Rich People’s Employees Are Sharing The Things That Surprised Them The Most

Not exactly "work for", since I only did it once, but I was a driver for a plastic surgeon. His brother is a famous celeb in southeast Asia. Anyway, he was in the states because he wanted to go skiing in the Rockies so I drove him to various ski resorts over the course of 5 days. On the way to the first resort, he was wondering where my gear was but I did not expect to go skiing with him nor did I own any gear (always rented or borrowed). He made me turn around and take him to the nearest outlet and then casually dropped like 7k on snowboarding gear as a gift to me. He then paid for my own hotel room, resort tickets, and food. He absolutely would not let me pay for anything because I'm "forced to spend time with an old guy". 10 years later, I still own and very much use the gifts he gave me.

Guy I used to work for was worth over 200m. I had personally seen balance sheets indicating 100m+ in cash at times. Older guy; you’d never know he had money if you randomly met him.

Drove a 12 year old truck like 500k miles. 5 acre lot in the country with a small home and not much in there.

He owned several companies but his personal office was a little former lawyers office with not much in there.

But man, outside of that town he had it going on. Private jet. He and his kids and grandkids took a big trip every summer. Every single time he would just buy a home on that vacation. He had acquired over 30 personal houses. Most of them large lodge-like houses on lakes and in forests.

And he loved to share it. Any employee could rent any of the houses up to a week for no charge except for a little cleaning fee. We could rent one every two or three years. One employee that worked for him battled cancer (and beat it!) for years, and he had to go to Minnesota or something for treatment. Every couple weeks the boss let him take the jet for no charge, and he stayed in one of his houses near that hospital. That guy is now a pretty high up manager.

During COVID they had their most profitable year ever. The company earned $20m more in profit than the previous year. It was insane. They issued a huge bonuses for every employee based on your tenure. I got $8000. I know a guy who had just started a month prior and he got $500.

He’d send people to school. If you were a good employee and you wanted to go back and study business or something related to a role, he’d pay all of the tuition as long as you made As.

Immensely lavish Christmas parties for employees. They gave away THOUSANDS of dollars of gifts. They’d draw a name for a car.

It’s astonishing what he’s done for so many people. He told me that he felt like he needed to do it because he inherited a business decades ago, giving him a head start.

He did a lot for me personally, and it k****d me to take another job. I just wanted something new in a new place. I was about to cry when I gave him my resignation. He congratulated me, and I was like “you’ve done a lot for me and I hope this is alright” and he said “just pay it forward. You owe me nothing.”

Very cool guy.

I sanded the hardwood floors with my uncle for the guy who started e trade. One of his many condos. The first time he showed up to the condo, the neighbor came out to meet him. Neighbor says, hey nice to meet you, selling my condo here next door for $1.5 million if you happen to know anyone who’s looking to buy. E trade guy writes him a check on the spot for $2 million & says, take care of all paperwork & let me know when you need me to sign. Neighbor was completely floored.

Ex worked for a very hooked up, edge of the 1% couple. They were definitely in the group and my ex took care of their kids as an au pair. She said that, despite all of them living in the same house, they were completely absent parents and basically hired her to have someone to blame when their kids scream at them.

I worked on a luxury electronic device for a client (actual billionaire), the device costs 175k.  He bought his neighbors 2million dollar house to put it in and turn into a game room/club house. He goes to tip me 100 bucks (tipping is VERY rare in my industry) I look surprised cuz that's a nice little bonus. He mistakes my surprise for it being too little and goes "i dont know how much i should tip I'm sorry" before i can thank him he hands me another 900 dollars. I try to refuse but he will have none of it he's just happy the work was done.


I just liked how he was aware that money holds no meaning to him, but it did to me, a working guy, and he was genuinely concerned to come off as stingy/insulting.    .

I taught English to an oligarch in Moscow while he was being driven to his meetings at the Kremlin. In the summer he took all of us staff with him and his family to St. Bart’s.
Rubbing elbows with Heidi Klum and Dimitri Peskov on the beach within the same hour was a weird mix. At the end when I was leaving he called me over he’s like “my friend… we don’t talk about anything that happens here, yes?” I literally saw nothing damning but still he’s in prison now because… Putin 🤷‍♂️

EDIT: This was during the 2016 election and while watching a clip of Stephen Colbert, he looked at me dead seriously and asked me to hire Kellyanne Conway for him or at least set up a meeting with her. Like mate who exactly do you think I am? A man who lives in a world where “no”and “can’t”don’t exist.

My cousin got rich by working his a*s off. I unfortunately grew up around rich people because I went to a private school, he didn’t. I hated them, we weren’t rich, we were just catholic. I got divorced and then got cancer . It was hard with 2 kids. He dropped off a card for me with 3,000.00 in it, I called to return it him and his wife refused saying how my mom and dad were always there for them. It really helped me a lot! Then unfortunately my father recently passed and he held a dinner in his honor after the service, it was beautiful ! He worked hard for what he’s got and he does good with his money!

I used to bartend private parties when I was in college. I worked at an event at this huge estate outside Milwaukee, WI. It was the first event I ever worked for my friend who hired me (he was a regular at the bar I worked at downtown MKE).

Fast forward to the night of the party and my friend said “I need you to wear a white buttoned up shirt with nothing under and be ready to take it off at some point during the party.” I was completely shook. Had no idea what this party was all about. I walk in to the house and the owners have a couple of pet pigs wearing tutus. I’m showed the dining room and told to set up in a corner while the guests arrived. Super fun party, I was allowed to drink during it and was ripping shots with the guests all night long. Eventually this super muscular gay guy walks up and asks me to to take my shirt off, and instinctively, I say “you first”. He does, he’s super ripped. Everyone’s cheering and yelling now as he tells me it’s my turn. So I do it, why not I’m feeling pretty tipsy. The guy busts out laughing, loving that I actually followed suit.

Tips me $50 on top of the $300 I made from working the party. I worked a lot of parties like this over the next couple of years and became good friends with some of the usuals that I would see at most of the parties. Really good source of income for broke college me. Good times!

I nannied for a wealthy family in the 90s .
They had a check sitting around for 180 000.00
They would look at it occasionally and say, "I really should get this to the bank."
They didn't deposit that check for at least 3 mos.

About half of them are not smarter than anyone else, just luckier.

How stingy they can be. It's shocking.

"I'm a billionaire and you expect me to pay $2 for water? That's insane!!!!"

The people my husband works for are billionaires and they are the biggest penny pinchers I've ever seen in my life.


***Edit - The people I am speaking of live in an estate worth about 45mil, drive limited edition Bentleys, provide Fiji water for their cat, bought their daughter a 20mil penthouse as a wedding gift, spent 200k on flower for the wedding, that kind of thing. .

They do not live frugally, at all. But they get weird about their money. If it is not something they WANT to spend their money on, they're cheap as cheap can be.

I didn’t work for, but dated a rich girl. Rich as in his father had a helicopter, they had an armored vehicle, bodyguards, etc. She and her environment lived inside a bubble. 

Once I took her to a normal area and she saw a shop, Hermes I think it was but not sure. She had a card from daddy to pay for things.

She liked a bag that was like 45.000 USD or something like that and bought it. I mentioned about how expensive that was for a purse. She looked at me confused and asked “45.000 USD is a lot of money?”.

She genuinely didn’t know the value of money, for her it was like tokens.

He went to the beach and instead of getting a hotel room he bought a house on the condition he got it immediately and all the contents. He said, "we need to find a restaurant, or actually let's check the kitchen." it was full of food because people lived there yesterday, and it surprised him they had food for some reason.

I dated a girl who was from a very rich family. Private Jets, property in every major city and celebrities over for Christmas Dinner.
The thing that amazed me the most was that socks weren't washed, they were just binned. The sock drawer was just full of brand new socks. Boxer shorts were exactly the same, but girls Underwear wasn't.
We're still friends now and I always joke with her about the socks 😅.

I grew up hunting, fishing, gardening, farming, a real country and forest life. A rich guy calls my friend who is basically my dad, asks to come to town for a long hunting weekend and he's looking for someone to set it up and be his guide through it.

I'm offered $500 + expenses in 1998 money and totally take the job. I rent a local cabin from another friend's dad, meet the rich guy and show him the plan, we set out for the weekend and it's basically me hunting and fishing but him pulling the trigger and him pulling fish out of the river. It's actually pretty nice. I'd taken many people on trips like this before, usually for free. At the end of the 4 day weekend I drive him to the airport about an hour away, he takes some of the meat with him, gives me the rest, and tells me the shotgun and rifle and ammo and fishing pole are mine, and that was awesome. I left them with a friend when I went into the service, that was almost 30 years ago, I'm told the shotgun and rifle are still fine.

Good fun.

I did some mechanic work for a guy in Vegas who had a passion for finding homeless junkies and taking them off the streets. he would set them up in an apartment and give them work to do like take care of the sick ones, clean the house, pick up meds etc, and he would also give them unlimited money to continue getting their fix. I was so confused, like if you're doing all this to get them off the street then why not get them off the dope and onto suboxone? I was constantly fixing one of the cars he bought the boys because they were trashing it. I was clean and sober for a few months just out of rehab and he never once offered me anything to help even after my sober living got suddenly shut down and I was homeless.

One story of many but the general trend is that rich people have NO clue how to spend their money.

Guy had his driveway and inside of his garage paved with f*****g *agate*. Like, insane. It was is beautiful. Probably one of the more unusual things I've seen.

I don't know what was beneath it, but it was agate coated with an epoxy resin.

I worked at a Fairmont hotel in banquets department and we had the owner (a rich Saudi prince) and his entourage come for a visit. We were briefed ahead of time on how to act around them. For instance, we were told not to look at the women at all.

They requested a buffet of McDonald’s food, so we ordered tons of food and organized it all into a buffet for them.

One evening we set up an outdoor event for them. It was cold/snowy so we had gas fireplace warmers around. A few guys from his entourage were standing around one, and I saw them put their phones into the fire, and watch, ensuring their phones were entirely melted/burnt up before leaving.

Always wondered why or what could have been on those phones..

Used to play a team sports and do outdoors stuff with some guys regularly years ago.

one of the guys - was very well off - a few million - owned a chain of jewelry stores.

Most of the guys did not even know - he did not flaunt it at all. He drove a beat up truck, average gear, was modest and a just a great guy. he never talked about it or anything (if you directly asked him "are you the guy..." he would admit it, he just did not talk about it or brag or anything).

it only really came up twice that I saw - once he showed up in a very nice BMW - his wife's car - his beat up truck was in the shop.

Another time, we were all volunteering working on a outdoor site - and it was hard work and we had missed lunch. he went out and brought back decent lunches for like 12 guys. Would not take money for it from anybody.

I think the differences are - in many of the comments here - the rich people who were not jerks - were self made - worked really hard - were not born into it.

When I was in high school I was a nanny for a wealthy family,with 3 kids. They had a handyman guy that always seemed to be there when the husband was not. Then,she was pregnant again. Hmmm. Baby is born,looks nothing like her other kids. Handyman is not around anymore. They divorced a few years later.