When Bob Dylan said, “Money doesn’t talk, it swears,” he could have been referring to some of these obnoxious examples of people with more money than brains. From tubs that cost as much as a Tesla to life-size sculptures of the Cat in the Hat playing pool and many more poor decisions, these Redditors’ spendy stories will definitely leave you speechless.
1. Don’t Wanna Wake Up From This Dream Job
I have a friend who was employed by a very famous old pop star. She lived on his property in a cute little cottage and was paid more than I am with the bonus of no rent or bills for said cottage.
Her job was laughable.
Every morning she would walk over to his mansion, open his bedroom curtains, put on classical music, and gently wake him up for the day. She would say things like, “Hey, hey, big star…I know you’re still sleepy, but it’s time to get up”.
I know this might sound kind of dirty, but she swears there was nothing untoward going on between her and this pop star.
2. Read The Room
The owner of the company where I work got a divorce and went on a shopping spree. He was so proud that he boasted about it to our receptionist and even showed her the receipt for tens of thousands of dollars.
What he spent was 80% of what she makes in a year.
She was really uncomfortable about the whole incident and ended up coming to me about it since I work in HR.
3. Big Log Energy
When I worked in construction management, one of our jobs involved building a log cabin for a very wealthy individual.
It was pretty epic: The largest diameter of the redwood logs was 110 cm (44 inches) and there was a two-story stone fireplace that included 12 hearths!
Unfortunately, when we were about 25% finished building the second floor, there was a change of plans…
The owner found out that the owner of a local car dealership had just completed his log cabin on the other side of the lake. The man I was working for got one of his employees to sneak onto the property at night and take measurements of the logs to confirm they were in fact bigger than the logs on his cabin. Stop the presses!
With a diameter of 115 cm (46 inches), the logs on the completed cabin across the lake were larger than the cabin I was working on. When we discovered this, the owner instructed us to take apart what we had already built and source new, bigger logs.
He insisted that the smallest log could not have a diameter smaller than 120 cm (48 inches).
He also told us to remove the architectural stone from the massive fireplace. This caused a new set of problems.
After about one-and-a-half years, with no limit on overtime spending, the cabin was completed.
The largest log was 172 cm (68 inches) in diameter and the smallest was 120 cm (48 inches).
I ended up running into a car dealership owner at the town market one day and told him about the cabin we were building and how we had to pretty much start from scratch due to the size of his logs (and my boss’s ego) and he simply replied, “I had no idea your boss even owned a cabin here”.
4. You’ve Yacht To Be Kidding Me
The first time I saw a yacht support vessel, my mind was completely blown.
A support vessel is a smaller yacht that accompanies your superyacht. It stores your watersports toys in its garage, houses your staff and additional guests, stores your supplies, extra parts, and fuel, and even provides a helipad and storage for a submarine.
5. A Night To Remember
The company I work for was invited to a Mardi Gras party in Galveston hosted by a very wealthy restaurateur with a company on Forbes top 400 in 2013, valued at $2+ billion. The shindig started on his private yacht, which was nicer than any house I’d ever been in.
It sleeps a dozen people and there is a private helicopter on the back of the yacht as well.
After we left the yacht, we boarded a fleet of fancy buses and had our own convoy of law enforcement to usher us to the public party. Can you believe that they stopped traffic so that a bunch of Mardi Gras revelers could get to the next part faster?
At the big, public party, the opulence was astounding. The place was massive and beautifully decked out. There were live models posing in Greek dress, just for folks to look at (and, yeah, they were all hot).
Inside the main ballroom, there was one bar in particular that I’ll never forget.
It was a martini bar, and there was a gorgeous, scantily clad woman in a bathtub full of olives. If you wanted one, she’d pluck an olive out of the tub for your drink. This was the closest to extreme wealth I’ll likely ever get.
To be fair, this person does do a good bit of philanthropy with his money and time.
And mind you, I thought I looked pretty sharp in my $100 suit when I pulled up to this thing. I’ve never had money. It kind of gave me a thrill to valet park my busted ol’ 2004 Pontiac Vibe, so at least I kinda got to feel rich.
6. One Hump Or Two?
I teach English as a Second Language and I receive a lot of gifts, but one of them was unforgettable. A boy I tutored came from a family that buys and sells expensive racing camels.
When the son graduated, the father allowed me to choose a camel that would be mine.
I am the proud owner of a racing camel in Saudi Arabia that probably lives in better conditions than I do.
7. Sweet Revenge
When I was younger, I worked retail selling electronics. One evening, a gentleman came in 15 minutes before we closed and said that he needed some computer stuff. This guy was the most haggard-looking fella I had seen in a while.
He had dirty sweatpants with holes, a stained hoody, and greasy hair. My manager wanted me to shoo him out of the building so he didn’t waste our time at closing.
I was slightly skeptical of the guy myself until I noticed that he was wearing very EXPENSIVE steel-toe marine boots.
So, against my manager’s wishes, I proceeded to help this guy find everything he needed and special ordered a few items—$31,000 in purchases. I asked him what he needed all this equipment for.
Turns out he runs a well-known fishing charter for wealthy tourists.
He asked why my manager kept looking over at us angrily, so I told him straight up. He just laughed and said, “Yeah, I get that. I probably would judge myself, too. Why did YOU decide to help me”?
So I told him that it was his boots.
“Good eye, kid. Want to see your manager get really embarrassed?” Of course, I answered, with a resounding “Yes”. Buddy went out to his vehicle and grabbed a dirty pink child’s backpack. Inside the backpack, there were ROLLS of $100 bills.
This guy walked over to the cash register with the backpack.
My manager asked how he wanted to pay and said that he would need ID for a credit card payment. The customer just smiled, opened the backpack, and dumped out about $50,000 in $100 bill rolls all over the counter and said, “I guess you’d better get counting. My friend [me] and I are going to go load up my vehicle”.
As we headed out, he turned and said, “And I know exactly how much is here and I’ll be counting it all again before I leave”. My manager was fuming so much that his face turned bright red, but he couldn’t turn down such a large sale.
When we were in the lot, Buddy asked what car was mine.
He ended up leaving me an envelope under the wipers.
It contained $200 and a thank-you note offering me a job if I ever wanted one.
8. Lightning McLaren
I had an amazing side gig teaching tech nerds how to drive their fancy cars at an HPDE (high-performance driving event).
One tech nerd shows up at the racetrack with a new McLaren 12C, delivered in a McLaren trailer and staffed by an entire crew of McLaren techs and engineers. Hmm, I thought, this is definitely going to be interesting.
Apparently, the driver had been complaining about how his $12,000 brakes would keep burning up after just one day at the track. This issue was escalated enough for McLaren to wonder if something was actually terribly wrong with the car.
After one session on the track, he huddled around a laptop with the engineers to find out what was causing the problem. The answer had me rolling.
Turns out, he was just a really terrible driver.
9. Fan Service
I used to be sort of part of an entourage for a billionaire (I’m being purposely vague). Sometimes this would involve flying with him to various tropical destinations. I got to see insane superyachts and his crazy expensive private jets—he had five—I think I traveled on three of them. But one of the craziest displays I saw was a little bit more unexpected.
He was extremely unhappy with the noise that the HVAC system was making in one of the rooms in his small office building. He asked his personal assistant to turn down the fan so that it would be quieter.
The assistant told him that he can’t change the fan speed without changing the temperature. Which introduced another problem…
This guy was VERY particular about temperature and would sit with a thermostat in front of him and often call his assistant into the room to adjust the temperature by a degree or two. After the assistant confirmed that you can’t change the fan speed without adjusting the temperature, the billionaire thought for a moment.
He then said, “Make it so that you can do that and have it done by Monday”. They had to get workers to change out the HVAC system in the whole six-story building.
I think the cost of the whole operation was roughly half a million dollars and they had it done by Monday—of course.
10. She’s Buying A Stairway To…?
I’m a custom metal worker and I did some work for the owners of the Plaza Hotel in Manhattan, who live in the penthouse. The penthouse floors were made of titanium plate and the owner’s wife had her own massive library. We were tasked with making a rolling staircase that was easy enough for an old woman to move.
We did, but when we delivered this gorgeous $80,000 piece of craftsmanship, there was a problem.
We were all really happy with the rolling staircase we’d made, but when we dropped it off, the wife said, “It’s too steep. Can you make another”?
It didn’t matter to her that it cost $80,000. Another staircase and another $80,000 later and she’s happy as a clam, and so is my buddy because he now has his very own rolling staircase at his workshop.
11. Egg-ceptionally Wealthy
I was born a rich boy, so I’ve seen my fair share of silly things, but the example that leaps to mind was when I was talking to my brother in front of the omelet guy at the country club. The country club omelet guy was available at any time, to immediately make the members a fancy custom omelet.
I liked mine with crab meat.
I always thought it was cool when the omelet guy would flip the omelet over in the pan with a big swish. He’d always play it cool and professional, but I could tell he took pride in the move. Anyway, rich people don’t usually talk about money, but on this day I was arguing with my brother about whether or not we were rich.
My brother insisted that we weren’t rich, because we don’t own our own island. At the exact moment that my brother said this, the omelet guy did the cool omelet flip move.
And I turned to him with a big smile like I always do, but I will never forget the look in his eye. He was staring back at me…and he just looked so tired.
That was 20 years ago but I still think about the omelet man.
I’m sorry we rich people are so up our own butts, omelet man.
12. As Luck Would Have It
I went to a casino where a friend worked as a croupier and sat at the roulette table where he was.
Every 10 minutes or so, I would put a few euros on black or red. In normal circumstances, I’d be moved on, but obviously, my friend wouldn’t do that to me. A tiny older lady came and sat right next to me.
We chatted a little and my friend clearly knew her well. My impression from our chat was that she owned an Asian restaurant in town. Much to my surprise, her first bet was for 100 euros on 3, 6, and 8.
I won a few euros and she lost. She then put 900 euros on 3, 6, and 8. She lost and I won a few more euros.
I put my remaining 12 euros on 6 for a laugh. It hits! She had put 900 on each and won 31,500.
I won 420 euros. I was chuffed to bits. I tipped my friend 50 and left to meet another friend. The following day, my friend told me that she ended up losing over 10,000 euros that night. Later, I found out the truth about that lady.
My friend clarified that she doesn’t “own a restaurant”, she basically owns a chain of 50 restaurants.
13. The Price Is Always Right When You’re Rich
My parents went on holiday with some old friends who could be right out of the movie Crazy Rich Asians. If you’re unfamiliar with property prices in Singapore, Google it. During the pandemic when everyone was strapped for cash, this one couple bought 13 commercial lots.
They also own the penthouses facing Marina Bay Sands.
Anyway, this friend group was on holiday in Milan and one of the women loved the hotel so much that when she checked out, she got the manager to contact the owners—so that she could buy the place. She spent $60 million and now owns it.
This was in 2018.
I just found out that she hasn’t even been back there and has forgotten what it’s called.
14. A Delicious Mystery
I was eating at my favorite breakfast place in my hometown. When I went to pay for my meal, the server said, “Don’t worry, it’s covered”. The next day, I went back, and once again, my meal was covered.
As this cycle kept repeating for the rest of the week, I became more and more baffled. I finally decided to ask the server what was going on.
Apparently, some rich dude ate breakfast there a week ago and liked it so much that he bought all orders for the following week.
He also tipped all the staff $10,000 to keep it a secret and cover tips for the week. It was a small mom-and-pop shop, but that gesture must have cost this guy around $100,000.
There was intentionally no hype and the other regulars and I were never told who it was.
15. Nanny State
I taught at a very expensive private school. At the beginning of the year, we tell the kids who are allowed to sign their weekly reports when we send them home. I told them it could be signed by a parent, grandparent, nanny, or au pair.
One kid asked, “What’s an au pair”?
Another kid blurted, “It’s a nanny but from another country. We have three of them”. This threw me a bit, so I asked, “Three? Why three”?
The kid looked at me like I was from another planet and said, “Umm, because there’s three of us”.
All of the kids in that family were close in age, went to the same school, and stayed in after-care, but just one au pair wouldn’t do. Seems like complete madness to me.
16. Lineups Are For Losers
One time, my husband and I were invited to a destination wedding in the Caribbean. The couple had hired out the whole resort for the long weekend, so their guests were the only ones in attendance.
When we arrived at the airport, the staff already had our names and we were able to bypass customs. It was truly a once-in-a-lifetime experience.
17. Sounds Like A Trap
There is a town near me that’s famous because it’s built around a lake and everyone there is filthy rich. All of the homes are in the millions—plural. As a teen, I used to do housecleaning there for money.
There was a super fancy gas station where my mom and I used to stop at for water.
When I was 16, just before Christmas, a woman approached me while I was at this gas station.
“Oh, you’re a cleaner,” she said (I was in uniform). “You are around my son’s size. We got him some stuff for Christmas, but he decided to go to Tokyo instead. Would you like to come over?
We can talk about hiring you and you can have his gifts”.
Of course, I gracefully accepted, and we went to their house. They hired us as cleaners and sent me off with a car full of gifts.
In the conversation, they said they are gonna send him cash instead—$20,000! All the gifts they gave me easily cost around $5,000. And they just gave them to me. It was literally like hitting the lotto.
18. Housing Crisis Solved?
When I worked at Blue Mountain, Justin Beiber tried to rent the whole resort to make it private on New Year’s Eve, but the staff wouldn’t let him, which I think is hilarious.
The area around the mountain has dozens of houses that are all valued well over $10 million and most of them sit empty.
Just a bunch of buildings that billionaires bought on a whim.
19. That Took A Turn
I once toured a 43,000-square -foot mansion in Dallas that was about 80% complete. The interior finishes were amazing. When I was there, the artisans were hand-carving the front door details and the indoor-outdoor pool was being tiled.
There was a bowling alley, a gift-wrapping room, a two-story master bedroom closet with a spiral staircase, and a ten-car garage with an oil change bay. I can’t believe what happened to it.
Shortly after I was there, it burned down under mysterious circumstances.
Its demise was even a cover story in the Wall Street Journal.
20. Judge Not…
I used to work at a suit store similar to Men’s Warehouse. One day, this guy came in looking kind of schlubby, but there were no other customers in the store so I went to help him.
I found him some stuff liked, but he ended up saying that he wanted to go check another place first. No problem, I told him, happens all the time.
He came back about an hour later and said that no one at the other store paid any attention to him, probably because he looked poor.
He then proceeded to tell me that he liked how I treated him with respect. He proceeded to buy a full wardrobe from me.
We’re talking 10 custom suits, 30 dress shirts, and 30 ties, plus casual shirts, shorts, pants, shoes, the whole deal.
I ended up ringing everything up and the total was around $20,000.
I made a 10% commission on everything and that was the most money I, as a broke college student, had ever received in a single paycheck. Thanks, Mark!
21. Be It Ever So Humble
My college roommate came from a very wealthy area.
One day, he mentioned that his neighbor—with whom he was good friends—had a cabin in the mountains near where we went to school and we could stay there for the weekend. Cabin? More like a $25 million mansion right on a ski run.
Matt Damon and Ben Affleck had rented said “cabin” to the tune of $10,000 a night. Two caretakers lived in the cabin and they would make you any food you wanted at the drop of a hat.
The bathtub in the master suite was made of solid copper and cost $35,000. It was so heavy that it had to be lifted into the house via crane during construction.
The whole place blew my mind, but the best part for me was that the cabin’s exterior was landscaped with underground radiant heating. This meant that you could walk to the in-ground jacuzzi tub in bare feet in the middle of winter since the radiant heating would not only melt the snow but also keep the paving stones warm.
22. Best Bosses Ever
My grandfather was a landscaper for one of the wealthiest families in his town. All through the years, the family was always very generous.
They would give him large Christmas bonuses and extra money during the year for jobs well done (for example, they loved the rich hue of the roses that year).
At age 86, Grandpa saw a doctor for the first time and received some scary news.
The doctor told him that he had to stop working because all of the bending over had caused pressure to build up behind his optic nerve, which could lead to blindness.
Despite this, the family continued to pay him his weekly salary and maintain his health insurance until he passed (at 100). They then sent $20,000 to the funeral home to defray some of the costs.
When he was still working, my mom and I would occasionally go up there to visit, and the matriarch was home she would come out and sit with us, and have us served iced tea with mint and the most delicious cookies.
They were really nice folks.
23. Win, Place, Show, Cry
Last year, I worked at Churchill Downs for the Kentucky Derby. For those who don’t know, there are races and events all week leading up to the main event. Each and every one of them have stupid amounts of money being thrown around.
One night, I was in an elevator when two guests stepped in. One jokingly said to the other, “So, how much of a donation did you make to Churchill today”? The other man replied, “It wasn’t too bad today, actually—only two and a half”. I should mention that this man was talking about millions.
Dude LOST $2 million in one day and he was straight-up laughing about it.
I also had another guest tell me that they brought $10 million with them for the weekend. Must be nice.
24. Nice Chunk Of Change
My sister-in-law works at an exclusive girls’ school. She said that the same thing happens at the end of every school year.
Thousands of dollars of high-end clothing, shoes, sporting goods, and makeup get left behind. I don’t remember the makeup brand, but she said one kid left behind about $800 worth of stuff.
These rich kids also didn’t care about their loose change. The last time the cleaning crew shared the change they gathered from the rooms, they ended up with around $6,000.
25. Just When It Couldn’t Get Any Weirder…
I used to be a nanny to celebrities and high-profile New York families. One time, the CEO of a famous athleticwear company and his model wife bought me an entire wardrobe to keep at their home.
You won’t believe why…
Every day I was instructed to go into the bathroom near the entrance and change out of my dirty street clothes and into “house” clothing because they didn’t want “outside clothes” contaminating their house or infant. I could only change back after I was finished with the baby for the day and was getting ready to leave.
26. A Boat Is A Hole In The Water You Throw Money Into
My next-door neighbor was the captain of a fancy yacht out of Miami. He had to go down there and stay on the yacht for three-month stints (three on and three off, which was shared with another captain).
I always thought he was going out on long voyages, but it turns out he was almost always sitting at the dock. The owner doesn’t even live in Florida.
My neighbor said the yacht was actively used for MAYBE three weeks a year.
He and all the other crew (chefs, stewards, etc) were just hanging out there in case the guy decided he wanted to fly in and use the boat. It was fully stocked with fancy food at all times.
The chef shopped for fresh stuff every four days so they could be ready at a moment’s notice in case the owner showed up. I just can’t get over how this guy was paying the yearly salaries for about 20 people just so he could occasionally use his boat at a moment’s notice.
27. That Poor $230,000 Car
A girl in my daughter’s sorority drives a 2022 Lamborghini Urus. Every time I visit my daughter, I see this car.
It’s always filthy and covered in dings and scratches. My daughter says it is always getting towed because the owner leaves it in campus no-parking zones even though she has a space at the sorority.
This girl also leaves the Lamborghini on the street near whichever bar she’s at and takes an Uber home. Every weekend she basically abandons the car until it gets impounded and then pays to get it back.
My daughter says this girl’s room is full of tens of thousands of dollars worth of designer clothes that the girl wore once and threw on the floor.
28. Bridezilla Nightmare Averted
I used to work in a museum that rents out part of the building for special events like receptions or dinner parties.
For one particular wedding reception, the bride (or perhaps her mother) strongly disliked the color of the walls in the large gallery where they wanted to have the reception. Seems like an easy fix, right?
However, we had to refuse her request to paint the walls a different color because the building is on a historic building register, which precludes making most kinds of alterations without a metric ton of paperwork. We even had to refuse when she offered to pay to have the walls painted for the reception and then repainted afterward.
The bride’s solution was jaw-dropping. Instead, she had a florist create walls of flowers in the actual color she wanted to hang on portable frames in front of the walls. We never learned the cost, but the florist said that it was the largest single order he had ever filled and it cost about as much as his shop would earn in a year.
For whatever it’s worth, it was really beautiful.
29. What, Me Worry?
In London during the summer, there are tons and tons of wrongfully parked supercars throughout the posh areas of Knightsbridge and Mayfair. I mentioned it when I was in Harrods and the woman serving me explained that it’s cheaper and easier to leave the car just anywhere and pay the fine than to find a spot and pay for parking around Harrods.
30. Missing Some Marbles
I had a friend who was a stonemason in Hawaii.
One time this billionaire’s wife ordered a marble wall and counters to be installed in the house. Now, she had flown to Italy to order a very specific marble for the house. The marble was delivered and my friend installed it impeccably.
Unfortunately, the billionaire’s wife wasn’t happy.
She told my friend that she’d get back to him. She then proceeds to fly back to Italy and visit the marble company. Apparently they “harvested the wrong wall in the quarry”. She then called my friend back to uninstall the wrong marble and reinstall the “correct marble”. Wow.
31. Can’t Buy Class
My roommate won $17 million in the lottery. No, wait, correction: His long-distance girlfriend, whom he had been planning to dump, won $17 million in the lottery. My friend proposed immediately and they bought a house together.
When I went to visit, he had a gigantic oil painting of Kramer from Seinfeld above his staircase. He also had a statue of the Cat in the Hat leaning over one of his pool tables lining up a shot.
Both items cost more than $20,000. I know that’s not a huge amount, but before that, we were just a couple of broke sailors.
I mean, this guy once taught me to how to hook up a three-course meal using one packet of ramen.
Money changes people.
32. Greta Would Not Be Impressed
I was working at a lesser-used airport one time and a 737-passenger airplane came in and parked. The ground crew put some luggage onto it. Then a person with a dog got on the plane and then got right off the plane without the dog.
The plane took off.
Apparently, this rich family sent an airliner-turned-private jet to pick up the family dog.
33. Regrets…I’ve Had A Few
For work, I once had to manage an early morning press conference for a very successful singer.
He flew in on his plane, got into his golf cart, and drove to the hangar for his press conference. He was so pleased with how it went that he wanted to take me out to eat.
I, of course, said yes, thinking we would grab something close to the airport.
That was not the case, however. He wanted to fly me to Italy on his private jet—for lunch. Sadly, I did not have my passport with me and needed to pick my son up from school later that afternoon.
Instead, we sat on his plane while he made cappuccinos for us. I still regret not saying “yes”.
To have that much freedom in life…to me, that is true wealth.
34. Baby, You’re A Rich Man
Forty years ago, I was a total bum.
For over a year, I had lived in other people’s homes and worked odd jobs when I could find them. For six months, I slept on a friend’s sofa and drove a taxi until my friend moved to another town and took his sofa with him. Then, one day, out of the blue, I experienced one of those serendipitous events that poor people rely upon.
My best friend called and invited me to drive out to Colorado and stay with his family for as long as I needed to.
I packed up my beater, bought enough bread and beans to last me for a few days, and got ready to leave California for a while. This little story is about the egregious display of wealth.
That was not it.
My Colorado buddy knew a guy who had made a lot of money in mineral extraction. This guy invited my buddy’s family to spend a weekend at their vacation home in Aspen. Of course, I was included in the invitation.
Cut to the display of wealth. This house was a beautiful log palace.
The interior was as opulent as any house I have seen, and I have been in the home of an oil executive.
On Saturday night, our host and I sat up drinking espresso and talking. He told me about all of the problems that accompanied his success—especially health problems.
He was suffering from ulcers and colitis from stress and had frequent migraines.
He was unable to unwind because he was obsessed with his business and compulsive overworking.
I then shared with him the memory I had created on my journey to Colorado: just me sitting on the back of my beater, eating bread and beans, and watching the sun rise over the desert—a poor, but free man.
35. Bath And Beyond
I worked at a tile shop and one customer wanted to buy a deep soaking tub made of solid travertine.
The dimensions were 178 cm (70 inches) long, 100 cm (40 inches) wide, and 110 cm (44 inches) deep. The thing weighed more than 2,000 kilograms (4,500 lbs) and cost $18,000. It was MASSIVE.
I sold her the tub, along with about $5,000 in other tiles for her bathroom.
While I was completing her purchase, I found out that for liability reasons we had to have a structural engineer certify the house as being capable of supporting the tub’s weight before we could release the tub into their contractor’s possession.
My company was adamant about this, and I was told that if I let them take the tub before this happened, I’d be out of a job. They purchased the tub and the engineer came back later to let me know the house didn’t pass the engineering check, but they were going to get it fixed.
They had to do more than $100,000 of work to structurally solidify the part of the house underneath where the tub would be.
It took them over six months to complete the project, but they did it. When they came to get the tub, I asked, stupidly, how they were going to get it in the house if they didn’t reinforce the floors in the hallways leading to the bathroom.
They replied that they would be cutting out the exterior wall and lifting it in by crane.
I felt very poor when I left for the day and got into my beat-up Chevy Cavalier.
36. London Calling
I worked with a guy many, many years ago whose family was stupidly wealthy. One time we were on a business trip traveling through London in a cab and he started yelling at the driver to stop. My coworker jumped out of the car and I followed him.
He ran up to a house, pulled out a key, and unlocked the door. I was all, “What the heck dude”?
It turned out that he owned the place. It was gorgeous, fully furnished, and spotless.
To top it off, he’d never actually been there before but had owned it for years. He had bought it sight unseen. Apparently, he even had people come in to clean it once a week.
37. They Just Sit And Spin
My boss built a 1,000-square-meter (11,000-square-foot) barn just to store his classic cars in. He has a collection of old cars from the 30s and 40s with a few “newer” cars from the 60s.
There are beautiful cherry wood wainscotting panels all the way around the barn and in the back corner, there is a turntable so his favorite car can spin around and impress people.
He never drives them and it drives his son crazy because they are just basically sitting there rotting.
38. The Great Castles of Arkansas
One of my elementary school friends came from a fantastically rich family. I’m talking the richest family in the state—we live in Arkansas and he’s a Walton.
One year his parents hired someone to literally build a giant play castle in their huge backyard.
Now, of course, it wasn’t life-sized, but it was bigger than a small house and had multiple rooms and decorations and everything.
The crazy thing was, this ungrateful little brat never even used it.
He just stayed inside and played video games all day. When I was a first grader, if I even had just a tiny castle in my backyard, you can bet chivalry, dragons, and all sorts of adventures would have gone down all day every day.
39. The Rich Are Different
My sister went to a private boarding school on an academic scholarship, but most of her classmates were there because they were royalty or the children of senators.
One weekend, my sister was invited to a classmate’s “school house” to play volleyball. It was a house that this girl’s out-of-state parents bought her, a 14-year-old so that she didn’t have to stay in the dorms on weekends.
When my mom went to pick up my sister from this girl’s house, the mother happened to be there visiting. She opened the door before my mother even got near it and explained to my bewildered mother that “the driveway rings”.
When my mom tried to peer through the mansion’s windows to see the volleyball court in the backyard, the mother explained, “Oh, the girls are in the basement. The pool’s on the left, the tennis court is on the right, and the volleyball court is straight ahead”.
40. Wait For It…
One evening a bride came into the shop where I worked doing bridal alterations.
She was a very lovely woman, but, man, she was clearly having this wedding to show off how rich she and/or her fiancé was. To start, she had two gowns—and not a ceremony gown and a formal dress for the reception like some brides do.
She had two huge and expensive gowns, both fully beaded, full lace hem, the whole nine yards.
During the fitting, she would ask if she could put on her veil and jewelry to see the complete look, and I, of course, obliged. She wore a tiara, cathedral-length beaded veil, bejeweled necklace and bracelets, and designer high-end heels.
Mind you, she had a different set of jewelry and shoes for each dress, of course. There must have been more than $10,000 worth of jewelry in my fitting room and each dress was about $5,000 to $7,000.
The funny thing was, her alterations came to a total of $450 for both gowns and she tried to haggle with me on it.
41. Sandwich Artist
When I was 18, I worked for one of the best art and antique restorers in New York City.
On one shift, we walked into an apartment in Gracie Square to polish an old lady’s furniture. Once we get in, the first thing I see is a huge painting by Monet! Then a Renoir!
Oh, another Renoir!
The woman was impressed by my knowledge of art and saw that I was obviously floored by her collection. She grabbed me by the hand and showed me her whole art collection.
There was easily over $100 million in art on the walls. Then she made me a sandwich!
Her servant later told me, “She doesn’t even make her own sandwiches”!
42. Let The Good Times Roll
A rich family I knew went to New Orleans for the first time and loved it.
They saw a house for sale in the Garden District and bought it on the spot. They even paid a year-round housekeeper to stay at the house so they could tell her they were flying into town and have her get groceries, put fresh sheets on the beds, etc.
They went back ONCE in four years.
So, basically, the housekeeper got paid a full salary for four years to just hang out around the house and watch TV. I lost my mind when they told me that they FORGOT THEY OWNED IT.
The only reason they were reminded they had it was because one of their accountants mentioned seeing it while he was on vacation.
43. The 1% Of The 1%
One time I found myself in attendance at a billionaire’s birthday party on the private island of a different billionaire. The host had hired two superstar musical acts as well as a band for the after-party.
Since it was on an island, they also had to buy out local ferries to transport all the gear and people over to the island and back.
Since the event required multiple days of setup and tear down, this required multiple trips to and from the shore with all the equipment.
The host also bought out a local hotel for six nights for the 100+ people they hired to work the party. There was also a catering crew and a few food trucks. Oh, and a mechanical bull.
Overall there were about 50 actual guests in attendance. I, of course, don’t know exactly how much they spent, but if I had to ballpark it I’d say a few million at least. The dude probably didn’t even notice the expense (although I’m sure his accountants figured out a way to deduct it from his taxes).
44. Messy Divorce Much?
I was on my break when I watched a guy walk out of a divorce attorney’s office and up to his Lamborghini. When a passerby commented on how nice it was, the guy offered to sell it to the passerby for whatever cash he had on him.
He said he didn’t care, he just didn’t want his wife to get it.
45. When Drywall Just Won’t Do
Metal worker here. One time we made a $250,000 anodized aluminum wall to act merely as a backdrop for the owner’s Brancusi sculpture.
46. Say No More!
I know a guy who owns a house in Toronto.
47. Life Lesson
My neighbor was a real estate agent in Florida and one day a long-haired hippy came walking into his real estate office. The man was wearing dirty jeans and a ripped shirt and no one wanted to help him.
Finally, a new kid on the job was forced to help this dirty hippy.
He turned out to be Gregg Allman and he ended up buying a massive penthouse suite.
48. At Least He Didn’t Drink And Drive
My friend’s dad owns a Fortune 500 company, so my buddy has never had to think about money. I remember when we were in college, he drove his $200,000 car to meet us at a party where he ended up having too much to drink.
He had his Dad’s driver come pick us all up and left his car at the frat house. But, like, he didn’t just leave it there until the next day…
He totally forgot about it. He didn’t even think to go pick it up again. When he did remember, he saw that it was gone.
We thought he’d had someone pick it up, but two months later, he was notified that it had been towed and he had to pay to get it back.
His response was, “I bought another one last week, anyway”. So wild.
My friend was on a working trip around the world and got a job at a very high-end cafe in Dubai. One day she was serving a customer who had a ton of shopping bags around her feet.
My friend asked the customer if she would like her to store them in the cloakroom for her to which the customer replied, “Oh, you can have them all. I can’t be bothered to carry them home”. After making sure the customer wasn’t joking, my friend, stored the bags until her shift ended.
The next day, my friend put on her best outfit and set off from the hostel she was staying at and returned as many of the items to the stores as she could…My friend ended up collecting $25,000 in cash and another $4,000 in very posh credit notes.
She had two items that she couldn’t return and she still has them 15 years later.
50. Not Quite The Happiest Place On Earth
I had a friend in middle school whose parents paid for her and three of her friends to go to Disneyland and stay at the Disneyland hotel.
I was lucky enough to be part of that group.
At one point during the trip, I cried in a corner of a store because my mom could only give me $20 to spend and everyone else bought whatever they wanted during the entire trip.