July 18, 2023 at 1:36 am

People Who Work For the Super Rich, What Have You Seen?

by Matthew Gilligan

ARWorkingRichPeople People Who Work For the Super Rich, What Have You Seen?

Really wealthy folks are a different breed.

They do things a heck of a lot different than you and I and sometimes they can be downright weird.

And today we’re going to hear from people who have worked for rich folks to get the inside scoop.

Take a look!

A jeweler’s wife.

“Jeweler here. Some random client quotes-

Client- “So I have some gemstones that have just been collecting dust (pulls out about a dozen amethyst, citrine, smoky quartz, most an inch or more across) what can we do with these? Can you make a crown? No, not a little flimsy” fake” one, a “real” one.

Me- (makes a 5lb silver and gold crown)

New client- “You’re going to see me a lot. This is going to be my new addiction. ”

Me- (ok, I’ll bite) “What was your last addiction?”

New client- “Collecting (fully grown) trees. I had 45 transported and replanted on my property last year.”

Client- “Have you seen my new car?”

Me- “I have not.”

Client- “They only made a few… (points out the window at a new, navy blue Bentley) I didn’t like the interior so I had them replace it all with bright orange leather. They added a plate inside with my name engraved on it. Isn’t it cool?”

55 year old client- “I want everything pink. Can you tell I’m obsessed with Barbie? (laughs) We’re even building a pink house. I want my engagement ring to be all pink.”

Me- “I can make it in rose gold.”

Client- “Great! Do you have any pink diamonds?”

Me- “Not in stock but I know of a supplier who has one.”

Client- “I’ll take it.”

Me- “It’s a natural Argyle pink. It would be about $220,000.”

Client- “How soon could you have it ready? Can you add more pink diamonds to the sides?””

I…don’t understand…

“I often do work for the wives of wealthy professionals. The thing that has always stood out to me is that if I tell them that something they want isn’t doable, they respond with literal confusion.

It isn’t anger. It’s confusion. They are so unaccustomed to not being given exactly what they want that it’s as if they don’t understand what is happening when they are told they can’t have something.”


“I used to work at a member’s only golf/country club. There were members who had been actors, athletes, race car drivers, former CEO of Google, some major money and egos going on.

There was one family that had 3 teenage kids, 2 girls and a boy. The mom and the girls were very attractive and knew it. They always looked amazing and had overly entitled attitudes to match. They were “fancy.” Well, the lady who washed the linens for the county club also did house cleaning for some members. This family was one of them. She said their multi-million dollar home was a disaster filth zone.

They basically did no house work in between having the cleaning lady there. Dishes piled with dried food that smelled, dirty clothes thrown everywhere, piles of crap all over, sticky floors, dog poop left on the floor. But the nastiest part was the bathrooms. She said they wouldn’t empty their bathroom trashes and the ladies of the house would throw their used tampons on top of overflowing trash so she had to pick up their used women’s products thrown on the floor not even wrapped in paper.

So these fancy bitches would walk around the club like they were so superior and look down on everyone then would go home and act like wild apes throwing their trash and period products on the ground. The thought of being so out of touch that you decide it is beneath you to even be sanitary because you can just pay someone to do that for you is just beyond insanity.”

The CEO.

“The CEO of the company I worked for was the founder’s son. Not an unintelligent guy for the most part.

His dad made him start with the most basic jobs in the company and work his way through the different departments. Managerial staff was ordered, upon penalty of termination, not to treat him any differently than a new hire.

So when he became CEO he wasn’t a bad guy to with for.

Now, this is a company of over 10,000. One night, I’m working overtime on the late shift and we get this call.

“Hey! You guys… Got… ‘Lectrician?” The guy is clearly drunk, we have no idea who it is or why he’s calling our maintenance/engineering group. We ask who he is and he informs us, light heartedly.

He wants someone to take a ride to his house and figure out why the internet isn’t working. This is an hour drive away.

I volunteer, I was bored off my nut anyway. I get to the house, entry gate is smashed, section of the white horse fencing is gone, Jaguar is stuck in the field.

Here in the house is dude, completely blasted. He’s got a huge cut on his hairline. “Are you ok, (boss)?”

“I’m fine! Why?” He asks, blood literally caked on his face.

I accompany him to the bathroom and help him clean himself up, wash off the gash and put some bandaging on it.

Then I corrected the Internet. Unplug-plug.

As I’m walking out, he asks me to do a shot with him. I comment, worried about my job, that it might be a bad idea. He agrees and hands me the bottle, “Take it home and do a shot later. Keep it.”

When I get back to work I look the stuff up… Never heard of it. It’s a $1500 bottle of scotch.

The next day I’m at work early. About eleven in the morning he comes walking up. “Uh… We’re not going to be… Talking about last night?” I tell him it’s all good, “Awesome.”

A little bit later I get an envelope. There’s a check attached for ‘Emergency Tech Support’ $5,000.'”

Money well spent.

“Had a client come into our 3D printing office.

His attention was immediately caught by a large industrial 3d printer in our showroom. Pulled out a credit card and bought a $250k machine on the spot. Best part was when we installed the machine at his facility.

First thing he wanted to print was a meter tall p**is. Few weeks after the install we got a photo of him standing next to the meter p**is.

Money well spent.”

Sure, I’ll take it.

“I was working for a kind of well off family during a summer. I went inside to get a drink and the mom was cleaning the kitchen putting things away and such.

She picks up a Macbook and says to me “hey, do you want this? No one uses it ” Got a brand new Macbook for college.”

Down in Florida.

“My brother in law builds custom homes in the Redneck Riviera belt of Florida.

One day, he called me to come over to this $15m beach house he was doing a complete remodel of. He was the original builder. He asked me to bring my truck and trailer. I show up, and he walks me through all four floors. He then says, “The owners have removed all the stuff they want to keep. She has told me to dispose of everything as I see fit. Get what you want.”

Furniture, appliances, outdoor furniture, rugs, lamps, artwork, you name it. I don’t know the value of everything I took home with me that day, but it was the highest end stuff I’ve ever seen. FOUR floors of it, and I only got one trailer load because I simply couldn’t fit anything else in my house. I likely had over $20k worth of furniture and appliances on that trailer.”


“Pumped a bunch of money into the Malibu City Council in order to change a few seats.

This would allow him to have the local ordinance changed so his front doors could be taller than 20 feet.”


“An old boss did extremely well and sold off the lion’s share of his ownership but wanted to stay involved in the company anyway, so he’d drive his absurd supercar to the office and just hang out.

One day he came in to the office and it was set up in such a way that the executive offices were in a little 2×2 office glass pod in the middle (with curtains for privacy if needed) and our rows were arrayed around them. He sat in his little glass office all day and cleaned his handg**s.

I’ll say this though, he wasn’t a bad dude. We may not have seen eye to eye on politics but if you worked for the company he knew your name and would hang around and chat. Super generous around the holidays with time off and the big holiday party/door prizes/stuff of that nature. The company went way down hill when he finally let go of the reigns completely.”

Money makes almost everybody crazy.