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’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 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.

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.

fucking lazy entitled assholes

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 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.

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.

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 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.