"He made me go out and buy him a new pair of underwear because he said his were 'unlucky'": 25+ People share the craziest things their millionaire bosses spent money on

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Feb 6, 2023 11:00 AM EST

If you've ever worked for someone extra rich, which of their spending habits caused you to raise your eyebrows? People who have done just that gave us their input, and the answers are actually not what I expected. Apparently, lots of wealthy folks are so tight-fisted with their money that they almost live like they have no money. 

One person shared that even though their father is pretty wealthy, he never washes his clothes. Instead, he apparently just wears them a few times, then tosses them in the garbage. He's really maximizing his environmental footprint by throwing away so many clothes! Instead of wearing high end brands, this guy is rocking secondhand clothing. Nothing wrong with that at all, but you really can wear clothes more than once. 

Next up, this woman was so annoyed at her sister for… making a nice dinner and expecting her family to show up to it. 

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  • 01
    Rectangle - AreaManThinks Was a chef for one back in the early 2000's. He asked me if we could have Abolone for dinner. I told him I wouldn't be able to get it to the house in time. He's like, "Dont worry...I'll get you some." One hour later a helicopter from San Fransico lands on the lawn...
    via Brock Wegner on Unsplash.com
  • 02
    Font - r/AskReddit Posted by u/4our20wentyLOL People who have worked for millionaires, what was the craziest thing you saw?
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  • 03
    Font - jenny_cosmasher One of the washing machines broke down in one of the half dozen apartment complexes he owns, and instead of calling a repair man to fix it, he goes into the laundry room with his tools, opens up the machine, and starts repairing it himself.
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  • 04
    Font - cantbelieveit1963 Rich people stay rich by not spending their money. 45+ Reply Share Saftigerkeks definition of gigachad
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  • 05
    Human body - Mobile-Present8542 Them rinsing out used zip locked baggies to reuse them again.
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  • 06
    Human body - jdhdjdindjdm They saved millions. One ziplock bag at a time.
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  • 07
    Cheezburger Image 9731992064
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  • 08
    Font - menscothegreat My old boss bought 4x 400,000 dollars condos over the phone on a snap decision then drives off on his 90 Toyota Tercel
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  • 09
    Font - Longjumping-Leave-52 Lol I know a lot of wealthy people like that. Contrary to popular imagination, most millionaires are not very flashy but just focused on being more successful.
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  • 10
    Font - SirJudasIscariot I was part of a mowing company that regularly took care of high-end properties. I got to see how some of the 1% lived. Anyways, the craziest guy we've ever dealt with was a cosplay weeb. Don't get me wrong, I like cosplay, I've done it myself a few times, but there is something inherently weird about watching a 50-something year old man prancing around as a magical girl. He even had the falsetto pitch down pat. It honestly creeped me out a little. I mean, you do you, but
    via r/AskReddit
  • 11
    Font - AreaManThinks Was a chef for one back in the early 2000's. He asked me if we could have Abolone for dinner. I told him I wouldn't be able to get it to the house in time. He's like, "Dont worry...I'll get you some." One hour later a helicopter from San Fransico lands on the lawn...
    via r/AskReddit
  • 12
    Cheezburger Image 9731991552
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  • 13
    Font - KP_Wrath My father: he's better about this now, but he used to wear the same clothes for about 4 days at a time, would buy a new outfit at goodwill, and throw the old away. Rinse and repeat. I also unfortunately know that he doesn't wear underwear.
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  • 14
    Font - madinsanewoman. This is so bizarre that I can't help but feel it's true. "You can't make this s*** up" kinda thing
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  • 15
    Font - pindadand I've done work for very wealthy people. However, the one thing I've seen about them is that they are so sick of getting by everyone that if there is any clue that you've taken advantage of them... you are gone. They were really pleasant and definitely didn't give the impression of looking down on other people. Many people assume that they won't notice if you overcharge them or that they won't care because the money has no significance to them. Just not true.
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  • 16
    Human body - madinsanewoman Who are they friends with? Genuine people???
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  • 17
    Font - lou_parr The whining when his new car wasn't compatible with his phone was sort of hilarious. Audi had a problem with iPhones for a while so he had the horrible choice of taking his new car back or buying a new Android phone. Watching him learn to use Android was funny (when someone else was helping him) and also horrible (when he was asking me).
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  • 18
    Font - Lordofdogmonsters I don't work directly for millionaires, but I'm a chef and I've cooked for some high profile clients. The worst ever was a private event I did for the owners of the Phoenix Suns and their entourage. They rented out the entire restaurant and spent an ungodly amount of money. I put together a 5 course meal for them (it was like 15 or 20 people maybe). The amount of food that they wasted was disgusting. It was like they just bought it to look at it and then threw it away. I
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  • 19
    Font - Hard RockGeologist He offered $10,000 for the return of his girlfriend's lost dog. It was found, and he paid the reward. He was the best boss ever, would do more for people that worked for him than he did for himself.
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  • 20
    Font - I_Like_Thanksgiving My company's CEO is a millionaire. He actually seems really normal, but I only meet with him every other Monday so...lol. But he wears whatever he wants (including trucker hats and flip flops sometimes, and we live in Colorado), so he just does his own thing after making his fortune
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  • 21
    Font - MaestroLogical 4 rooms filled floor to ceiling with Tivo boxes. . This was 2004, so Tivo was pretty much brand new, I was installing light fixtures in an 8 room, 6 bath house in a gated community. The house was... strange. Felt like a museum that never got visited. The vast majority of the house was just fancy antique furniture and expensive art, but it was covered in plastic. Went in one room and was shocked to see it literally filled with Tivo boxes, but they were all empty. Went in ano
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  • 22
    Font - The fact that they were empty is what puzzles me so much, had they been unopened I'd have just assumed it was theft ring or some rich guy buying up a stores inventory to jack up prices or something. I had to install light fixtures in every room... except those 4. The owner simply said he didn't need light in those rooms when I asked about moving the boxes so I could get in one. I opted to not ask questions and just did my job but over a decade later I still occasionally wonder wtf that wa
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  • 23
    Font - biopticstream I worked as a personal assistant for this millionaire and let me tell you, the craziest thing I saw was when he made me go out and buy him a new pair of underwear because he said his were "unlucky." Like bro, just do your laundry. But hey, when you're a millionaire I guess you can just buy yourself a new pair of undies instead of dealing with your own laundry. And honestly, that's just the tip of the iceberg. The amount of entitlement and lack of basic life skills these peop
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  • 24
    Font - eric_ts I worked for a millionaire who was to become a billionaire a couple of years after. He was/is a fundamentalist Libertarian who didn't believe in handouts of any kind, so throughout the year he would collect extra condiment packets and on Halloween he would sit by his door, sipping 25-year-old single-malt and throwing the packets into the kids' bags. "Happy, happy Halloween!"
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  • 25
    Font - explodingladybugs A three dimensional shadow box picture in his office, the coolest thing I've ever seen
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  • 26
    Font - siciowaThe9 My best friends boss is a multi-multi millionaire, he sent my friend who has worked for him and is very successful himself, to view a property he wanted to buy, he wanted my friend to assess if it was suitable, price was no option. this was the house https://thewilliamsestates.com/listin g/1175-billionaires-row-trousdale- beverly-hills-ca-90210/ He ended up not buying it as it didn't meet his needs.....
    via r/AskReddit
  • 27
    Font - dedokta I was doing IT work for a guy that fancied himself a bit of a musician. He could sing and play fairly well, but he was so into it that he rented a unit in an industrial estate and built a full recording studio there. Large screen TVs, bathroom with shower, seperate vocal booth, sound insulated space and separate mixing room with high end equipment. I built a computer system to mass replicate CDs, set up his network etc. I don't think he ever got a single person to record the, it w
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  • 28
    Font - He worked get me to come to his house and set up his sound system and networks, all high end gear at but he had no idea how to plug anything in. Had me trying to install a full 7.1 sound system into a room about 3x2 metre. Total overkill. The guy moved into a new place with a pool surrounded by a good quality glass fence (barrier?) all around. He didn't like it so he removed it, even though I told him he legally had to have a fence around it. The council made him put a new fence around it
    via r/AskReddit

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millionaire wealth employees billionaire rich
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