Rich people live completely different lives than everyone else. Having access to large sums of money gives them a certain degree of power, and with that power, they either do good or bad things. The ones who opt for the latter often conduct their shady dealings in secret—but little do they know that some people are silently observing them in the background. Here are some of the most shocking conversations chauffeurs, workers, and friends of rich people have overheard.
1. 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.
2. 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.
3. 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…
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. 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.
27. 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.
28. 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.
29. 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.
30. 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.
31. 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.”
32. 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.
33. 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.
34. 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.
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.
36. 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.
37. 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.
38. 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.
39. 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.
40. 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.
41. 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.
42. 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.
43. 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.
44. 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.
45. 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.
46. 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.
47. 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.
48. 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.
49. 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.
50. 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…
51. 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.