‘He told me never to buy a helicopter, only planes’: People Share 25+ Most Entertaining ‘Rich People’ Stories

Author image for Eleonora Bader
Eleonora Bader
Mar 20, 2024 6:00 PM EDT

When I was a kid, I wanted to be rich and famous. Now, I just want to be rich, you can scratch the famous part. I don't need people eyeing my every move… But I do want the freedom of being able to build a castle on an island I bought so that I can get away from people. That's the kind of wealth I want to obtain. Today, that's kind of hard to do, unless you come from old money (or are a tech genius, which I'm not).

I love imagining what it would be like to walk into a store and not think about the price tag on items. Wouldn't that be a treat? Well, rich people don't even go to stores, they just send people to go shopping for them. Scroll down for the funniest, most entertaining (and frankly shocking) things that the wealthy have said or done in front of Redditors.

Bro, my car doesn't even have air conditioning.

Next, check out these micromanaging stories by fed-up employees who were done with their boss.

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  • 01
    What is the most rich thing you've seen wealthy people say/do casually?
    via u/CoolCoast7853
  • 02
    nightpop 14 hr. ago My friends bought a house in Palm Springs but the renovation was taking too long so they just bought a second house in Beverly Hills to live in during the renovations. They kept both 6.8k Reply Share Suz626 10 hr. ago A relative bought a house in Malibu Colony (right on the beach) to live in while their Palisades home was being remodeled. Then they told me they kept the Malibu home because it was just easier than driving back to the Palisades after a day at the beach. 521 Rep
    via u/nightpop, u/Suz626
  • 03
    karamellokoala · 12 hr. ago I rented a little apartment in a nice, brand new complex a few years ago. The lovely family upstairs that lived in the $3+ million penthouse bought it as they were renovating their $10+ million house nearby and didnt want to rent during the process. 1.4k Reply Share ...
    via u/karamellokoala
  • 04
    Udbbrhehhdnsidjrbsj · 14 hr. ago My dad knows a billionaire who had a french chateau disassembled and reassembled in the US. He acted like it was just a normal as building a house. My dads been there a few time and said it's an insane property with a huge man made lake and huge sprawling lawns. 2.7k Reply Share Expensive Structure2 12 hr. ago I went to a guy's house one time that has been a church in the UK. Apparently it was going to be torn down so he had it shipped to the US and then built a
    via u/Udbbrhehhdnsidjrbsj, u/Expensive_Structure2
  • 05
    God HatesPOGsv2025 · 16 hr. ago Going to their apt in the city so they have a place to hang out in between shopping at stores. Their apt is only for that purpose. 2.7k Reply Share ...
    via u/GodHatesPOGsV2025
  • 06
    closetklepto 14 hr. ago Was at a bar with the multi-billionaire ceo of the company I worked for. He made fun of Oprah for only having one jet, then went on to tell me to never buy helicopters because they are built by the lowest bidder - planes are the better choice. Bob, my car didn't even have air conditioning... 6.9k Reply Share
    via u/closetklepto
  • 07
    bluebonnetcafe 11 hr. ago I once stayed at a place that was $10,000 a night, amenities included. Luckily my health insurance paid 90% since I'd met my deductible. 1.9k Reply Share westberry82 7 hr. ago I see you too have stayed at hotel AH -SPEH THAL 211 Reply Share
    via u/bluebonnetcafe, u/westberry82
  • 08
    GarryWisherman · 17 hr. ago I used to work at a jeweler and the stories are endless. Clients would talk about how they just got back from a months long trip on a yacht or some exotic island. I'm just like cool I put in 60+ hours this week and have worked every day of the week lol. The that I wouldn't get at all is the watch guys. I had a client come in one time and ask for the cheapest watch we had, so he didn't have to worry about it on his trip. He ended up going with a $800 watch (not the che
    via u/GarryWisherman
  • 09
    notice buffed out. Id explain to them that they're shaving precious metal off every time and ruining the integrity of the watch, but they dgaf because their egos are so massive. We'd hold private events and encourage clients to bring their friends and itd always turn into a d ck swinging contest of who can spend more. Absolutely wild environment and I was absolutely burnt out after 2 years. Most money I ever made, but most miserable I've ever been. 2.8k Reply Share
    via u/GarryWisherman
  • 10
    reffak 13 hr. ago Contactor here. lady did not like the shape of the pool at the new house.Gets the job to change the shape. Does the job. So I tell her we can guarantee the workmanship for 5 years, but not any longer. She says cool, we are only here for 3
    via u/reffak
  • 11
    capybarramundi · 13 hr. ago Pay USPS to keep the local branch of their post office open (it had been selected to close) so they didn't have to drive as far to go to the post office.
    via u/capybarramundi
  • 12
    bored88 14 hr. ago edited 11 hr. ago I photograph luxury homes and architecture for a living. There's a neighborhood I do a lot of work in called Silverleaf and it's probably the most exclusive neighborhood in the valley. The bottom part of the neighborhood is your typical wealthy people's homes. Doctors, lawyers, business owners, etc.. extremely nice houses but still attainable for anyone who wants to put in the effort to work those types of careers. As you drive towards the back of the neighbo
    via u/bored88
  • 13
    I work Upper Canyon every month or two and even though all of the houses are owned, half or less are lived in. For some, it's a vacation home they might visit for a few weeks or months of the year, and for others, it's an investment and a place to park their money. I photographed a 15-million-dollar house there a few years ago. The owner was selling it because he bought a 29 million dollar house literally 2 or 3 lots up because he liked the views more. He's a Canadian business owner and spends m
    via u/bored88
  • 14
    georgekourounis · 15 hr. ago I once saw Jeff Bezos pay $100,000 to get a guy off the stage at an auction event. The guy on stage wasn't going to leave until he reached his goal, and Jeff was tired of listening to him. Bye Felicia. $$ 1.4k Reply Share
    via u/georgekourounis
  • 15
    holdonwhileipoop. 10 hr. ago It was from an 8-year old! My very wealthy friend got remarried and her son said he wouldn't mind staying with me while they went on their honeymoon. As we took our seats on the plane, he looked so confused. He sheepishly asked, "Who are all these people on your plane?". Oh, my little dude... ⇧ 526 ↓ Reply Share
    via u/holdonwhileipoop
  • 16
    TeslasAndKids. 14 hr. ago I worked in a sporting goods store in my early 20's and got absolutely screamed at by an old man for not knowing who he was when I asked him for ID. Apparently he owned like half the town and others at the store would kiss his a s. At $9 an hour I wasn't paid enough to kiss his as even if I cared who he was. I wasn't from there and had only seen him come in a few times to buy random sh t. But either way, the federal fɩ ng government requires you produce ID to purchase a
    via u/TeslasAndKids
  • 17
    La_Murano 13 hr. ago Ha ha ha! I work the front door at a s. > club and I will get people coming in all the time trying to not pay the $20 to get in! My favorite is when they say do you know who I am? And I say No sir. Will the be cash or card? And then they usually say sometime like "I can't believe you don't know who I am!" I always reply with I'm sorry sir that information is probably in your wallet on your identification if you've forgotten. Oh and the ones that scoff when I say its $20 and
    via u/La_Murano
  • 18
    noyou42 13 hr. ago I know an almost billionaire who is very very sweet. He kept his oceanfront condo for his mother in law to stay at for like month a year, and went to it every day to feed the stray cats who lived around it. The place is paid off mind you but has high fees, a paid parking spot, utilities ect cost almost 20 grand a year. 645 Reply Share
    via u/noyou42
  • 19
    Cool Koala_818 · 12 hr. ago Someone once asked me where I summer (never felt so poor than saying um... here? Using summer as a VERB, is a sign we are not in the same tax bracket 755 Reply Share
    via u/Cool_Koala_818
  • 20
    SwoopnBuffalo. 14 hr. ago I had a friend of mine casually ask if I wanted to go to Dubai for a week to do some skydiving training in a couple of weeks. My response was "no, I have to work for a living". Blew my mind when they asked me like it was no biggie to duck out for a week and blow $15k. 793 Reply Share SlapHappyDude . 9 hr. ago Casual, spontaneous international travel really is a Hallmark of the super rich. 210 Reply Share
    via u/SwoopnBuffalo, u/SlapHappyDude
  • 21
    cmontgomeryburnz. 17 hr. ago Get stressed from a true crime podcast and book a tropical getaway to decompress. 866 Reply Share SentientOrigin. 14 hr. ago I day dream about that kinda stuff I 172 Reply Share
    via u/cmontegomeryburnz, u/SentientOrigin
  • 22
    Ki ngCookies 13 hr. ago I live not far from an old (now abandoned) castle in France. It was bought decades ago by a Chinese couple, they had the staircase taken out and shipped to China and just left the place and never returned. It's been neglected since. 329 Reply Share
    via u/KingCookies
  • 23
    dpj2001 15 hr. ago My millionaire aunt scoffing at the idea that my single mother taking care of me and my younger brother couldn't find a place to live because $3,000/month is "easily affordable." Edit: $3,000/month being the average rent in the area. Reply Share 845
    via u/dpj2001
  • 24
    ntgco 13 hr. ago There is a large liquor store near me, they have VERY expensive bottles in the back room. One Xmas I was standing in line. The man in front of me, had one case of wine, 12 bottles of various variety. The checker said..... OK that will be $27,455. WTF??! Guy hands over his Credit card. Followed him out, Drove away in a Bentley. 323 Reply Share
    via u/ntgo
  • 25
    vunzya 12 hr. ago Years ago I helped coordinate an event in the Cayman Islands for my job for the companies main clients. I worked closely with a small business that sets up events. Not only did they make my work infinitely easier, but they offered us discounts on several events. Really good people that would work around the clock to make sure everything was getting set up properly. On the island, right before we were going to one of the events, my boss's wife tells my boss (and me indirectly, a
    via u/vunzya
  • 26
    tour which ended with swimming with the stingrays for a few hours and it was for about 20 people. I had to call the company and ask them for the discount while apologizing profusely. The boss's wife wanted to knock $4,000 off the total. After a lot of conversation and back and fourth I got the discount. I was disgusted with the look on her face after I told her we got the discount. For the rest of the trip I stayed away from her, as I knew that she would continuously ask for me to fight for disc
    via u/vunzya
  • 27
    nothing to that family, like finding pennies in your couch cushions. My boss and his wife had kids who felt neglected and the oldest would, without fail, destroy something expensive. I was in the room when a secretary told the wife that her son had destroyed another antique roadster (the boss collected them). She barely shrugged her shoulders. I think she just wanted the discount because she was such an empty person, maybe the power trip makes them feel something. 205 Reply Share
    via u/vunzya
  • 28
    BrokeFartFountain · 18 hr. ago Not taking free expensive stuff given to them because they probably already have a lot and/or they think it's something only poor people do. It's ironic because all these brands try to give those they perceive as rich more free stuff that they don't want or need. 616 Reply Share
    via u/BrokeFartFountain
  • 29
    gloomwithtea 11 hr. ago I had a friend whose parents obscenely wealthy. Like, she'd pay $100k every year to bring her horses from Canada to FL for the summer to ride at the stable I was working at, and her horses were worth $300k+. She offered to bring me back with her to Canada to take care of her 3 horses full time lol. She'd always take the free stuff and pass it along to me. It was awesome to use- I never could have afforded it otherwise. I had no idea how much they got! 411 ⇓ Reply Share
    via u/gloomwithtea
  • 30
    . Drogdar 14 hr. ago Had one of the outside salesmen drop in and we were talking about clothes for some reason. He said he donates his clothes to charity every year so he doesn't buy the "very expensive shirts"... his shirts are $300 each. Then he tells me he does buy "decent" shoes though. He showed me a company online where most of the shoes cost more than my car. How do we work for the same company and live that differently? 422 Reply Share
    via u/Drogdar

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