phone number but had her agent’s; though he was not accepting calls.
She had in the meantime taken a cab to the gig, thinking she had been forgotten. Lots of apologies eventually ensued and there were no repercussions.
97. 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.
98. The Most Expensive Sushi Roll
I’ll never forget my twisted experiences with this one rich guy. He shared a stock I should invest in called Teledoc. Their rich friends puked shellfish in the back seat. He hired Anthony Bourdain’s food scout to travel the world and try interesting dishes, no matter the price. $10,000 USD for a roll of sushi? Done. But one thing he said really showed how vile he was.
He told me his wife doesn’t get intimate with him anymore while she was in the car.
99. Hotel Havoc
I used to work as a front desk agent at a boutique hotel. A guy who was obviously very full of himself came in with an online reservation that he had booked at a shockingly cheap nightly rate. He proceeded to give me a hard time about EVERYTHING, from telling me he shouldn’t have to give me his credit card info since he had prepaid his reservation, to telling me “Um yeah, I’m pretty sure I can find the elevators, I’m not stupid.”
He was just being an all-around jerk. About 10 minutes after checking him in, he came down and demanded that we give him a bigger room with a king bed and a view, even though he had booked a standard queen bed online. I complied, as we had extra king beds available. 10 minutes later, he came down again to complain about the size of the room.
He told me, “I’m only going to give you one more chance to make me happy,” and asked for the general manager. After much arguing between him and my manager, we ended up giving him our nicest suite AND free parking since we had “Given him trouble.” He got all this for a way cheaper rate, like $40 per night! Oh, but he outdid himself.
Get this: He informed us shortly after the ordeal, while on his way out to dinner, that he was not even going to be in the room for the majority of his stay, as he was visiting friends and would be staying at their home. What the heck! So I made it my personal mission to make his life a living nightmare from that point on.
I reset his room keys every time I saw him leave the hotel—which was quite frequently, 3-4 times a day. It was particularly funny when he came back tired from a night out and had to come all the way down to the front desk to get his keys fixed. Needless to say, he was very frustrated by the end of his stay. I doubt he’ll be staying with us again.
100. He’s Just Thirsty
Billy Bob Thornton was doing radio press for a movie about to come out, meaning he had to stop by six to seven radio stations for interviews. He wanted to have a drink in the vehicle on the way to the next interview but I had to let him know our company has a no drinking policy in our vehicles. He asked me to call the owner to make an exception, but the owner said no and it would be a $250 cleaning fee if he drank in the vehicle. His reaction was unforgettable.
He asked to stop by a bank, then came out and handed me $5,000 cash. “Here’s for the whole dang pack.” He drank in the car the rest of the trip. Later, I got up the nerve to ask him if that was the most expensive six-pack he’d ever bought. All he said was “not even close” and never explained it further. I think about him often…
101. Freaky Hobbies
Not all of them were rich, but a few were. I drove my boss’ friends around so they could meet up and swing. Sometimes, they’d rent out space by a local lake and sometimes it’d be at a “normal” upper-middle-class looking home. Other times, it’d be a home where “floor-to-ceiling glass windows” that went 30 feet in the air and among the top residential mansions.
90% of the driving around was to either pick up people, drop people off, or get drinks. One time, I ordered 100 taquitos from Whataburger the morning after. Nothing too weird about it, but people did prefer to be picked up and dropped off alone or with their +1. Carpooling was a big no-no. Nobody wore robes, but I did see some people had those masquerade ball masks.
People were friendly and talkative before being dropped off. Normally, they slept on the ride home. Few occasions that stuck out were a guy who had taken Viagra for the first time and told me all about it, and another guy who took his contacts out beforehand and always asked to borrow my contact solution and case.
If you hadn’t known they were swingers you’d think they were just hiring a designated driver to keep people from getting into trouble. Especially because none of them were particularly attractive, at least to me.