20 Stories From People Who Had Unexpected Experiences with a Super-Rich

Ever wondered what it’s like to rub shoulders with the ultra-wealthy? Spoiler alert: it’s not all sports cars and luxury handbags (though let’s be honest, that happens too). From bizarre flexes and outrageous spending sprees to jaw-dropping displays of wealth, these stories pull back the curtain on the super-rich, proving that their lives can be even stranger than we ever imagined.

• I used to work as a personal trainer, and one of my clients was this super-wealthy guy who, over time, started showing extra interest in me. He would always linger after our sessions, asking personal questions and trying to flirt. Eventually, he started trying to monopolize my time by bribing me to cancel sessions with other clients, saying things like, ’I’d rather spend more time with you.’
  
  One day, he offered me a six-figure salary to train him exclusively, which I refused. Drop all my old clients and dedicate all my time to just him with 24/7 support. No matter how tempting this offer was, it felt way too controlling.
  
  The next day, he came to the gym bringing his equipment, saying, ’I can afford better anyway.’ We stopped working together shortly after that, but his persistence was on another level. It was one of the most bizarre experiences I’ve had.

• I’m an art student working as a gardener. My client is a super wealthy guy. When he learned about my studies, he invited me inside to show something. I agreed but grew nervous as he led me to the bathroom. My heart sank when I walked in and saw an original Picasso above the toilet. © useroftheinternet999 / Reddit

• I briefly worked with one of the top Saudi Arabian crown princes in the 80s. He would buy out the top three floors of the best hotels (like the Four Seasons, etc.). Two floors were for maids, help, and security, while the top floor was reserved for the Royal family. Once, it was just the prince and his three wives. It was unbelievable. © Elysian-Visions / Reddit

• I used to work for a billionaire family as a tutor for their daughter. One day, we were in her room studying when she suddenly yelled, ’Daddy’s home!’ and ran to the window. She had heard a helicopter and knew it was about to land on the lawn. © DiscombobulatedBabu / Reddit

• My dad works in shipping and has many friends who have worked on superyachts. In the 90s, one of his mates was called up to bring the yacht of a particular Australian media tycoon billionaire from Sydney to New York, with instructions to anchor in a specific bay at an exact time with a lunch spread for 50 people prepared.
  
  So, they arrived, set up the food, and waited. The guy never showed up. It turned out he was hosting a party for wealthy friends in a building overlooking the harbor and wanted to be able to point down and say, ’That’s my boat.’ He wanted the lunch prepared just in case he decided to take his friends down to the yacht, but he didn’t feel like it that day, so all the food was wasted, and they sailed back to Australia without ever seeing him. © clovisson / Reddit

• A friend did some work on Sylvester Stallone’s home. Apparently there’s a ton of statues and art of himself, some of which are naked. © CaravelClerihew / Reddit

• I went to a New England prep school for high school on a full-ride sports scholarship. There were a decent number of foreign national students — mainly from Asia — who came from extremely wealthy families. One of those students’ parents bought him a brand new, fully loaded BMW 5 Series when he got his license during his junior year.
  
  When we graduated a year later, he was returning to Korea and obviously couldn’t take the car, so he gave it to his best friend. That kid got an $80k car at 17 years old, just for being good friends with the right guy! I’ll never forget that. © JAG23 / Reddit

• "A woman who owned a small private jet business once told me that someone paid them about $45,000 to fly their dog (by itself) to New York for training. No other passengers. © aticho / Reddit

• I became personal friends with my boss and his wife; they are super nice people. The wife turned out to be a heiress and would buy me whatever I mentioned, even casually during a conversation.
  
  I learned that gifts were how she was raised to show love. I’ve trained myself to only talk about things I already own unless I find something useful she might like and suggest it to her.
  © Lazyassbummer / Reddit

• Keith Urban bought a couple of guitar pedals for a local kid here in one of the guitar shops. The kid had a budget and was struggling to pick one, so Keith just bought them both for the kid by quietly paying the shop owner on the way out the door before the kid even knew what he’d done. By all reports, he’s a genuine decent, down-to-earth bloke. © kizzt / Reddit

• Some extremely wealthy people I’ve been around have a heightened awareness of their own time and mortality, which often leads to impatience. They understand how amazing their lives are, making them feel even shorter.
  
  I knew a guy whose vintage yacht broke down before summer, so he bought another one just for that upcoming summer. His reasoning was that he likely had only 20 healthy summers left in his life, and he didn’t want to spend one without a boat, considering he had the means to avoid it. Honestly, I can’t argue with that logic. © cholula_is_good / Reddit

• I had a client that lived right outside NYC. They were ’new money’ in an area that was mostly old money. Hated their neighbors, but played nice face to face. Every time the neighbor’s wife would buy something and try to show it off, they would buy a more expensive/rare version, or buy two of the same if that wasn’t possible. The vast majority of it was displayed in the front room. They were a bit eclectic but were nice people. © Unknown author / Reddit

• I used to petsit. I remember a rich person asking me to petsit their cat. There were a lot of TVs, in almost every room. The weirdest was the bathroom. Sorry, cat bathroom. There was a TV playing cat cartoons, an overly fancy litter box, and paintings of cats. © Kpop_TWD / Reddit

• Family friends were having marital issues. Their marriage counselor figured out a lot of their problems were overcooking meals. The counselor reminded them that they are rich and can just cater all their meals, and it would be cheaper than getting a divorce. They listened to the counselor and now are happily married again. © waterloograd / Reddit

• I had a friend who grew up fairly wealthy and married wealthy men. Not crazy rich, but millionaires and extremely comfortable.
  
  She used to talk about wanting to write a cookbook for poor people, but her recipes always involved stuff like grass-fed, organic ground beef.
  
  She got divorced at one point and her income took a hit, she wondered if she’d qualify for public assistance. Like, lady you live in a $3,500/mo apartment, drive a luxury car, travel overseas 3x a year, have a maid... I don’t think you’ll qualify lol. © 321dawg / Reddit

• I live near a company that builds yachts. One day there was an odd-looking yacht. A crew member explained to me that was a ’shadow yacht’.
  
  You see when you get hyper-rich and have multiple yachts. You wouldn’t want to ruin the aesthetic of your nice yachts with jetskis and helicopters. Nor would you want your crew to sleep on the nice yacht. So you buy a shadow yacht to store your toys and to house your crew. This shadow yacht follows your fleet of nice yachts around. © Doppar / Reddit

• Client was a mega millionaire in the 60s so even richer when I met him. He’d ride the bus to the office to have free coffee. Every day.
  
  He was the founder of a company that had its name emblazoned on shipping containers being transported via big rig trucks in the states, but also international shipping and logistics. Came into financial offices daily for the free coffee. Didn’t even talk about his finances, just for the coffee, and then would skedaddle. © sunlitglo / Reddit

• Some kids have plans and strategies they practice to prevent being kidnapped by stalkers. One kid I worked with was the child of a big Hollywood player, and people would stalk the kid in an attempt to get to the parent.
  
  One time, a nutjob wielding a screenplay broke in and cornered the kid. I thought I was going to have to physically intervene, but the kid dove into a nearby dog kennel and locked himself inside. He couldn’t get out, but the intruder couldn’t get in either, so he just threw the screenplay at the kid through the kennel bars. Meanwhile, I had called the cops.
  
  I was so impressed by the kid’s quick thinking and asked how he got the idea. He said that he always keeps an eye out for a way to escape and gets ready to run when he sees someone he doesn’t recognize approaching. I felt awful that this kid had to live like that. If I hadn’t seen it happen myself, I would have thought it was just paranoia. © harpejjist / Reddit

• I work at a university offshoot, where a billionaire has donated a few buildings. He’ll drive through now and then to take a look at them. He’ll stop and chat with us lowly workers, and occasionally give us tickets to the games in the arena he donated to the university.
  
  Well, this blew up more than I expected. No one’s guessed his name so far, but he keeps a low profile so you wouldn’t recognize his name unless you were in the know. © II_Confused / Reddit

• My grandpa was a piano tuner. He couldn’t drive due to epilepsy, so family members would take him to jobs.
  
  One day, my dad took him to a job and got talking to the owner. He said the guy lived in the biggest, nicest mansion he had ever seen, with everything in the house being incredibly expensive. But the owner and his wife were very down-to-earth and normal, if a bit rough around the edges.
  
  Finally, his curiosity got the better of him, and my dad asked how they made their money. The guy said he used to drive a truck and got tired of having to carry around bottles of ketchup. That’s how my dad met the creator of the ketchup packet. © blitzbom / Reddit

Want more? Check out 20+ Stories About How Rich People Really Live Like.