rSlash - r/Askreddit What's it Like Working in $50,000,000 Households?

Episode Date: June 26, 2026

0:00 Intro 0:03 Todays question 0:12 Homeless 1:17 Hamptons house 1:53 Drugs 3:51 Property management 4:28 Fines 5:13 Penthouse 5:26 Yacht 6:41 Landscaping 7:33 Cleaning 8:35 Flying 9:59 Art handler 10:29 Cars 10:50 Painting 11:15 Watch 11:32 Allowance Learn more about your ad choices. Visit megaphone.fm/adchoices

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Welcome to R-Slas Ask Reddit where people answer the question, people working in ultra-wealthy households. We're talking 50 million plus. What's the most out-of-touch thing you've witnessed? Our next reply is from Big Routine. In my previous job, the two heads of the household, collectively worth about $30 billion, were engaged in a very lengthy and protracted set of discussions for how best to stop homeless people from congregating near their compound in Hawaii. The homeless were ruining the vibe. Some options discussed ranged from donating to political groups to influence the mayoral candidates to get someone more hardline against homelessness.

Another idea was simply paying people to go and vandalize the place so badly that people would leave. They settled on just having private security, constantly patrol the area, and take pictures to stir up fears that the homeless were robbing people and houses. It worked. Wow. Kind of crazy that somewhere in that discussion, it never came up, what if we just bought them houses or some sort of cheap, affordable apartment where we could give them a place to stay and, you know, give them the help they need to get off the street?

Instead, it's, let's turn them into villains and turn the community against them. I feel like this post is a foreshadowing of what's to come on this thread. Our next reply is from Original P. My mom's boss was taking a stroll on the beach in the Hamptons and liked the house that we walked past. She left a check in the mailbox for the owner and a note asking to buy the house. Long story short, she has a great Hampton's house now. And beneath that, another reply from Stoloka.

My mom did this. We were playing in the park one day, and she decided she really liked the look of a house across the street. She knocked on the door, asked if she could buy it, and we moved in a few months later. Of course, this was in 2004, and the house cost was $200,000. Our next reply is from Cotton was King. In my misspent youth, I sold drugs, primarily cocaine and weed, but also literally anything else someone wanted that I could find, which was most things. However, I was also a terrible cocaine and heroin addict, so while I handled thousands of dollars every couple of days, I was perpetually broke. Anyway, I got a DUI one night.

Luckily, I didn't have drugs on me and had just enough money to bail out of jail. One of my buyers called me looking for an eight ball the next day, so I go out to his house and make the sale. This is a guy a little older than me at the time. I was 21, so he's probably very early 30s. An old money family with still paying out shipping ties to the Mississippi River. I have no idea what this family is worth. I told him that he should find another hookup most likely, as I'm broke and can't afford to keep myself out of jail for this screw up. that I'll hit him up when I'm back out and up and running, and I hope he understands. This man proceeds to tell me that he can't afford to find someone else that he trusts.

He gets me in a pre-trial diversion program, pays for it himself to the tune of $10,000, all because he wanted to maintain convenient access to cocaine and oxycodone. We're both clean now and still talk a couple of times a year. A really good dude, actually. And a similar story from One Big Red. President John Skipper had hid his blow habit for ages until he once had to use an unknown plug. The dude recognized who he was and started to blackmail him. He decided to come clean rather than be blackmailed, and Disney let him go instantly.

People who have something to lose definitely understand how valuable trust is, unless they're idiots. Well, normally rich people have their employees sign NDAs, but you can't really have someone sign an NDA saying, I won't tell people about all these drugs I sold you. Our next reply is from giving you the high hats. A friend helped to look after some properties for a very famous individual. Dozens of employees, massive upkeep for houses, nobody was ever in. Then one day they came in and found this famous person asleep on the couch. The famous person left a couple of hours later.

A $20 million house used for a nap once. Hey, let's keep in mind, it isn't just a 20. million house. It's a $20 million house plus taxes, plus electricity and plumbing and all those fees, plus all the employees to watch it and do landscaping and all that stuff. Our next reply is from 1320. We built a house for a Middle Eastern type guy in Corona del Mar, California. He bought four smaller adjoining houses and bulldozed them. That right there has to be $8 million. Anyway, since this was a city street and a neighborhood, there was nowhere to store lumber or heavy equipment, but on city street and sidewalks. On more than one occasion, I saw and heard him talking to code enforcement

while writing them a check for $25,000 and telling them to come back when it ran out. Yeah, one thing I hear a lot is that rich people park their cars wherever they want because they get a ticket, but the ticket's like, I don't know, $150. And when you're worth a billion dollars, that's a really cheap price to be able to park wherever you want in a very crowded city. Our next reply is from Mr. Bulldog. I dated a girl whose grandfather is. very wealthy. He purchased the penthouse above his and converted it into a terrarium-type environment for his cactuses. Our next reply from Let's Go Gators. I worked for a high net worth doctor who had sold outpatient surgery centers to private equity for over $100 million. I'm a CPA

and ran his family office for close to a year. When I needed to take time off for my sick 11-month-old, he asked why we didn't have live-in help. But the biggest thing, and not much right, rattles me after 20 years of looking at crazy numbers on a screen, was the cost of owning a yacht. The boat itself was only a few million. But the captain, first mate, food, gas, repairs, cost of going through the Panama Canal was insane. In the neighborhood of 500K a year, easily, he would fly out to it to go fishing for the weekend, and he didn't even eat fish. He was vegan.

In general, he was fairly normal, had immigrated from Cuba on a raft type of. story. But the yacht was crazy. Instead of rags to riches, he went from raft to yacht. Then a similar reply from Salamook, My daughter's ex-boyfriend's family has a yacht that they use four to five weeks a year with three or four person full-time staff, but they also have a charter license for it during peak season. It's booked solid for like $80,000 a week.

Our next reply is from Hog Chief. I worked for a shipwright out of Newport, Rhode Island. He had about 80 acres of gorgeous. farmland in my hometown. The property was full of old stone walls, which he paid two of us twenty bucks an hour to keep the weeds and vines from growing over the walls. The property had a beautiful old house that was immaculate and rented out to a local judge. He also had a large barn with a beautiful crisscraft boat and assorted British cars all in perfect condition. Anyway, he would pull up in a two-wheel drive, 15-year-old truck, looking like Jimmy Buffett,

ask how much he owed us and hand us cash. It was a great summer for me. A few little weeks later, the property next to his went up for sale. It used to be a farm as well, but someone had bought it and built a five or six million dollar house on it. When this guy bought it, he hired a company to come tear the house down because he preferred the look of farmland. Our next replies from Vanilla with Flake. I was a cleaner and I was paid to join a family to go to their holiday home upstate and clean the holiday home while they were there. They were only there Saturday and Sunday, but they wanted me to clean throughout. I changed the bed every day and cleaned up like I'd do at a hotel. When we got back, the chauffeur had a problem, so they just organized a local cab company. The husband sat in front,

I sat in the back with the wife. The husband started smoking. The cab driver said he couldn't smoke. The husband said, I'll pay you money to get the car cleaned. The cab driver said, no, if you smoke, I'll get a fine. The husband told the wife to pass him her very expensive Irmez handbag. The husband went into the bag, took out a huge pile of cash, about $1,000 and put it on the dash. He said to the driver, it's fine, I got you covered. And then he just started smoking. Once again, we have another post that confirms that fines only prohibit poor people from doing stuff. For rich people, it's barely even an inconvenience. Our next replies from Worried Eb. I used to fly corporate jets before I started flying for a major U.S. airline. Many rich people who own private jets will

frequently broker them out to charter for people who wish to pay. It's a great way to reduce your operating costs and make money. Often, I'd pick up overtime work that paid a minimum of $3,000 a day, plus expenses. This contract was for a very rich celebrity who must get his fish for a private event the following night from a specific company in Chile, and he needed 150 pounds of it. So I picked up the charter from the broker, and I was flown in first class from my home. home in New York to the Jets location in Louisiana on Thursday, where I met my co-pilot, and off we go to fly to this small town in Chile and fly it to the chef and event in Santa Barbara. Minus an 11-hour rest in Chile, we flew about 17 hours in two days. The charter cost 250k.

My expenses were 10K and another 10K for the co-pilot. That fish cost $350,000 when you factor in all the fishing, handling, packaging costs, customs, etc. Each package was sealed to prevent smelling or leaking. The owner's assistant met us at the airplane and tipped as each an additional $3,000 in cash. Blows my mind. Our next replies from a trippy mouse. I work as an art handler in a major city. Their collection consisted of antiques, things that would usually be reserved for museums. Think 2,200-year-old bases, figurines, etc. On the desk of the client, there was a small Athenian chalice painted in the iconic orange figure black background style, developed around 2,500 years ago. Inside of it was paper clips, spare change, and chewed gum.

Our next reply is from Ashton. This family has a summer cabin. They get five brand new four-wheel drive vehicles delivered every year to this cabin, and the old ones are hauled off. They can go five plus years without ever visiting the cabin. Whether they touch the old cars or not, new cars are delivered every spring. Our next reply is from Whole Chocolate Milk. A buddy of mine owns a high-end house painting business. So he does a lot of these insane houses that overlook the Pacific Ocean in Southern California. Last week, he was telling me about one of his clients who lost his keys to a Ferrari.

So it's just been sitting in his garage, basically as a paperweight, for two years. Because the guy can't be bothered to get a new set of keys. for his Ferrari. Our next reply is from Seal. I did a job and a small favor for a Middle Eastern guy. I mentioned in conversation that I liked his watch. He took it off his wrist and gave it to me. He wouldn't take no for an answer. It turned out to be worth about half my annual salary. Our next replies from Angry Deuce. This is probably pretty tame, but one of my clients is a billionaire, and I happened to see her kids' allowances printed out on a sheet of paper when we were in a meeting once. smallest allowance on that paper was 250k a year. The person receiving this allowance was a six-month-old

grandchild. The child's parent allowance was $2.5 million a year. That was our slash-ask Reddit, and if you like this content, be sure to follow my podcast because I put out new Reddit podcast episodes every single day.