#1
We went out for drinks one night, and I didn’t have much money on me, so she spotted me a couple of rounds. The next day, I went over to repay her the $20 she had spent on me.
She actually got emotional and said, “Nobody has ever paid me back before. They all figure, she can afford it..”
This was in the 1980s, and I was making s**t money as a secretary.. But I actually felt sorry for her. 💔.
#2
#3
People are people, but let’s be honest, financial status can change how they live and how the world treats them. When it comes to the ultra-wealthy, most of us can’t help but feel a little curious. We see glamorized versions of their lives in movies or on social media, but that’s only one side. The real story? That often comes from the people who see them up close, day in and day out.
We’re talking about the staff, those who work for them and experience both the perks and pitfalls. Their tax consultants, private chefs, chauffeurs, gardeners, housekeepers—they all have a front-row seat. They get to see what money hides and what it reveals. And sometimes, the things they witness are as strange as they are shocking. It’s a world of wealth, yes, but also of secrets, rules, and contradictions.
#4
By contrast, blue-collar people were almost always the nicest, laid-back, sincere, grateful, and high-tipping clients, with actual friends and family, who had a wedding for all the right reasons.
Old-money people and self-made successful people (i.e. people who worked construction then launched their own businesses) were night and day different from new money (mostly IT) douchebags, obsessed with impressing The Joneses.
#5
#6
They don’t always have some deep dark thing that is unique to wealth. They’re human, and the things, the emotions, the tenancies they exhibit are the same across the entire human spectrum. I’ve come away seeing wealth just makes you more of what you are. If you’re mean, you’re more mean. If you’re nice, you’re more nice.
They still have problems, and some of that is tied to their wealth, which is family drama, having access to the wealth, and raising children to be humble or entitled.
They are more insulated from legal or political consequences.
We spoke with Leslie, now an IT professional, who used to babysit for ultra-wealthy families in her early twenties. “I was in college, and it paid better than any other part-time gig,” she says. She babysat for families in her upscale neighborhood, getting a close look at luxury and everything that came with it. “The houses were like museums,” she recalls. “But working in them wasn’t always comfortable.” What she saw left a lasting impression.
#7
The actual billionaire I worked for was super cool. Self made. I had monthly meetings with him (and about 16 others) and to see his ability to connect with hourly workers to senior executives was impressive.
#8
Sorry to disappoint you, but some of these people were wonderful humans. Yes, some were jerks too, and most were somewhere in between, just like the rest of us. Most of them genuinely cared about the people these charities were reaching, you could tell by the questions they asked when I would give them a presentation.
Sorry, I know it's uncool to fail to s**t on the wealthy, but I found them to be just like the rest of us in that some were total jerks, some were exemplary humans, and most were somewhere in between.
#9
A lot of ultra wealthy people don't dress up when they go out, they can be plain or even sloppy. It was important to never assume someone's status.
They are petty and will throw you under the bus in a millisecond if it will even slightly benefit them. While I worked there I was screamed at, had things thrown at me, I saw grown men throw huge tantrums. They do it because they know they will get something out of it. Your work had to be beyond perfection because they would purposely try to find faults to exploit. I hated that their behavior was always rewarded. I preferred it when their assistants were the ones we helped.
Many of them seem incredibly isolated and lonely. Some would come and talk politics at us because they had no one else who would listen. Though, to be honest, we weren't allowed to express any of our own thoughts so it was pretty one sided conversation.
“The money is good,” Leslie says, “but it’s never easy.” Babysitting in these homes meant walking on eggshells. Everything had rules: what to touch, where to sit, even how to close the fridge. “They didn’t say it outright, but you always felt like a guest, not an employee.” She often found herself adjusting to the tiniest of expectations. “Good pay came with invisible pressure,” she adds.
“There are rules, so many of them,” she explains. Some families had entire booklets for babysitters. Things like how to fold the child’s blanket or what music was allowed near bedtime. “One family didn’t let their kid hear any pop music. Only classical.” Leslie says she memorized the guidelines just to avoid awkward moments. “And if you messed up? Even slightly, it was noticed.”
#10
Very consistently joyless, entitled, arrogant and cheap, often overlaid with substance abuse issues. With notable exceptions.
One of the richest, multiple billionaire, would occasionally come out and work with me. I was doing landscaping, maintenance, whatever. He asked me to help plant some strawberry’s, worked with me the whole time and described high finance, how to shift risk to the other guy while retaining control and the lions share of the profit. Easy going, super nice guy.
#11
#12
Also **NO ONE** loves free s**t more than rich people.
“Everything is expensive. Designer cups, designer bibs,” Leslie laughs. “You could never relax.” One time, she nearly cried after a toddler spilled juice on a white velvet couch. “It wasn’t even my fault, but I kept apologizing.” She says it felt less like childcare and more like guarding a priceless art exhibit. “You’re not just babysitting the kid, you’re babysitting the brand.”
#13
Just... so much a***e of EVERY kind. Beat. Starved. Locked out. Tortured. SA'd.
People dont call because there's no point because the authorities won't even go, let alone actually DO anything.
The richer they are, the more f****d their kids are if there is anything off in the family.
#14
#15
Later, I was sitting in that lounge, and a woman walked up to the concierge, gave him a piece of paper with her measurements on it and asked him to have some workout clothes/shoes sent up to her room so she could use the gym. As if they just have a magical chamber downstairs with everyones exact size of shoes and clothes sitting there. She seemed perplexed when he explained they didn't, and suggested a Lululemon store a few blocks away. She then said "excellent! Send someone over to pick some things up. I prefer earth tones. Just charge it to my room." She didn't even wait for a reply before walking away.
It's mind blowing. They are just used to getting everything they need, all the time, at a moment's notice. They are utterly dumbfounded when they hear the word no.
“Once, the dad came home with another woman,” Leslie shares. “He didn’t realize I was still there.” She had been upstairs with the child when she overheard voices. “I stayed quiet, but it was awkward,” she recalls. “The next day, the mom acted like everything was fine.” She never brought it up. “It wasn’t my place, but it left me shaken.”
“Some of them don’t want to correct their kids at all,” she says. “One little boy told me to shut up on day one.” Leslie looked to the mom, expecting a reaction, but none came. “They think their kids are untouchable.” She says it’s like the kids are raised to believe they’re royalty. “I wasn’t just the help, I was beneath them, and they knew it.”
#16
His biggest secret was that he knew most people only liked him for his wealth, including his present wife, 2 kids and 2 step kids, and they’d cut ties in a heartbeat if it disappeared.
#17
He died with a ten million dollar cellar.
#18
“One family didn’t even pay me,” she recalls with disbelief. “They said letting me be in their 'beautiful space' was enough.” Instead, they offered her leftovers. “It’s caviar,” they said, as if that excused the unpaid work. “I left that job and never went back.” For all their wealth, some families showed little basic respect. “It was insulting,” she adds.
#19
I remember eating a $32 hamburger, listening to a man brag about influencing elections in developing nations to support his commercial interests. He spoke so casually– like he was sharing old college stories. He shared missteps he had made in his political schemes that had caused civil wars, and lamented on the tens of thousands of lives that his errors had indirectly taken. Drunk, at a bar on a mountain, he talked through *literal crimes* with the tone of someone who had f**ked up at their day job.
I remember that he believed it was his duty to 'influence', that whatever underlying meritocracy granted him enough power to buy elections also required him to guide the poor, silly populations underneath him.
He left me with the check for his beer.
#20
