For most of us, the lives of the “1 percent” are a complete mystery. When people have that much money, what could they possibly be spending it on? If you’re imagining elaborately decorated private jets and spontaneous trips around the world, you might not be too far off.
Someone asked people on Reddit who work directly for the super wealthy to share some of their best (and worst) stories, and many of these employees delivered. We’ve gathered some of the wildest tales about these affluent employers and what they spend their money on, so we can all get some insight into the mysterious world of the wealthy. We even were able to speak with personal finance expert and creator of the blog Making Sense of Cents Michelle Schroeder-Gardner to hear what it’s really like working with rich clients.
Enjoy this list and if you’re hungry for more of these stories afterwards, be sure to check out Bored Panda’s previous publication on the same topic right here.
#1
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: tf2hipster
#2
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: TexasFordTough, sofatutor
#3
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: nellirn
#4
I’m not sure of their net worth, but my aunt and uncle are easily worth multiple millions of dollars. My aunt used to be CFO/Vice-President of a well-known home goods/wares/furnishings company, before transitioning to be CFO of a major electronics company. My uncle was CFO for a scientific equipment company, before retiring when they were bought out. He retired in his early 50s and is not planning on ever working again, because he doesn’t need to.
They live in Minneapolis in a huge, beautiful condo. They own an apartment in Chicago that they visit maybe a few times a year, but allow friends and family to use whenever it’s free. They’re building a house in Palm Springs, and have invited my family to spend Christmas 2016 there. Every Christmas they give each family member some amount of money (the lowest amount given to my family members was $1,900 to each of us kids, the highest was $10,000 to my grandma). They also give expensive gifts and gift cards, even to significant others. They bought me my first college laptop, as well as my sister’s (and I assume they’ll do the same when my brother attends college next fall). They paid off my student loan debt after I graduated, as well as paying for my grad school. They paid my sister’s way through undergrad, and are now paying for her to go back to school to get a second bachelor’s. When I was 17 and my sister 15, they took us to Rome and London for a week on their dime, and this summer they took my 17-year-old brother to Paris, London, and Rome with a friend of his. They do all of this for my aunt’s side of the family as well (uncle is mom’s brother, aunt by marriage), and her side has way more people on it.
They are two of the kindest, most generous people I have ever met. They will help in any way possible, not just monetarily, when called upon. They have both reviewed resumes for me, assisted with job searches, helped my sister get a wonderful internship with St. Jude’s, and have supported and encouraged every family member in some way. Their basic philosophy is that it makes more sense to spend their money on the people they care for and love now, than to give it to them posthumously. That way they can enjoy it too.
tl;dr: my aunt and uncle fit this bill (heh), and are generous, kind, loving, wonderful people.
Image source: ICantWink
#5
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: LordXeeloBob, Wikipedia
#6
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: xxbearillaxx, Jurij Kenda
#7
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: SayHeyItsAThrowaway, kyo azuma
#8
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: JamAndDai, Etienne Martin
#9
I worked with 3 men that were all worth well over 20 million and they were all so kind and very humble. I talked to 2 of them for hours ever so often and I couldn’t get enough of their stories. One time, one of them sat down with me and sorted nuts and bolts for a few hours. He taught me about all kinds of different bolts and although it wouldn’t normally be fun, It was amazing. Just having a self made millionaire taking the time out of their day to teach you about something so small is just such an awesome thing.
Image source: Tezuka_Boy
#10
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: anon, Brina Blum
#11
My dad used to work for a private airfield. They had a ton of people fly in. but most of the richer clients always flew in at night. One time in high school, I had to do a ‘job shadow’ thing and went to work with my dad. They had the owner of a California airport fly in for the weekend, and my job was to stand outside with an umbrella. His wife tipped me $20 and said, ‘The sandwich trays are real silver — have at it, kid.’ After they got in their car, I asked my dad what she meant. Apparently, when some richer folks fly, they let the people who detail their planes have the platters and other serving items. I always wondered how we got so many weird serving trays.
“Another time I visited my dad at work, I got to hold an albino kangaroo. Most adorable and softest animal I’ve ever touched.
Image source: eggtasticness
#12
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 caterering 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: A2KB, Ashley West Edwards
#13
I don’t know if this counts or not, but my dad used to work directly under the CEO of a pretty descent 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 honer. 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: bitch-im-the-witch, John Arano
#14
I have a good one, I interned for this wealthy CEO in Houston. He was traveling to Mexico and had forgot 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: mustangswon1, Andras Vas
#15
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: waterloograd
#16
A coworker used to be a housekeeper for an ultra wealthy natural gas tycoon (~$100,000,000 net worth) and she said it was the easiest money she ever made. His daughter, who worked for him, frequently flew around the country for business and this guy would pay my coworker between 5 and 15 thousand dollars simply to accompany the daughter and keep her company on business trips that lasted a few days. Everything was top of the line luxury and all expenses paid. Private jet, 5 star hotels (she had her own room every time), 5 star restaurants, etc.
Image source: anon
#17
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: LifeIsBizarre, Pixabay
#18
I fell into a job that made me an apprentice groundskeeper for a man that owns a majority share in the local sports team. Best/worst? Nothing bad to say so far. It’s been a year now. I barely interact with him but when I do, I can just picture dollar signs floating above his head. His wife is super nice and down to earth. They had an employee appreciation party and I blew up pool floaties with her and she talked about getting three pairs of glasses for nine dollars at the store. The best is being on the property five days a week and looking out over the water, listening to music. Also he has a daughter that comes by from time to time and uses the pool with her friends. I’ve gotten a raise and two bonuses since being there. The bonuses were my 80 hour paycheck, matched. And I guess every once in a while there’s tickets to the ball game right above the dugout, but I really don’t care about sports, so it’s nice to go just for the novelty.
Edit: oh, also one time they gave me two six packs of beer to show thanks.
Image source: pregnantbaby
#19
Once as a caddy I was given a 20 minute lecture/demonstration on how to open a Porsche door correctly. Subsequently, I resigned the fallowing day.
Image source: superjew101, Marcel Strauß
#20
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: Elysian-Visions, Saad Khan
#21
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 oreceeded 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 to long to say hi, s**t like that. Everyone hated her. Other than that, these people were really cool.
Image source: ChuckMastaT
#22
I used to work in a private school, and a few dozen of the students were children of the local super-rich from Bay street. One mother started coming into the school every day to visit the uniform shop and buy new uniform items for her child. This went on for a week straight before the shop attendant asked her if everything was okay, the child keeping track of their clothes, etc.
The mom responds with, “Oh, we’re fine. It’s just that our nanny is on vacation for two weeks, and I have no idea how to use the laundry machines at home.” I was stunned into silence when the shop attendant passed that one along to me.
Image source: north49er
#23
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: luther_williams, Jeff Tumale
#24
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: mikedub9er, Pixabay
#25
I worked for a guy who is approaching billionaire status. Hes a complete a*****e. I wont say what business he is in but he flies around in his jets visiting his businesses every few weeks. He is also major booster for a big college. His kids are OK, one is a party hound / coke head. The other is poised to take over the corporation. He treats his employees like complete s**t, only seeing them as dollar signs. If you aren’t making money for him you are expendable. His employee turnover rate is huge. Managers can expect to be out of a job within 18 months (keep in mind he has over 40 stores that are managed). He is also the biggest chauvinist I’ve ever seen. He hits on every woman he comes across to the point of many lawsuits, which he doesn’t care about, his accountants write checks. He once told a black guy that a monkey could do his job……he had to write a check. His quarterly meetings were all about how great he is and how we should all be like him and work 80+ hours a week. I don’t miss that piece of s**t.
Image source: thorgott
#26
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
Image source: DANK_SINATRA13, Ravi Sharma
#27
One of my boss’ vacation homes were featured in architectural digest. I came across the article just after I received my “bonus” for working 90+ hour weeks for two months straight. It ended up being a $50 Amazon giftcard
Image source: Mr1988
#28
I nannied for two upper class social ladder climber families.
The first family was much more well off than the second, and they were awesome. Paid for me to accompany them to Disney World “in case they wanted me to watch the kids one evening so they could have dinner.” They ended up buying me all the alcohol and we got ridiculously wasted in Epcot and in our rental house every evening. They even paid me my salary while on the trip. It was fantastic, they were very generous and very sweet. I miss them and their kids a lot.
The second family was not as well off, but still fairly wealthy and they were awful. Passive aggressive notes about not doing laundry correctly (not only were they particular about the setting everyone’s laundry was on, but the husband could not wash his own clothing, seriously had no idea how to work the machine), the kids were bratty and made comments about how I made the beds wrong (wtf kid doesn’t make their own bed?!) and I need to correct it because “that’s what our mom pays you for.” They under paid me to not only nanny but “light house keeping” which turned into cleaning all four levels of their house every day.
They basically treated me like an appliance, had no regard for my time (would come home late all the time, no phone call etc but would passively aggressively b***h at me when I requested a day off here or there for school or family visits). It was super uncomfortable.
Oh also-the husband and wife of the second family had separate living quarters. Like, she had the master bedroom and bathroom and he had the “bonus room” above the garage with an attached bathroom. It was super strange.
And I off handedly made a comment to my husband that my employer seemed like the kind of woman who would have a surrogate carry her children as to not mess up her own physical appearance, and wouldn’t you know that at least 2 of her kids were carried by surrogates (her kids confirmed it, but they also told me not to say anything because it’s a huge secret). I know that makes me sound very insensitive, but the amount of importance that she put on appearances made it plausible.
Image source: TJ4President
#29
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: amber_binkin
#30
I used to.
Nothing really bad, with the exception of thinking that because he paid me marginally above minimum wage, I was his f*****g slave. Due to this there was a steady increase in daily expenditures.
He didn’t usually sweat the small s**t though, except for the time I got into a fender bender in one of his cars I used for work. Literally a dent in the pass door, that could be popped out, with no paint damage. He threw a hissy fit, and I was like, f**k this, I’m out. A few weeks later he apologized and hired me back, because no one else could tolerate him.
He is a mostly decent guy, we got along fine otherwise.
Image source: f**ktamilbullsh*t
Follow Us
