People Who Have Worked For Super Rich Employers Are Sharing Their Wildest Stories, Here Are 84 Of The Best (New Stories)

For most of us, the lives of the “1 percent” are a complete mystery. When people have that much money, what could they possibly be spending it on? If you’re imagining elaborately decorated private jets and spontaneous trips around the world, you might not be too far off.

Someone asked people on Reddit who work directly for the super wealthy to share some of their best (and worst) stories, and many of these employees delivered. We’ve gathered some of the wildest tales about these affluent employers and what they spend their money on, so we can all get some insight into the mysterious world of the wealthy.

Enjoy this list and if you’re hungry for more of these stories afterwards, be sure to check out Bored Panda’s previous publication on the same topic right here.


I used to do some financial work for someone who became very wealthy through their very popular chain of surf gear. I had run through their tax position and had found a way for them to save a little over 2 million in taxes a year by reshuffling some of their entities. Would have taken them around an hour to sit down and change everything, lots of signatures on paperwork, then maybe an hour extra of their time a year to administer. Their response?
"Nah, I don't want to waste that much time with paperwork, that's what I pay you guys for."
I can't even imagine what it would be like to be in a position where a bit of paperwork wasn't worth that much money. (Heck, offer me $20 and I will gladly fill out paperwork for an hour for you!)

Image credits: LifeIsBizarre

There’s absolutely nothing wrong with being rich, wealth is something many people aspire to have, but having money does not give people the right to do whatever they want. Well, it shouldn’t. But the unfortunate truth is that money is power. In many of the examples on this list of rich people acting entitled and treating their employees poorly, their money is exactly what allows them to do that. The people sharing these stories relied on their wealthy employers to buy groceries, pay rent and provide for their families. That’s a lot of power to have, and sadly, not everyone with power knows how to maintain their ego.

Rich people have a lot of influence in society as well, particularly in politics. A 2015 report from the New York Times found that less than 400 families were responsible for almost half of all the money raised in the 2016 presidential campaign. And what's the impact of this? As Paul Krugman of the New York Times states, “Wealthy donors have access to politicians in a way ordinary Americans don’t and play a disproportionate role in shaping policymakers’ worldview.”


My dad worked for an extremely wealthy man as his personal accountant. One day my dad was driving him to a meeting, he was super old, and the man asked to swing through McDonald's. After ordering a coffee for $1.06, they began pulling forward. The man asked my dad to reverse his car to the speaker to let them know he had a senior discount card. A man worth well over 20 mil, in a massive and nice luxury car, was not about to miss out on saving four cents at McDonald's.

Image credits: xxbearillaxx


I used to work for a composer who is worth around $100 million. He was generally a really nice guy and was genuinely hilarious. There would be some times where he was in a really bad mood and would lash out at people, specifically when it came to preparing food for him. One guy got chewed out for handing him a can of coke by holding onto the top of it rather than around the side. One specific incident that sticks out was when somebody went to get a whole lobster for his dinner and set it out on the table. Our boss hadn't come out to eat it for hours, and it was probably around midnight at this point, so the kid just sat down and started eating. Whaddaya know, big boss comes into the dining room to eat his lobster and sees an intern sat down at the table wearing a bib eating his super expensive (now cold) lobster dinner. That kid didn't come into work anymore

Image credits: DANK_SINATRA13

It’s no coincidence that wealth inequality continues to rise in the United States, as rich people are behind the curtain pulling the strings of politicians. Wealthy people tend to be much more concerned about tax cuts and clinging onto their money than supporting policies that would benefit the lower classes. But the problem with a small amount of rich families influencing the politics of a nation is that they don’t accurately represent the needs of the entire population. The New York Times published a piece breaking down the demographics of the 158 families that contributed the most (over $250,000 each) to the 2016 presidential campaigns, and not surprisingly, “The families investing the most in presidential politics overwhelmingly lean right, contributing tens of millions of dollars to support Republican candidates who have pledged to pare regulations; cut taxes on income, capital gains and inheritances; and shrink entitlement programs.”

Most of these families also live in the same 9 cities across the country, including neighborhoods like Bel Air and Brentwood in Los Angeles and River Oaks, a wealthy suburb of Houston. The industries they work in are also overwhelmingly similar, with half working in either finance or energy and natural resources. 


A good friend worked for a certain GOP elite political family who had a member running in the 2012 US presidential race. This family actually hired a high-end caterering service to cater a food fight for a 7-year-old's birthday party. The staff set up a big tent outside, and then had the nannies lay out special painter's coveralls for the 25 kids at the party. Then, the kids destroyed 6k worth of food. My friend and the catering staff were horrified. The kid's parents all stood around watching and cracking up. The kids and families all got gift baskets worth 2-3k each as well. Vulgar, to say the least.

Image credits: A2KB


I have a super rich great uncle who's probably worth at least that much. I spent a week one summer house sitting for him in his beach front bungalow on Balboa Island while he was out of the country on business. He paid me very generously and I got to live on f*****g Balboa island for a week. Uncle Fred is a kind, down to earth man, and his whole family is rich as f**k. Overall the experience was very nice, except for one thing, cousin Chad.

Chad is his grandson, my age who played waterpolo for USC a while back and won some major National Title. His victory ring cost thousands and thousands of dollars, solid gold, diamonds, like those world series or superbowl rings, except for college waterpolo. More on this later.

Cousin Chad was a total c**t, the stereotype of the University of Spoiled Children all the way. Throw money at the school and play a sport, boom degree in communications. During that week he used the house as his love pad/party house, despite strict instructions that he could only use it with my permission and only for himself and a few other approved people. Invariably after he was done he abandoned the place and let the non written into the will pleb (me) clean up.

He also had a habit of showing me this absurd victory ring. He said "if you promise to be careful, you can hold it if you want." Towards the end of the week i accepted, because i had a prank in mind. I took a dollar coin (gold colored), and put it into my hand and discreetly pocketed his ring. i said "hey, Chad" and he turned back to me from his phone in time to see me chuck the dollar coin down into the canal that bordered the house.

Chad punched me in the face (i deserved it), and then dived into the canal to look for it. I put the real ring on top of his wallet which was on the table inside and left while Chad dove up and down in the canal to find his ring.

Uncle Fred thought the whole thing was funny when he got back, but Chad and his family haven't spoken to my family since.

Image credits: LordXeeloBob


I have a good one, I interned for this wealthy CEO in Houston. He was traveling to Mexico and had forgot his laptop which had all of his stuff that he needed on it. He called the company and asked to have it sent to him, they said it would take 3 days to ship it even with priority. He paid me $500, plus a plane ticket, and for a hotel for me to stay in for the night to fly his laptop down there so he could have it within 12 hours.

Image credits: mustangswon1

When it comes to who is acquiring wealth nowadays, it is largely out of the control of individuals. In fact, almost two thirds of Americans say that people become rich from having more advantages in life, and 71% of Americans believe that poor people have faced “more obstacles in life”. According to a report by Wealth X, many rich people did inherit their wealth, or at least got a huge head start from their families. The report found that people with over $100 million in net worth are expected to be responsible for over 60% of wealth transfers in Europe and Asia until 2030. And it's not much better in North America, where people at the same level of wealth are anticipated to be responsible for 38% of “passed-on wealth on the continent by 2030". Even if someone appears "self-made", they might have had generations of affluent family members preceding them.


My sister-in-law worked on the maid staff for a mega-wealthy (1+ billion) guy for several years. She was pregnant for a bit, then gave birth 2 months premature. You can imagine this was time consuming and expensive. The rich family gave her all the time she needed, and paid for the entire process (wound up costing over $100k). My niece is now 33 years old.

So my experience was pretty positive.


An old high school teacher of mine is an extremely successful private tutor and does a lot of work in the wealthy neighborhoods in the area. Once, he was tutoring a kid and helped him get prepared and pass his college-level physics class; at the end of their last session, the kid told him to wait there and went into his dad’s office and came out with his payment and an extra $1,000.
My teacher tried to refuse it, saying it was too much, but the kid said his dad asked him to give a tip


I was working (as an architectural model maker) for a developer who was trying to put up an ugly f*****g building in the middle of Mansion House London. Anyways he had this dog super special trained so that it would only obey his commands. So I was working on adding some stuff to a display in his office and the dog was under my feet, so I said really nicely 'Can you go lay down over there please?' and it did.

I was fired on the spot.

Despite knowing about wealth inequality, it can be hard to have an objective view on what is realistic for our future bank accounts. According to CNBC, over half of millennials in 2018 thought that they would become millionaires at some point in their lives, including 70% of millennial men. But the reality is that it might be much harder to achieve that goal than many millennials realize, as much of the generation is plagued by student debt and will be responsible for their own retirement funds. “They face an economic future with projections of lower rates of return and economic growth than in the past,” says a report from the Brookings Institution. “These factors make accumulating sufficient funds for retirement more difficult for millennials relative to previous generations.”  


Once as a caddy I was given a 20 minute lecture/demonstration on how to open a Porsche door correctly. Subsequently, I resigned the fallowing day.


Not work for, friends with.

Not a best or worst story, but an observation. My friend rarely demands special treatment. She's proud of this, and it's true.... but what she doesn't always seem to understand is that she gets it anyway.

Example: Kid attends private school. Multiple parents are grumbling about curriculum change. Head of school calls her to hear her thoughts. The HoS may explain "we were just checking in with some parents to see..." and Friend might believe that everyone is being contacted. As far as she knows, every parent is getting their say. But in fact, the school is not calling everyone. They may not be calling anyone else at all. She's being reached out to because she's a big donor and the school thinks they can't afford to have her unhappy. She hasn't threatened anything, she hasn't thrown her weight around, she hasn't demanded that they hear her opinion--but she's being catered to because the school respects her checkbook.

Multiply this times however many organizations and businesses all over the city, & you get a person who goes through life with a somewhat different experience than other people, but they're not demanding it, and may not even be very aware of it. They think everyone gets the kind of attentive service and outreach that they enjoy.


I briefly worked with one of the top Saudi Arabian crown princes in the '80s. He would buy out the top three floors of the best hotels (Four Seasons, etc.); two floors were for maids/help/security, and the top floor was for the royal family. Once it was only the prince and his three wives. Wild.

However, millennials are not completely doomed. Financial experts recommend younger generations start saving as soon as they can, with whatever amount is possible for them. Savings accrue interest, so starting to set aside $1000 a month when you're 25 can leave you with over $1 million by the time you retire. “People feel like, ‘Oh, I can’t start, I don’t have any money,’” Denise Nostrom, a New York-based financial advisor, told CNBC. “But even if you can do $25, $50 per week or per month — when you see it accumulate, it motivates you to want to do it more.”


Some family friends were having marital issues. Their marriage counselor figured out a lot of their problems were over cooking meals. The counselor reminded them that they are rich and can just cater all their meals, and it would be cheaper than getting a divorce. They listened to the counselor and now are happily married again.


I don't know if this counts or not, but my dad used to work directly under the CEO of a pretty descent sized construction company when I was in high school. I met him a few times, he lent me his lake house over spring break once, but I wouldn't say I really knew the guy all that well.

but when I graduated high school with top honors, he like took it upon himself to throw my graduation party, and bused a bunch of my friends down to his ranch, and had one of his pigs slaughtered (and then one of his cows, when he found out a lot of my friends were Jewish), and just threw this big a*s opulent party in my honer. I think he did that for a lot of people in the company, just because he likes to entertain, but it was still dope as hell.


I was a bank teller. Two stories here.

First: person my age, about 20, came in. Was a delight. He came in once a year to take his trust which was 100 million dollars, and take the interest out, about 48,000 dollars. Once a year. That's all he lived off of. He was content, and was modest. I loved it.

Second: girl came in with her mom. Actively whined at me for 10 minutes about how unfair it was her mom had all this money in her account and was making her live in poverty, with all her university fees paid, her rent and car covered, and she was only getting a tiny payment of $5,000 a month. She couldn't fathom surviving off it. The mother turns to me and says "well I don't know. I thought that would be enough to live off of? Should I give her more? " I meekly said "That's 60,000 a year. I make 20,000 a year, am going to college full time and have a baby on the way..." they both got really quiet and left. Never saw either of them again.

Also, Mike Tyson banked there, but I won't talk about that. You said only people who were wealthy. ;)

One interesting thing about wealth is that it's not entirely objective. Sure, there’s a clear difference between living paycheck to paycheck and having enough disposable income to take a trip to Greece ever summer. But according to most Americans, you only need to make over $100,000 annually to be considered “rich”. Of course, a person's wealth depends on the size of their household as well. Buying groceries and clothing for a family of five living in a two-story home is very different from providing for one person residing in a studio apartment. So to be considered “upper-class”, a household of one needs an annual income of over $78,000, while a family of five needs to make at least $175,000 a year.  


A coworker used to be a housekeeper for an ultra wealthy natural gas tycoon (~$100,000,000 net worth) and she said it was the easiest money she ever made. His daughter, who worked for him, frequently flew around the country for business and this guy would pay my coworker between 5 and 15 thousand dollars simply to accompany the daughter and keep her company on business trips that lasted a few days. Everything was top of the line luxury and all expenses paid. Private jet, 5 star hotels (she had her own room every time), 5 star restaurants, etc.


I used to work in a private school, and a few dozen of the students were children of the local super-rich from Bay street. One mother started coming into the school every day to visit the uniform shop and buy new uniform items for her child. This went on for a week straight before the shop attendant asked her if everything was okay, the child keeping track of their clothes, etc.

The mom responds with, "Oh, we're fine. It's just that our nanny is on vacation for two weeks, and I have no idea how to use the laundry machines at home." I was stunned into silence when the shop attendant passed that one along to me.


I worked for an upscale condo complex, starting at 500k and up, so most of these people were pretty wealthy. Most people were really nice, I got all kinds of Christmas gifts and even left over things I didn't care about like clothes and food.

Best story, I was talking to a guy about why he drives a beat up car compared to everyone else, it was like a 1998 Yukon, and he said his thing was jets. Then oreceeded to take me to his private hanger after work, showed me his 3 private jets and offered to fly me anywhere l, anytime I needed, just ask. Never took him up unfortunately.

The worst was a lady who was just never happy with anything we did. Just hated all employees. We were too nice, took too long to get her car, got her car too fast and was wasting gas, took to long to say hi, s**t like that. Everyone hated her. Other than that, these people were really cool.

It’s also possible that you are even richer than you think, in comparison to the entire world. According to a 2015 report by Oxfam, the 62 richest people in the world had a combined level of wealth that was greater than the combined net worth of the world’s poorest 3.6 billion people. While there’s no question that the richest individuals are extremely wealthy, the poorest people in the world are also experiencing severe poverty. To fall into the category of the wealthiest half of the world in 2015, one only needed to have about $3,210 worth of assets, which equates to about $3,915 today. For example, if you own a car, especially one made in the last 10 years, that’s probably enough to land you in the wealthiest half of the world.


When rich people want to buy a Jaguar in the UK, they get assigned a special sales person who is incredibly knowledgeable, meet in a special fancy office, and special arrangements can be made. This was my friend Chris's job; he had access to things that a normal Jaguar sales person wouldn't have. Once, a Saudi prince wanted to buy a new Jaguar that had been released, so they met up and spent a full day spec'ing the Jaguar out; the final price was, like, £125,000 for the vehicle. The factory had 16 different color options for this model, and the prince asked if he could sleep on it as it was getting late, so they set a time to meet tomorrow. The next morning, he decided to just order one of EACH color.
"They quoted delivery time, the prince agreed, and he was presented with ocean travel options, to which he said, 'What about air cargo?' In the end, 16 of the same Jaguars in different colors ended up being loaded on a plane and flown to Saudi Arabia — and the total cost was around £2.5 million.


I fell into a job that made me an apprentice groundskeeper for a man that owns a majority share in the local sports team. Best/worst? Nothing bad to say so far. It's been a year now. I barely interact with him but when I do, I can just picture dollar signs floating above his head. His wife is super nice and down to earth. They had an employee appreciation party and I blew up pool floaties with her and she talked about getting three pairs of glasses for nine dollars at the store. The best is being on the property five days a week and looking out over the water, listening to music. Also he has a daughter that comes by from time to time and uses the pool with her friends. I've gotten a raise and two bonuses since being there. The bonuses were my 80 hour paycheck, matched. And I guess every once in a while there's tickets to the ball game right above the dugout, but I really don't care about sports, so it's nice to go just for the novelty.

Edit: oh, also one time they gave me two six packs of beer to show thanks.


I worked with 3 men that were all worth well over 20 million and they were all so kind and very humble. I talked to 2 of them for hours ever so often and I couldn't get enough of their stories. One time, one of them sat down with me and sorted nuts and bolts for a few hours. He taught me about all kinds of different bolts and although it wouldn't normally be fun, It was amazing. Just having a self made millionaire taking the time out of their day to teach you about something so small is just such an awesome thing.

Being aware of all the devastating poverty in the world only makes it harder to accept that billionaires are simultaneously hoarding wealth. According to a 2020 report from Humana, “Getting the richest one percent to pay just 0.5 percent extra tax on their wealth over the next 10 years would equal the investment needed to create 117 million jobs in sectors such as elderly and childcare, education and health.” And as Humana India’s CEO Amitabh Behar points out, it should not be up to individuals to solve the issue of wealth inequality.

“Governments created the inequality crisis —they must act now to end it. They must ensure corporations and wealthy individuals pay their fair share of tax and increase investment in public services and infrastructure. They must pass laws to tackle the huge amount of care work done by women and girls, and ensure that people who do some of the most important jobs in our society —caring for our parents, our children and the most vulnerable— are paid a living wage. Governments must prioritize care as being as important as all other sectors in order to build more human economies that work for everyone, not just a fortunate few.”


Worked at a restaurant where a few of the regulars were the children of billionaires. After being asked how she has so much money, I once heard a student say, 'I told my parents that my tuition costs $500,000.' Another time, I was serving a table and was asked to bring a tray of 60 Patrón shots ($600 for a 19-year-old student). I must have had an incredulous look on my face because his only response to assuage my concern was, 'My father owns diamond mines in Africa.'


One of my boss' vacation homes were featured in architectural digest. I came across the article just after I received my "bonus" for working 90+ hour weeks for two months straight. It ended up being a $50 Amazon giftcard


I nannied for two upper class social ladder climber families.

The first family was much more well off than the second, and they were awesome. Paid for me to accompany them to Disney World "in case they wanted me to watch the kids one evening so they could have dinner." They ended up buying me all the alcohol and we got ridiculously wasted in Epcot and in our rental house every evening. They even paid me my salary while on the trip. It was fantastic, they were very generous and very sweet. I miss them and their kids a lot.

The second family was not as well off, but still fairly wealthy and they were awful. Passive aggressive notes about not doing laundry correctly (not only were they particular about the setting everyone's laundry was on, but the husband could not wash his own clothing, seriously had no idea how to work the machine), the kids were bratty and made comments about how I made the beds wrong (wtf kid doesn't make their own bed?!) and I need to correct it because "that's what our mom pays you for." They under paid me to not only nanny but "light house keeping" which turned into cleaning all four levels of their house every day.

They basically treated me like an appliance, had no regard for my time (would come home late all the time, no phone call etc but would passively aggressively b***h at me when I requested a day off here or there for school or family visits). It was super uncomfortable.

Oh also-the husband and wife of the second family had separate living quarters. Like, she had the master bedroom and bathroom and he had the "bonus room" above the garage with an attached bathroom. It was super strange.

And I off handedly made a comment to my husband that my employer seemed like the kind of woman who would have a surrogate carry her children as to not mess up her own physical appearance, and wouldn't you know that at least 2 of her kids were carried by surrogates (her kids confirmed it, but they also told me not to say anything because it's a huge secret). I know that makes me sound very insensitive, but the amount of importance that she put on appearances made it plausible.

It’s almost impossible to even comprehend the wealth of the world’s richest people, especially those in the top two slots: Elon Musk and Jeff Bezos. However, there is one website that can help you understand their riches a little better. On Simple Texting’s blog post “How Long Does It Take Tech CEOs to Earn Your Salary?”, visitors can choose one of 14 tech CEOs and insert their personal salaries, mortgage payments, or student loan debts to see how long it takes these CEOs to earn that amount of money. For example, if you earn $100,000 a year from your job, Elon musk earns that same amount in only 23 minutes. He also earns $260,736 per hour and over $6 million a day. Jeff Bezos, on the other hand, earns a modest $149,353 per minute. These numbers are hard to conceptualize, but they make it understandable why some people pose the question, “Should billionaires even exist?”


My dad used to work for a private airfield. They had a ton of people fly in. but most of the richer clients always flew in at night. One time in high school, I had to do a 'job shadow' thing and went to work with my dad. They had the owner of a California airport fly in for the weekend, and my job was to stand outside with an umbrella. His wife tipped me $20 and said, 'The sandwich trays are real silver — have at it, kid.' After they got in their car, I asked my dad what she meant. Apparently, when some richer folks fly, they let the people who detail their planes have the platters and other serving items. I always wondered how we got so many weird serving trays.
"Another time I visited my dad at work, I got to hold an albino kangaroo. Most adorable and softest animal I've ever touched.


I used to.

Nothing really bad, with the exception of thinking that because he paid me marginally above minimum wage, I was his f*****g slave. Due to this there was a steady increase in daily expenditures.

He didn't usually sweat the small s**t though, except for the time I got into a fender bender in one of his cars I used for work. Literally a dent in the pass door, that could be popped out, with no paint damage. He threw a hissy fit, and I was like, f**k this, I'm out. A few weeks later he apologized and hired me back, because no one else could tolerate him.

He is a mostly decent guy, we got along fine otherwise.


This was ages ago; I worked in a DVD store, and a woman came in with five, double-sided A4 pages of movie titles and just asked me to fetch what we had. I ran about and collected DVDs and Blu-rays close to $1,000 worth. I asked what they were for — she was a PA for a billionaire and getting them for his yacht.

There will always be people flaunting their extravagant wealth and others with much less in the bank working for them. But clearly, as the stories on this list show us, money can't always buy you a great personality. I'm happy to live a modest lifestyle where I never have to worry about personal employees sharing crazy stories about me on the internet. Enjoy reading the rest of this list, and don't forget to upvote your favorite posts. Then let us know in the comments if you've ever worked for a wealthy person or witnessed ridiculous displays of affluence, we'd love to hear from you!


I worked for a super wealthy russian family.

I had (mostly) only good interactions with them, but I had the benefit of being an american. They hired a maid from nepal and were terrible to her.

At times, their wealth would be super apparent, but at other times, when we'd be stacking firewood or foraging in the forest for mushrooms to cook that night, I really never thought about their money.


I worked for a guy who is approaching billionaire status. Hes a complete a*****e. I wont say what business he is in but he flies around in his jets visiting his businesses every few weeks. He is also major booster for a big college. His kids are OK, one is a party hound / coke head. The other is poised to take over the corporation. He treats his employees like complete s**t, only seeing them as dollar signs. If you aren't making money for him you are expendable. His employee turnover rate is huge. Managers can expect to be out of a job within 18 months (keep in mind he has over 40 stores that are managed). He is also the biggest chauvinist I've ever seen. He hits on every woman he comes across to the point of many lawsuits, which he doesn't care about, his accountants write checks. He once told a black guy that a monkey could do his job......he had to write a check. His quarterly meetings were all about how great he is and how we should all be like him and work 80+ hours a week. I don't miss that piece of s**t.


I don't "work" for him exactly, but I have a startup and our investor is a multi-millionaire that owns the first facility outside of China to mass produce L-Arginine as a supplement, as well as a large private labeling company for supplements and a huge packaging facility. We get to use his facilities at cost, and he frequently comes along with me when I'm going to oversee a manufacturing or packaging run of our products. It's weird when I get to catch glimpses of him outside of his office, because he is in no small way a "bro" deep down. I went to his house last week, and he had random things like a fridge that was a dedicated beer tap or tacticool AR-15s laying around mixed in with all of his typical old-money commodities. It's weird, because I see him as an older, more mature business man/scientist but the moment that he cuts loose he lives essentially the fantasy life of a frat bro.


i worked in a think tank sponsored by a billionaire. I was working late one night when he came in, and he asked: Those coca-colas in the fridge, whose are those? I said, they are mine, but you can just take one. He then handed me 20 Euro's and said thank you. Brilliance was: I only bought those coca-colas and kept them in the fridge, for if a client or someone important ever would want a coke :)


I used to work for a billionaire Russian family as a tutor for their daughter. One day, we’re in her room studying, and suddenly, she yells, 'Daddy’s home!' and runs to the window. She’d heard a helicopter and knew it was about to land on the lawn.


I worked for a large travel agency in my city, where I was employed to do IT work.

It was exciting because it was my first real IT job, and I had a lot of fun doing it. The experience I gained from that job has been and continues to be invaluable.

Unfortunately, it wasn't the best place to work. I worked directly with the owner, and he liked to micromanage to the point where it was impossible to work independently. He was not a big fan of technology either and felt that he was 'forced' into the internet age, so he treated me and my team very poorly. Many of my coworkers were very disgruntled about this, myself included.

The worst part was, after nine months of working there, the boss decided to quite significantly CUT my pay, citing that I had 'cost the company money and time' due to a mistake that was blamed on me that I had no part of; Long story short, a client was mad when they missed a payment date and their booking was cancelled. Instead of calling the customer out, my boss pointed the finger at me.

At that point I'd had enough. I quit without bothering to give notice, and the rest of my team soon followed suit. I last heard he had to hire an entirely new IT department; I wish them all the best :)

As for those of us that quit, we all got different jobs; though I'm actually self-employed.


I worked for an owner of the biggest strip bars in Canada, probably worth about 300 million now(yes he owns a lot more than the strip bars) and one night right after 9/11 he came in drunk and made me shut the music off on a busy night to start singing these serbian songs over the mic, being on the US/Canada border, there are usually 90% americans in the bar at any given time. When the customers started saying "put the music back on", he responded with "go to your new york city and listen to the taliban music theyre playing there for you now"....I was shocked and worried about what was going to happen to him after that so I just went to the bar and sat down and had a beer like I was just a customer. Luckily they just started leaving instead of lynching his drunk a*s...


Not me nor my friend but my friends friend works for this, what I can only describe as borderline bond villain if not for how silly he was, so more of just a bizzare eccentric millionaire type. Anyways, my friends friend more or less gets paid something like 500,000 a year to perform bizzare tasks and errands, for example there was an instance where he had to drive the guys 800,000 dollar car across a couple states because he didn't want to pay to have it moved because he didn't trust movers or some s**t. The guy was strange but hey that's a sweet gig until you're asked to bury a dead hooker.


As the butler for a billionaire family, you need a strong stomach to put up with the insatiable needs, voracious appetites, and non-stop whining the rich are capable of. Not to mention their lack of appreciation for anything anyone does for them. On the other hand you might be lucky enough to work for a kindly family that treats you well, although it's rare! But overall, I'd not recommend private service as a wholesome career. Better to work for the rich in a luxury hotel where they come and go quickly!!!


Super weird stereotypical rich guy. Enormous house with an enormous collection of Asian art, and he would always walk around in a silk robe with slippers on. His son's room was roughly 100 yards away in the guest house with a massive sh*tton of expensive electronics and guns. I couldn't believe my eyes.


Worked for a company owned by a hundred-millionaire up until recently. I heard back in the early 2000's from one of his insiders that he crossed over into billionaire status with the tech boom, but I think he's back to a measly hundred-millionaire again. I can't even mention some of the stories of his legendary cheapness because they're too specific, but he would get involved in issues over a $500 loss at times down through multiple layers of management. Nice guy generally and easy to deal with, unless you f**k with his money somehow. I heard that he made a sorta bet with a VP once when the VP was bragging about his investment skills, he provided something like 1M, the VP was to invest the money however he saw fit, and would keep a percentage of what he made, and owe all of what he lost within a set period. I heard that he lost a lot of it. The guy wasn't a VP much longer after that.


I worked at the home of a millionaire (supposedly around $100-150 mil). Just did property management at their home and different vacation homes. They paid me very well, and treated me more like a friend than an employee. They were the nicest family you could ever know and lived their life just like a normal middle class family. If, or should I say when, I get to be as successful as him I can only hope to be as good of a person. The only thing that I never understood was their favorite thing to spend money on... Mardi Gras partying. They easily spent 150-200k on one day of partying once a year.


I worked graveyards as a valet at an ultra-luxury boutique hotel. It's quite shocking how some of these people live, and you'd never have a clue by just looking at them on the street. One weekday at 2 a.m., a guest asked to bring around his Bentley; he was a regular-looking dude, came out with a backpack, got in, and left. Not even 30 minutes later, the same dude pulls up in a Ferrari and now has a briefcase instead of a backpack. An hour later, he orders five shot glasses to his hotel room. I go up, and it's two guys in robes and two naked women on the couch. They have lines of coke and booze on the coffee table.
They tip me $50 for the shot glasses, and I leave. Two hours later, just as the sun was rising, the two guys come out together in suits looking like they were heading to the office. The women left shortly after. Drugs and sex workers were nothing new, but the car swap middle of the night was a bit strange.


My buddy was dating this girl with insanely rich parents. The dad was the breadwinner and the wife only drank wine and decorated their amazing 5.000 square feet prime location apartment. One day she felt she was "done" with the decorating and complained that she was now bored.

Daddy solved this by simply buying the rest of the floor and knocked down some walls. So now they have a 10.000 square feet apartment and she can keep decorating. To give you a sense of scale i'll tell you the carpenters doing the renovations played basketball in the entrance hall on their lunch brake...

I guess when she's "done" the next time they need to buy another floor and build some stairs...


Have some family members who are in your wealth classification range. They are very nice and very down to earth. They don't go flashy in very many things but do enjoy the amenities of wealth, for example, they have their own full staffed kitchen/restaurant building on their property. Shoot, they have a service elevator to get to the pantry for the restaurant thingy. Plus distant relatives, and their landscapers, cooks, cleaners etc. families are welcome to go swimming in their pool and ride horses on their property.
Some other, less than standard thread wealth, I know will commonly have basketball courts or football fields inside their homes (generally NOT full size of course). Some of those families had children grow up to play professional sports, so money was never an issue to some of these athletes at any point in their life.


Not me, but I know someone who dated Stanley Kubrick's daughter (I assume he was quite wealthy) and he got to see some of his films before they came out officially.


I'm a driving instructor, and one group rented the track to drive their supercars for the day. At the end of the day, they all partnered up and got into their cars to leave. After they were gone, we realized that they had forgotten their Lamborghini Aventador at the track.


I used to ‘work’ for an Arab billionaire’s son, a 'Daddy’s money' guy and terrible, garbage human being. Once, saw him spend $16,000 on a wallet...a fancy one with little gold spikes on it and stuff. He had shoes with gold on them. One year for his birthday, he received, like, 30+ cakes — big fancy cakes — and he told us to leave them on the floor in the hallway outside his room."
We walked by those cakes every day for two weeks waiting for instruction, and after the two weeks, we were told to throw them away.


My dad works in shipping and has a lot of friends who have worked on super yachts. In the '90s, one of his mates got a call to bring the yacht of a particular Australian media tycoon billionaire (not that one) from Sydney to New York — with instructions to be anchored in a particular bay at an exact time with a lunch spread for 50 people ready. So, they got there, set up the food, and the guy never showed up. Turns out, he was having a rich dude party in a building overlooking the harbor and just wanted to be able to point down and say, 'That’s my boat.'
He wanted the lunch in case he decided to take his rich friends down to his yacht, but he didn’t feel like it that day, so all the food got wasted, and they sailed back to Australia without seeing him.


I used to work for a company that modified aircrafts for really rich people. (I’m talking 747s, not Gulfstreams.) This company had made several aircrafts for this one customer, who purchased a new one solely because his spiritual advisor had told him that one of his current planes was bad luck. He still let his wife use it for her personal travel. To me, one of the most exquisite features of these planes wasn’t the gold-plated everything or rare wood veneers — it was the silk carpet.
"That stuff cost over $1,000 per square foot and feels like walking on a bed of angel feathers harvested in the most inhumane way possible. Granted, these guys don’t deck out the whole plane, just their personal areas (the aft third is usually reserved for staff and such, and is more like a fancy economy class), but yeah…silk carpet.


My dad is a mid-level hedge fund manager, so he's probably worth like 8-10 million, but some of the higher ups at his firm are probably worth nearly a billion. I also go to private school, so I've been exposed to my fair share of super rich individuals.

Rich people are weirdos. Everyone has small quirks and odd habits, but for the ultra rich, they can actually alter situations around them so that these strange desires can always be fulfilled. To give an example: founder of my dads firm, probably worth around 900M, refuses to get gas in his car. This guy is totally self made, grew up poor, and obviously had to deal with getting his own gas for a while, but now he just has his 'butler' do it. This 'butler' is more his personal assistant, managing his other house employees and making sure everything is to his liking. Hedge fund billionaire has 6 different cars, but only likes driving his Porsche Macan, so he has two identical ones of those. Just alternates them every few days so his butler can always keep one gassed up. Other than that he's a super nice, down to earth guy, always very generous by giving gifts for my birthdays and bringing stuff when he comes to my house for dinner, but he has this weird hatred of gasoline.

Another funny story about these hedge fund managers that always makes me laugh- the top 20 or so at the firm do this big gift giving every Christmas time, where all of them buy around 10,000 dollars of something, usually high end alcohol, which is put into a big pool and split up between them. Last year, my dad contributed a ton of fancy champagne, and he received around 80 bottles of champagne and a bottle of high end scotch. However, my dad doesn't drink much champagne or scotch, he's more of a wine guy, so he took it to the liquor store and traded it in for wine (they valued all his champagne just over 10k). When he was talking to one of the other top guys, he said that most people ended up exchanging the alcohol for stuff they wanted, because no one drinks that much champagne, but everyone sees it as the most traditional gift. They also realize it would be awkward to just give cash or gift cards, so they go through the hassle of buying a ton of alcohol none of them want that ends up all being exchanged later.


I'm an art student working as a gardener. We work in one of the wealthiest areas in my country. Some customers are really eager to show me their collection of artwork that they have hanging on their walls once they find out that I study it. I remember one time standing in a bathroom — with my dirty gardening clothes — and there was a Picasso above the toilet.


I work for an estate planning law firm, and we have a lot of wealthy clients that come to us for wills/trusts. Our attorney always does his little spiel about how he would suggest leaving the money in a trust that pays out every few years rather than giving money to kids outright, because a young person suddenly inheriting millions might make poor financial decisions.

Cue one couple, who planned to give each child $50,000 at age 16, then $100k at 20, $100k at 30, etc., until 50 when they could withdraw the whole inheritance. My boss kind of hesitated and said he wouldn't recommend giving fifty thousand dollars to a teenager, and the husband goes, "It's just $50 grand, what'll it buy, a car?"

I was thrown until I went through their list of assets later on. The *cheapest* car they owned was $72k.


I used to pet-sit. I remember a rich person asking me to watch their cat. There was a lot of TVs, in almost every room. The weirdest was the bathroom — sorry, the cat bathroom. There was a TV playing cat cartoons, an overly fancy litter box, and paintings of cats.


I worked in landscaping for one of the wealthiest people in New Zealand, his property is the most expensive ever sold here at 15 Million NZD (it even came with a Maserati). He and his wife own some businesses, he never really talked about what they were.

Super chill people, never had a negative experience with them, even when I interrupted him smoking what i assume was weed (may have been a legal high). He just laughed it off.


I've been working for the super rich for sometime. Wildest thing I've seen was a brand-new 90-meter multimillion-pound (GBP) yacht that was built in Netherlands. Maiden voyage to Antibes in France. The owner came on board and left after a few hours. Next week, we got sent to Genoa, Italy, where all the bathrooms on board were ripped out and upgraded. I'm talking about brand-new marble sinks, showers, floors, and lobbies all crowbarred out and chucked in skips. New, polished marble colors and patterns arrived in the weeks following."
"There's feed-me money, there's f**k-you money, and there's it's-not-even-a-thought money.


I became personal friends with my boss and his wife; they were super-nice people. The wife turned out to be an heiress and would buy me whatever I mentioned, like in passing during a conversation. I learned gifts were how she was raised to show love. I’ve trained myself to only talk about things I already own, unless I find something useful she might like and suggest it for her.


I used to work in the diving sector - mostly military and research diving, we have had one special customer from saudi arabia, who was worth millions over millions probably billions, I am not sure.

Well how ever, he bought a mini ROV for underwater use (he did not want to dive, so he used the roboter which is made for usually biological research, just to look at the colourfull fishes). The thing itself is worth about 200k €.

How ever he also bought some safety equipment for his yard etc.

Well to the story.

This dude wanted us to do the service for the equipment, all over it would take about 5 - 6 hours.

Well he said no problem I pay for a week, make sure your technician is at the airport when I say it.

So our technician went to the airport got picked up in the private jet, worked there 5 hours and could dive 4 more days on a private beach where nobody is allowed to dive or do anything and was flewn back then.

This guy was the most friendly rich dude I ever met and he was really nice to everyone not just people he wanted something from, sure he was a bit crazy when it comes to investments, but what ever he had the money.

BTW this is/was his ship, sadly he died in 2011 or 2012 I think

If you do a bit of research you know who it is I am talking about.


I worked for a very rich man who owned a string of retail stores. I was a college student and one day I went to work quite ill. The owner insisted I visit an Urgent Care center. When I returned, he asked what had transpired. I replied that I had a sinus infection, etc. and that I didn't fill my prescriptions because they cost too much money. He pulled out his wallet and peeled off a $100 bill and insisted I go straight to the pharmacy. I repaid every penny, but I never forgot how much it meant to me that he cared enough to send a lowly part time college student retail worker to Urgent Care then take the time to follow up to see if I was okay.


I worked for some guys who were probably in the 5-15 mil range. They paid me to do ridiculous s**t. One guy paid me $150 cash to put lights on his Christmas tree since he and his wife always fought over how to do it. The damn tree was 12 feet tall and it took me a while.

Another one paid me to be his designated driver for holiday parties because he was making a run for governor. So basically I chauffeured him around in his Range Rover and hung out at his multimillion dollar home while he was boozing it up with other socialites.

These guys seemed to live in a world that was completely different from mine, but the stress and responsibilities they put up with were also more strenuous.


I befriended and stayed with the daughter of Russian oligarchs who lived in Paris. The mom was a famous writer, and the dad did something in business. Their grandfather was a famous Soviet writer, and so in general, they lived a very cultured life. They lived in the richest part of Paris called Neuilly-sur-Seine and had houses in the Alps, Crimea, and Moscow. The rather sad part was that the daughter only had a few options for a career; she could be a doctor, a lawyer, or a businesswoman. In this family, if you didn’t have a natural artistic talent, you only had those three career prospects to chose from.
Their son was lucky enough to study at the Geneva Conservatory, but that was only because he was really talented. I had the impression that the daughter was rather depressed about how limited her options were and how much pressure was put on her to succeed.


I'm not sure of their net worth, but my aunt and uncle are easily worth multiple millions of dollars. My aunt used to be CFO/Vice-President of a well-known home goods/wares/furnishings company, before transitioning to be CFO of a major electronics company. My uncle was CFO for a scientific equipment company, before retiring when they were bought out. He retired in his early 50s and is not planning on ever working again, because he doesn't need to.

They live in Minneapolis in a huge, beautiful condo. They own an apartment in Chicago that they visit maybe a few times a year, but allow friends and family to use whenever it's free. They're building a house in Palm Springs, and have invited my family to spend Christmas 2016 there. Every Christmas they give each family member some amount of money (the lowest amount given to my family members was $1,900 to each of us kids, the highest was $10,000 to my grandma). They also give expensive gifts and gift cards, even to significant others. They bought me my first college laptop, as well as my sister's (and I assume they'll do the same when my brother attends college next fall). They paid off my student loan debt after I graduated, as well as paying for my grad school. They paid my sister's way through undergrad, and are now paying for her to go back to school to get a second bachelor's. When I was 17 and my sister 15, they took us to Rome and London for a week on their dime, and this summer they took my 17-year-old brother to Paris, London, and Rome with a friend of his. They do all of this for my aunt's side of the family as well (uncle is mom's brother, aunt by marriage), and her side has way more people on it.

They are two of the kindest, most generous people I have ever met. They will help in any way possible, not just monetarily, when called upon. They have both reviewed resumes for me, assisted with job searches, helped my sister get a wonderful internship with St. Jude's, and have supported and encouraged every family member in some way. Their basic philosophy is that it makes more sense to spend their money on the people they care for and love now, than to give it to them posthumously. That way they can enjoy it too.

tl;dr: my aunt and uncle fit this bill (heh), and are generous, kind, loving, wonderful people.


I tutored a wealthy 5-year-old. I got paid good money to spend an hour drawing, coloring, and playing with this kindergartener — but all in French. He had been to more places in the world by 5 than I’ll ever go to in my lifetime, probably. The best part of the job were the perks, though. They would take me and my S.O. out to dinner at fancy restaurants and pay the bill no matter what it was. They would invite us over to eat some delicacy they prepared, and they’d always have some house guest staying with some wild résumé; for example, one time they had a diplomat for the Netherlands there to do business.
They also had houses in my city and in San Francisco and would fly there all the time. I was invited on several occasions, but I never had time to go.


I worked for an attorney who is worth around 20+ mill. These guys deal with a lot of frustrating people and situations. So when my boss fired me for buying the wrong printer paper for the office, I was less than surprised. It's tough, you have to be on point all the time.


Last job I worked at the founder was a billionaire, and all the initial MD's were worth $10mm-$300mm. Founder was really cool, multiple houses, his own g6, etc. There was a company event at his main house, but by the guest house. His estate was so massive we couldn't even see his actual house from the guest house (which was much bigger than most normal houses). The other MD's had varying personalities, some were nice, some were a-holes. They were all very demanding and perfectionists.

I remember one of them coming in on Saturday to work, and his 8 year old daughter called because she wanted to play with him. He explained that he needed to work so he could buy all the nice things she likes. She said that she didn't want anymore vacation houses or yahts, she wanted to see him more.

Current boss is a billionaire and co-founded the firm. He and two other co-founders tried to buy the Clippers a couple years ago, but were short of Ballmer. Good guy, but very conservative. Not nearly as much as a perfectionist as the last couple people i worked for. Donates a lot to charity.


My grandfather died with a $20 million portfolio. He lived in a one-bedroom condo that was build in the '50s, drove a rusted-out Honda, and his entire wardrobe came from Walmart and was 10 years old. At his will reading, a bunch of distant relatives showed up hoping to get a piece. In his will, he made fun of all of them, then spent 10 pages detailing how and where he wanted all of his money donated to specific charities and foundations.
Some of it was even really surprising, as nobody besides him was aware that he casually owned 160 acres of land in Vermont that was just forest. The land was donated to a land trust, and turned into hiking trails.


The biggest thing is you run on 'their time'. They show up/leave when they want.


I can't quite say directly but I worked at a bike shop in a very wealthy part of New York. There were a lot of rich people coming in and they were often in two categories.

The first category would spend hours in the shop trying out every piece of equipment and clothing we had in the store before purchasing a single item or nothing at all. These people could be just mildly annoying or quite infuriating. One woman who was married to a man worth $70 million wanted to get the exact same bike she had already so she could give it to her brother who really liked her bike. I looked around to see if we had it and she asked about another bike that was just the same manufacturer and the same color. I just said it was a different bike than what she was looking for so that I could get back to looking for the bike she'd asked for. Then she got upset with me for not knowing anything about the bikes. You were very specific about wanting the exact bike you were asking for so I thought you wouldn't be interested in any other bike! Next time she came in with her father, she pointed at me and said "that's the one you don't want to talk to about bikes". Jeez, lady.

The other group just seem like ordinary customers but they smile and crack jokes. The are just overall pleasant to be around because you can just have a conversation with them rather than work but if the store is suddenly busy, they'll let you take care of other customers; they're in no rush and don't want to rush you. One man went around and gave every employee a $100 bill after we just swapped out his handlebars.


My boss is really chill. He treats everyone with respect and is always ready to learn something from someone. No superiority complex or unethical beliefs. Genuinely seems like a decent guy. Made me not trust him at first, as I assumed anyone that rich that's that nice is hiding something, but he's really genuinely a good person.


A friend dated a girl who's dad was worth about 2.8B. This was nearly 20 years ago. When she turned 18 (driving age in our country), she asked for a car. He bought her a second hand Golf or something. We all expected a new Merc or something even nicer, but no. He was like "Well, all you're going to do is scratch it parking or something. And anyway, you're 18, you need to have some room for improvement and not just start at the top." We laughed quite a bit. He also made a point of always being home for dinner. I guess he'd go back to work form home after.


after graduating from university in 2012, i moved to southern france to work on megayachts for the super wealthy and famous. one of the biggest yachts i worked on was [silver angel](

after my visa in europe ran out, i came back to the states and worked on two other private yachts for families with a net worth in the hundreds of million and billion usd. what was fascinating was how money wasn't an object for some things, but they freaked out over other little costs.

the first family i worked as the chief officer on their 120 foot long motor yacht that had 6 guest suites and 4 crew cabins. the funny thing is, they only used their yacht one day a week for lunch on sundays. every sunday they would show up with their entourage of butlers, maids, and private chefs to do a 3 hour lunch cruise. best part of the job was i had 6 days off a week, paid a full salary with benefits, lived on the yacht so had free room/board with one of the private chefs making us every meal. they also consumed exclusively fiji bottled water--everything from their lemonade to the water the pasta was boiled in all came from those damn square fiji bottles. the biggest time i ever got chewed out on the job was when i filled their dogs water bowl with tap water and was promptly and forcefully told that if i ever gave the dog anything other fiji bottled water i would need to find another job.


I worked for a guy who had some pretty major stakes in the oil business, he was pretty cool, but very weird about his money. He wanted these crazy projects done but he always hired local kids to work for him, I was his landscaper (only had a 2 year landscape degree at the time) and didn't make all that much money.

His wife owned like 100+ sheep, just because she found it fun.

His entire basement was full of survival supplies for when the world ends.

He once asked me to price out installing a helicopter landing pad in his backyard in case anyone ever has a heart attack at one of his dinner parties.

He had a second house on site, which he used to house his German Shepherds.


I worked for a very wealthy legally blind guy who owned a Tesla Model S. He couldn't drive it and his chauffeur drove him around in a different luxury car, so it was a bit bizarre that he owned one.


I used to do pool and spa maintenance in my 20s. I worked on one property with a mountainside, 10-bedroom, 14-bath mansion with a saltwater pool, tennis courts, a guest mansion, and a servants' house that was 4-bedroom, 5-bath. The property had so much more stuff, but here's the wildest thing: I worked on this property for two years, year-round, five days a week, and not a single person was ever there. The middle-aged, single woman who owned it lived in a city about four hours away and just didn't come to the property, because she was so busy with work. A multi-multi-multi-million dollar compound, just empty. All the time.
"Finally, after two years, my boss called me on my day off and asked if I could go to the house to put some pool floats away. He apologized, because it was my day off, but said the owner would pay me $500 for the job. I was confused as to why there were even pool floats out anyway, because nobody was ever there, but I figured why not — $500 for 10 minutes. I show up to the house, and the woman's adult children were staying at the house with about 10+ kids between them all, and they were having a massive pool party/cookout. I awkwardly walked up and said to one of the parents, 'Sorry, it must have been a mistake, but I was told to come put pool floats away, but you're obviously here so I'll leave.' The woman's adult son said, 'Oh, no, we're getting ready to leave. You can take them.' Then, he instructed the kids to push them toward me. I literally grabbed one inner tube float and four pool noodles, brought them 10 feet into the pool house, and put them away. Then, I told them they were all set and went to leave. The son thanked me and handed me a folded mass of $20 bills; it was $400. I was expecting $500 from my boss for payment, but I figured $400 cash was still overpayment, so I didn't mention it. The next day at work, my boss gave me $1,000. I told him the son had already paid me $400, which was fine. He said the son told the woman how great a job I did, so she wanted to pay me $1,000 instead of $500, and the $400 was a tip from her son — for 10 minutes of work. She actually called my boss the next day to ask if she should reimburse me for gas, since it was 15 minutes from my house. I told him that I was all set.


I have a friend who is worth several hundred million. He's a super nice and generous guy. You'd expect him to be conservative (wanting tax cuts and such) but he's not. He grew up in a country with universal healthcare and believes we should have it here in the US.


I do masonry work. We were doing a backyard bbq, pizza oven, and an indoor remodel on a restaurant owners house. Half way through the job he gets arrested for possession of cocaine. Still rich enough we continue to work and get paid for it.


My relatives have a few million, and they think they are the super rich. They had to live on a boat for years to afford to build their house. I just got an email from his wife saying they were 'on island,' meaning they are at their beach house. Who talks like that? Oh, they are so annoying, new money and no class. They don't know that people just don't talk like that. You should see the photos of their trip to Europe (which of course they had to send to everybody as a brag, and not even a humble brag). My mother and I called it "the Clampetts go to Europe". People with big money don't act like that and they don't realize how foolish they sound. Most super rich are careful to be humble and gracious. Everything they brag about are things I grew up with, so it's just bad taste to me and my family who laugh at them. He'd still be broke and working at my aunt's restaurant if his brother hadn't set him up in business.


I worked for a guy that was worth about half a billion. Incredibly complicated individual. His flaws and greatness were so tightly bound up together, that you couldn't tell what was good and what was bad.

I think he was bi-polar. His mood swings were terrifying. He really was a genius, but he had a peculiar "outsiders" understanding of everything. His emotional impact was completely separate from his physical existence. When he was angry, he filled the entire room, you couldn't see anything else. When we was calm, he as a 5'8" guy you wouldn't look twice at on the street. He built 4 companies from nothing. He lost everything 3 times after selling out to "retire".

Great stories, everything from schmoozing with millionaires to living in poverty. He ran drugs at one point to keep his company afloat, and later donated lots of time and materials to law enforcement for free. It was like working for Hemingway, he had been everywhere and done everything. He was still very human, but you didn't get to see that very often.

My favorite story is about technical terms. I was doing computer stuff, and we had a very peculiar disk layout on top of a lot of high end SAN. We started having problems we didn't understand at the time (we were overloading the back-end, but that wasn't clear then). I got called in, and spent 8 hours trying to get s**t working. He asked me what was wrong, and I told him "The partitions are screwed up". We got everything running again, and went home at 2 am, completely exhausted.

The next morning I walked into the office at 8am, and all of the partitions between the desks were gone. He had hired people, in the middle of the night with no planning, to come in and remove the cube walls. He later claimed that he was trying to improve communication, but the cube walls were only 10 inches over the desks, we had un-obstructed views of each other at all times. All of us technical drones looked at each other with wide eyes, dude was seriously hard core when he wanted something done.

He handled everything like that. He was all about extremes, sometimes insane ones.


I worked for a guy that started the young millionaires club for my city.
He owned several BMWs, Maseratis, etc. Parked them in the furniture warehouse, usually directly in the way of the guys trying to load up the office furniture orders (you know, the stuff making him money). Regularly he would go out on a networking lunch with local architects, designers, anyone who might specify the office furniture systems we sold (everything from cubicles, to wall systems to high end furniture made of alpaca hair) And he would show off by calling us mid lunch hour and telling us to specify an entire office, top to bottom, complete with 3D renderings and priced, before he got back from lunch. We didnt get paid for this.
There was a wage freeze for 3 years, yet he bought a $10,000 door for his office. (several warehouse guys walked in on him banging the VP in the conference room. He didnt see them tho. Made the monday morning meeting weird. Also made sitting with his wife at Christmas super awkward)
We would work a full day at below industry wages and have more work, so we would work an extra 6+ hours at no extra pay (or banked time) a bunch of us were looking into getting second jobs, so he made us sign a contract giving us a at a whopping $10 an hour when we worked past normal hours. As that was more than what we would make at a part time job. (His logic) I pointed out that this was against labour laws in our province. Magically our design group started being paid proper OT, and had to sign another contract saying we would not disclose this to anyone else in the company and i was magically laid off 2 weeks later. Apparently i didnt 'fit in with the culture'. Worst 3.5 years of my life.


Know a few people in 2-3mil category and a few in the 20+, one is an uncle who works as a CFO for a Renewables Fund, and the other being parents friends who inherited their wealth. Both are really nice, but my uncle use to race cars on the weekend, and often spent 30-40k a week on this hobby. I should also point out, he was very nearly declared bankrupt, I think this has actually happened again in the past.


Wealthy client dispatched his pilot to fly the private jet from Pittsburgh to DC to pick up a Rolex at a jeweler in Tysons Corner. It was a gift for wealthy Guy's wife - it was her birthday and he'd waited till last day to begin looking for the $22,500 diamond encrusted watch she wanted.


I once got to write a check for 3 million dollars. Just being the person who wrote a check that large floored me.

It was just an inter-account transfer check but I ostensibly held 3 million dollars.


Accountant here, I think what surpised me most was, most people who keep around a million in liquid are usually deeply spiritual, meditation/yoga/ follow Jesus but not church goers, well educated but not rational they nearly always follow their emotions, the funny thing is the poor and the rich are the same in terms of beliefs and lifestyles, rich people dress like poor people they simply could not give a f**k about fashion or television. I've never met a self proclaimed atheist rich person, that is exclusively for the Middle to upperclass the people who ARE preoccupied with current affairs and television, also most rich people I've met are self made business men, engineers,and farmers not inheretred wealth.


I used to work for a guy who owned a temp agency in Charleston, SC. As the owner of a temp agency, he knew how little working people made, but this didn't stop him from one day berating the two girls who worked as his receptionists/office managers (making $7 an hour) because his take-home profit from the business had dropped from $40,000 a month to $25,000 a month. I could see the Karl Marx silhouettes forming in their eyes as he spoke.


At former job, my boss came over to a group of young employees, me included, seeking commiseration about the exorbitant cost of maintaining a 100 foot yacht.


I worked for someone in the past who is close to that rich and maybe is. There is so much money in the family I don't think she really knows how much she is worth as there is unlimited money and much more will come her way anytime there is a death in the family. Her family is so messed up that the money just seems sad. It isn't really the money that messed them up but the money allows all the messed up people to make a lot of really bad decisions with very few consequences furthering the mess. They were the unhappiest family I have ever worked for. Every person in that family needed a year in some intensive therapy resort somewhere. They were very generous but they were also always suspicious that people were after their money. They were nice to me and the other workers but horrible to each other. The kids were absolute nightmares to their parents and to each other. It was just sad to see something (money) that can improve your life instead end up just making really unhappy people even more miserable.


Worked for a multi-million dollar company a while back. The owner/CEO was a super awesome guy. He would often come into the break room right before my shift started and make coffee and shoot the breeze. He was super humble and an all around likable guy.
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