Most of us have encountered workplace gossip: some of it juicy, and some not worth a second thought. But when it comes to the ultra-wealthy, the secrets can go from surprising to downright shocking.
Someone online posed the question: “People who have worked for the ultrawealthy, what are some of their deepest, darkest secrets?” And the answers did not disappoint. From being unbelievably cheap to wildly inconsiderate, these behind-the-scenes confessions pull back the curtain on what life is really like around extreme wealth.
#1
Had a friend who was an heiress to a family name you all would know. She was a granddaughter, not a daughter, so her wealth was not as great, but she was beyond comfortable.
We went out for drinks one night, and I didn’t have much money on me, so she spotted me a couple of rounds. The next day, I went over to repay her the $20 she had spent on me.
She actually got emotional and said, “Nobody has ever paid me back before. They all figure, she can afford it..”
This was in the 1980s, and I was making s**t money as a secretary.. But I actually felt sorry for her. 💔.
Image credits: Roseallnut
#2
Changed out some home security stuff for a very wealthy older couple. Like 10B+. The wife was incredibly kind and if encountered in the wild she would be totally normal appearing. It was the little things in their home that blew me away. Hand crafted everything. They even sent me and my guys home with a bunch of stuff from their garden.
Image credits: jordanr01
#3
I worked in the wedding business for 8 years. After awhile, I was able to sniff out ultra wealthy clients during initial phone calls/emails and always turned them down. Newly-rich people have one objective: impress others. That’s it. Nothing was ever, *EVER* good enough. Most wedding clients had timelines, which at most were broken into 30-minute blocks. I had one wealthy mother in law who had her timeline in 5-minute blocks. Yes, 5-minute blocks. After the wedding, she emailed me SIX PAGES of criticism, absolutely heartbroken that her daughter’s “golden hour” sunset photos were delayed by 10 minutes because our champagne service was not efficient enough. I had one bride email me 6 months after her wedding, to complain that we provided her a new staff member for her reception. Mind you, this person was *extra labor* - she was provided an *extra* server for free, as I always paid extensively for new hires to have on-the-job training before they were given real shifts. One rich bride was enraged that my employees put 2, and not 1, orange slices in her cocktail.
By contrast, blue-collar people were almost always the nicest, laid-back, sincere, grateful, and high-tipping clients, with actual friends and family, who had a wedding for all the right reasons.
Old-money people and self-made successful people (i.e. people who worked construction then launched their own businesses) were night and day different from new money (mostly IT) douchebags, obsessed with impressing The Joneses.
Image credits: TheeNeilski
People are people, but let’s be honest, financial status can change how they live and how the world treats them. When it comes to the ultra-wealthy, most of us can’t help but feel a little curious. We see glamorized versions of their lives in movies or on social media, but that’s only one side. The real story? That often comes from the people who see them up close, day in and day out.
We’re talking about the staff, those who work for them and experience both the perks and pitfalls. Their tax consultants, private chefs, chauffeurs, gardeners, housekeepers—they all have a front-row seat. They get to see what money hides and what it reveals. And sometimes, the things they witness are as strange as they are shocking. It’s a world of wealth, yes, but also of secrets, rules, and contradictions.
#4
My dad cleans houses, ranging from the tiniest studio apartment to houses with their own security guard and driveway in SoCal. The biggest houses the cheapest and most judgmental people. I once went to a house where their master closet was bigger than our house (1800sqft). The owner was the nastiest person I’ve ever met. Middle class people were the best. They always tipped and gave free food to my parents.
Image credits: Appropriate_Sky_6571
#5
I worked for a guy doing a remodel on one of his bedrooms.one day I was driving to his place and my truck broke down .I called to tell him I would be latedue to break down .he sent me to the Ford dealership and put a f350 on his amx card about 80 k and called it a bonus.
Image credits: SpecificBenefit1323
#6
I worked at a place that sold very expensive watches and jewelry which was frequented by the rich and famous. I would get in trouble sometimes because I didn't recognize them (Basketball players wives, for example) These were a specific type of rich person, the ones who wanted others to know exactly how rich they were. I learned that there are brands that cater specifically to these people, and are mostly only recognized within their own circles.
A lot of ultra wealthy people don't dress up when they go out, they can be plain or even sloppy. It was important to never assume someone's status.
They are petty and will throw you under the bus in a millisecond if it will even slightly benefit them. While I worked there I was screamed at, had things thrown at me, I saw grown men throw huge tantrums. They do it because they know they will get something out of it. Your work had to be beyond perfection because they would purposely try to find faults to exploit. I hated that their behavior was always rewarded. I preferred it when their assistants were the ones we helped.
Many of them seem incredibly isolated and lonely. Some would come and talk politics at us because they had no one else who would listen. Though, to be honest, we weren't allowed to express any of our own thoughts so it was pretty one sided conversation.
Image credits: Artwaste
We spoke with Leslie, now an IT professional, who used to babysit for ultra-wealthy families in her early twenties. “I was in college, and it paid better than any other part-time gig,” she says. She babysat for families in her upscale neighborhood, getting a close look at luxury and everything that came with it. “The houses were like museums,” she recalls. “But working in them wasn’t always comfortable.” What she saw left a lasting impression.
#7
I have flown private jets for various wealthy individuals. People you would likely never know, they don’t exist in the public sphere in the way someone like Bezos does.
They don’t always have some deep dark thing that is unique to wealth. They’re human, and the things, the emotions, the tenancies they exhibit are the same across the entire human spectrum. I’ve come away seeing wealth just makes you more of what you are. If you’re mean, you’re more mean. If you’re nice, you’re more nice.
They still have problems, and some of that is tied to their wealth, which is family drama, having access to the wealth, and raising children to be humble or entitled.
They are more insulated from legal or political consequences.
Image credits: MavenAloft
#8
This is 50 years ago, worked for dozens of the most wealthy, think 100 M and up crowd.
Very consistently joyless, entitled, arrogant and cheap, often overlaid with substance abuse issues. With notable exceptions.
One of the richest, multiple billionaire, would occasionally come out and work with me. I was doing landscaping, maintenance, whatever. He asked me to help plant some strawberry’s, worked with me the whole time and described high finance, how to shift risk to the other guy while retaining control and the lions share of the profit. Easy going, super nice guy.
Image credits: ever-inquisitive
#9
I have been acquainted with a few billionaires and several multi-millionaires, most of them board members of non-profit charities I have worked for. Non-profit organizations in the US must have boards, and the board members are usually wealthy individuals.
Sorry to disappoint you, but some of these people were wonderful humans. Yes, some were jerks too, and most were somewhere in between, just like the rest of us. Most of them genuinely cared about the people these charities were reaching, you could tell by the questions they asked when I would give them a presentation.
Sorry, I know it's uncool to fail to s**t on the wealthy, but I found them to be just like the rest of us in that some were total jerks, some were exemplary humans, and most were somewhere in between.
Image credits: Traditional-Tank3994
“The money is good,” Leslie says, “but it’s never easy.” Babysitting in these homes meant walking on eggshells. Everything had rules: what to touch, where to sit, even how to close the fridge. “They didn’t say it outright, but you always felt like a guest, not an employee.” She often found herself adjusting to the tiniest of expectations. “Good pay came with invisible pressure,” she adds.
“There are rules, so many of them,” she explains. Some families had entire booklets for babysitters. Things like how to fold the child’s blanket or what music was allowed near bedtime. “One family didn’t let their kid hear any pop music. Only classical.” Leslie says she memorized the guidelines just to avoid awkward moments. “And if you messed up? Even slightly, it was noticed.”
#10
That they are painfully detached from regular struggles and genuinely seem to think that their success is tied to meritocracy even when born into extreme wealth and when it is earned they will not accept luck played a factor. Also they fundamentally can't understand the word no and you have to explain things to them so that they think that they are right. For example when they try to break specific rules you will often have to say "I will make sure to share your suggestions so hopefully we can change that rule in the future".
Also **NO ONE** loves free s**t more than rich people.
Image credits: teachmeyourstory
#11
I attended a private boarding school with many ultrawealthy students.
Just... so much a***e of EVERY kind. Beat. Starved. Locked out. Tortured. SA'd.
People dont call because there's no point because the authorities won't even go, let alone actually DO anything.
The richer they are, the more f****d their kids are if there is anything off in the family.
Image credits: kifferella
#12
One of my best friends in my teens was the son of the one-time richest man in the region. They were completely normal other than their house's interior. There were at least a dozen other houses in their neighborhood better than theirs. It's quaint by today's standard of country club. But absolutely everything was best available. Commercial huge Subzero refrigerators disguised as cabinetry. High flush toilets that were completely silent. A wired smart house as much as that existed in 1990, which is more than you think. Subtle touches, understated wealth. Lots of accessory-type bland original art, like Audubon or landscapes. Mom drove a station wagon, dad a buick. They were generous and kind. They raised their kids to be accountable and treat people right. Dad was self made, mom 2nd generation wealth.
The actual billionaire I worked for was super cool. Self made. I had monthly meetings with him (and about 16 others) and to see his ability to connect with hourly workers to senior executives was impressive.
Image credits: beaudujour
“Everything is expensive. Designer cups, designer bibs,” Leslie laughs. “You could never relax.” One time, she nearly cried after a toddler spilled juice on a white velvet couch. “It wasn’t even my fault, but I kept apologizing.” She says it felt less like childcare and more like guarding a priceless art exhibit. “You’re not just babysitting the kid, you’re babysitting the brand.”
#13
I have a neighbor… we are both 78 years old. When he was about 19 or 20 he worked for Jackie Onassis as a handyman around her horse ranch in New York. He once assembled a motorcycle for her son, John, that she had shipped in from Italy. He said she was the nicest person you could imagine. She even cooked him breakfast a couple of times when he was all sweaty after doing early morning chores.
Image credits: genehil
#14
I got upgraded recently by a very kind hotel staff member, got to stay at the hotels "exclusive floor". The rooms were really nice, but it was all the extra stuff. Exclusive lounge with free 'canapes', a selection of custom scents for your room, and a lovely dedicated concierge who seemed deeply confused I didn't need him to do anything for me. Access to a spa.
Later, I was sitting in that lounge, and a woman walked up to the concierge, gave him a piece of paper with her measurements on it and asked him to have some workout clothes/shoes sent up to her room so she could use the gym. As if they just have a magical chamber downstairs with everyones exact size of shoes and clothes sitting there. She seemed perplexed when he explained they didn't, and suggested a Lululemon store a few blocks away. She then said "excellent! Send someone over to pick some things up. I prefer earth tones. Just charge it to my room." She didn't even wait for a reply before walking away.
It's mind blowing. They are just used to getting everything they need, all the time, at a moment's notice. They are utterly dumbfounded when they hear the word no.
Image credits: raw_copium
#15
They are unusually cheap, or most I've worked for are. I'm in wine sales and cellar management, and I had a client who had over ten million dollars in First Growth Bordeaux and Grand Crus Burgundy, and he served $20 Pinot and bubbles (Cava) at his Xmas party for his best friends and celebrities.
He died with a ten million dollar cellar.
Image credits: investinlove
“Once, the dad came home with another woman,” Leslie shares. “He didn’t realize I was still there.” She had been upstairs with the child when she overheard voices. “I stayed quiet, but it was awkward,” she recalls. “The next day, the mom acted like everything was fine.” She never brought it up. “It wasn’t my place, but it left me shaken.”
“Some of them don’t want to correct their kids at all,” she says. “One little boy told me to shut up on day one.” Leslie looked to the mom, expecting a reaction, but none came. “They think their kids are untouchable.” She says it’s like the kids are raised to believe they’re royalty. “I wasn’t just the help, I was beneath them, and they knew it.”
#16
A surprising number of them are hoarders. Like... mansion-level filth hidden behind marble gates. Rich doesn’t mean clean.
Image credits: blissdoll_
#17
They can actually be quite cheap when nobody is looking; penny pinching is pretty common. They will use the lowest bidders on stuff like cleaning and lawn service, then stiff people on payment over minor disputes.
They're also poor tippers when nobody is around. I've been out to dinner with a wealthy friend, the table order was quite expensive, but she only tipped a $5 bill. She slid it quickly under a napkin so nobody could see how little she left. Now if she'd been with her other wealthy friends, I'm sure the tip would have been much larger.
That same friend also bought me a drink once while we were out, a soda, not an alcoholic beverage. It was $1.50, no big deal for someone with a bank account bursting at the seams. When we got back to her place, she asked me to repay her because she was nearing her "budget" for the week on snacks and stuff. I did, gave her two $1 bills, she kept the change.
#18
So I don’t work with ultra wealthy, but I’ve lived next to one for ten years and just realized it maybe a year ago. Nicest neighbors ever. Standard suburban house, decent cars but not flashy. It was only when I noticed they were gone for like 2-3 months I asked the wife and she said she was traveling with her husband to India, Japan, Italy, Iceland, amongst others. Turns out he’s a ceo of a massive global company and they must be worth close to 500mm plus.
Image credits: Darrksharrk
“One family didn’t even pay me,” she recalls with disbelief. “They said letting me be in their 'beautiful space' was enough.” Instead, they offered her leftovers. “It’s caviar,” they said, as if that excused the unpaid work. “I left that job and never went back.” For all their wealth, some families showed little basic respect. “It was insulting,” she adds.
#19
I did a personal IT service for a incredible wealthy guy in Tucson. House overlooking the city from the foothills, 8ft single pane windows, etc. He had a ranch of at least 40k acres in Texas, and most of his $ was from oil.
His biggest secret was that he knew most people only liked him for his wealth, including his present wife, 2 kids and 2 step kids, and they’d cut ties in a heartbeat if it disappeared.
Image credits: ratherBwarm
#20
Worked for? No. But I worked for a high end furniture store and delivered furniture to them for years when I was young. Most of them try to squeeze as much as they can out of you while paying as little as possible. So many times.. SO MANY TIMES we would show up with furniture and they'd be trying to get us to move the whole f*****g house around for them like we were United Van Lines. If we refused they would call the manager and tell them we have to do it or they'd refuse the furniture, we can just leave and they'd leave a bad review. Eventually the manager made it clear to all customers we are delivery service, Not a move your s**t around service.
Once that was solved, they'd try to bribe us with tips. A few times when we were broke we agreed and then they'd not give us the tip either by pretending they forgot and hope we wouldn't say anything or they'd make up some b******t reason to not tip us. "Yeah, when you carried that 300 lb armoire down to the basement, the third step is creaking now. It didn't do that before. We're going to have to use that tip money to contribute to the carpenter who is going to fix that step"
Then when we'd give them the bill, they'd act like we were asking them for a small kidney and carry on about how much it was like we were stealing from them... like they didn't f*****g know how much it cost when they ordered the thing. 🙄 I f*****g hate rich people. I know SOME of them are ok but based on my experiences, I'd say a good 90% of them are the cheapest most power abusing a******s I've had the misfortune of dealing with.
#21
Worked in the tech investor/ startup space. Ended up at WEF in Davos one year.
I remember eating a $32 hamburger, listening to a man brag about influencing elections in developing nations to support his commercial interests. He spoke so casually– like he was sharing old college stories. He shared missteps he had made in his political schemes that had caused civil wars, and lamented on the tens of thousands of lives that his errors had indirectly taken. Drunk, at a bar on a mountain, he talked through *literal crimes* with the tone of someone who had f**ked up at their day job.
I remember that he believed it was his duty to 'influence', that whatever underlying meritocracy granted him enough power to buy elections also required him to guide the poor, silly populations underneath him.
He left me with the check for his beer.
“Some were downright rude,” she admits. “No greetings, no thank yous. Just orders.” She says she felt invisible in those homes, even when she was doing her best. “They’d talk about me like I wasn’t there.” Leslie believes some people assume money replaces kindness. “It doesn’t,” she says. “In fact, it exposes who they really are.”
#22
He was "divorced" and "married" a second wife. He never divorced, and the second wife is a mistress that he parades around as his wife.
Actual wife doesn't give a s**t as long as they're still rich, but won't let his second batch of kids inherit their joint assets, so he had to buy his second wife some income properties for security. She'll be okay though. He bought her 100 mil worth of income properties.
Image credits: SleepoDisa
#23
Long time lurker, first time poster. Have not worked for any, but my stepfather is one. I remember one instance where he was planning a flight and his plane needed maintenance before flying, and instead of waiting the time (I think it was a couple weeks or so) for the plane to be fixed, he just bought another plane.
He believes that money can solve everything, which to no surprise, it does not. He has this idea that he can just pay people to either shut up or ignore issues. Including family. He has constant arguments with my mom that often involve him completely ignoring the problem and giving her some rather large gift thinking that it will solve the issue. It usually doesn’t.
His kids are completely messed up. They spent their entire lives never being told “no”. And now they are becoming adults and have been slapped in the face (metaphorically) with the fact that most people actually have to work for a living. They don’t get the “concept” of it.
The whole thing about having assets in different countries and hiding transactions under the guise of “charity” is completely true. I don’t think he does it out of malice, but purely because he believes his only worth is his money. In actuality he’s a really kind person, but he sees all relationships as transactions. I often feel sad for him when hearing from various family members about how he sweeps real problems under the rug and covers it up with money, because he thinks that’s the only solution.
It’s also quite sad seeing how much of life you miss when you feel like you can’t go anywhere without needing “protection”. We come from a third-world country in which the rich are specifically known as such and targeted often, and as a result, there is always a “need” for hiding either yourself or your money. Just as an example, my stepfather’s mother (I guess my step-grandma?) has not left the gated property that she lives in for maybe 5 years because she is afraid that if she leaves/goes out in public, she will be kidnapped for ransom or other similar situations. She lives about a 45 minute drive away from one of the most beautiful beaches in the world, and has never gone to see it. And she’s so lonely. She has a hired staff member specifically to keep her company. As in someone is paid to hang around with her, because she’s lonely and doesn’t know how to make friends that aren’t in it for the money.
Money does solve a lot of problems, but it also gets to a point where it creates them.
Image credits: LankyEntrepreneur267
#24
I have provided construction services and the NDA was always in place. Almost all of the clients were lonely and their wives were unhappy. The children had nanny’s and were well cared for and the men all had PA’s. Latest thing I’ve noticed, the wealthy love pickleball (the sport). I have ate food and drank alcohol with these people and it is fascinating. Oh….the women love online shopping….there were deliveries everyday. Helicopters are a big deal too, especially A-Star. If any women are reading this post, I have never seen so many women’s high-end shoes in my life…like hundreds of pairs in dedicated closets. Sorry I’m rambling, I think I have sunstroke.
“But hey,” she smiles, “there were kind ones too.” Not every family was cold or out of touch. “Some were incredibly sweet, offered me dinner, asked about my studies.” One mom even wrote her a glowing reference letter. “That kind of kindness stays with you.” It reminded her that wealth doesn’t always erase humanity. “Some people were genuinely good.”
#25
Back in the day worked on an estate for a celeb couple. Neurotic is an understatement, phone calls at four am saying I needed to go and buy "organic lavender oil" as she couldn't sleep. 8 hour round trip to deliver a bacon sandwich cooked by his own chef as he didn't like onsite catering. He was married to arguably one of the most beautiful women to have ever lived had a awesome job, multi multi millionaire . . .and was miserable as f**k.
The second estate had old money husband he had the title and land but was cash poor. The wife as new money or would be new money when she Inherited from her father. The difference in the way they dealt with money begged belief. She was spending too much and the accountant told her to reel it in, her response was to fire the accountant. She expected me to sail her yacht for her on the weekend, no overtime because "it's fun".
I could go on for days.
#26
I didn’t work for the ultra-wealthy but my mother (who was extremely beautiful but not wealthy) grew up as a socialite, the kind who was a debutant and was supposed to marry an ultra-wealthy man. Instead, she married my dad who was a struggling artist.
But one of her best friends came to visit our humble home when I was 12 years old in 1992. She was an heiress to a huge fortune, and she had just come from Paris where she had seen the Calvin Klein runway show. She had liked the clothes so much, that she bought the entire collection. However, since it was literally the pieces worn by the models, instead of off-the-rack, they didn’t really fit the way they should and sometimes, her shirt just fell off. Luckily for her, she had just gotten a new b**b-job and was happy to show it off.
She was on a lot of prescription pills and drank alcohol from dawn to dusk, and also chain-smoked. We didn’t have a guest room, so she shared my bed. She would periodically wake up, take pills, and smoke, burning holes in my comforter. One night, she suddenly screamed in her sleep, “YOU BETTER GET THAT B***H OUT OF MY HOUSE OR IM CALLING THE COPS!”
12-year-old me thought she was facinating and hilarious. The night she woke me up screaming and cursing, I got out of bed and went in the living room, to find my father watching the LA Riots on tv because he said, “it’s a lot more peaceful than what’s going on here!”.
Image credits: HippieFortuneTeller
#27
I worked as a PA for a billionaire. He was delusional. But his wife was something else. She would have breakdowns and start screaming and crying in her office which was glass so the whole floor could see and hear her. It could be over something as simple as her lunch being late or wrong (Luckily I was not her PA. She went through a few of them quickly.) One time she was supposed to speak at a company event and it was raining. I was told we pushed her slot to avoid rain so called her hair dresser who was doing her hair at a rented mansion. She still showed up for the original time and had an absolute meltdown about it being rainy and muddy and her slot being pushed. My boss was pissed at me and didn’t want to hear any of it in terms of me calling ahead. Just took it and said sorry. Told me “sorry is for losers.” Ok bro.
There’s a show and documentary about them which gives a glimpse into who they are. Gave me PTSD watching them.
Well, these posts definitely reveal a darker, more unfiltered side of extreme wealth. From shocking behavior to complete disregard for others, it’s a glimpse into a world not many get to see up close. What are your thoughts? Have you ever had an encounter with a wealthy person that left you surprised, uncomfortable, or just plain speechless? Share your experience in the comments—we’re all ears!
#28
Managed private golf, country, and social/city clubs for more than 2 decades. I have worked with, for, and befriended many of the top 1%.
They are just like us - imagine your favorite , happy go lucky, helpful best friend .... now give that friend the means to help anyone in the world. There are many like that.
Imagine that nasty, spiteful, bully from your high school or neighborhood who took joy in making the lives of others miserable.... now give them all the resources in the world to continue to do that. Yep, I've met them too.
What am I most shocked by? The hypocrisy (most popular example - support fervent gun control & open boarders but often make use of armed guards, gated communities etc....)
Also shocked about the anti Semitic attitude I saw between liberal-Jewish people and more orthodox/conservative Jewish people.
One club I worked at a lonely wife of a uber wealthy man would leave uber expensive jewelry behind at the spa, gym, card room I think just because she wanted attention. Eventually one of her RM watches was never found. I suspect I know who took it... I just hope she found a way to p**n it for 10 times her annual average salary.
I probably have as many positive uplifting stories as I do examples of miserable human beings from my experience. I will say I have never come to trust even the nicest ones to pick one of us normal folks over one of their fellow uber elite friends. Even if they know a friend / acquaintance is in the wrong ... they will never side with the help over one of their own.
#29
I had a very wealthy boss who really had no boundaries about 20 years ago. I worked at an art gallery and was paid literally peanuts.
One night after a big party I ended up at his house with an agent from out of town, I was just PR babysitting. I discovered all he had in his house to eat was champagne, a block of Parmesan and c*****e. I left asap.
He had me break up with women he invited up to his cabin for the weekend, one was a rockette who forgot her cellphone and I had to priority fedex it back to her. I also had his Chase Manhattan PIN numbers and dealt with his expenses. He’s d**n lucky I’m an honest person because I cannot stress to you enough, I was only 27 🫣.
#30
My mom was a primary teacher in a European school that jillionaires around the world send their kids to. She was trying to teach kids to be considerate of the cleaning staff and not throw s**t on the ground, and she said the kids would reply with "but my parents told me that making a mess is how we give these people jobs". Anyways the parents started to complain that the mean teacher wouldn't let them make a mess...
Another time she and the principal called the parents of a kid with learning disabilities to discuss what kind of job the kid would be capable of having in the future. Mom blew a gasket from the insinuation that any child of hers would have to work a day in their lives.
#31
Worked for a landscaping company who had some wealthy clients. One day one of our customers legit talked about how we should line all poor people up and shoot them in the back of the head e*******n style. Like dude who do you think takes care of your lawn? I wasn't surprised by what he said. It just confirmed my suspicions.
#32
There’s a few but having a n**e painting of yourself in the foyer of guest house was one. I couldn’t believe it. Lol.
Image credits: Goldenpeanut88
#33
I did a week worth of work on the ranch of the guy who invented the fleshlight. Man was loaded. He had a giant house with a Spanish fountain out front, a spa/gym/office with a huge roman style pool and statuary, an attached walled garden with stone Buddha statue and an Indian tiger tower, a massive barn, and his own disco/club. It was quite the compound.
His dark secret was that he was kinda boring and down to earth for what he’s famous for. Everyday he’d drive a UTV around and look at the birds. His wife was quite nice too, though maybe a little out of touch. She complained about how hard it was to buy legitimate antiques (the aforementioned statues, etc) because countries were cracking down on exporting cultural relics.
They treated me well. Would come around to check and see if I had enough water. Would come chat with me for a bit each day. Honestly pretty nice people.
#34
They're cheap and stingy but strangely generous to the chosen few they let in.
Also they don't think they're ultra wealthy because they're constantly comparing themselves to anyone who has more/newer/better than them.
Also their wealth to them is also subjective in the context of their own perceived rise and fall. They are very insecure about anything they've lost. They will feel their empire has fallen as they age.
Image credits: IronOk4535
#35
Not me but my parents. They went to school with a girl who was from a poor farm family and became rich after high school. The girl and her roommate were in college and created the first “storyline” of a very popular video game. she went to school for computer science and got a degree along with the royalties that came with selling said storyline. She worked for company that purchased the storyline for a while and decided to retire early. My parents stayed in touch with her from time to time but haven’t seen her in many years until very recent when her mother died from cancer. The last time she spoke to my mom she became very lonely after having several relationships fail due to various reasons. She went into a bad depression and used some of her money to basically “shelter” herself away from other people. When my parents reconnected with her during her mother funeral, they said she looked very aged and worn out like she hasn’t slept in years. Turned out she was on various depression and anxiety meds that weren’t working well and she stayed up for over 48 hours before the funeral. Her father said she was losing weight fast and told my parents the money changed her. It was evident she thinks and lives life one day at a time and hoping the day is done quickly so she can go to bed. It broke my parents hearts knowing she became successful and yet struggles with her own insecurities and mental health issues herself.
#36
Their days are, many times, filled with busywork and nonsense and can be quite boring. They would send me to find their little dog. It usually took me a couple of hours because the mansion was so large. This was nearly a daily thing.
#37
I was an electrician and worked on the home of a very famous pro wrestler. We were adding a bathroom to the guest house on his property, the bathroom in said guest house was 1200ft²... Just to give you an idea of how ungodly rich this guy is.
The main house was basically a castle, easily 30,000ft² and they had 6 great danes that would s**t all over the place and they'd just let the giant piles of dog s**t sit on the marble floors of their gawdy a*s mansion until the cleaners came every day to clean it up. They're not the only wealthy people I've known who were like this. They're pigs. They'll live in their own filth until whoever they pay to clean up after them comes along and rescues them.
#38
Had to entertain an oligarch for an afternoon once but had no idea he was a legit oligarch with destroy the world amounts of wealth.
The only secret I gleaned was you never know who somebody is. He dressed, acted, and enjoyed in all the ways a normal person on a budget would. I didn’t get the impression that was an act for me but he definitely appreciated that I didn’t know or give a f**k who he was.
I took him to a dive bar and for tacos after. My boss said the oligarch reported a great time and made sure I got the recognition.
#39
Worked for 3-4 billionaires. Was in Construction Management and did multi year remodels of some homes and some new builds. I’ve been on their jets, yachts, visited 3 of their 9 homes, drove their cars, helped move Picassos across the 30,000 sqft house…you name it.
My biggest take aways are 1.) that many of them have no real understanding how the real world works & 2.) it’s often a lonely, fearful, and sad life.
They stress over who is trying to take advantage of them. My wealthiest client ever drove a Prius because she was afraid of being targeted. They paid to have 24/7 security at the house cause they fear the “eat the rich crowd” and live in paranoia. Their kids have nothing to aspire to, no dreams, and any accomplishments are mere expectations.
I got out of it cause the stress was unbearable when pulling a rabbit out of your a*s becomes what you’re known for and the expectations are that you will always be able to do that. They throw money at your bosses and your boss agrees to the impossible and then you have to get it done.
#40
Nepotism out the a*s. Routing all sorts of favors, money laundering, and bribes thru various 501(c)3s and family foundations and making sure they are photographed at their “charitable” events so everyone sees their “philanthropy”. .
#41
In my past work I met and spent time with celebrities, mostly singers. The old school people were the best. People like Ricky Skaggs and Merl Haggard were just people who sang for a living and happy that people enjoyed their work. So many “ New” talent ( Terri Clark, Taylor S) are supreme snobs. Dolly will sit and talk like you’re in the office waiting for your appointment. Kelly Clarkson you can have. She did a fundraiser for breast cancer and wanted a red carpet. She also did not want the band to look at her. Two hugely popular venues here in Nashville have stage musicians ( interesting fact: some can’t read music so the sheet music is numbered instead of notes. It’s all kept in a cage backstage.) They played for her and she wasn’t very grateful…
It’s sad, because when she first made it big one of my exes was a huge fan, like goofy fan. Got to meet Kelly who was so kind and warm. Even chatted for a bit.
#42
My gpa worked for one of the 5 richest families in the state. He saved up forever to buy something for his baby daughter at a nice store only to be turned away on account of his race and the assumption he couldn’t afford anything. He was disappointed but continued on with his day. His boss saw he was not his normal self and asked what happened. Gpa didn’t want to say as it was not relevant to his job but boss was persistent. Gpa finally admitted what happened and that he was a bit disappointed. Unknown to gpa, boss went to store, and said he understood that someone tried to purchase there but was declined on the understanding that they/their money (obviously because of race) was not good enough. Boss said since he was the one who paid that person. He understands HIS money is not good enough and would let all his (rich) friends know that their money was no good at that store…. The store closed and did a “private sale “. For my gpa to buy the dress he wanted for his only baby girl….
#43
I dunno if it’s a deep secret but they did seem to hide the reality from the image. They seemed like a standup family guy who’d created an empire from nothing.
Their child committed s*****e. On Father’s Day. And it was a CLEAR statement of why they were doing it on THAT day from people who were close enough. But the death was very much hidden and written off as an “accident” and portrayed as something other than what it was.
It wasn’t an accident. It was a tortured souls last outcry to their horrible, a*****e father who was a piece of s**t as an employer so I can only imagine the horror he was as a parent. They chose THAT day to end their life and even though I was a child when it happened…I remember realizing how much the day they chose was impactful in the grim circumstances.
#44
Paul Allen and his family were the worst. The news articles about the sexual harassment are true. Their (in house) lawyer left all the correspondence and documents out in an unlocked office while the cleaning crew and us security staff chaperoning them were there. I guess they figured no one late at night there read English.
#45
I worked for a large company owned by a single family and they couldn’t all fly in their private jet at once, just in case the plane went down. They also had a small preamble to important meetings about what would happen if the patriarch died during or after the meeting and the succession plan.
#46
Work for a few of them on high end acquisitions. Mostly classic cars.
The guys in the nine plus digits for wealth go two very different ways. For 80% of them they are down to earth and very nice to be around. Their problems are different than ours for sure but the self made ones are super chill. 10% are using me as a service to say time and they go into it that way, like I never even speak to them.
The last 10% treat everyone like staff and they suck and I change extra for being treated that way even if they don't know it.
People in the high 7-mid 8 digit net-worth are all over the place. You have old money that is super cheap, you have new money that is trying to skip the line and wait to get a car that is in demand and think they don't have to pay over sticker. You have people like me who daily old F150s because that is how they made their money and they don't ever act out of how they were raised right.
Like everything people are different. 2nd generation wealth can go suck an egg though. Most if not all of them are entitled brats.
#47
People are not going to like this but
**Stealth Wealth is a lie**
They only do that in front of the camera because a normal person would much rather buy a product that profits a CEO living a "normal life" rather than profiting a CEO that takes 10minute jet rides.
In private events they love to show off more than anyone else. Everyone is wearing a RM, that costs between an average home to a mega yacht.
#48
I worked as an architectural designer for the incredibly rich. It was the least fulfilling position I ever had. Most of the builds were 5th vacation homes only their lawyers would use. I was told it gave them a tax break though I still have no idea how. I had total design freedom in most cases, every designers dream. I did a Japanese-Hawaiian 50s surf theme in one kitchen with a vintage surf board as the bar top. After a while, I started calling these palaces of dust because no one ever used them. Many were on a private ranch the firm managed and the maintenance tasks were depressing to look at because of how obvious it was the properties were unused. And they were gorgeous. The very few clients who got personally involved were the reason I got out of high end design. They would walk all over boundaries such as not calling in the middle of the night to tell me they decided they want the kitchen window back in its original position (pre-build). But the worst ended in two deaths. It was winter in an area where that really means something. This build was nearing completion and the owner flew in unannounced on the day the home theater was being installed. The installers were coming from what would be a 45 min drive in the summer, and what the locals called the s*****e road to attempt with ice. The theater company attempted to cancel due to weather. I was told to call and let them know the owner was in town and they’d have to make it. I refused. A 20 year old drafting assistant was given the task. She called and they agreed to send their guys. Some 20 min later, I was again told to call. This time I did, hoping they had changed their mind. Instead I was given their cell numbers. I refused to call the guys in the car since I knew by that point, they would be going through a canyon with black ice, next to a river with no guardrail. The assistant called. They were on the way, but she let them know the owner was waiting. Then the other architectural designer called. Then the assistant. I asked them not to but the impatient owner trumped all. Then they stopped answering. They had hit a patch of black ice and careened into a ditch and a light pole. Speed was a factor. They both had families with young children. Neither the architectural firm nor the home theater company ever mentioned the phone calls to anyone. As for the owner, he was annoyed at the delay.
#49
My boss got mad by people offering him free money.
Galas, diners, test drivers in cars yet to be launched, concerts, free stuffs (expensive wines, delicatesses, tickets to parks, etc...) are all handled by her secretary because it annoyed him.
People used to call offering to him be part of lucratives already closed deals just to strength their relations with him. I saw it happens. It was in real state bubble but still.
He was silent partner in some (shade) deals that just conclude after it proved to be lucrative. The insinuation of his name is what make the deal happens so he make a profit before even investing his money.
He complained about those things a lot while got more and more rich just because he was already rich.
PS.: Beer, Casinos and telecommunications was his business. I worked as a waiter for him and he love me - what put me in troubles with his son and made me quit.
#50
I used to be close friends with a kid who was best friends with a kid a little younger whose mom’s family was probably worth $5 billion. We would go over to his house and do whatever activity you could dream of, it was there. Every single night there were sterno pans with dinner from one of the local high end restaurant if a chef didn’t come in and make something.
We would take the family jet to his apartment in a large city every couple months: limo to hanger, get on, laid out food on flight, limo directly off plane and to apartment. One time his marijuana dealer in the city was out of town so he asked me to bring an ounce for him, back when it was $400/oz for high end. I had made the flight before, so I knew security was no issue; but as a 20 year old kid(guessing) that was a huge expense. I felt awful bringing it up after everything we didn’t pay for and I did smoke, but not at his rate. I. We always sat court side at basketball games, went to a club afterwards and spent north of $25,000, ate at the best places, etc. so I just ate it. We were in limo back to plane after that weekend and he was f*****g around with his bag and pulled out a thousand in an envelope and was like my bad man, I totally forgot to get you this. He was young dude, kind, soft spoken. Haven’t seen him in probably 15 years.
#51
I’ve done work for quite a few wealthy people. A couple were lovely. A few were just regular. Most are a******s, and one (and his wife) were straight up evil, satan spawned scumbags.
#52
The more money they have, the more problems they create to not pay you. Sign a contract, get a guarantee with clawbacks and wait. Rich people are rich because they don’t prefer to spend money, and they know they can out litigate the little guy to avoid paying for it. CYA. Money = nothing if you don’t get it up front, the wealthier they are the more you should protect against them up front. Billionaire client? Do a 70 up front and a 30 back end, and know who they trust to sign off so if they aren’t around you can get THAT guy if they are off jet setting and unavailable. Best advice I can give.
#53
All these people saying uberwealthy people are cheap or detached from regular struggles probably have not worked close to one of these people, or at least maybe not a self-made $100M+ person.
They definitely have struggles you can relate to like dogs dying, car trouble, health, etc. the difference is they can handle those things for what they are and not really concern themselves with the cost to repair. They can just have their emotions where normal folks also bear the burden to stress about the money involved.
They also are usually not cheap, but instead have an extremely precise valuation mechanism. That is probably how they got so much rich in the first place. Having this strong valuation is sometimes incorrect due to a lack of risk for them personally, but the value they attribute is often better than a normal person who is overvaluing something.
Source: worked with three people like this and they were all pretty much had the same personality, and very much valued their personal things and all dressed like they were lounging at home no matter where they were.
#54
Nothing exciting. Just being horrible business people driving their five generation family company into the ground because they grew up wealthy and refuse to take advice from the people they hire to advise them.
Buying or starting businesses they know nothing about, way overspend/overpay for, think they can grow any kind of business because of their self-perceived operational and business expertise they think drove the success of other businesses they owned that, in reality, got super lucky in a hot market.
Then, paying the people that are giving them good advice and working their a*s off way under market, treat them like s**t generally, not believe in Covid and want them back on planes four times a week in September 2020, when they have an anti-imune disorder and aren't ready to come out the gate and get on a bunch of planes and stay at hotels.
#55
They are completely inept but do not think they are. They can’t make a decision to save their lives and cannot fathom the idea of the working class reality losing all empathy for actual humans. They cannot understand the ease and privilege wealth gives them. They can afford to fail over and over again and always get more chances to make the same mistakes and not learn from them. It’s been an interesting few years working for an ultra wealthy person.
#56
It's not a secret but more like a fact : they have lifetime concierge taking care of all theire life and mental load.
also
they use fake names all the time everywhere.
#57
I was a substance a***e counsellor in South East Asia for almost a decade. I’ve met quite a few billionaires, and got through many counselling sessions I think I’ve gotten quite a good picture of the ultra wealthy and their families.
My main take away is that they just do not care about the rest of us. Its solely about wealth preservation. I’ve seen how they treat others, their PA’s, our support staff and it was always void of seeing their humanity.
They only fear few things, but mainly time. They fear death and the end of their mortal life. They fear parents, siblings, uncles or whatever family member who can take away even a smidge of their wealthy.
They get away with murder as if it’s nothing. I spoke with one young man, who’s father is one of the richest people in Hong Kong, who killed two people. One in a driving accident, and one he shot dead. People were paid off and nothing came of it.
Later in life I came to read “pedagogy of the oppressed” by Freire. In it he states that not only are the oppressed victims of oppression done by the oppressors, so are the oppressors victim of the system. As oppressing other robs you of your humanity. I full heartedly agree with this statement.
#58
I knew people who would buy multi million dollar homes in a resort area and live there for peak season one maybe two years then sell them just as quickly for a huge profit…they considered that their jobs cause they would make hundreds of thousands just by holding a property for a year or two.
#59
Worked with finances of ultra wealthy. The darkest "secret" that I ran over was that the kids of the parents who built up their wealthy had messed up personalities. Seemed to have no passion, d**g addictions, empty on the inside to the extent that I could see.
#60
They rarely pull permits for construction because it’s more advantageous to pay a fine when caught…since that apparently doesn’t flag the assessor but a permit does. 🫢.
#61
They'll pay you big money to lie for them in court. Long story short I refused to testify that they didn't undercut the government and used substandard parts for a multi million dollar construction project.
