60 Employees Of Ultra-Wealthy Families Reveal The Most Absurd Things They Witnessed

Not me but my wife

She was a nanny for a fairly wealthy family

They were actually pretty down to earth. Really nice people. Always flew commercial and the father drove an older model Volvo

But that $8M original Monet that hung on the dining room wall was something else.

In my misspent youth. I sold d***s. Primarily c*****e and w***d but also literally anything else someone wanted that I could find. Which was most things.

However I was also a terrible c*****e and h****n a****t so while I handled thousands of dollars every couple days. I was perpetually broke.

Anyway I got a DUI one night. Luckily didn’t have d***s on me and had just enough money to bail out of jail.

One of my buyers called me looking for an 8ball the next day so I go out to his house to make the sale.

This a guy a little older than me at the time. I was 21 so he’s probably very early 30s. Old money Ag family with still paying out shipping ties on the Mississippi River. I have no idea what they’re worth.

I told him then that he should find another hookup most likely. As I’m broke and can’t afford to keep myself out of jail for this f**kup. That I’ll hit him up when I’m back out and up and running and I hope he understands.

This man proceeds to tell me that he can’t afford to find someone else he trusts, gets me in a pretrial diversion program and pays for it himself to the tune of around $10k.

All because he wanted to maintain convenient access to c*****e and oxycodone.

We’re both clean now and still talk a couple times a year. Really good dude actually.

I work as an art handler in a major city. Their collection consisted of antiquities, things that would usually be reserved for museums. Think 2nd century BCE vases, figurines, etc.

On the desk of the client, there was a small Athenian chalice painted in the iconic orange-figure-black-background style, developed around 500 BCE.

Inside of it was paper clips, spare change, and chewed gum.

My fiancé used to nanny for a very wealthy family. They were renewing their vows at a high end country club in Florida. She was brought along to tend to the kids at times and they let me come and paid for literally everything. Hotel, luxury rental car, room service, meals literally everything. We didn’t spend 1 dollar in 7 days and they thanked me for coming!

Anytime lol.

I think I read this story on reddit. Florist in a mall had a regular customer who ordered flowers several times a week. When the customer found out the florist was going to close because of expenses exceeding income they bought the ENITRE MALL and never charged the florist rent.

I worked for a shipwright out of Newport, RI. He had about 80 acres of gorgeous farmland in my hometown. The property was full of old stone walls which he paid two of us $20 an hour (1995 money) to keep the weeds and vines from growing over the walls. The property has a beautiful old house that was immaculate and rented out to a local judge. He also had a large barn with a beautiful Chris-Craft boat and assorted British cars all in perfect condition.

Anyway, he would pull up in a 2 wheel drive 15 year old truck looking like Jimmy Buffett, ask how much he owed us and hand us cash. It was a great summer for me.

A few years later the property next to his went up for sale. Used to be a farm as well, but someone had bought it and built a 5-6 million dollar house on it. When he bought it he hired a company to come tear down the house because he preferred the look of the farmland.

In my previous job, the two heads of the household (collectively worth about $30 billion) were engaged in a very lengthy and protracted set of discussions for how best to stop homeless people from congregating near their compound in Hawaii. They were ruining the vibe. Some options discussed ranged from donating to political groups to influence the mayoral candidates to get someone more hardline against homelessness. Another idea was simply paying people to go and vandalize the place so badly that the people would leave. They settled on just having private security constantly patrol the area and take pictures to stir up fears that the homeless were robbing people and houses. It worked.

Did a job, and small favour, for a Middle Eastern guy, mentioned in conversation I liked his watch, he took it off his wrist and gave it to me, wouldn’t take no for an answer. Turned out to be worth about half my annual salary.

The Dad usually has a "humble" hobby to get away from his family.

Two families come to mind. The first Dad bought a comically small tractor just so he could mow the acres of land at his country house all day and no one bothers him. The second Dad was a carpenter and would build custom wine cellars for his friends for free.

We build (framed) a house for a Middle Eastern type guy in Corona Del Mar, California. He bought 4 smaller adjoining houses and bulldozed them. That right there has to be $8M. Anyway since this was a city street in a neighborhood there was nowhere to store Lumber or heavy equipment but on the city street and sidewalks. On more than one occasion I saw and heard him talking to Code Enforcement while writing them a check for $25,000 and telling them to come back when it ran out.

I was a cleaner and I was paid to join the family go to their holiday home upstate and clean the holiday home while they were there. They were only there Saturday and Sunday but they wanted me to clean throughout. I changed the bed every day and cleaned up like I would do at a hotel.

When we came back, the chauffeur had a problem so they just organised a local cab company. The husband sat in the front, I sat at back with the wife. The husband started smoking. The cab driver said he could not smoke. The husband said, I'll pay you money to get the car cleaned.

The cab driver said no, if you smoke I will get a fine. The husband told the wife to pass him her (very expensive) Hermes handbag. The husband went into the bag, took out a huge pile of cash... about $1,000 and put it on the dash. He said to the driver, it's fine, I got you covered and then he started smoking!!

My moms boss was taking a stroll on the beach in the hamptons and liked the house we walked past. She left a check in the mailbox for the owner and a note asking to buy the house. Long story short, she has a great Hamptons house now.

After I got out of the Navy I went to Graduate school full time. I was unemployed and using the GI Bill.


My parents have a friend that owns a very successful software company and he's in the 100 million range. He's also a complete f*****g p***k.

There was a bad thunderstorm one night and he called me the next day and asked me to come clear some trees that had fallen over on his property during the storm. I needed some extra cash so I said yes. He said he would be in the area and he'd come pick me up.

He pulled up in his $100k+ Mercedes S Class that was less than a year old. He said he needed to make a stop at the Mercedes dealership on the way. I said okay.

We pull up and there is a NEW Mercedes waiting for him. We get out and move to the newer one and sit in it. I figured we are just doing a test drive or something, or he's using this as a loaner while his car is getting serviced.

The Dealership Manager (not a regular sales guy) comes to him with a clipboard and he signs a bunch of papers.

The D****r looks at him and says "Black Card?"

My parents' friend says "Yeah, put it on the Black Card"

We drive away. It wasn't until we were a few miles down the road that I realized that he had just BOUGHT the car.

That's when I realized that ultra rich people just do things differently than us regular folks, including how they buy cars.

I used to fly corporate jets before I got on flying for a major US airline. Many rich people who own private jets will frequently broker them out to charter for people who wish to pay etc. a great way to reduce your operating costs and make money.

Often, I’d pick up overtime(contract) work that paid a minimum of $3,000/day plus expenses. This contract was for a very rich celebrity who MUST get his fish for a private event the following night from a specific company in Chile. And he needed 150lbs of it. So, I picked up the charter from the broker and was airlined in first class from my home in NY to the jet’s location in Louisiana on Thursday where I met my copilot and off we go to fly to this small town in Chile and fly it to the chef/ event in Santa Barbara.

Minus an 11h rest in this town in chile, we flew about 17hours in 2- days.

The charter cost $250,000. My expenses were $10k and $10 for the co pilot.

The fish cost $350,000 when you factor in all fishing, handling, packaging costs, customs etc.


Each package was sealed to prevent smelling or leaking.


The owners assistant met us at the airplane and tipped us each an additional $3,000 in cash.


Blows my mind.

Not me but my wife nannied for a family back in the day. They wouldn't eat leftovers the next day no matter what it was, how good it was or how much they liked it. Imagine having a dish you actually like a lot but don't look forward to having a bit of it the next day for lunch because you always have fresh hot meals prepared for you or you just order food delivered from your favorite high end restaurants.

Also, she was once working while they hosted a dinner party in their home. She sat at and managed the kids at their table. She overheard the parents and their friends talking. One of the couple she worked for said something like, "I've wanted to try one of those dishes in a pan that people make at home but how embarrassing. What's it called? I can't remember the word". And after some going round and round they realized it was "casserole". Apparently only the poor eat casseroles and they thought it very quaint that people would cook that way, mixing everything together in a mass dish everyone gets served from.

It's not the extra cars or the vacation homes in Europe but it's the little things like this that really stand out to me. Not being willing to eat perfectly good and safe food that's less than a day old in your own home where no one is watching or judging is super weird.

I walked into a friends of a friends apartment once and recognized a painting on the wall. I sat down, amazed that someone actually had this piece in their apartment. Then I started looking around. Everything in their place was a masterpiece. Stickley, maloof, eames. Thank goodness this was before nanny cams, or they would have a funny video of me, walking around, flipping things over and fan boying. I was surprised not to recognize the label on the dining room table and chairs, despite the style being distinctive. This was flip phone era, so I took a grainy pic and looked it up. Didn’t find anything, so the next time I came over I sled about them. They were custom Frank Lloyd wright. I couldn’t ever get comfortable, I was aware of my limbs at all times.

Did some private cheffing of a family that had a net worth above 10 billion, their 2 dogs were cloned from the original dog who died at 18 y old. they had health issues all the time so we were required also to cut the dog food to specific grammage etc.

Hate that I’m late to this because my entire job is working with the 1% of the 1%.

My favorite moment was at a multi billionaire’s estate (10b+ net worth), he stopped and asked me if I knew how to use one of his bathroom sinks. I thought at first he was testing me or something, but I genuinely hadn’t been on that floor, so I said “no.” He looked at me with a smirk and said “me neither.” This was his main house too.

I fish on a guys boat in Marlin tournaments a couple times a year. 1 of the 1st times he invited me, I asked about dates n such and mentioned "now all I need to do is find a place for the family to come stay for the week in the area"...so he says "My friend has a beach house available for around $12K a week."...which i replied, "Bud, that decimal needs to move 2 places to the left for me to afford it!". His response was cool though. "Sorry, sometimes I forget." Then gave me a number to call and mention him. Got a beach Condo for $1500 for the week, which was about 1/3rd the going rate!

I worked for a high net worth doctor who had sold outpatient surgery centers to private equity for over $100 million. I’m a CPA and ran his family office for close to a year.

When I needed time off for my sick 11 month old, he asked why we didn’t have live in help.

But the biggest thing, and not much rattles me after 20 years of looking at crazy numbers on a screen, was the cost of owning a yacht. The boat itself was only a few million - but the captain, first mate, food, gas, repairs, cost of going through the Panama Canal was insane. In the neighborhood of $500k a year, easily. He would fly out to it to go fishing for the weekend and he didn’t even eat fish he was vegan.

In general he was fairly normal. Had emigrated from Cuba on a raft type story. But the yacht was crazy.