92 People Who Worked For The Super Rich Reveal The Craziest Things They Have Seen While On Duty

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If you had all the money in the world, would you spend it on private jets and luxury cars, or would you rather ensure there were adorable bunnies hopping around your garden at all times? 

For most of us, the lives of the ultra wealthy are shrouded in mystery, as it can be hard to relate to them when we think splurging is buying organic bananas once in a while. But some people have had a glimpse into the fascinating lives of the super wealthy, through working for them, and they've recently been sharing the wildest things they’ve seen on Reddit. So enjoy this peek into how the rich spend their money, and be sure to upvote the stories that you find most shocking!


Not the craziest thing but wild to me.

I was working for a kind of well off family during a summer.
I went inside to get a drink and the mom was cleaning the kitchen putting things away and such.

She picks up a macbook and says to me "hey, do you want this? No one uses it " Got a brand new mac book for college.

Image credits: kingJoffi


I moved the guy that created ebay. He had Aretha Franklin's grand piano (played it) and Elvis Presley's coat (didn't wear it).

Image credits: Interesting-Step-654


The owner of my company had a customer pay off a giant debt by signing over a yacht to him.

When he went to the marina to get the storage info transferred to his name and saw how much it costs to store the yacht there, he bought the marina.

Image credits: UncleGrako


Had a Client who purchased a newly built penthouse apartment and wanted a jacuzzi on the balcony. It would’ve meant a structural column was needed in the middle of the balcony below which the contractor who built the apartment block wouldn’t go for as it would impact selling that apartment.

Client buys the apartment below, approves the column, jacuzzi is installed, then privately sells the apartment below. Voila problem solved.

Image credits: kl_dudey


I had a client gamble away 220,000 in one night.

Image credits: TruthYeller54


You weren’t allowed to hand him or his family things that have already been opened or used. That bottle of sunscreen that was only used once. Don’t even think about it. Everything has to be new. There was a desk that had bottles and bottles of just sunscreen that they only used once and never again.

The interesting thing was this guy owned an eco resort.

Image credits: TheMysticalPlatypus


I've seen my boss walk into an Audi showroom in NYC and driving off in an R8 (years ago) because: 1) It was frustrating trying to haul a cab and 2) His kid was turning 16 in a couple of months so he was going to buy a car anyways.
It's amazing how fast you can drive out with a new car if you're not financing.

Image credits: UstasMom


My mother used to run a landscaping business. One of her clients was a local big business owner with a HUGE house and a lot of land.

They owned zebras. Yes, I got to pet them.

Image credits: Chiaseedmess


My aunt used to clean rich people's houses. I helped her once and I saw a tanning bed in the loft bedroom of a little girl (12 or so years old).

Image credits: nevercursd


Have a buddy that owns a window cleaning business. Came out to an estate to bid on the job, inside and out for the entire property. Owner decided to just do half…and it was over $13k and two days for a large crew to complete. When my friend cashed the check he noticed the memo, “windows, house #5”.

Image credits: Blueshockeylover


Bartending at a fancy party in a very wealthy older couple's house where these people had art on display they had bought from museums. I was working in a room where three walls were glass and you could see this beautiful manicured garden with sculptures. When the sun started to set these big floppy eared white bunnies started to appear and frolic around the yard. I asked someone who worked in the house about the rabbits. The rich people bought them as a garden feature. Every once in a while they had to cull the rabbit population. The rabbits were decorations!!

This was also the night when I was making an older man a drink and he decided to ask me "so, what are the poor people doing tonight?"

Image credits: CindeeSlickbooty


I did a Manny (Male Nanny) job for a rich couple who wanted someone to care for thier kids. The wife didn't want a female nanny and I was in college so it helped pay the bills. One day they asked "Do you want to go to Hawaii?" Turns out the company that the husband was the COO of was doing an executive retreat in Hawaii. Instead of finding daycare in Hawaii for their kids they thought it'd be easier to just pay for me to fly to Hawaii, care for the kids during the day, and then have my evenings or their "family time" free.

So I went to Hawaii on their dime, had my own hotel room, they paid me for my time and gave me a large stipend for my own food/entertainment. I ended up with pretty much every evening off so I got to spend it. During the day I brought their kids to the beach, we went hiking, and did some touristy running around. On top of that they gave me $5k in "spending money" in case any of the kids wanted anything. I had to show reciepts, but when I tried to turn in the receipts the wife just said "Oh don't worry about it, it's only a couple grand" and never verified how I'd spent some of that money. I couldn't tell if she just trusted me implicitly by that point or if she truely thought the amount was so small it didn't matter.

They were a really nice family, just very well off which made just spending money on any problems the easiest answer. I actually got invited to the oldest daughter's high school graduation because she considered me a friend.

Image credits: DrGrizzley


Worked in recruitment finding crew for super yachts many years ago.

Put forward a candidate for a chief engineer on a very well known yacht owned by a very well known individual. Was the perfect fit of knowledge and experience and the guy was super friendly and nice as well.

They turned him down because "he wears glasses and the owner doesn't want anyone with disabilities working on board".

Edit: I didn't expect this to get so much attention. To answer a few things that keep popping up.

Why didn't I tell the candidate so he could sue them/Is that even legal?
I had signed various NDA's so i would have been destroyed.
I was told this over the phone so there was no proof.
They have a whole company of lawyers.
If the candidate did decide to sue he would have failed.
The yacht industry is small, especially at the top end.
It would have been the end of both of our careers. Neither of us would have worked in the industry again.
They were registered under a different countries "flag" so would have made it even more difficult.

They could have payed for Lasik?
This was over a decade ago, maybe 2. Yes it was probably still available but why the hell would they? It was one of the top jobs in the industry at the time and they could have anyone they wanted, why waste the money when they can get someone else the has the right knowledge/experience and fits their "requirements".

Why don't I name them?
Lol ummm f**k no. Even though it was a very long time ago and I have nothing to do with the industry anymore I do not want to f**k with these people.

Image credits: Duranis


I babysat for an "old money" family as a teenager. Massive house that had passageways in walls that the kids would use to play hide and seek. Basement had a passageway to a weird underground cave/cellar that had been bricked off for decades. One day the dad, who was the coolest dude I've ever met, asked if I wanted to earn an extra 200 bucks. I sat sure and he wants me to help him knock down this brick wall because after 40 years he can't stand it and has to know what's behind it. We go down and knock this wall out only to find that in the late 1800s his family had slaves and instead of setting them free when slavery was abolished they put these 4 poor women in a good cellar and walled them in. The smell when that wall csme down was awful and even 20 years later we have no idea what their names were or anything other than they were women. They buried them in the old family cemetery at the back of the property, right next to the relatives that walled them in to die. I still visit the family, as I'm great friends with the older kids, and always go back and out flowers on those women's graves. They have headstones that simply say in memoriam since we don't actually know their names.


Getting a charted jet stocked with lobster and other expensive food only to show up late with McDonald's.


This guys house had a rotating elevator for his car collection that were all stored underground. The elevator rotated so that he never had to put any of his cars in reverse when taking them out or parking.


My sister is a butler for a super wealthy family she told me a couple crazy stories :- The family once got this super expensive rare breed cat and a few months later the wife tells my sister she can feel the cat isn't quite happy in their house so she asks her to take their private jet to drop the cat off in their mansion on Lake Como, Italy so it could spend a holiday in the sun. That same woman would then sometimes berate my sister for buying soap in plastic dispensers instead of just soap bars because it's bad for our planet- They bought this insanely huge super luxurious cabin in one the most expensive ski stations in Switzerland. They realized the cabin ( more like a mansion really ) right next to theirs was for sale and then bought that one as well just so they wouldn't have close neighbors

Image credits: Inequitom


Worked as one of four full time groundskeepers at a large estate. 46 acres of lawn to mow twice a week. 2 clay tennis courts, 3 pools, one for the main house and one for each of the two guest houses. 100+ acre private lake with boat house. No clue how big the whole estate was including the woods. Personal favorite was the 3 mile personal race track. But what really blew my mind was that he hosted his niece's wedding one summer, paid $350k to have this massive willow tree trucked in and planted by the lake for wedding photos. Only to pay another $50k to have it removed and the landscaping returned to its original state after the wedding because he did not like the look of it.

Image credits: Rarnah


Billionaire company owner took the new sales team out for a fancy dinner. Super fancy. When the bill came they all knew it was going to be astronomical.

He got everyone to put their credit cards in a bowl, then said he was going to pick a card out and that will be the one to pay the bill.

Everyone sweating and not sure if he was serious, he picked out a card then went to the card machine, then stopped and said that he’d pay off the guys biggest debt. It was his mortgage and he dutifully paid it off.

Billionaires literally have f**k you money


Had a client come into our 3d printing office.
His attention was immediately caught by a large industrial 3d printer in our showroom.
Pulled out a credit card and bought a $250k machine on the spot.
Best part was when we installed the machine at his facility.
First thing he wanted to print was a meter tall penis.
Few weeks after the install we got a photo of him standing next to the meter penis.

Money well spent.

Image credits: robertcboe


I worked at a house in which both father and mother were so busy making money in order to give their children a better quality of life that the eldest son who was at my school joined a gang.
That guy didn't lack money but he lacked empathy, love for other people, respect towards others, control of emotions.

Image credits: GabrielOmarCY


My mom's cousin(my 2nd cousin) worked for a billionaire in China, building a hospital as his general contractor. Well he came home and found out he had a package waiting for him that weighed over 700lbs. Turns out he bought him a statue he remarked on that was a recreation of a terra cotta warrior statue. Even as a recreation it predated christ


My wife is a veterinarian and she went to a house where you could not see the main house from the stables. But you could see the 8 car garage, the swimming pool, the helicopter pad, and the guest house. This by the way as at least their second home.


I did a clerical job for very rich man, and mostly worked at his office. But once I was at his home for some business reason, and heard him in the background telling family members to get fake passports and cash together and get ready to flee the country. Apparently he had been engaged in some sort of illegal business activity.

The next day I went to work. The office was closed and padlocked.

I never did find out if he outran the law or not


Years ago I used to work carpentry mainly doing sunrooms. One of our clients was a brain surgeon who was married to a lawyer and they subsequently had a massive house on a large property. Their son was also some type of neuroscientist and with his parents' permission, had yet another massive house built on this same property. Problem is, city ordinances prohibit 2 separate livable dwellings on the same property.

Mind you these houses were about a quarter mile away from each other. So to comply with the ordinances, THEY BUILD A F*****G WALL BETWEEN THE HOUSES. And this isn't just some dinky picket fence type of wall, it's a massive medieval style wall that has round towers with merlons and crenels, a gym midway through, AND a massive $750k+ all-glass sunroom all the while being wide enough to have room for a walking path and a road for golf carts.... inside the wall.

The city ordinance said only one livable dwelling can be on their property, so they just made a massive hallway between their houses.....

Edit: I was able to find the video I took from years ago on my computer when we were on the jobsite scouting it out. My memory wasn't exactly correct but this gives you a good look at what it looked like. The steel structure you see near the end is where the sunroom was going to go. All we were providing was the glass.


Image credits: Bombxing


I worked on a billionaires home installing his custom pool. He ordered a custom iridescent tile. For the whole pool it cost $440KUSD for material alone and another $400K to install it. We informed him that it was a special order and couldn't be changed once ordered. He approved. We installed it. Walks out, it looks amazing (all the people working on it thought so) says he doesn't like it tear it out and replace it. All told he blew like 2.4 million dollars on his pool tile before he got done.

F****r didn't bat an eye

Also worked on a house in that same area that had a $250K fish tank. Can't share pictures of that cause it was in someone's house but still.

For scale. The boat in the pictures behind the pool is 90 feet long

Image credits: Lousyfer


I was the Project Manager for a mansion build for one of the founders of a major health insurance company here in the US. This guy was one of (if not the) best billionaire I’ve ever worked for. He showed up nearly every day in shorts and flip flops and would treat all of us like equals.

This was around the time that President Obama was about to put out Obamacare. I was in a meeting with the owner and President Obama called him, on his cell, to discuss the plan. He (the owner) tells us to hold on, the president is calling, to which someone jokingly made a comment about (thinking he was joking). The owner asks Obama to say hi to the team, and he did! It was surreal to be at the table with him when the call came through. And an experience I will never forget.


*He was a founder but sold his shares (prior to Obama becoming president) and was in retirement, working on passion projects. Not an active member of the company.

**I’m not going to disclose his name for NDA purposes.

***I will say that his story is pretty all American. Did not come from money. Served in Vietnam and started out as an insurance salesman. Built his own company up from that.

Image credits: Nuxul006


I do high end florals in very rich area. See tons of obscene shows of wealth all the time. The amount of money some of these people spend on flowers alone is unfathomable. The one that I always come back to is a client who we were decorating their house for Christmas, and as I was hanging garland around their 6 car garage (a separate garage than the one connected to the house), I look in to see each of the 6 spots has a car elevator and is 3 cars deep. So there were 18 of the same exact $350k+ car. Why would anyone need 18 of the same exact car? let alone one that expensive!?!


used to work for a real estate development company, the boss was the riches guy in town. the second biggest office was given to his wife who did nothing. Her office was entirely bright pink, they put in a private bathroom just for her, her parking space was double wide because she couldn't park straight and she used employees to run all her personal errands. It was very annoying, but we were told we had to do everything she said. I remember she once asked me to print out a website for her.


He lives on a lake, but his wine cellar is in a building across the lake. So he takes his boat to the wine cellar in a building also on the lake. He wanted a bigger cellar so he paid them to expand the building to accommodate his wine. Once said and done, he created a code specifically for the wine cellar. Being it’s across the lake he takes multiple boxes at a time. While he’s there he scans them with a little 3d scanner that automatically orders the wine from various places/ emails his assistant to order certain wines. He once threw me a bottle of wine and said “good thing you caught it, that was 10k”.


Bodyguarded someone filthy rich with next to no class whatsoever. He bought a very sought after rare classic car from a renowned Italian carmaker, had the roof taken off, painted it a ridiculous pink sparkle color and put it on the roof of one of his most central buildings in the middle of a large European city. The Italian carmaker offered to buy the car presumably because they were absolutely disgusted with what he’d done to the car and didn’t want the abomination to get further exposure as they felt it damaged their brand tremendously. He sold it to them. Was then banned from ever purchasing factory new models from that brand ever again globally.


I interned a long time ago where we had to clear every single check or credit card charge with a guys parent because he got conned into joining a cult and the leader kept getting him to p**s away his trust fund. Once there were enough checks and balances in place he got kicked out of the cult for not paying up anymore. I felt bad for the guy, he was actually pretty nice but his parents just pawned him off on the help while they traveled and he was an easy mark because the cult made him feel loved.


* I've regularly seen people $50k+ for a single tree.
* Had a client buy seven trees to the tune of $485k.
* One client gets 20ft+ palm trees from key west trucked up to the north east and planted by his pool all summer. When the winter comes they get ripped out and put through a wood chipper because it's cheaper for him than finding an adequately sized green house to store them over the winter.
* I know of a rock collector who sells field stone. He sold one boulder he dug out of the ground for $80k.
* Multiple homes with full size outdoor hockey rinks NHL style boards/glass, painted lines, score boards, lights and zambonis. During construction on one house the rink was build before the house so they kids could come practice over the winter while the house was being build. The power company came out to see what was going on because there was such a ridiculous amount of power being consumed.
* A client who buys all his neighbors homes when the opportunity arises itself just to knock them down. The homes that are being leveled are all $2+ million, 2+ acre, 4+ bed, 3+ bath homes that the majority of people would give their left arm to live in.


This'll be buried, but I lived-in with a billionaire woman, she just needed someone around the house I think. There were no issues and we got along fine.

The most absurd, was I was in Grad School looking to do a study abroad for six weeks, and she chartered a flight for me - just me - on a private jet to/from, as well as an allowance for me to buy as much as I could while I was in Tunisia and Spain for her and to have couriers ship it to her: she arranged a person to be with me. She doesn't like travel.

The other graduate students looked at me when I spent $38,000USD on two champagne flutes. And so on. Let me be clear: I was not rich at all, but the experience was eye-opening.


I was a trainee sailing on a container ship going from Dubai to Tokyo and back (via all the big ports). One day the route was changed and now we would go from Singapore to LA. Because this change wasn't planned we (the 2 trainees) didn't have visas for the US, meaning we couldn't leave the boat once we docked. For us it was not a problem, we'd only be there for 2/3 days at most. The company decided we should get the visas. They flew us from Hong Kong to our home countries, got us a 10 year work permit for the US in a matter of days, and then flew us back to Dubai to join the ship. I've never seen money thrown around like that for little to no reason. It was crazy.


As a house keeper. Sex dungeon, weird art, lots of casual nudity. Imagine you have infinite money in Sims and are building a house. Also, you have already traveled a bunch and been to every theme park and fancy restaurant and spa. You start really having fetish stuff at home. There is so much sex stuff that it's not even weird to me anymore.

Overall weirdest top three.
3, Brass copies of the home owners genitals.
2, a room dedicated to fascism and sexual kinks.
1, body parts removed incased in plastic from surgery.


Re-did a ladies shower one time during the middle of a nasty divorce. The shower was 6'x10' with the entire ceiling covered in shower heads. "Since he was off with half the office I figured I'd get the other half all in here". Lady was a baller- $500 tip for everyone who worked on that bathroom because it was her ex's money.

EDIT: We redid the glass to her shower when I was at a glass shop. How the actual plumbing and stuff worked is beyond me. My job was to bring in giant panes of glass, attach them to the wall/floors, waterproof the seals, and dip. With how large her house was and the other 2 'smaller' houses that were attached I'm sure she had enough money to throw at someone to solve those plumbing problems.


Jeweler here. Some random client quotes-

Client- "So I have some gemstones that have just been collecting dust (pulls out about a dozen amethyst, citrine, smoky quartz, most an inch or more across) what can we do with these? Can you make a crown? No, not a little flimsy" fake" one, a "real" one.

Me- (makes a 5lb silver and gold crown)

New client- "You're going to see me a lot. This is going to be my new addiction. "

Me- (ok, I'll bite) "What was your last addiction?"

New client- "Collecting (fully grown) trees. I had 45 transported and replanted on my property last year."

Client- "Have you seen my new car?"

Me- "I have not."

Client- "They only made a few... (points out the window at a new, navy blue Bentley) I didn't like the interior so I had them replace it all with bright orange leather. They added a plate inside with my name engraved on it. Isn't it cool?"

55 year old client- "I want everything pink. Can you tell I'm obsessed with Barbie? (laughs) We're even building a pink house. I want my engagement ring to be all pink."

Me- "I can make it in rose gold."

Client- "Great! Do you have any pink diamonds?"

Me- "Not in stock but I know of a supplier who has one."

Client- "I'll take it."

Me- "It's a natural Argyle pink. It would be about $220,000."

Client- "How soon could you have it ready? Can you add more pink diamonds to the sides?"


Didn’t work for the wealthy, just grew up pretty well-off.

A portion of my childhood was spent in a very expensive village and the house I lived in at the time was on the nicest street. To make a long story slightly shorter, there was a tennis club owned by a very wealthy couple who lived on the same street, and they were known for being extremely rich (huge mansion and all). From what I heard from my parents years later, this couple’s tennis club was actually just a swinger’s club in disguise and they would select couples from around the village for membership and invite them round to a private barn they owned on the outskirts of the village. In that barn they would have their… sessions. Thankfully, my parents were never apart of this but I did hear a number of stories involving parents of kids I knew personally. Just shows what the extremely wealthy do when they’re bored lol.


The CEO of the company I worked for was the founder's son. Not an unintelligent guy for the most part. His dad made him start with the most basic jobs in the company and work his way through the different departments. Managerial staff was ordered, upon penalty of termination, not to treat him any differently than a new hire.

So when he became CEO he wasn't a bad guy to with for.

Now, this is a company of over 10,000. One night, I'm working overtime on the late shift and we get this call.

"Hey! You guys... Got... 'Lectrician?" The guy is clearly drunk, we have no idea who it is or why he's calling our maintenance/engineering group. We ask who he is and he informs us, light heartedly.

He wants someone to take a ride to his house and figure out why the internet isn't working. This is an hour drive away.

I volunteer, I was bored off my nut anyway. I get to the house, entry gate is smashed, section of the white horse fencing is gone, Jaguar is stuck in the field.

Here in the house is dude, completely blasted. He's got a huge cut on his hairline. "Are you ok, (boss)?"

"I'm fine! Why?" He asks, blood literally caked on his face.

I accompany him to the bathroom and help him clean himself up, wash off the gash and put some bandaging on it.

Then I corrected the Internet. Unplug-plug.

As I'm walking out, he asks me to do a shot with him. I comment, worried about my job, that it might be a bad idea. He agrees and hands me the bottle, "Take it home and do a shot later. Keep it."

When I get back to work I look the stuff up... Never heard of it. It's a $1500 bottle of scotch.

The next day I'm at work early. About eleven in the morning he comes walking up. "Uh... We're not going to be... Talking about last night?" I tell him it's all good, "Awesome."

A little bit later I get an envelope. There's a check attached for 'Emergency Tech Support' $5,000.


Grew up with the children of a very famous musician, think someone who has dozens of songs you'd recognize immediately. Their house had 4 stories and 3 elevators. The kids room (identical twins) was two stories itself and bigger than my family's (nice) two story home with a pool.

Every toy you could imagine, dirt bike track, baseball field. One of the twins was very kind and I really liked him. The other had a bit of a chip on his shoulder and his personality would change a lot, but he wasnt a bad guy- at least when I knew him. I believe the "nice" one joined the military for a big then when he got out joined helping to support the business. Not sure what happened to the other.

His parents were very kind. My dad about had a heart attack when he showed up at our house to drop me off one day, he recognized him immediately.

Funny enough they just wanted to be normal. We all wanted to go to their house but they really just wanted to come hang out with us and not be treated differently. Didn't understand it at the time but definitely do now. Hope they are all doing alright


I have a friend who owns his own business.

He was in this house one time doing some work...and as he passed a room, he saw a Gibson Les Paul leaned up in the corner.

He mentioned it to the owner of the home...just making a statement. "Hey, I saw that Les Paul up there. Do you play?"

The owner basically said that they had purchased the guitar for their son when he was in high school, but he had since gone off to college and the guitar probably hadn't been touched by anyone except their maid in over 5 years

My buddy was like "Cool. Well that's a pretty nice guitar. It's a shame it doesn't get played more often" and then went back to working. That was it. No more conversation

As he was walking out after finishing the job, the owner came down with the guitar in his hand and asked my buddy if he wanted it

He tried to say no but the person wouldn't take no for an answer

And that is how my buddy got a 10,000 dollar Gibson Les Paul for free


I don’t know why I love this story but I always bring it up to show how the real wealthy treat money.

My father was the private chef for a billionaire. He’s famous-ish, and would travel with him on his private jet, make him anything he wanted etc..

He was a very very genuine man the billionaire and was very good to my father and us as his family. That being said one story always stood out.

He wanted a smoothie. They had just arrived at his house X in beautiful location Y and my dad hadn’t been in that kitchen in quite a while. He couldn’t find the blender and was told to go out and buy one (high end of course) and make a smoothie. He does this, makes smoothie, boss is happy, and while cleaning found 10 blenders in obscure spots likely done by the cleaning crew.

It just to me puts things in perspective at a real level. This man had thousands of dollars worth of pristine high end blenders I probably wouldn’t even entertain buying because it’d be to much for me to justify for a blender, and could care less. I don’t know but to me it was a very real example of wealth at a human level if that makes sense.


My friend is a mechanic. A wealthy, fat, famous and all round unlikable entrepreneur came into his work one day and took a liking to his co-worker. He asked my friends co-worker to come and work for him maintaining his car collection. It was really good pay and he got to work on some cool cars so he thought why not.

His days were spent working on old, rare sports cars on his sprawling property but every now and again he'd get sent to Europe or the United States to check out cars said entrepreneur was interested buying. He'd get sent to auctions all the time and ring up said entrepreneur while it was happening so he could bid on the car on his behalf.

EDIT: Not Jay Leno. If you can figure out the country I'm in, you'll 100% know who it is. Not Clarkson either.

Yep, it was Clive.


I did carpentry for a summer to save up money for school. We would go to huge mansions and amazing houses that needed work done. Usually easy stuff, decorative things so most times it would be 1-2 days of work. Most times we would work the family would be home. It’s not a problem, very normal. Once a family had kids and they watched a tiktok video on what poor people eat and it was about how to cook things like 10 cent ramen and bread with sausages to make hotdogs. They laughed and thought it was fun so made the food to try in the kitchen. They hated it all. This was the food I grew up eating my whole life.. that packet of ramen was the same as the dinner waiting for me at home..


My brother in law builds custom homes in the redneck riviera belt of Florida.

One day, he called me to come over to this $15m beach house he was doing a complete remodel of. He was the original builder. He asked me to bring my truck and trailer. I show up, and he walks me through all four floors. He then says, "The owners have removed all the stuff they want to keep. She has told me to dispose of everything as I see fit. Get what you want."

Furniture, appliances, outdoor furniture, rugs, lamps, artwork, you name it. I don't know the value of everything I took home with me that day, but it was the highest end stuff I've ever seen. FOUR floors of it, and I only got one trailer load because I simply couldn't fit anything else in my house. I likely had over $20k worth of furniture and appliances on that trailer.


I dated the heir of a family worth billions. He had a Black Amex that was paid off every month - he never knew who paid it or anything like that. He regularly planned vacations that cost $50-100k (usually to super remote areas).

Waking up every day with nobody expecting anything of you makes a person weird. He was a very kind person but just…out of touch.


I didn’t work directly but I was a chauffeur picking up a family in Atherton. All the children had their own iPads and one child got upset and threw his iPad on the ground breaking it. Some assistant/nanny went inside and brought out a brand new iPad in the box and gave it to the child. Nothing was said. I despair for the future.


It’s crazy how many try to get out of paying for things. Makes you wonder if that’s how they got wealthy in the first place. But as for material things I’ve seen, I worked on a house that had a huge swimming pool with a 1/3 mile long lazy river. He also had a movie theatre that sat about 20 and a $60,000 aquarium in his basement/private bar.


My friend is an aeronautical engineer, worked for some Saudi family's airport in the US. Got sent all over the world to work on and retrieve private jets. Insane. He quit to be closer to his wife and newborn kid.


Pumped a bunch of money into the Malibu City counsel in order to change a few seats. This would allow him to have the local ordinance changed so his front doors could be taller than 20 feet.


Not me but my mum, she was a chef to the queen's cousin. (any British person will know its not that impressive) one thing my mum always mentions whenever she tells people this is that one day when she was working a wedding apparently all the guests looked extremely similar in some way or another. **Especially** the bride and groom, one of my mum's friends said she swore they were siblings. She always jokes about them all being incestuous but how she described it and knowing the royals it's highly likely that the couple were related (this was in the 90's i think)


I worked landscape construction for a boutique company in high school and college. We had a good relationship with a prominent landscape architect who traveled across the county every week for projects. The jobs he referred us to were the most interesting. Two come to mind:

• There was a client who spent $5m renovating a $2m house just because they liked the trees on the property. There was a particular tree we couldn’t even go near with sharp-edged or power tools, it was written into the contract.

• Another client was a fledgling-software mogul who had a vacation house in the area. They wanted to replace a specific type of shell that lined the property, and only after we laid it and finished the job did we find that it wasn’t the exact same type. We had to contact vendors across the country to find the right type and had it trucked 800 miles to the property. The client had no qualm about paying for any of this. They just wanted it to their specifications.

As someone who grew up in extreme poverty, it was a shakeup to see people routinely throw tens to hundreds of thousands of dollars at vanity projects to impress their neighbors. Ironically, a lot of the richest clients and neighbors of clients we serviced (hundred millionaires to billionaires) would hire the cheapest maintenance crews and keep their run of the mill native grasses. You’d get done working on a $30k project for a multi-millionaire and then farther up the street in their gated community was a billionaire having their lawn mowed by workers who were picked up that morning at a 7/11.

Overall, besides the extravagant projects, on the day-to-day we dealt with a-lot of elderly people who were fairly successful and saved well. They were always very particular about what they wanted, and most made sure to let us hear it if we strayed from their vision. A-lot of them loved to talk to us, but there usually was a sense of superiority from them. They’d brag about their grandkids or children who were going to various colleges and in the same breath couldn’t believe it when they found out I was going to an as good/more prestigious school. It made me realize quickly that even if you work hard, play your cards the right way, and find success, you still probably won’t make it into their world. “It’s a big club, and you ain’t in it”.


Worked for a really wealthy guy who had one of those builtin sub zero fridges solely for Fiji waters. Not sure why that stood out to me more than anything.


I dated a girl for a year whose parents were very wealthy, like live in servant, parents flown on private jets in and out of NYC multiple times per week, wealthy

Both her and her brother were some of the most emotionally unavailable people I’ve ever met, like completely focused on work at all times and it consumed their entire lives and completely detached from reality

In an honest moment (probably the one she had with me in a year) she told me how miserable her and her entire immediate family were all the time


It is perfectly legal to declare children beneficiaries of a trust before they are even born. There are unborn children’s trusts out there funded in multi-millions.

Something to think about. I’ve seen some figures in my day - no matter how hard you work, even if you’re making $200-$300k a year and invest in aggressively, you’ll never match the inheritance awaiting some of the not-even-born-yet children I’ve witnessed.


Spent a summer working with my dad doing loss prevention. He had to inspect a construction job on a residence. It’s was a 20 m house. A dude from Iran bought just for his girls to go to school in Canada. He also bought the lots on either side for 10-15 m each. So they could have some privacy.


Guy had six houses. Hated using computers, only had the most rudimentary knowledge of them. He had a pc in every house, all exactly the same. If we replaced one, we replaced all six to make sure they were always exactly the same. If we installed software on one, we installed it on all six. Made sure all the icons on the desktop were in exactly the same positions, same printers, same mice, same everything, and he’d fly us in the jet to wherever we needed to work on one of the machines. And then on to the other houses, to do the same thing.



I do high performance MEP/FPand HVAC design for mostly high-end residential clients.

As I write this I’m working on a house with 8 washers and 8 dryers in one house. Don’t ask me why. 20000 square feet, but only 3 bedrooms. Pool in the basement, next to the commercial staff kitchen and the archives.

Honestly the lifestyle these people lead is so alien to a normal person, it really is another world.


I was previously engaged to an insanely wealthy man, and could write a book on the insanity that was my life for two years. He was in his 20s and owned a Bugatti, Lamborghinis, Rolls, etc etc. it was the classic love bombing beginning, and then i found out how insane he was.

His friends never lasted long, and all of his “friends” were always getting something out of him. They were never equals. I was always a supporting roll also. When my family dog of 18 years died he was annoyed that i was sad, and told me “i wish my problems were that small.”

He had extreme control issues, so he’d never drink or do drugs to always be in control. Which correlated with his bizzarre body issues. His diet and workout regimen was extremely controlled and of the utmost importance. This man would literally suck and lick the powder off chips, but not eat them to save the calories…

He also was obsessed with Michael Jackson…. This was like 6 years ago. And it was all we would listen to. Insane.

When it would be a hotter week, he would book penthouse hotel rooms in the town over cuz their air conditioning worked better.

He’s also in the middle of his third court case with a third ex girlfriend for domestic abuse. Not to bury either of the leads here, but he was also very much into the idea of cuckholding. So, there’s that.


Spending $200K on light fixtures for the spare bathroom.

Spending over $2M on a garage for their motorhome.

Building a "home" where the Kids wing was about a 5 to 10 minute walk from the parents wing.

Building a 10k square foot guest house for company.

I could go on and on about the utter waste of money the ultra wealthy is willing to spend on. One thing they will never overspend on and will fight you tooth and nail over is labor to build/install anything.


I was working in Dubai for a time and i didn’t directly work for him but i worked with an Emirati prince. Aside from the usual outlandish stuff like a new super car every week or holding our meetings on a yacht in which he would come via helicopter. The best was he ejected out of a fighter jet that he barely knew how to fly.


I've seen my boss tip his drivers several thousand dollars in cash. Just a stack of $100's.

He also would put a couple hundred thousand dollars in his daughter's pink backpack that she wore around while they were traveling.


Wife is PA for wealthy and incredibly powerful man. Self made, humble. Uncomfortable in small social gatherings, but a lion in a business setting. Understated houses. What I found most interesting is the guy would think nothing of dropping 5 figures on jewelry or other luxury items, but come the end of the day Friday that guy is in the kitchen at the office taking home all the leftover bagels from the morning.


I briefly cleaned houses one summer and these houses were INSANE. Some had elevators. Some had STALLS in their master bathroom (edit: corrected from bedroom). One had a literal cave manufactured in the bathroom, with showerheads all thoroughout it—you could walk from one end and come out the other side of the bathroom (split by a massive hot tub).

What struck me as odd, in almost every house, was the sense of disuse. They had grand pianos covered in dust. Expensive lamps and throw pillows with the tags still on them. Sprawling playrooms with every toy any child could want, totally devoid of playing children.

The weirdest house I cleaned though, wasn’t huge and it wasn’t gorgeous. It was pretty normal on the outside. But inside, the entire house was FILLED with piles of clothes. Everywhere. I pulled aside my fellow cleaner and asked, with all sincerity, how to clean this house. She told me to “go around the piles as best you can.”

They had a mountain of clothes in the living room, like something out of a cartoon. Every couch had stacks of brand new clothes with tags on them. They were the only folded clothes anywhere. In the bedroom it was the same. Smaller piles in every corner, couldn’t fully open or close doors around them. The kids’ bathroom didn’t even have a shower curtain.

Best guess after “cleaning” that house as best we could, is that they don’t wash clothes. I think they just buy more, and discard the dirty clothes into the piles.

I think about that house a lot, and wonder if they ever got their s**t together.

Edit to add: it was like metal bathroom stall cubicles. And the elevators and stalls did not seem related to accessibility, my apologies for any misunderstanding


“Never work for millionaires. They’re just trying to prove something. Work for billionaires. They know what they want and will just pay what it costs to get it right.” - a caretaker getting paid six American figures for keeping up a multimillion dollar house that gets used two weeks a year.


Their kids (all young 20s) never shut the door when using the bathroom. Plenty times while cleaning the house I'd walk past the bathroom and see one of their daughters on the can, they'd often wave or say hi. F****n odd.


I’ll change a few details to protect the innocent, but I used to give guitar lessons in a very rich area and the company I worked for had a lot of celebrity and/or just ridiculously rich clients. I saw in-home rivers, elevators, waterfalls, live-in chefs, 40-car garages, fully automated mansions that could “change the season” indoors, etc. The thing that stood out most to me was the boredom of humanity. Like one guy I became friends with had 17 off-road vehicles, a house bigger than his Laker-star neighbor (and his Chicago Bull star neighbor for that matter), and traveled to different extreme game competitions every weekend, but when I came over for the lesson, he just wanted to talk about Nirvana, watch tv, learn Pearl Jam bass riffs, and go to shows.

The second thing that stood out to me was that the ratio of cool people to screwed up people seemed relatively the same between the super rich and the normies. Like there was one guy who wanted lessons with his very young son to connect with him, but only lasted 3 minutes every lesson before he had to take an important call or run off to an emergency board meeting. You could see the kid was in a giant playground of a mansion but was just crushed. However, I also gave lessons to a family where the parents were two high-powered lawyers (one of whom is now running for Congress) and they were absolutely amazing to those kids. Always attentive, would drop calls from celeb clients to fix a tricycle wheel, would lovingly enforce homework rules, etc. Great people. That was about the same ratio amongst my middle class clients and amongst my poor clients.

The last thing that stood out as the one really obvious advantage to being rich was the people’s physical appearance. By and large, they were almost all very good looking people at any age, and most without surgery. It’s actually kind of incredible what the body can do when you’re able to always feed it healthy foods (live-in chefs), exercise whenever you want in a variety of ways with or without leaving your home (in-mansion gyms, indoor-outdoor multi-tiered waterfall pools, week-long skiing trips, personal trainers, etc), and the lack of daily, grinding mental stress. I’m not saying they didn’t have stress or they didn’t work hard, but most did not have that existential stress about what might happen if they got fired because they didn’t work the extra Saturday, or the stress of a boss breathing down your neck when you’re at a dead end job just hoping for a living wage. There is something to be said for the mental benefit of hope and joy and inner calm and unfortunately, money does help with those things. So I did see a large health benefit to people with loads of money also.

And lastly, I don’t believe any of these people were self-made. This type of wealth is not just working hard and climbing the corporate ladder using nothing but your bootstraps. This type of money is generational wealth with decades-long investment accounts from things set up by ancestors. I’m not saying they haven’t worked hard, but turning $100 into $1000 and turning $100,000,000 into $110,000,000 are two very different things and the latter is inarguably easier from both a percentage and opportunity standpoint.


I did pest control for the ceo of a pretty big candy company. Dude had cases and cases of gummy bears in his basement. Like enough to fill a small Uhaul.


Worked for the son of the CEO of Rolls Royce America, he would routinely charge the company when he went to the brothels, and his wife was the company accountant.


I often do work for the wives of wealthy professionals. The thing that has always stood out to me is that if I tell them that something they want isn't doable, they respond with literal confusion. It isn't anger. It's confusion. They are so unaccustomed to not being given exactly what they want that it's as if they don't understand what is happening when they are told they can't have something.


I set up a party for a family out in the hamptons that bought the house next door just to level it and set up a giant temporary party tent on the plot. Wild s**t.


Radiant heated driveways to melt snow.

A turntable to rotate their car so they didn't have to back out of their driveway.

Lifts in the garage so they can park cars underneath each other.


Once when I told my boss that we have completed the work well before time, he removed his expensive watch and gave it to me and said "good job".


I did a catering job years ago for John Paul Dejoria, Patron Tequila and Paul Mitchell, and his house was awesome. River side texas hill country. Beautiful place. We were packing up at the end of the night and the security guard came by and said stay away from the windows we are locking up. We said ok and about 5 minutes later these metal drop down armor plates came out of the roof it seemed and covered each window and door. Thick metal plating armor.


My bro worked on a super yacht, quit the day he saw a 14 year old take a massive s**t on the deck and tell him to “clean it up”.


Not me, but my cousin teaches English to foreign students in London, sometimes they're kids. She was once asked to go to a wealthy Arab's home to help their kids learn English. The house was stunning, the usual opulence, but the liquid hand soap was watered down. Despite being incredibly rich, they skimped on basic items like soap, loo roll, etc. It was all cheap brands, or, as I said, watered down


I knew a DJ working for the super wealthy. Not a famous DJ however the guy was good and low key. The one thing that always stood out for me were the orgies he played for. He always told me after dark you would not believe the people f*****g and swapping wife’s. And drugs, so many drugs.


I worked for an owner of a large, construction company. Back when we had the recession in around 2008, I saw him layoff workers and stop pay rises, at the same time of ordering in a brand new Rolls Royce for himself. His money, but didn't sit right with me.


Did appliance repair.

One lady had a 10x12 walk in wine cooler. Floor to ceiling stocked with wine.

In her living room.

Another person's house was made of imported stone and had a library the size of two car garage.

My favorite was an old lady who just had nice stuff. She took care of what she had. Everytime I went she gave me 40 bucks for " a nice beer with your lady" I would always refuse but she insisted and was basically the typical granny everyone would want.


I work as a private chef, and the New York, New Jersey, Connecticut area. For mostly high net worth families. VCs, CEOs, owners of sports teams. S**t like that.

Here’s what I’ve seen:

-They don’t raise their kids. Every single family has house staff. Sometimes one for each child. They are not well adjusted, all attend private school, have drivers, and don’t understand how anything works. I had to explain what public school is to a kid once.

-They shop differently then we do. When we go to a the store we buy what we need. A 12 pack of seltzer, only the paper towels or snacks we need. These families order everything and in bulk. It’s not one 12 pack of Spindrift, it’s whole cases. And everything is ordered and delivered. I’ve been to homes with floor to ceiling cabinets of just beverages.

-They do not take the subway or public transportation, ever.

-A room dedicated only to silverware and another just for servings platters.

-The amount of money spent weekly on fresh flowers is obscene. They are beautiful, but damn.

-A dining room table that cost $250k.

-Elon Musk (not by choice, he just happened to be at a dinner I was working.)

-They spend more money on kitchens they’ll never use that most people will ever spend on a vehicle. I’ve worked on $20k+ ranges in private homes. You can find a picture of one in my post history.

-The homes. I work for a family during the summer of last year that has at least $75mil across three properties alone. It’s absolutely wild.

-They will often try to undercut you. Only a few times have I had a billionaire look at my rate and not try to get me to take less. I’ve been standing in a $40 mil Hamptons home listening to a woman try to negotiate me down.

-They eat way simpler than you could imagine. I’ve written extensive fine dining menus for private dinners only to be asked for something as simple as steak, smashed potatoes, and broccoli rabe. No s**t, this is a standing dish for a client of mine. So f*****g simple.

-They will give you all expenses paid trips just so they don’t have to worry about cooking their own meals. Aspen, Cabo, Hamptons, Jackson Hole. It doesn’t matter. They don’t want to cook.

I might be missing a few things, but this is just off the top of my head.


$40k/year on sports coaching and travel, each, for two kids.

It was a better option than having them get into drugs or blow money in other destructive ways.

When the oldest kid turned 22 he got mad at his mom and yelled at her "All I know about is !"

She said "I know. But you don't have a cocaine addiction and three pregnant strippers like your Uncle Mark."


$300 dollar baby cashmere sweater that will fit for 6 months and probably get thrown up on.


I coached sailing to the child of a CEO from one of the biggest US service industry conglomerates.

When his child did well he would take me out to dinner sometimes with his buddies. The many stories they each told of cheating on their wives, drug taking, tax evasion and general scumbaggery genuinely shocked me especially when I had a close relationship with some of his children.


What struck me the most is how extremely picky they are, and how angry they get at anything that isn't exactly how they want it. Because I'm noticing myself drift towards that, even though I'm nowhere near wealthy. It makes me question what I feel entitled to.

Everything else, I categorize as alien behavior that I could never understand. This is the only one where I see a bit of myself.


Used to perform a religious service for a multi-Billionaire on weekends. Saw some interesting things for sure. One of my favorite frivolous spending I saw was when he wanted to lower the fan on the AC system without changing the temperature, and his staff told him the system can't do that.

He thought for a moment then said something like "Make it so it can do that. Have it done by Monday". This was Saturday. You bet there was a new HVAC system in that 6 story building by Monday, cost a few hundred grand.

There was a lot of other stuff but that stood out for how casual it was.


Worked for a 3 person dog walking/doggy daycare company. Ended up getting some VERY wealthy clients.They traveled for fun so often my boss and I had their dog for more days out of the year than they did. It was to the point that people at my favorite dog-park thought he was my dog!! As you can imagine the dog misbehaved a fair amount, but he was also sweet.

The same couple also employed a pool guy. I helped him out one day when their pool cover got stuck and he offered to pay me cash next time he came by. He asked where he could leave an envelope and I told him just to leave it on the counter inside. He looked at me incredulously and said, "Do you really think they let me in their house?". I never knew what to think of that lol. He seemed like a professional guy, and had started working for them just a few months after me.


I used to work at a member's only golf/country club. There were members who had been actors, athletes, race car drivers, former CEO of Google, some major money and egos going on. There was one family that had 3 teenage kids, 2 girls and a boy. The mom and the girls were very attractive and knew it. They always looked amazing and had overly entitled attitudes to match. They were "fancy." Well, the lady who washed the linens for the county club also did house cleaning for some members. This family was one of them. She said their multi-million dollar home was a disaster filth zone. They basically did no house work in between having the cleaning lady there. Dishes piled with dried food that smelled, dirty clothes thrown everywhere, piles of c**p all over, sticky floors, dog poop left on the floor. But the nastiest part was the bathrooms. She said they wouldn't empty their bathroom trashes and the ladies of the house would throw their used tampons on top of overflowing trash so she had to pick up their used women's products thrown on the floor not even wrapped in paper. So these fancy bitches would walk around the club like they were so superior and look down on everyone then would go home and act like wild apes throwing their trash and period products on the ground. The thought of being so out of touch that you decide it is beneath you to even be sanitary bc you can just pay someone to do that for you is just beyond insanity.


I am a dentist and used to own a dental office in an extremely wealthy area. I feel like really rich people come in 2 flavors, very humble and generous or just 100% a-hole. Most are the A-hole. Not much in the middle. True wealthy people care a lot about time, not money. If there was any hiccup in a procedure or something wasn’t correct they would FLIP out. 99% of the issues they would flip out about I could fix but that meant they had to make another dentist appointment which “wasted” their time. I HATED working on rich people. Best day of my life is when I sold that dental office.


My dad is currently working as a landscaper for an obscenely rich man, one day he struck up a conversation with my dad who mentioned he just moved to the area and was saving up for some new basic appliances like a washing machine etc...

Turns out, Mr richypants is the type to throw out perfectly good and functional stuff just because a new model comes out, perfectly good furniture gets dumped because his wife saw a dining room set, couch etc... that she liked better. So, my dad could just take home a washer, a dryer, a new fridge, a dining room table, a BBQ etc... and basically outfitted his whole place with fancy s**t he never thought he'd have just by taking it from the shed of discarded stuff of this rich guy.

And this is like, bottom of the barrel nepotism for this guy, he's a co-owner of an international shipping company, a bona-fide billionaire. Hell, he's not even at this estate dad works at 95% of the time. It's a vast estate up the coast from Brisbane, a few hundred kilometres from the city with a private beach and all that. From this guy's perspective he basically lets the staff pick through the trash.

This is the kinda guy who gives his nephews private jets for their birthday.

Most of the stuff isn't even used! Like, all the appliances but the fridge still had the plastic film on it!

Such wasteful people.


I worked on a school project with a girl whose family net worth is more than $9 Billion. They have a consumer products company that is a household name everyone would recognize, and it is family run. Two stories:

First: at dinner one night, she made an offhand comment, “Growing up, my parents would tell me to eat all the food on my plate,”. And I thought, ‘yeah, me too’. Until she continued, “because when I’m running the family business, it will offend our overseas suppliers if we don’t eat all the food they serve”.

Second: I was writing a fluff article for the school newspaper about an event: ‘It was fun, many people including John Park, Jose Gonzales, and Mary Jones all attended.’ I gave them each an FYI before submitting. She replied immediately very agitated and said I couldn’t include her. I thought she misunderstood and said it would only show up buried at the back. She replied, “You don’t understand. If my name shows up in the paper at all, I will get angry calls from my whole family - parents, aunts, uncles, everyone”


I did personal shopping for a pop star for about seven months before they moved out of my area.

The main thing I witnessed was inconsistency. Day 1, go find me this exact rug and find some picture frames that would compliment this room. Great, I put in a little extra foot work and found that rug discounted. Well, they didn't want it discounted when they can afford full price.

Day 2, while they were out the other day, they saw this fantastic sculpture at a home goods store. Can I find it? Hey, turns out I can! No problem. Wait, but if I found that rug from yesterday discounted, why couldn't I put in the time to find this discounted?

NDA runs out in 2030, but otherwise I have nothing but praise. They were a joy to work with. It was just very much never knowing what would strike their fancy and when, then not knowing if I should go the extra mile to save money or find a newer model, or just get paid for a full day's work for walking about a mile to Bed, Bath, and Beyond.