“Cases And Cases Of Gummy Bears In His Basement”: 30 Of The Wildest Things People Have Seen While Working For The Ultra Wealthy

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.

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.

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.

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 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.

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.

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.

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.

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

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.

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).

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

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.

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.

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”.

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.

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?"

“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.

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.