20 People Who Worked For The Super-Rich Reveal The Most Surprising Things That Happened While On Duty

Published 2 years ago

Have you ever wondered what the rich spend their money on? We instantly think of private jets, real estate, remote islands, cars, ridiculously expensive art pieces, superyachts, etc. Just FYI, the sales for yachts increased by 25% in 2021. The time when many were dealing with the financial hardship caused by the pandemic. And the truth is, many actually do spend their wealth on luxury items. Yet, despite their lavish indulgences, many billionaires also donate billions to charity.

Recently someone reached out to people who have worked for the rich and asked them to share their best and worst experiences. And many did, from hosting an employee’s son’s graduation party at their ranch to firing an employee for something so absurd as giving their dog a command. We’ve compiled a list of some of the most riveting tales people had to share so yall can get some insight into the secretive world of the moneyed.

Related post: 20 Casual Things Wealthy People Say Or Do That Scream That They’re Well-Heeled

More info: Reddit

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Image source: bitch-im-the-witch, John Arano

I don’t know if this counts or not, but my dad used to work directly under the CEO of a pretty decent-sized construction company when I was in high school. I met him a few times, he lent me his lake house over spring break once, but I wouldn’t say I really knew the guy all that well.

but when I graduated high school with top honors, he like took it upon himself to throw my graduation party, and bused a bunch of my friends down to his ranch, and had one of his pigs slaughtered (and then one of his cows, when he found out a lot of my friends were Jewish), and just threw this big a*s opulent party in my honor. I think he did that for a lot of people in the company, just because he likes to entertain, but it was still dope as hell.


Image source: xxbearillaxx, Jurij Kenda

My dad worked for an extremely wealthy man as his personal accountant. One day my dad was driving him to a meeting, he was super old, and the man asked to swing through McDonald’s. After ordering a coffee for $1.06, they began pulling forward. The man asked my dad to reverse his car to the speaker to let them know he had a senior discount card. A man worth well over 20 mil, in a massive and nice luxury car, was not about to miss out on saving four cents at McDonald’s.


Image source: tf2hipster

My sister-in-law worked on the maid staff for a mega-wealthy (1+ billion) guy for several years. She was pregnant for a bit, then gave birth 2 months premature. You can imagine this was time-consuming and expensive. The rich family gave her all the time she needed and paid for the entire process (wound up costing over $100k). My niece is now 33 years old.

So my experience was pretty positive.


Image source: mustangswon1, Andras Vas

I have a good one, I interned for this wealthy CEO in Houston. He was traveling to Mexico and had forgotten his laptop which had all of his stuff that he needed on it. He called the company and asked to have it sent to him, they said it would take 3 days to ship it even with priority. He paid me $500, plus a plane ticket, and for a hotel for me to stay in for the night to fly his laptop down there so he could have it within 12 hours.


Image source: superjew101, Marcel Strauß

Once as a caddy I was given a 20-minute lecture/demonstration on how to open a Porsche door correctly. Subsequently, I resigned the following day.


Image source: LordXeeloBob, Wikipedia

I have a super rich great uncle who’s probably worth at least that much. I spent a week one summer house sitting for him in his beach front bungalow on Balboa Island while he was out of the country on business. He paid me very generously and I got to live on f*****g Balboa island for a week. Uncle Fred is a kind, down-to-earth man, and his whole family is rich as f**k. Overall the experience was very nice, except for one thing, cousin Chad.

Chad is his grandson, my age who played waterpolo for USC a while back and won some major National Title. His victory ring cost thousands and thousands of dollars, solid gold, diamonds, like those world series or superbowl rings, except for college waterpolo. More on this later.

Cousin Chad was a total c**t, the stereotype of the University of Spoiled Children all the way. Throw money at the school and play a sport, boom degree in communications. During that week he used the house as his love pad/party house, despite strict instructions that he could only use it with my permission and only for himself and a few other approved people. Invariably after he was done he abandoned the place and let the non written into the will pleb (me) clean up.

He also had a habit of showing me this absurd victory ring. He said, “if you promise to be careful, you can hold it if you want.” Towards the end of the week, I accepted, because I had a prank in mind. I took a dollar coin (gold colored), and put it into my hand and discreetly pocketed his ring. I said “hey, Chad” and he turned back to me from his phone in time to see me chuck the dollar coin down into the canal that bordered the house.

Chad punched me in the face (I deserved it), and then dived into the canal to look for it. I put the real ring on top of his wallet which was on the table inside and left while Chad dove up and down in the canal to find his ring.

Uncle Fred thought the whole thing was funny when he got back, but Chad and his family haven’t spoken to my family since.


Image source: TexasFordTough, sofatutor

An old high school teacher of mine is an extremely successful private tutor and does a lot of work in the wealthy neighborhoods in the area. Once, he was tutoring a kid and helped him get prepared and pass his college-level physics class; at the end of their last session, the kid told him to wait there and went into his dad’s office and came out with his payment and an extra $1,000.
My teacher tried to refuse it, saying it was too much, but the kid said his dad asked him to give a tip


Image source: nellirn, Pixabay

I worked for a very rich man who owned a string of retail stores. I was a college student and one day I went to work quite ill. The owner insisted I visit an Urgent Care center. When I returned, he asked what had transpired. I replied that I had a sinus infection, etc. and that I didn’t fill my prescriptions because they cost too much money. He pulled out his wallet and peeled off a $100 bill and insisted I go straight to the pharmacy. I repaid every penny, but I never forgot how much it meant to me that he cared enough to send a lowly part-time college student retail worker to Urgent Care then take the time to follow up to see if I was okay.


Image source: ChuckMastaT

I worked for an upscale condo complex, starting at 500k and up, so most of these people were pretty wealthy. Most people were really nice, I got all kinds of Christmas gifts and even left over things I didn’t care about like clothes and food.

Best story, I was talking to a guy about why he drives a beat up car compared to everyone else, it was like a 1998 Yukon, and he said his thing was jets. Then proceeded to take me to his private hanger after work, showed me his 3 private jets and offered to fly me anywhere l, anytime I needed, just ask. Never took him up, unfortunately.

The worst was a lady who was just never happy with anything we did. Just hated all employees. We were too nice, took too long to get her car, got her car too fast and was wasting gas, took too long to say hi, s**t like that. Everyone hated her. Other than that, these people were really cool.


Image source: anon, Brina Blum

I was working (as an architectural model maker) for a developer who was trying to put up an ugly f*****g building in the middle of Mansion House London. Anyways he had this dog super special trained so that it would only obey his commands. So I was working on adding some stuff to a display in his office and the dog was under my feet, so I said really nicely ‘Can you go lay down over there please?’ and it did.

I was fired on the spot.


Image source: A2KB, Ashley West Edwards

A good friend worked for a certain GOP elite political family who had a member running in the 2012 US presidential race. This family actually hired a high-end catering service to cater a food fight for a 7-year-old’s birthday party. The staff set up a big tent outside and then had the nannies lay out special painter’s coveralls for the 25 kids at the party. Then, the kids destroyed 6k worth of food. My friend and the catering staff were horrified. The kid’s parents all stood around watching and cracking up. The kids and families all got gift baskets worth 2-3k each as well. Vulgar, to say the least.


Image source: mikedub9er, Pixabay

Worked at a restaurant where a few of the regulars were the children of billionaires. After being asked how she has so much money, I once heard a student say, ‘I told my parents that my tuition costs $500,000.’ Another time, I was serving a table and was asked to bring a tray of 60 Patrón shots ($600 for a 19-year-old student). I must have had an incredulous look on my face because his only response to assuage my concern was, ‘My father owns diamond mines in Africa.’


Image source: SayHeyItsAThrowaway, kyo azuma

Not work for, friends with.

Not a best or worst story, but an observation. My friend rarely demands special treatment. She’s proud of this, and it’s true…. but what she doesn’t always seem to understand is that she gets it anyway.

Example: Kid attends private school. Multiple parents are grumbling about curriculum change. Head of school calls her to hear her thoughts. The HoS may explain “we were just checking in with some parents to see…” and Friend might believe that everyone is being contacted. As far as she knows, every parent is getting their say. But in fact, the school is not calling everyone. They may not be calling anyone else at all. She’s being reached out to because she’s a big donor and the school thinks they can’t afford to have her unhappy. She hasn’t threatened anything, she hasn’t thrown her weight around, she hasn’t demanded that they hear her opinion–but she’s being catered to because the school respects her checkbook.

Multiply this times however many organizations and businesses all over the city, & you get a person who goes through life with a somewhat different experience than other people, but they’re not demanding it, and may not even be very aware of it. They think everyone gets the kind of attentive service and outreach that they enjoy.


Image source: amber_binkin

This was ages ago; I worked in a DVD store, and a woman came in with five, double-sided A4 pages of movie titles and just asked me to fetch what we had. I ran about and collected DVDs and Blu-rays close to $1,000 worth. I asked what they were for — she was a PA for a billionaire and getting them for his yacht.


Image source: luther_williams, Jeff Tumale

When rich people want to buy a Jaguar in the UK, they get assigned a special sales person who is incredibly knowledgeable, meet in a special fancy office, and special arrangements can be made. This was my friend Chris’s job; he had access to things that a normal Jaguar sales person wouldn’t have. Once, a Saudi prince wanted to buy a new Jaguar that had been released, so they met up and spent a full day spec’ing the Jaguar out; the final price was, like, £125,000 for the vehicle. The factory had 16 different color options for this model, and the prince asked if he could sleep on it as it was getting late, so they set a time to meet tomorrow. The next morning, he decided to just order one of EACH color.
“They quoted delivery time, the prince agreed, and he was presented with ocean travel options, to which he said, ‘What about air cargo?’ In the end, 16 of the same Jaguars in different colors ended up being loaded on a plane and flown to Saudi Arabia — and the total cost was around £2.5 million.


Image source: LifeIsBizarre, Pixabay

I used to do some financial work for someone who became very wealthy through their very popular chain of surf gear. I had run through their tax position and had found a way for them to save a little over 2 million in taxes a year by reshuffling some of their entities. Would have taken them around an hour to sit down and change everything, lots of signatures on paperwork, then maybe an hour extra of their time a year to administer. Their response?
“Nah, I don’t want to waste that much time with paperwork, that’s what I pay you guys for.”
I can’t even imagine what it would be like to be in a position where a bit of paperwork wasn’t worth that much money. (Heck, offer me $20 and I will gladly fill out paperwork for an hour for you!)


Image source: waterloograd, cottonbro

Some family friends were having marital issues. Their marriage counselor figured out a lot of their problems were over cooking meals. The counselor reminded them that they are rich and can just cater all their meals, and it would be cheaper than getting a divorce. They listened to the counselor and now are happily married again.


Image source: JamAndDai, Etienne Martin

I was a bank teller. Two stories here.

First: person my age, about 20, came in. Was a delight. He came in once a year to take his trust which was 100 million dollars, and take the interest out, about 48,000 dollars. Once a year. That’s all he lived off of. He was content, and was modest. I loved it.

Second: girl came in with her mom. Actively whined at me for 10 minutes about how unfair it was her mom had all this money in her account and was making her live in poverty, with all her university fees paid, her rent and car covered, and she was only getting a tiny payment of $5,000 a month. She couldn’t fathom surviving off it. The mother turns to me and says “well I don’t know. I thought that would be enough to live off of? Should I give her more? ” I meekly said “That’s 60,000 a year. I make 20,000 a year, am going to college full time and have a baby on the way…” they both got really quiet and left. Never saw either of them again.

Also, Mike Tyson banked there, but I won’t talk about that. You said only people who were wealthy. ;)


Image source: Elysian-Visions, Saad Khan

I briefly worked with one of the top Saudi Arabian crown princes in the ’80s. He would buy out the top three floors of the best hotels (Four Seasons, etc.); two floors were for maids/help/security, and the top floor was for the royal family. Once it was only the prince and his three wives. Wild.


Image source: DANK_SINATRA13, Ravi Sharma

I used to work for a composer who is worth around $100 million. He was generally a really nice guy and was genuinely hilarious. There would be some times where he was in a really bad mood and would lash out at people, specifically when it came to preparing food for him. One guy got chewed out for handing him a can of coke by holding onto the top of it rather than around the side. One specific incident that sticks out was when somebody went to get a whole lobster for his dinner and set it out on the table. Our boss hadn’t come out to eat it for hours, and it was probably around midnight at this point, so the kid just sat down and started eating. Whaddaya know, big boss comes into the dining room to eat his lobster and sees an intern sat down at the table wearing a bib eating his super expensive (now cold) lobster dinner. That kid didn’t come into work anymore

Violeta Lyskoit

Violeta is one free soul. She feels the most alive when traveling to new places and seeing the beautiful world out there.

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