30 People Share Their Shocking Experiences With The Ultra-Rich

My wife and I bought a nice house in a middle/slightly upper middle class neighborhood. Not many European cars, parents didn’t send their kids to private schools. Everyone was doing fine, but seemingly not rich.

One day, a neighbors kid (age 6) passed out. Went to the hospital and within a few days was diagnosed with brain cancer of a type that was pretty much a death sentence. He was given 6 months to live.

A week later there was the previously scheduled block party and Frank (single guy, mid 60s, quiet neighbor 6 houses down) shows up and overhears people talking about the neighbor kid with cancer.

He asked me if I had the parents phone number, which I did and gave it to him.

The next day Frank had flown the entire family on his private jet across the country to a research center in California to meet with his best friend / former college roommate who happened to be conducting cutting edge immunotherapy research (basically reprogramming your body’s cells to fight specific strains of cancer).

As it turns out, Frank, the quiet guy living down the street who drove a 7 year old Toyota Camry was worth $750M (he started a company in the 90s that was bought by Oracle in the early 2000s and made him ultra rich).

Fast forward 5 months. Frank had paid for the entire family to move to CA for treatment which cost him just over $2.2M out of pocket. The kid was in remission after some next level, Star Trek crazy medical treatment. For a family he didn’t even know. Amazingly enough that wasn’t the extent of it…

Come to find out, we all learned Frank was sponsoring orphans in the system in our state and paying for college or trade school educations for every single orphan in the system in the state and had been for 20 years. He had sent more than 1,500 orphans to college or a trade school of their choice, spending $230M to do so.

The quiet dude down the street driving an old Toyota. He died 2 years ago. Left all his money to his foundation to continue to send state orphans to college.

The world would a significantly better place if only a fraction of the world’s ultra wealthy followed his example.

A buddy of mine, who has since passed away from cancer, while going through treatment was working at a bike shop. One of the customers was/still is a Wall Street guy who is a billionaire several times over. My buddy mentioned to the rich guy that he got denied getting into a cancer treatment trial at UNC. The rich guy said “ hmm, somebody should do something about that”

And 2 days later, my buddy got a call and they told that “due to recent events” he is in the trial.

I always thought that was cool.

I was invited to play the North course of the Los Angeles Country Club--an epic track that is very difficult to get on, especially for a lowly winemaker. But I sold the GM some wine and he invited me out, so I got there at 6:45 am for an 8 am tee time--clubhouse is supposed to open at 7.

But as I pulled up, a guy came down in an LACC windbreaker, took my clubs and asked if I wanted a cup of coffee.

After we were all set up and chilling in the locker room, I asked him:

"I'm not sure how it works here, my good man. Are you able to receive cash tips? (Some clubs don't allow.)"

"Oh I don't work here," he laughed. "I'm a member."

Later I saw him leaving in a Lambo--dude could have bought and sold me 1000x over, but still showed amazing hospitality to a visitor to his club.

Boss I worked for. Filthy rich, but wears the same old clothes all the time. 
His wife wouldn't spend money on a new bikini at the hotel shop in the hotel they own, because she has one.


Plainest, nicest people. Also loaded.

Waiting to check out of a five-star hotel. The guy in front asked the Receptionist to order a car to take him to the airport.

Receptionist: “Of course, what time’s your flight?”

Guy: “Whenever I arrive”.

I used to be a big-time Jeep 4x4 off-road guy. I made friends with one of the guys behind the counter of a local 4x4 store. We'd occasionally go out for beers or dinner and got to be pretty close. I knew he had a degree in mechanical engineering, but he never spoke much about himself or his family. One day, he called me up and asked me if I was interested in going to watch a big GT Daytona 24 Type car race in PHX. I laughed and said I'd love to, but I can't afford that s**t. His response was, "my Dad will swing by Denver and pick us up in his jet, and then we'll fly onto the race. He's fielding a new Daytona Prototype car. I'll cover everything". It was an awesome trip I'll never forget. Turns out his family was/is ridiculously wealthy. The next race we went to was THE 24 hours of Daytona. Both races were in Luxury boxes. Unlimited food and booze. Pit passes.

A local family with generational wealth and smart business minds grew their businesses to become multi billionaires. But they'd still stop at the chain of corner stores they owned to get coffee and snacks.

I went there for coffee after they switched from very bad coffee to very good coffee, and there was the patriarch of the family getting his coffee at the coffee bar. I introduced myself, shook his hand, and congratulated him on the massive improvement in his stores' coffee. I asked him what was behind the change after decades of selling the same less-then-average coffee.

"My brother and I were stopped for coffee one day," he said, " and he took a big gulp and he looked at me and he says, 'Tell me again why we sell such s****y coffee.'" LOL!

A friend in college was from Japan. His father owned a plastics company and was crazy rich. One day he asked to borrow $1000 until his allowance came. I said I didn't have $1000. And he was like, "I don't mean cash, you can write me a check." And I said, no, I literally didn't have $1000. He was dumbfounded.

I once broke like $15,000 worth of marble because a piece wasn't installed correctly. I was a pool tech in Florida working on 'millionaire pools' basically people who lived too far away or their pools were too large for regular pool companies. It encompassed everything from driving 3 hours to clean a pool or flip a switch to actual tech stuff and troubleshooting leaks or doing repairs on fun pools built very oddly to say the least.

Anyways I'm just walking along the edge of the pool A which is an Infinity style pool that shared an edge and 20' drop with pool B. I was standing where I was supposed too, the marble feature I was standing on wasn't secured when installed and began to slide under my feet. The pool being very elevated left me in a weird spot, I jumped over the wall and to the side about a 10' drop and I cleared the base of a marble staircase. The 8' curved slab of marble wobbled back over the edge and took out 3 marble steps and some of the sandstone floor.

Guy comes outside yelling and says 'tell me you weren't standing on that' me: 'I was standing on that' and you watched all the anger leave his face. The money and damage meant nothing to him, likely an insured inconvenience. He thought I'd lie to him and he'd have some justification for the anger. Instead he goes inside, comes back out like 5 minutes later while I'm on the phone with my boss with a tablet and tells me I was like Spiderman as he shows me leaping over staircase, and me standing where I should be able to stand and the marble wobbling under me. We investigate the ledge, lo and behold none of the adhesive made contact with the slab. It had just been existing there due to gravity and pressure of other slabs. I handed him my phone with boss, his insurance ended up covering it and he was able to sue the company that installed it... but watching all the anger leave his face left taught me a cool lesson.

20 years ago. A casual friend asked me to be his +1 to a destination wedding. He is gay but was told he needed to bring a female. We were friendly but I didn’t know much about him, other than he was cool people and when we all went out in our friend group, he always looked amazing. I was like, ok how much? “No worries, I got it”. Turns out it was one of those many-day long Indian weddings. In India. He flew us there on his family’s private plane, we stayed in separate suites at a gorgeous hotel. All kinds of wealthy and famous people were there. I think my jaw was on the floor the entire trip. I received a “gift bag” with like $20k worth of jewelry, local luxury goods, and tech devices. He offered me his bag bc he didn’t need a macbook..?! Hell yeah.

I never thought I would enjoy a big a*s wedding like that but I also never thought I’d get to see so many famous people up close either. Hands down incredible. .

Told a customer (I clean for a living) they were out of paper towels. She then asked me “where would I get more? My personal shopper is on maternity leave and her replacement has not come yet…” as she stared off in the distance, afraid of the horrors of the grocery store.

I work at a private high school, and every year each class starts with an overnight class retreat. One year, we couldn't find a location that would take the junior class, so one of the parents just casually BOUGHT A SUMMER CAMP, and the junior class had their retreat there.

This Saudi girl I met at uni was super chill, really cool and down to earth and grounded, always dressed very low key in oversized hoodies and didn’t really wear any notable jewelry. Anyway, she told me that she didn’t live on campus because her mum had bought a place nearby as both her and her sister were going to the same uni. So like a bit weird but okay! Then she invited me to a party at her place that her mum was throwing and when I got there my jaw dropped to the floor. Turns out her mum had bought an entire estate complete with huge grounds, there were marquees set up in the garden set up as cocktail bars and shisha spaces, incredible mixologists and countless wait staff serving around the most amazing canapés. Ivana Trump was there. I was like WHAT THE F**K?! And she just looked at me like it was all nothing. Crazy. Went to many more parties she threw - the best one being a casino night where they essentially built a casino inside a marquee in their garden with all the games you’d expect and proper dealers and all. Blew my mind how insanely rich they were and you’d never guess from just seeing them out and about, and they were the nicest, sweetest most down to earth family (not that rich people can’t be nice but obviously that’s the stereotype!).

Threw a €800 kids Dior jacket in the kitchen bin because it got wet…in the rain…it’s a rain jacket.

Two things come to mind that I haven’t seen mentioned:

1. The amount of people who absolutely kiss their a*s, even family, hoping to get a cut of their fortune. It’s almost like they have a level of worship or mystique in other people’s mind that is really gross to witness upfront. 

2. It’s almost easy for them to find new ways to make money. Example: a $20M property development that falls apart and the bank needs someone to step in and complete it. Bank wants $15M for it, they negotiate $10M. Put in $2m to complete it and it’s worth $20M. So it cost them $12M to make $20M so they manage to net $8M just by being someone who can get it done. Negligible to their overall worth but to the average person, they could do that once and never have to work a day again in their life. .

Not sure if he is considered “ultra” rich but it was definitely a different bracket than mine. I used to work in a restaurant and there was an older gentleman who would come in maybe once or twice a month and he ALWAYS knew someone at two or three tables. He’d come up to the host stand and make it known that he’d be paying for all their bills. Every time. It was the one and only time I’ve ever handled a black Amex. Those things are THICK. He was very nice and always left a humongous tip for whoever was serving the tables.

That they're usually pretty nice. Back in the 90s I delivered pizzas in a pretty exclusive area. This was one of the towns that some of the pro athletes lived in. Then various business owners, CEO's, etc.

Anyway, most of the people were really nice. One guy and his wife were concerned that I didn't have an investment plan started. I mean this in a good way. Like they were worried about my future. There were other similar gestures from others that were also well meaning.

Now, their kids could be a******s sometimes. The people who actually earned the money though? More often than not they were solid people.

The richest person I met, worth billions, refused to pay $5 for a Diet Coke, argued it, and drove a 20 year old regular car.

I was in a drive through for a coffee shop and there was a Ferrari 458 in front of me. Really cool car and not something I get to see often so I was enjoying getting a close look. The driver goes to pull around to the window after ordering and drags the side of the car against the yellow bollard. Crunches the door pretty hard. I audibly yelled. The driver gets out and is understandably freaking out, looking at the car, the bollard, hoping some magic would happen to undue what had been done. Then the passenger gets out and he's laughing. What an a*****e to be laughing at his distraught friend who had just smashed up their expensive car. It soon became clear that the passenger was the owner and the driver was their friend who had just crunched the car. The owner was calming their friend down explaining it was no big deal he'd just get the car fixed and not to worry about it.

I worked with a guy for 20 years who was worth $400 million when he died in 2008. We did a lot of deals with other multi multi millionaires. What amazed me was with some not all was their absolute love of accumulating wealth. They loved their assets more than they loved their children. I remember one day when I walked into his office and he was crying. I asked what was wrong, what happened??? His answer was”interest rates had risen”.