54 People Share What Surprised Them Most After Hanging Out In Wealthy Circles

Worked on Capitol Hill for 2 years. Had a congressperson tell me "We make the rules here, we don't have to follow them". That was 15 years ago, and I haven't forgot.

Edit: Todd Akin was the person.

Went to uni with a girl who had a billionaire father - she thought the average American made a million dollars a year. Told her the number was closer 60k and she glitched out for a sec and said 'that's half of my allowance'

Eye opening chat for everyone involved.

They’re not as smart as you might think. Definitely not as smart as they think.

I was briefly involved with a very wealthy woman, so I got to hang out with her social circle.

Most people I met who had money-money, whether they earned it themselves or were born into it, felt that being rich meant they were somehow special or gifted. And poor people, weren't. "If they were smarter/harder working, they'd be rich."

TL;DR: Rich people believe poor people deserve to be poor. It's a character flaw to not have money.

My ex-wife was in a wealthy family. Her friends were even more wealthy. I'm talking about the kind of wealth where I met a guy who had a room bigger than most people's apartments and it was dedicated to a single Egyptian vase in the middle. (I never asked why) I could tell you all sorts of weird stories.

With that said, what surprised me most about how they operate is that money is literally never a thought to them. Like quite literally.

Pause and take a moment to think about how money for the average person rules much of their life. They worry about bills, groceries, budgeting, etc. Now consider there are people out there who grew up never needing to think about any of that. For all intents and purposes from their perspective everything *feels* free.

Due to this, since money is not a factor, a lot of their thinking is around resources. Who are you connected to, what can you obtain, etc. and boy do they love rarity and exclusivity. That is their essential means of communication at their level.

It's never "how much" it's always "what do you want in exchange". Now that I'm thinking about this out loud, they essentially revert back to traditional barter trade, lol.

I could rant about them all day so I'll stop here.

Every extremely wealthy person I have ever personally known was incredibly lazy but thought that they were exceptionally hard-working, just oblivious about how much harder the average working-class or poor person is compared to them & how hard life in general is for people.

How little empathy they have for poor people.

Going against the grain here, and the intent of the question.


They have the same cross section of people as anyone else I met (anecdotally).


Some were lazy, some were hardworking. Some cheap, some prodigal. Some humble, some arrogant. Some were showy, others werent. There really wasnt a universal truth about them.

They're cheap about really weird things.

Corruption to them is not a big deal.

I married rich and I have a number of rich friends-in-law. Most of them aren't bad people. There's just these interesting breaks in reality because they lack broader context.

A friend didn't realize that steak was expensive, because they're parents have it so frequently. They thought is was similar to "meatloaf" or "peanut butter and jelly" where it's a commonly shared everyday food experience.

Generally, their critical thinking is pretty good. They've attended good schools their whole life. But at the same time, I think they can view themselves as *exceptional* rather than *privileged*. If that makes sense? Like they worked hard to get into good schools, but they also went to top high schools, access to tutors, academic legacies, and could focus on their education rather than working.

Similarly they can often be very emotionally sensitive. It's not a bad thing, but I think they're more used to having their feelings validated. So sometimes I've noticed they can lack the ability to compartmentalize. This isn't true for all of them. But it's probably a thing that they didn't have to develop coping strategies for.

I would say that despite that they've all obviously grew up super wealthy, the vast majority still refer to themselves as *Upper-Middle Class*. It's like because they only have *summer home* money rather than *yacht* money, that they aren't actually rich.

This isn't all of them. But one person in particular when they were in graduate school they were temporarily cut off from the family credit card. They had to make a budget for meals, and they absolutely didn't know how. So they went to costco and got a pallet of canned baked beans. And proceeded to eat them cold in their apartment. Some of that is certainly performative, but they're idea of not having money somehow became being an early twentieth century boxcar hobo.

How untouched they are with reality. A student spilt water on their desk at a school in Dubai. When asked to clean it up, she said “ana?” meaning “me?” And proceeded to call her nanny to wipe it off for her.

There are different classes of rich people and they don’t interact.

My friend works for 1%ers.

Nobody likes free stuff more than wealthy people.

Money is just this thing that's there; nobody is really fussed about it - mainly expenses when it comes to going out, or shopping.

It's like having running water - it's there, and perfectly normal.

You know how the average american is stupid enough to think that if they work hard enough, they'll be a billionaire? Well, that's about the same level of stupid that wealthy people operate on. The average wealthy person just doesn't understand how much luck they have with their connections and inheritance. Just as the average Joe thinks that everyone starts at the same base level and earns their billions, the wealthy think that the average Joe starts with a few million in their families and then make bad choices to lose their "opportunities."

I was trained by the Forbes program through a Relais & Chateaux property, and they straight up tell you that not only are wealthy people completely out of touch, the average person that comes into wealth will lose touch within 3 years. And it doesn't take *that* much to feel "wealthy." Once you get near $1M/yr you'll almost certainly start losing grasp on average prices and standard budgeting. You start equating your time with higher values, which heavily influences your day to day judgments.

They're right, too. Ever have a good paycheck or bonus and feel the relief of not having to look at the pump while you fill up your car? Imagine not caring about price of an entire *fleet* of private jets just because you don't know which interior you like more. That's a convo I've heard in the back of a car I drove.

And then there's guys like a certain "asset manager" firm owner who bought a historical mansion in town and gave his architects and contractors a blank check budget. This has resulted in many, many issues with historical preservation and local ordinances that are just done anyway with the fines paid. And since the property has become usable, he has since flown in several times on his helicopter, using his hastily built helipad, and simply paid any and all FAA fines as if they're just part of his usual travel expenses. His likewise generationally wealthy neighbors have consistently complained about his helicopter usage, but he's just at such another level that nothing happens.

Wealthy people genuinely live in another reality than you. They don't believe in things like climate change affecting them because they literally think and act as if they are on a different planet than us.

What surprised me most is how normal and informal it all is on the surface—no constant power flexing—while everything important happens quietly. Decisions are made over casual conversations, opportunities move through relationships rather than merit alone, and favors are remembered long-term. It’s less about obvious wealth and more about access, confidence, and knowing the right people without having to announce it.

They really think the only reason they’re wealthy is because they earned/deserve it. So few people acknowledge the luck that got them there.

Lack of consideration with money.

I helped some folks book a vacation to Disney, and the woman spent $20k before she'd even told her husband they were going on vacation. They buy a whole different kind of groceries, too. Grassfed butter, $7/half gallon milk, etc. I'm over here going "I got this Kirkland butter. Feeling pretty good" and then......

They do not love their children. I stopped working for super wealthy clients because their kids would get so desperately attached to me (and any other available adult.) Seeing the megabillionaire spending exactly 15 minutes per day with his 12 year old son even though he had an extra few billion dollars to donate to a conservative business school was the last straw.