“Cases And Cases Of Gummy Bears In His Basem*nt”: 30 Of The Wildest Things People Have Seen While Working For The Ultra Wealthy (2024)

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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.

DrGrizzley , Juliane Liebermann Report

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.

kingJoffi , Crystal Collis Report

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. Basem*nt 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.

colobirdy85 Report

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

The__Riker__Maneuver Report

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.

wjescott Report

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.

kl_dudey , vilnis Izotovs Report

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

_Diskreet_ Report

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.

robertcboe , Minku Kang Report

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.

**Edit:**

*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.

Nuxul006 , wikipedia Report

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

ATribeOfAfricans Report

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.

UncleGrako , Eugene Chystiakov Report

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).

Interesting-Step-654 , Michal Balog Report

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

Inequitom Report

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.

grexbear Report

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.

TheMysticalPlatypus , BATCH by Wisconsin Hemp Scientific Report

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”.

Blueshockeylover Report

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.

Rarnah , CHUTTERSNAP Report

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?"

CindeeSlickbooty , Andy Brunner Report

“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.

TheNoisyNomad Report

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.

Ilookbetterthanyou Report

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.

Chiaseedmess Report

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.

Duranis , Alina Kacharho Report

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

C_Beeftank Report

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.

anonymous10472011048 Report

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!?!

Spade18 Report

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.

UstasMom , Tyler Clemmensen Report

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.

https://www.youtube.com/watch?v=05k6g8Ak2jE

Bombxing , Mary Hammel Report

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

Lousyfer , Lousyfer Report

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

TruthYeller54 , Chris Liverani Report

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).

nevercursd , thuhang bp Report

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