The lives of rich people are clouded in mystery, as many of them value privacy and try to avoid unwanted attention. But this only makes the rest of us more curious to know how differently they live from us and what kind of luxuries complete financial freedom can buy. So when, once in a while, we get a peek inside, we can’t just keep it to ourselves. That’s exactly what was happening under this thread, where people who found themselves in events hosted by the wealthy enthusiastically shared the craziest things they witnessed there. Scroll down to check them out for yourself, and don’t forget to upvote those that surprised you the most!
I was at a political fundraising dinner around 20 years ago. There were many affluent rich people there but only one billionaire. At one point I naively asked him why he didn’t run for office. He laughed and looked me directly in they eyes and said, “ son, why would I be a politician when I can own one?” F****d me up then. Nothing has changed.
Image credits: mrmastomas
I don’t think it qualifies as a “rich people event” but my wife works for bank, and unless you are management at a bank, you don’t make s**t. At her company holiday party a few years ago, the president of the bank comes out on stage and starts shooting dollar bills out of an air cannon. The site of a reasonable wealthy head of a bank shooting dollars at his underpaid (~$17/hour) employees, that they then have to scramble on the floor in their eveningwear to pick up turned my stomach. I don’t know how a supposedly smart and successful person could be so tone deaf. It was gross.
Image credits: Mr-Young
When I was in school I got paid $20 to work silent auctions for fundraising events in NYC. Most of them were for private schools in Manhattan. I swiped a credit card for a woman who bid $25,000 for her 5 year old to be principal for a day.
Image credits: krobs42
I was a server at a really nice restaurant and ended up working a dinner in our private room for the president of a major movie production studio’s birthday. One of the guests at the dinner was apparently a major producer and insanely rich.
I heard them discussing how he had decided to collect EVERY BOTTLE of a very nice wine maker’s specific vintage (to put into context this bottle would probably go for about $2000 per in a restaurant, not sure what retail would be) and had a full time employee tracking down private collections and restaurant wine cellars that might have bottles. At that point he had over 4000 bottles of the one wine, organized by serial number in a custom-made cellar.
He told a story about how Martin Scorsese had badmouthed a franchise he funded and when he later called looking for funding for The Irishman he told him to “go f**k himself”.
At one point in the dinner his assistant (one of three assistants sitting at the end of the long dinner table) informed him that the first truffles of the season had been delivered to some chef in Tokyo. So producer guy goes “Great! Anyone want to go to Tokyo this weekend for a truffle tasting?” A couple of people said yes so he instructed the assistant to “make sure one of the jets is available” for the trip.
They stayed 3 hours after we closed. Bought every bottle of the same brand of wine (different vintage) we had in our cellar “for the road”, let me taste a 1989 Chateau Haut-Brion and tipped $3600 for the lateness of their departure.
Wild night.
Edit: It wasn’t Kevin Feige for those trying to guess. He wasn’t American.
Image credits: ammonite13
I was in the Peace Corps in Zambia. We used to hang out at the casino in Lusaka cause they gave you free food, drinks, and cigarettes while you played. We would play like $2 hands of blackjack just to get fed.
But I went to the roulette table and some guy put down $10,000 in USD all over the table. Lost his spin, and just shrugged his shoulders and walked away.
Coming from the village where we sh*t in holes and pumped our own water, I was floored by the amount of wealth that existed right around from us.
Image credits: Sure-Scarcity-2436
My friend had a friend who is one of those “crazy rich asian” type of dude. Watch the movie and you will know what i mean.
One day, this rich dude was driving his Ferrari in the toll road, my friend was in another car following him for a car meetup event. This dude crashed his Ferrari to another car, and then stopped in the side of the road. He went out, called someone and waited while smoking with my friend. He acted like normal nothing happened, my friend said.
In 10 minutes, suddenly there was a yellow Lamborghini came up. The Lambo driver went out, took the Ferrari key from the rich dude hands, and then sit inside the crashed Ferrari.
The rich dude drove the Lambo and continue the journey. Apparently the new driver will take the fall for every single crash related problem.
Oh yeah, Police was there the whole time, and they did not bother to talk or approaching the rich dude before the lambo driver came up.
Image credits: jembutbrodol
“There’s not a huge difference in lifestyle between 10 and 30 million.”
I literally had nothing to relate to. He’s one of my best friends and the kindest guy you’d meet. He drives an older truck from the early 2000s and likes t-shirts and shorts.
Image credits: hobbes8889
Not at an event, but at my then 9yr old sons friends house. They were VERY wealthy, and it was the Dads birthday dinner. They were having fillet steak, seafood etc.
Their two sons were disgusted that hey were having fillet steak-AGAIN. And one threw his away, and the other huffed off to his room and demanded his Dad (whose birthday it was) take him to get a pizza.
Dad actually DID! And my macaroni eating kid sat there scoffing his steak and witnessing the majesty of life.
Image credits: Vegetable_Waltz4374
“So anyway, I had to buy the maid a 1M dollar house so she could live closer to me to do my cleaning everyday. And now she’s not my maid anymore”
Gee I wonder why…
How I wish I was joking 😑.
Image credits: jenlou289
They had a ‘poor people’ themed costume party. I wish I was joking!
Image credits: theblondestar
Learned about the yacht life. I once had super wealthy bosses and they they were talking about their friend who owned several buildings. And who had a big yacht.
So the yacht was always ready to go. Which meant that it had a full complement of personnel, paid full time, down to chefs and servers. It was basically a hotel at sea.
The thing is, the guy rarely used it. So you had a boatload of bored people who had nothing much to do. If the guy goes to Europe, he would rather fly there — and have the yacht head there ahead, *just in case* he felt like using it. Which wasn’t all the time.
Image credits: KarmicPotato
My buddy took me on a cruise with our local Ferrari club. The house we went to was owned by a member who had 8 Ferrari’s in his garage, at this house, he also had a real Michael Schumacher F1 car and a Ford GT. While we were there he unveiled his new car a custom built Daytona SP3 that was all completely custom. The base price of the car is around $2.2 million so with the customizations it was closer to $3 million the way he had it.
The crazy part was the story he told about it, this was supposed to be an early build number car but it was delayed. He had to ask Ferrari about why his $3 million dollar car was taking so long while he was putting in another order for a completely custom Ferrari that is probably worth even more than that.
Spending more money on 2 cars than I’ll probably make in my whole life was a pretty wild story to hear while in a garage with cars that collectively are worth more than my family has made all together for a couple of generations really puts the wealth gap into perspective.
Image credits: sirbobbinhood
I worked a private event as a waiter, it was a rehearsal dinner. The father of the bride was telling everyone he chartered a private jet for his daughter and son in law to fly to Bali for their 6 week honeymoon, which he has also paid for. The jet was to stay there for their use for the duration of the trip in case they wanted to visit other places if they got bored. The rehearsal dinner for 20 people was about 20k. Working that event was probably the most I ever made in one night at that job, certainly the easiest.
Image credits: pleasantly-dumb
Having to chase someone down because they paid a power bill for a family in need at a charity event, It was $2200 they wrote the check for $22000 said they just heard wrong.
Image credits: cantpanick86
Through some odd connections I found myself at a private dinner that included the then-current Treasurer of a US state (this was decades ago).
His wife was young and gorgeous and everyone (not me) was drinking steadily. As the night wore on the State Treasurer demonstrated his ability to touch the tip of his nose with his tongue and my connection (the one who got me invited) said, “that’s why he always has a beautiful blond in his arm!”
Raucous laughter all around. Later I said something to my connection about the Treasurer’s wife and they laughed, rolled their eyes and said, *THAT’S* not his wife, that’s his girlfriend – well, one of ’em.
After further discussion it was revealed that every woman there was either a side piece or casual/open thing and most of the men (all VIPs/rich) had wives at home.
Meanwhile I was from a small, coastal (Gulf of Mexico) fishing village and this was the kind of thing I only saw watching *Dallas*. Tame by current “standards”, but back then it was scandalous.
Image credits: EngineerBoy00
Eating sushi off super hot naked girls.
I was tending bar at a party at a 50 million dollar mansion in East Hampton. If I named the owner/host you’d all know who it was. There were movie stars and musicians there. There was a lot of crazy s**t there. What made the sushi thing so weird is nobody really paid any attention to the woman. It actually creeped me out and reinforced how different really rich people are.
Image credits: jeffweet
I worked at the montage resort in laguna Beach,ca. A centi-millionaire threw a birthday party for himself. He hired John legend and Don Henley to put on a show for him. Henley cost 750k for a couple songs and John Legend was 250k.
Image credits: Eattherich187
When we were poor our daughter went to a private preschool that was great for her disability and they accepted us at hardly any tuition in exchange for speaking at fundraising events for them on our daughters benefit from being at the school.
At their big fancy yearly ball dinner we were speakers and they sat us at a donor table. We were literally stealing dinner rolls to make our Carl buddig sandwich meat better. At the auction portion one of the ladies explained that last year she bid on and won the African safari but she didn’t have anyone to go with her so she donated it back to this years event. As that vacation came up for bid she goes “wait my niece loves animals and travel, I’ll take her” and she went and bought it for he second year in a row.
Image credits: bzzltyr
I was hired to be a photographer at a wedding. They had rented the venue at a very expensive vineyard. There was a mansion there and as part of the deal the bridal party got to stay at the mansion. The owner is almost never actually there. He lives in a big White House, if you know what I mean.
I show up early the morning of the wedding and I’m greeted by the butler. Who’s more or less exactly like what you’d think, but younger and not English. Throughout the day I was all over the mansion taking pictures. During a lull I was chatting up the butler.
The weird thing was that he said it’s shift work, that there are basically three of them (maybe another guy for filling in, I’m not sure) and it’s 8 hour shifts. So I was asking, since wedding stuff is kinda seasonal and it gets cold here, like if I showed up at 2am in January one of you would be here, all alone in the mansion, just knocking around on the odd chance the big guy shows up? And he was like yeah, someone’s always here.
That just kinda blew my mind. Can you imagine just being the dude who sits alone in someone else’s mansion polishing the silver waiting to see if they show up? 85% chance I’d let my guard down and they’d catch me running around in my boxers dry h*****g the statues while blasting AC/DC or something.
Image credits: Metalhed69
Hot tip for anyone that likes art, the best place to see art in places like New York? Auction houses. They change their art every month, most of it will go into private collections and never be seen again, and they are free to visit.
I’ve stood in a room at Sotheby’s in NYC by myself with 5 or 6 Monets….probably $70-80 million worth.
But the two crazy things I’ve seen is you won’t even find rich collectors there. They send their assistants.
And one time I was at Sotheby’s and they were auctioning off a bunch of Tiffany Vases. Some assistant was checking them out, flipping them over, bare hands, just almost tossing them around like soho cups. I was shocked.
Image credits: RudyRusso
Special service. It was a ritzy wedding and someone there was a congressman. So we had secret service throughout the wedding pretending like they were guests while also not engaging with anyone to be distracted. They were like real life NPCs.
Image credits: bilbobaggginz
I used to work for an eye doctor, and he sent me to a charity event in town. There was a silent auction, the kind where you write your bids down, and someone would come behind you and bid a little more. The doctor asked me to bid on this ski package and gave me a blank check and a maximum price. As dinner finished and the auction began, I knew that I was in the wrong room. I decided that instead of hanging around the ski package, I would just write down the maximum and hit up the open bar. It wasn’t my money. As I was backing away from the table, the guy behind me was a local developer. Big real-estate, big money. He looked at what I wrote down, looked at me, and said, “There is no way you have that kind of money, and I bet that you don’t even ski.” He then turned around, wrote $10K as a bid and looked at me, and said, “You ruined my fun. I think I will ruin everyone else’s fun.” He walked around the room and bid $5k to $10K on all of the luxury items. The charity broke a fundraising record, but people were pissed. I could care less. When I told the doctor the story, he thought it was funny.
Worked for a guy who said he shouldn’t have to pay taxes because he doesn’t use the welfare programs it pays for… I get where he comes from but taxes pay for so much more, than just welfare… same guy also said that he lies on his taxes because if he gets audited then he’ll just pay what he owes, but if he doesn’t then it’s free money….
Image credits: Consistent-Golf-1048
I attended a rich person dinner in Bel Air. My girlfriend and I hardly knew anyone there but slowly got the sense everyone there was “wealthy.” The house where the dinner was held was listed for $80MM on my Zillow app. At the actual dinner, I began to make small talk with the guy seated next to me. We started talking about traveling, and he said his friend recently “raced with the Porsches in Germany.” I looked at him, and said “oh, you mean he raced Porsches in Germany, that’s great.”
He looked at me confused and said “no, he raced with the Porsche *family*” and rattled off a couple names of the Porsche heirs that apparently they were friendly with.
Years and years ago, assisted a photographer at a fundraising event at the country club for a very, very, VERY private gated community in the NC mountains. The turn INTO the entire community was all but disguised as a junky old “mountain hollar” driveway. No signage, missed it the first two times. Absolutely GRILLED at the guard house before they let me through and then about 30 years into driving up: holy s**t, the Garden of Eden. It was WILD how well hidden everything was.
The event was at the country club and there were some very famous names in attendance. It was my job to stand beside the photographer and write down the names of those in attendance as they lined up for their photo op with the famous names. During the dinner, was upstairs inserting photos and polishing already-immaculate solid sterling picture frames that had to have weighed a couple of pounds each. And then passing them off to a handful of staff with thousand-yard stares, to be arranged on tables by the doors upon exit (after the event ended).
Then standing downstairs beside that table, checking names off a list as the donors/attendees left (and were supposed to pick up their parting gift). Except it never really got that far, because….
The SHEER VOLUME of people who saw their photos in those frames just *tried to f*****g steal them.* Nevermind that they were clearly intended as a donor GIFT— that part didn’t even matter. I was hired help, I had nothing to do with anything except the expectation that I’d hand them off and check a name off a list, **assuming** that the event organizers had shared that information with the attendees/donors. I guess they didn’t? People were literally swiping them and shoving them into their jackets, pockets, down pants and/or purses and hauling a*s for the door while I stood there desperately trying to explain “It’s a gift! If you don’t mind, what’s your name so I may check it off that you received yours?”
That went down like a lead balloon. Apparently being told that something was intended as a gift **after you already f*****g stole it** was considered rude. Maybe you should have asked before you tried to shove it down your pants???
I’ve witnessed wealth, I don’t possess it but I’ve been in the company of more than plenty and sometimes to the point of excess. But this was on a level of its own: these people collectively possessed more f**k-you money than some small countries, but behaved no better than a flash-mob on an Apple Store in San Francisco. I’ve just never seen anything like it, before or since.
My dad cooked a small dinner at a very privately wealthy families house, in which D**k Cheney was a guest and they flew in Elton John to play piano for the night.
That same family put on a birthday party for their 4 year old granddaughter, who wanted “a carnival” for her birthday, so they invited all of the country clubs staffs families to “make the place look alive”. Free carnival rides and food all day and night. In their backyard.
Image credits: Afitz93
I went to school with a lot of crazy rich kids, the richest of whom were normally Russian. A few stick out to me:
It was a boarding school so we had all our stuff there all term. At the end of term one kid piled his stuff on the side of the road, and got into an all-white Rolls Royce as it pulled up. As it left a second all-white Rolls Royce pulled up and collected all his things.
One of the nicest kids you’ll ever meet decided he wasn’t going to go into student accommodation at uni, so he decided to buy a house. I asked him out of interest how much money he had access to. His dad had given him £3.2 million in ‘spending money’ to last him 5 years.
We also had a designated helicopter landing pitch for anyone who flew in.
Good friend of mine catered Zuckerberg’s birthday party a while back, and the dude had an entire “McDonalds”—with all the food, packaging, and such—flown in to his f*****g backyard. None of the cooks were McDonalds employees, but *fine-dining* line chefs making Big Macs and other s**t while the rest of them made all the “real” food for the sober adults….
Image credits: rawwwse
Went to a wedding in San Francisco 30 years ago. My wife was good friends with the groom. Lots of nice people that I’d never met. Casual conversation with anonymous attendee, he asks me what I do professionally. I tell him that I’m a public employee Union advocate. He tells me I’m the problem with the world and turns his back to me. Similar thing happened to me when a mutual friend introduced me to Reince Preibus. In both instances, “tell me you’re a class warrior on the wrong side of the battle without telling me”. The rich don’t care about being polite or getting along. They drive the steamrollers.
Roomate/sports teammate in college got married. They flew me in to be a groomsmen. I knew he had money but not “whatever the f**k I want money”. Dad came up to me bragging about hiring a 30 person black choir to sing with him at the dinner after wedding. He really did and f*****g danced and sang his a*s off. Then he caught me in the walk in portable semi truck size fridge. I found the Dom Perignon and had never had any but always heard about it. He hands me three cases one at a time and said get out there and start a Dom fight. So I did.
Then he introduced me to the two state senators and the owner of the Chicago Bears.
I drunkenly got to talking with the wedding planner and asked how much. 1.5 million. I was the quirky white trash friend who stopped people from bothering him or fought while he left the bar cause of some a*****e losing money on him in college.
I woke up hung over in their f*****g palatial mansion to a maid putting breakfast on my bed and asking if I “Mr. Southernjeb” needing anything further.
Orders of magnitude greater wealth than anything I could have imagined.
Go gators.
I work for a company that provides a platform to host auctions, so I’ve been to a lot of these type of events here in the North East. I’ll never forget what happened at this one event for a ritzy private school. During the live auction for a yacht trip around France/Paris or something of the sorts, this one woman, who I guess helped secure the package or had friends who donated it, WAS NOT happy with the bid price that was going to win, basically saw it as an insult. She got up on stage, b**ched everyone out, then said fine, if you all won’t spend the right amount I’ll do it. Lady spent $60K on the trip out of spite. Walked off stage, grabbed her purse and just walked out.
I was invited once to a party with very rich people here in México City, nothing too crazy but a guy was casually talking about his new island near Cancún like It was nothing.
Image credits: Spascucci
“There should be a line at the DMV for people like us, then another line for everyone else…”
For context, he’s a super rich lawyer that thinks laws and mores don’t apply to him and others of his status.
I once celebrated New Year’s eve at the big house of a rich family.
He was the boyfriend of my girl’s college roommate, met the guy before and he was really friendly.
When outside for a smoke with his best friend he told me the guy was gifted a small castle with 12 permanent staff for his 21st bday.
Image credits: JackFourj4
An investor of my company bought a new Bentley SUV because his Cadillac’s battery died.
Image credits: JJGBM
At my former employer we had a client book one of the largest aircraft in the fleet to fly her son to private school in Europe and she accompanied him. She then stopped at a smaller city in Italy for her to visit a restaurant she liked and then returned to the west coast of the US. The bill for this was well over 100k…to drop her kid off at school for the year.
I went to a famous person’s birthday party in Beverly Hills. I won’t say who it was, just in case. But when my girlfriend and I got there, we were escorted up his driveway in a golf cart. Security brought us into his front room where there was a gold piano and then they escorted us to the backyard. First thing I saw was a woman in lingerie in one of those big inflatable spheres floating in the pool. But that was just the side pool. We kept going to the main backyard where there were trapeze artists, more lingerie girls in the bigger pool, a cigar wrapping station, Topher Grace sitting by himself (didn’t seem like he knew anyone there), and a big jazz band playing.
It was the most Los Angeles thing I’ve ever done and honestly didn’t enjoy my time there. We left early because of how self important everyone seemed.
I work at a high end country club. It was raining so we closed the tennis/pickleball/basketball courts. A group of teens came in and asked if they could play basketball. When I told them the court was wet and slippery and they weren’t allowed to play one kid said, there are towels in the locker room, grab some and go dry it off!” It was pouring rain when he said this.
Not me but my friend worked catering at this fancy charity auction and said people were casually bidding $50k on a weekend trip like it was pocket change.
The wildest part was when someone bid $20k on a bottle of wine just to immediately gift it to someone else at the table.
Meanwhile my friend was making minimum wage serving them and stressing about rent that month”…”.
At a very rich people wedding. The grooms father talking about what a sound financial investment it was for this other rich girl to marry his son. To top it all off the groom was 200% gay.
I was once at an all you can eat lobster dinner put on by a company as a reward for high performing employees and a drunk millionaire started yelling at his bosses who were worth hundreds times more than him, because the wine selection was sub par.
I was once told to get my pilot license after complaining about being in a long distance relationship.
Very pricey political fundraiser in NYC.
The former Police Commissioner of NYC said from the podium that the then-recent graffiti on the Christopher Columbus statue was proof that discrimination against Italian-Americans was alive and well in the US. This got applause.
To this day, this is the most WTF thing I’ve ever heard someone say with a straight face.
My uncle is a concierge at the Pitkin County Airport in Colorado. He found a briefcase someone left on a plane with $20,000 CASH, knew the person and called them to come back & pick it up. Who forgets $20,000 cash?!?! My uncle also gets dibs on lost & found items so I make requests for “gifts”: so far I’ve gotten a pair of Ray-Ban aviator sunglasses and Sony Bose noise canceling sport earbuds.
I worked in catering while in law school. Worked a super rich family’s daughter’s wedding where the dessert course was a whole show. A giant ice sculpture of a dove was carted out. Probably 10 ft high. In the middle there was a giant gold ball. Once it got set they pushed two racks of glasses up next to the sculpture on opposing sides. Then, two guys with chrom bore drills drilled into the sides of the sculpture and desert wine came pouring out of the internal globe into the waiting glasses. According to the wedding planner the sculpture was 15k. The wine in the sculpture was close to 50k.
I hate being late to the party, but I was invited to a sports booster alumni fundraiser for a college (they get their friends to give $10,000+ to the college football team in exchange for club seats and booze that acts as a bonus business tax expense writeoff).
That’s the backstory. Here’s the f****d up part:
One of the night activities was a dinner and an entrepreneur brainstorming session for the club where they would take all of these rich a******s in one room, get them all drunk and then see what business ideas they could come up with to make the club even more money. *Over the course of an hour or so, these business owners came up with ideas for absolutely diabolical scams.*
One scheme included sending fake bills that the recipient would just pay because it would be too much work to question it.
I remember there were employees for a catering company who were in the room working late at 10pm at night and the look of f*****g disgust on their faces is something I’ll never forget.
I was at a party in New Orleans, and I saw a shiny object out of the corner of my eye.
Upon speaking to the person who possessed the shiny object, I found out it was one of the biggest yellow diamonds in existence, or an expensive diamond beyond compare.
Yeah. Whatever…
It was her next statement that drew my undivided attention.
She said, “I shot my husband dead one night after I found out he was having an affair with another man. The judge gave me 6 years in a psych ward, but let me keep the ring.”
That was the moment I realized I was chatting with a m******r.
Not as out there as some of these others.
Went to a New Year’s Eve party with a lady I was seeing who runs in pretty high international political circles (she works for one of the larger defence contractors). So it was pretty ritzy. Definitely a lot of cash splashing around (I think my date was wearing a solid 15k in dress and jewels), definitely hijinks in the boots and bathrooms. I may be bred from illiterate cannon fodder stock, but I’ve drank from the golden cup, eaten from the silver spoon etc etc before so I can fit in for a New Year’s party.
But when one of my dates friends admonished the party for having **the same ice sculpture fountain from last year for the aperol spritz**… I didn’t know how to respond because I know a guillotine joke wouldn’t stick the landing with those bourgeoisie f***s.
Not a gala or event, a friend’s wife worked at an HOA in a rich area where some celebs and pro athletes lived. One resident asked her if the airplane paths overhead could be changed to avoid the area. They weren’t even close to the airport, maybe 20 miles.
Private jet sent from Las Vegas back to the Bay Area to pick up leftover brisket from a party hosted by someone in the VC world.
Image credits: jammastergeneral
I worked one of the top 10 billionaires weddings. It was a 3 day event, he flew his private wine collection out on his private jet that cost around 30k just for the wine. The flowers alone were a million dollars. They had a live band till 11pm and then a pretty famous DJ rose up from the floor and played till 3am. The wedding total cost easily over 3 million.
Worked a bar mitzvah and he flew every one out in his private jet. Had a professional cowboy hat maker there to make hats for everyone. Had a live band and had at 10pm the kids all left and he brought in a weed dispensary with any and everything for anyone to partake. That cost over 2 million dollars.
Both tipped like s**t and both are s****y humans.
