I work in finance, so I know plenty of rich guys. Despite the stereotypes, many are pretty down to earth guys who just happened to luck out and be raised insanely interested in something very profitable. But the truly rich dudes, the CEOs and CIOs I worked with, are for the most part sociopaths

I can only speak about some executives I have met in my work life.

Almost all have been clueless, generally useless people with a clear focus on optics above all else. They throw some money at a bunch of stuff, end up with a return, and act like they “worked” for it. Then they give advice about how to “work”, as if their return wasn’t just a systematic result of having the money first.

Entitled, idiotic people.

My second ex-wife came from a very wealthy family. I didn’t hold it against her, because while they were superficial, judgemental, unempathetic assholes, she wasn’t. I was wrong. She was, it was just better hidden.

When I went to university in Regina, there was a very wealthy Indian family whose children I was in a peripheral social group of.

The daughter specifically was in several of my classes and often needed assistance, so I got to know her really well. Not “friends” but certainly “commonly seen together”.

I think she was one of the single most clueless people I have ever met in my life. She expressed, for example, surprise that we didn’t all have maids. Because “everyone has a maid”. We’d pressed her by asking if her maids had maids, but it never clicked for her. She just couldn’t comprehend that you could go through life without servants. (Not slaves, though. PAID servants.)

She was a genuinely nice person, but so utterly disconnected from reality that talking to her was often the conversational equivalent of an out of body experience. Her father was a decent man, too. He was “self-made” (in that he didn’t inherit wealth, just some privilege and contacts) and thus pretty grounded. He contributed to his community and was by all accounts a good neighbour.

His eldest son, Sunil, however, was an asshole, pure and simple. He would be just the kind of person that would turn into a “Fred Trump” once his father’s moderating influence was gone.

They don’t live in the same reality as we poors. I don’t mean that figuratively either.

Seriously rich?

Kinda hard to pin down where the line is. Like, I’ve never met a billionaire that I know of.

Most of the millionaires I’ve met, I didn’t meet long enough to have a fair evaluation of them. Not to the standards where I’m willing to make a claim about their state as a human being, rather than their behavior are that point in time.

Plus, other than one specific celebrity that I had only minor interactions with when I was dating his ex, it’s nobody famous.

But, while I’ll start with that guy, I’m not going to name him because not only would it pin my location down too close, it just seems rude because it would also mean the same for our ex, who was and is a wonderful woman.

That being said, he was a NASCAR driver. In our direct interactions, he was actually really polite, never crossed any lines, wasn’t an arrogant prick, never even tried to say anything shitty because I was dating his ex. However, indirectly, with how I saw him behave towards others, he had gotten to the point in his wealth that a lot of people do; servants become background noise instead of people. I’m not saying he was bad to anyone, he wasn’t. But he just went with the assumption that since they were being paid, no extra effort was needed.

And that is super common among people that can essentially pay multiple people a yearly salary and still have fuck you money left over

I was a nurse’s assistant, and did home health. It may or may not surprise you to discover that a lot of wealthy folks retire to the mountains, or near them. Plus, there’s always local individuals that manage to reach the kind of wealth where they have multiple people providing services in their homes.

So, with me being me, I ended up working for a decent number of that kind of household. Money can’t buy you immunity to cancer, or Parkinson’s, or Alzheimer’s, or much of anything else that I was particularly in demand for.

Overall, it was actually the less wealthy ones that were less than you might hope. The folks that ran local banks and made good investments, the lower end of the millionaire ranks. Enough of those were either dicks, or had family that were dicks, that it was noticeable. Usually family more than the patients or their spouses. The kids were usually more prone to being arrogant shits than their parents that had “worked” for the money.

Still, never anything where I ended up punching anyone! Wanted to a few times, but the statement that if they kept it up, I’d not come back either ended the problem, or I ended up doing exactly that. See, back then, I’m my area, male caregivers could be counted on fingers. Out of the handful, I was absolutely the strongest, and one of three that had serious experience and went beyond the basic education needed to be certified.

So, I could pick my cases if I wanted to. If I said I was leaving, it meant that they would end up with second or third best, and maybe someone that couldn’t physically hack the job. You get a 200 pound dude with severe contractures post stroke, it takes a strong caregiver to get the job done right, even with lifts and other gear.

Anyway, point is that when the person is the one that built the wealth, they tend to be decent to people, but still treat employees like employees, even when it isn’t necessary or useful. Like, handing something to a maid without saying anything and just expecting it to be handled, even if it wasn’t actually their job. That kind of impersonal thing.

And, not all of the kids were bad. But, when the kids of the wealthy were less than bare minimum decent, they tended to be outright assholes I didn’t put up with that shit after my early twenties, but i saw plenty of maids and groundskeepers and such treated like dirt. Most of the time, I kept my mouth shut because I ain’t fucking with someone else’s livelihood. I raise hell, and maybe they lose their job. Sometimes, I’d have a word with the patient or their spouse, or a more reasonable family member, but not usually.

But the higher end crowd, where the amount of millions started climbing to nasty levels, they were mostly really easy to work for. Much more relaxed, less prone to expecting perfection all the time, way less concerned about costs too. Like, one lady whose husband was my patient dealt with a problem with the van we used for transportation by just buying two more vans so that one was always going to be ready. If I said we needed “chucks” a whole damn pallet of them was in the store room the next day. That kind of not caring. You’d see some of the little m millionaires wanting to keep track of how many of them would get used. Not many, just some of them. But not the big M ones. They did not give a fuck about supply usage at all lol.

Now, one thing that seems good on the surface that the “little m” ones were prone to that the big ones weren’t was gifts and tips. It only applied to folks like me, where we have an ethical obligation that precludes accepting such things without extra paperwork. The really, really rich ones, you’d explain that, they’d say “of course”, and if they wanted to do something extra, the paperwork was handled before they did or gave whatever it was. The less rich ones were fairly often kinda dicks about it, like the rules didn’t apply to them, that the fact it protects us as much or more than them wasn’t important. Most of those types of patients were very generous, even the ones that are assholes. But it was the less wealthy ones that tended to think it didn’t matter, or that their desire to be generous trumped all else.

But, that’s the kind of thing the NASCAR guy was prone to. Not being a dick, just not really thinking about the people as people, and more like entities that exist for a function.

Mind you, he was a dick in other ways, hence the ex part of things. But they had business interests they still shared, so they had to interact a good bit. He’d only be in the area maybe five times a year, though, he didn’t live here, just had property here. So I may have just not seen him being a dick.

I think the only truly bad experience I had with folks in that wealth range, as in bad enough I almost busted someone’s face, was the son of a banker. He was the point of contact for the company I worked for, meaning he more or less called the shots.

Well, we were contracted for both of his parents. Generally, that meant two caregivers. But this fuckstick was prone to “sending home” a caregiver, but expecting the other one to still provide care to both.

Now, I came into the case after he’d burnt through a dozen or more caregivers. His dad wasn’t out of range for smaller caregivers to provide care to in a home setting, and didn’t need the kind of extras my bosses tended to reserve me for.

He tried sending me home twice. I let him know I’d have to contact my supervisor before I left. The first time, he didn’t raise a fuss. I called, she sighed, and told me to go home. The second time, he said to just get out, or he was calling the office instead. Fine, whatever, I just hit a pay phone and called.

Well, after that, my dander got raised. I made it very clear that if I got sent back, and he wanted me to leave, I damn well expected to get paid for my drive time and fuel expenses. Having already burned through a lot of the staff at that company (and a previous one), he actually agreed to that.

And then tried sending the other caregiver home a few days later. And then wanted me to take care of his mom as well as his dad. Which, I have no issues taking caren of multiple patients, I used to do nursing homes. And I have no issues with female patients, though some male caregivers won’t do it even if the patient requests or doesn’t care.

What I did object to is that not only did that company require an extra form to be filled out for a male caregiver with a female patient, but I sure as fuck wasn’t getting paid to do two patients. There was actually a different rate they’d charge, and I got better pay. But only when that’s what the contract was for.

So I said no. I reminded him that I was sent out for his dad, that me taking care of his mom might mean insurance wouldn’t cover any liability, and that the fee scale was different.

He pulled the whole “I’m paying your salary” bullshit.

I have no fucking clue how, but I kept my cool. Told him to call the company if he wanted to change the contract and plan of care.

The office said “just for tonight”. So, fine, whatever, the boss lady was incredible, and I knew I’d get paid the extra, so no worries

But, then I’m upstairs taking care of his mom. Because, you know, she hadn’t had anyone checking on her while he was swinging dick. She needed care, and I went to provide it after securing his dad. Made sure he was clean, dry, and safe.

This asshat starts yelling up the stairs at me that his dad was wet, and I needed to get to it.

I inform him that I’m unable to do so because his mom is in similar condition.

He flips his shit and starts crossing the line into nastiness instead of just being a generic dick that thinks his money is important. I finish up his mom’s care, come down the stairs and walk right to the phone and tell my supervisor she needs to find someone to relieve me or I’m going to walk. He’s ranting in the background, so she’s understanding, but we both know damn good and well there’s nobody else that can or will drive out there at 11 pm with no warning.

I turn to the guy and tell him that he’s going to need to provide care, and if he wants to talk to my supervisor, she’s right on the phone, and hand it out to him.

He doesn’t take it, so I drop it and start packing my bags. I’m past the point where I give a fuck. He’s screaming at the phone, then at me, then the phone, and I’m walking out the damn door.

Hit the character limit, will finish

I licensed some music to my biological brother’s company. After years of enduring abuse to protect what was my main source of income, he terminated the contract and ghosted me right before a major milestone for the business so he got to keep my windfall despite him already being a multimillionaire in his early 30s. Great guy.

I worked in middle management for a relatively unknown billionaire. I’m not sure just how rich he is but when I left that company in 2021 he had at least five private jets. I met him a couple of times. He was born into the wealth, third generation. He was a little on the clueless side. Definitely grew up sheltered (though at this point he was on up there in age). I didn’t get the impression that he was a bad person, but at the same time he’s not someone I would have entrusted any important decisions to, either.

His company is getting taken over slowly by grifters and cons. I don’t know if it will make it to the fourth generation.

I happened to go to school in a public school district that had both middle-class and upper-class families. My neighborhood was lower-middle-class to middle-class, so my neighborhood was dubbed “the hood.” The school district, likely due to donations and a good stream of funds from property taxes was just as good or even better in some eyes than going to a private school. Some of the rich families preferred their children going to the public school, as long as it was good, for the character. I grew up with this mix of friends.

Later in life, I’ve had jobs which cater to who these richer kids became as adults. CEOs and other execs of multi-billion dollar organizations and the like. Perhaps I’m good at it because of the exposure and how I’m not intimidated by them. Depending on the person, they sometimes appreciate being treated like a normal human being for a change.

In a nutshell, there’s new money and old money. As children, the new money kids were more normal, but a hell of a lot more fun. The old money, quite boring. Mainly because they were all the fucking same. Same hair, same clothes, same interests. They tended to be more elitist and lacking in empathy. Big surprise?

That somewhat translates to the adult versions. Old money rich people are incredibly boring. You see, rich people don’t have the same struggles as normal people have. Think of it this way: Imagine that money was like water out of the tap. You want some more for now? Just turn on the tap. Of course, it would be concerning if for some reason the tap didn’t work or that the water didn’t flow, but if it’s been so reliable your entire life, it’s not one of your major concerns. New money people also have that same tap, but may come from a family or background where things didn’t always work that way. The tap is still seen as this awesome achievement.

I’ve only gotten to know the richest people as an adult on a very superficial level. From what I’ve gathered, there are some that are perfectly fine with their boring lives, but only because they’ve found some line of work that they like. Those that haven’t tend to have secret vices and debauchery at a level a poorer person could never get away with.

They live in a completely different world. Imagine if the world you lived in conditioned you in a way in which you could only identify with other rich people. I suspect they are quite lonely. Boo hoo, right? Those of us who aren’t rich but are also lonely for other reasons have such ire for these people. But such is the way of things.

I’ll refrain from making more generalizations than that, as we’re talking about human beings. Everybody is different. There are exceptions to every rule. Some rich kids go on to become wonderful, dynamic people that happen to have the freedom to affect change in the world. Some grow up to become complete leeches on society. Just as you’d expect.

The biggest takeaway: Usually, not always, they’re actually pretty boring compared to normal people. The crazy stories you hear are actually the minority.

fucking lazy entitled assholes

Met 3 that you’d never guess we’re wealthy. They were kind and quiet folks, and tipped well…

The other 7 I’ve known were absolute abusive douchebags. Exactly the stereotype that would stiff tips and cuts people of on the road. Made the absolute worst bosses or lunch companions etc.

I think of myself lucky with the first 3… 1 was a very kind old WW2 vet, the others were bosses from different firms I worked. Amazing and smart dudes.

As to most of the 7 dbags, you wouldn’t want to be near… They are nice enough while they think you can give them something but they turn face as soon as they doing think you can give them anything.

I’ve known some that were just like the guy next door, you wouldn’t know. Down to earth, didn’t drive new or fancy cars, normal house.

I’ve also known a couple who were the opposite - nice cars, really nice house, etc.

I’ve seen assholes in both camps.

I’ve met 4 self made billionaires. They are alright, just very focused and no time for any distractions.

Kids of billionaires are a different story, it’s hard work to ensure they become balanced human beings.

I mean they range from selfish entitled cunts all the way to very nice people just like most groups. They just tend to be the first one more often.

I did high end installations in some of the most expensive homes in California. Some of them tell you to make yourself at home while you’re working in their house and some tell you not to touch any surface in their home with any part of your body at any point because you’re a disgusting filthy poor.

It is kinda hard to haggle on prices for services when they are having conversations about spending more money than you’ve ever had in your life on some ridiculous luxury in the other room and you can hear it all.

The only rich person I knew was, ironically, one of my two best friends who is the daughter of an extremely wealthy Canadian. She was wonderful even if a little naive and was always surprised enough at how differently people live that she would try to fix it. Probably an exaggeration, but if you did so much as tell her that a family she was staying at was saving money and using sporks instead of spoons and forks, she’s the kind of person who you’d expect to say “you can’t pay for silverware? In Upstate New York? That’s like Africa tier lifestyle. I’ll give you a thousand dollars to fix the issue, nobody should be living like this.” So she was kind of like a reverse form of uptight. She was also a devout Baha’i with Libertarian leanings, possibly with her father’s Masonic activities rubbing off on her, and aside from being made of money, was the most street-smart of us.