Doing the math on how long it would take to earn a million dollars on an average salary is a depressing reality check. Especially when you compare it to the wealth some people casually sit on.
But some got a rare glimpse into that lifestyle by working for the ultra rich. And they took to Reddit to share what they witnessed: the bizarre, the unexpected, and the kind of stories that make you question reality.
We’ve gathered the best ones below. Take a look and upvote the ones that made your jaw drop.
#21

Worked on some house renovations for extremely rich clients.
Wife of rich guy in perth decides she wants to update the house. We literally stripped the house of every bit of flooring, furniture, finishing etc and they were just going to dump it all. The foreman bagged a huge stainless steel kitchen unit that he sold for 15,000aud. Another guy salvaged all the marble and resurfaced his kitchen. I got a brand new in its plastic mattress that was worth something like 6000aud. It was absolutely disgusting how little respect they had for money.
Worked in another house in L.A. fireplace was white hand carved italian marble. Guys lifting the obscenely big flat screen into place dropped it and chipped the fireplace and cracked the screen. Thought i was about to witness someone being m******d. The woman who lived there calmly said it's fine, it was an accident. She was just upset she would have to wait another few months for a new fireplace.
Same house had built a raised platform off the side of a hill so they could put down a few hundred square feet of AstroTurf. Whole thing cost over a million dollars.
To be honest most of the really rich people i met were very down to earth and nice but when it came to money it was surreal how they would find ways to waste it.
Wife of rich guy in perth decides she wants to update the house. We literally stripped the house of every bit of flooring, furniture, finishing etc and they were just going to dump it all. The foreman bagged a huge stainless steel kitchen unit that he sold for 15,000aud. Another guy salvaged all the marble and resurfaced his kitchen. I got a brand new in its plastic mattress that was worth something like 6000aud. It was absolutely disgusting how little respect they had for money.
Worked in another house in L.A. fireplace was white hand carved italian marble. Guys lifting the obscenely big flat screen into place dropped it and chipped the fireplace and cracked the screen. Thought i was about to witness someone being m******d. The woman who lived there calmly said it's fine, it was an accident. She was just upset she would have to wait another few months for a new fireplace.
Same house had built a raised platform off the side of a hill so they could put down a few hundred square feet of AstroTurf. Whole thing cost over a million dollars.
To be honest most of the really rich people i met were very down to earth and nice but when it came to money it was surreal how they would find ways to waste it.
13points
#22

Owner of my last company flew 5 of us to New England to a funeral of a coworkers parent. We were there for 10 minutes, loaded up and flew home.
13points
#23

My ex and I stopped in a major tourist attraction city on the way to visit family in another state. We just happened to run into a rich guy and his wife at one of the bars we chose to go to and hit it off. He said he was the head engineer at some company, and was vacationing with his wife. They ended up spending the whole night with us, going from bar to bar, buying expensive champagne and liquor, and footed the whole bill everywhere we went. They even took us to a strip club, rented out the whole VIP section, paid for a few dancers to spend the night with all of us (no, nothing happened aside from a lot of lap dances, chatting, drinking, and pot smoking), and just acted like it was no big deal. We tried to decline and pay for ourselves on a few occasions, but he insisted and said he wanted to. When I asked why he was being so generous he said “you two are fun to be around and you made my wife smile” like it was the most normal thing in the world. At the end of the night, they paid for a luxury cab to get us back to our hotel and that was that. In hindsight, that totally could’ve ended up turning into the start of a trafficking/horror movie, and I’d definitely never do something like that now, but it’s still a fond memory.
13points
#24

Worked for a guy who owned a bunch of hotels. Loved his booger sugar (died from it actually). Several nights I'd see guys come in rolling briefcases and was told if his wife asked he was never there. Half hour or so later they'd leave with nothing in hand. Interesting guy. Gave me a couch once geeked out of his mind cause I mentioned I needed one lol.
12points
#25

My wife's best friend works for one of the richest women in the world. I have been to one of her houses before and know many details. But honestly, it's all pretty mundane. She is pretty normal and has many of the same issues we all face. Problematic kids, always striving for what's next, and a complex about her money and perception. What was wild was seeing pictures of people in the room I was standing in. Some of the most powerful people in the world stood where I was, which was pretty cool.
All in all, I guess my interactions are boring because she happens to be a normal "billionaire.".
All in all, I guess my interactions are boring because she happens to be a normal "billionaire.".
11points
#26

I was shocked by how much they discriminate against each other.
In my line of business I work for a lot of celebrities and the ultra wealthy. One day I was chatting with a multi millionaire client at his house when he suddenly looks over to his neighbors property with a look of absolute disgust. He proceeds to spend the next 5mins complaining about how his new neighbor is “new money” and a “dot com billionaire” and doesn’t fit in the neighborhood. Like.. this dude was literally disgusted and mad about it. “All our neighbors are embarrassed to have him in the neighborhood”.
Here I am, a $25 an hour employee trying my best to act sympathetic to this guy’s “dot com billionaire” problem while internally trying not to scream.
In my line of business I work for a lot of celebrities and the ultra wealthy. One day I was chatting with a multi millionaire client at his house when he suddenly looks over to his neighbors property with a look of absolute disgust. He proceeds to spend the next 5mins complaining about how his new neighbor is “new money” and a “dot com billionaire” and doesn’t fit in the neighborhood. Like.. this dude was literally disgusted and mad about it. “All our neighbors are embarrassed to have him in the neighborhood”.
Here I am, a $25 an hour employee trying my best to act sympathetic to this guy’s “dot com billionaire” problem while internally trying not to scream.
11points
#27

I worked for a billionaire who was building a 30,000 sq ft home. The guest house was over 6,000 sq ft. He didn’t care for how long the cabinetry was going to take so he actually bought a cabinet company and had them work on his home exclusively until all the cabinetry and built ins were installed and completed. He also owned a few Gulfstream jets and I got to sit in the pilot’s seat while the mechanic would ask me to press this lever or that as he was maintaining them.
10points
#28

I came to work one day and saw a Ferrari parked. I was like wow who’s Ferrari is that? He said oh sorry my Porsche is in the shop getting fixed so I had to drive my Ferrari.
10points
#29
We became freinds with a rich couple because our children got along really well. For some reason they started to really like us as friends, even though we are lower middle class. We started getting invited to Christmas parties and events they put on.
These were the kind of people who have a huge gated property with multi car garage. The husband owns a bunch of online tourism websites or something really random.
One day hes talking with me and hes asking what he can do for ideas for his parents retirement. Not sure why my opinion mattered but he seemed to really value it.
Eventually we got to the conclusion he should buy his parents a self sustaining business. Right then and there he decided to buy his parents a huge orchard farm worth millions that was already largely profitable. It was like it took no thought at all to just drop a few million to buy it for his dad.
He ended up thanking me for my advice lol. I dont think I really contributed at all. Haha.
These were the kind of people who have a huge gated property with multi car garage. The husband owns a bunch of online tourism websites or something really random.
One day hes talking with me and hes asking what he can do for ideas for his parents retirement. Not sure why my opinion mattered but he seemed to really value it.
Eventually we got to the conclusion he should buy his parents a self sustaining business. Right then and there he decided to buy his parents a huge orchard farm worth millions that was already largely profitable. It was like it took no thought at all to just drop a few million to buy it for his dad.
He ended up thanking me for my advice lol. I dont think I really contributed at all. Haha.
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10points
#30
The first and last time I had an ultra rich friend, from true privilege, was at university. Don't get me wrong I do think she was a nice girl and we had good times, but I think we eventually realised our backgrounds were making us incompatible.
The last time I hung out with her she was talking about her trip to Tuscany which looked absolutely delightful on her social media. I was asking her questions about it and ventured how I would love to go to Italy some day. She suddenly burst out laughing, the rich people laugh, and said, "What do you mean you have never been to Italy? Just rent a villa - they're so cheap!"
That was about 9 years ago now and I am still yet to follow her advice.
The last time I hung out with her she was talking about her trip to Tuscany which looked absolutely delightful on her social media. I was asking her questions about it and ventured how I would love to go to Italy some day. She suddenly burst out laughing, the rich people laugh, and said, "What do you mean you have never been to Italy? Just rent a villa - they're so cheap!"
That was about 9 years ago now and I am still yet to follow her advice.
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10points
#31
My boss is a multi millionaire and the amount of times he tries to cut corners, only to just end up spending way more money is baffling to me. He’ll hire a contractor to do something, then 60% of the way he’ll change his mind and ask for not only something different to be done, but also add like 2X the amount of work originally planned. He will just get a wild hair up his a*s and then one day we’re trying to work and then “Oh s**t, The Boss bought 4000lbs of fine wood flooring that we need to figure out where to put it, everything has to be put on hold” Then that wood just sits there for two years before anything gets done, a lot just gets damaged over time because we just don’t have a good place to store it.
So it’s just every couple of months we have to deal with some weird curveball b******t that doesn’t make sense.
So it’s just every couple of months we have to deal with some weird curveball b******t that doesn’t make sense.
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10points
#32
When I was in the Navy, my bunk mate came from good old money. We'd go out on the town together and he'd drop money like it was nothing when I was barely affording to survive. PS4's came out and he said lets go get some and I couldn't afford it so told him I'd come along. He bought two PS4s, every accessory the store had for him and me, and two copies of every game they had there.
If he ever ran out of money he just called his daddy and would have money in his account by the end of the day. Like $20,000 just transferred.
And man had no idea what a regular tip at a restaurant was him. We go out and eat together with friends, tab would be $25 for him and he'd go and leave a $100 tip thinking that was normal.
If he ever ran out of money he just called his daddy and would have money in his account by the end of the day. Like $20,000 just transferred.
And man had no idea what a regular tip at a restaurant was him. We go out and eat together with friends, tab would be $25 for him and he'd go and leave a $100 tip thinking that was normal.
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10points
#33

I've seen clients with so much money, up in age, barley able to get around, litterly getting around with the assistance of a personal nurse.Spending more money than anyone could imagine, bringing Bali, Rome, Tuscany, all places they've traveled into there home's environment, in this particular case we're talking a dessert zone in California, we litterly created Micro Climates, in order to accomplish some of there visions. Money was not a concern, so long as they ended up with the same Tropical environment they experienced in Bali. It was insane the entire time I was working on this once In a life time project, pulling off Scapes that I'd never be able to repeat again. It was impossible to fathom another client like this, with so much money to burn, I recall on one particular area the Tuscan zone of there property, I failed to capture the true flavor of Tuscany. Fact was I didn't spend the kind of money to import fully established Olive trees, not pleased with the wave of there hand they had me replace the 52" box Olive trees, with bigger Olive trees, it was a over 1.3 million dollars worth of Trees, irrigation, established shrubs planted from 36" box containers, that were torn out. I obviously transplanted what I could and took them to lm my nursery.
9points
#34

In my early 20's I was hired as security along with nine other guys for some big important party. We were given three piece tailored suits. I still have mine though I was much skinnier back then. The party was at a big estate and the owner and host was a big name where I live but I didn't recognize until my co-workers were talking about it the next day. I was posted at the lower basement. There were two basements and no one was allowed in the lower basement. It was an easy gig. I just sat there, watched TV, and they gave me food. I only had one incident where a drunk older lady was looking for a man and somehow wandered all the way to me and kept grabbing me. We were tipped 500 on top of the promised pay the next day.
8points
#35

Guy who lives in a climate that is not hospitable for palm trees…..at all. I’m taking all the way northern US. But he didn’t care, he wants palm trees. So every year, when the palm trees inevitibly die, he just gets new ones delivered and planted.
8points
#36
Worked for an Uber rich Afghan man, he would hand me wads of cash and multiple credit cards with different names/addresses on them. He would then have me take his kids wherever they wanted to do whatever they want. Didn’t ever ask for a receipt, but I brought him back receipts and kept exact change.
He also lived in a very safe wealthy neighborhood, but hired private armed security for his home if he was ever traveling.
He also lived in a very safe wealthy neighborhood, but hired private armed security for his home if he was ever traveling.
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8points
#37
They have the capacity to help way more than poor people do, and most of them do it. They arnt the greedy swine most make them out to be.
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8points
#38
I live in an area where there are billionaires amongst us. I lived here for 15+ years and noticed there were a lot of helicopters around. I would joke and say “on that’s the CEO of _____.” Come to find out, the billionaires get around on helicopters so they don’t have to wait in traffic lol.
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8points
#39

I know someone who pays a company to clean out his charcoal grill and big egg smoker. Yes, there are apparently companies who do this and people pay good money for this service. I didn’t even know this was an option in life.
8points
#40
I worked for a billionaire that is constantly embroiled in legal battles. I was the head of a new business venture for him. He placed his family and kids into top positions and eventually had them making decisions while they had zero experience. The guy was extremely rude and I left the role pretty quickly.
What I found out though was that he played a billionaire game of not paying any business debts and forcing suppliers or whatever companies that were owed money to always settle for pennies on the dollar, which ultimately screwed over everyone except for him. It made me realize how unfair the world is for the 99% of people.
What I found out though was that he played a billionaire game of not paying any business debts and forcing suppliers or whatever companies that were owed money to always settle for pennies on the dollar, which ultimately screwed over everyone except for him. It made me realize how unfair the world is for the 99% of people.
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7points


