35 People Who Worked Will Billionaires and Millionaires Share the Differences Between Rich People and Regulars

Roy

2 years ago

Prepare for a voyeuristic peek into the world of the haves and have-nots with 35 observations that make you question if you're living life or just trying to survive. These aren't just your run-of-the-mill habits; they're the quirks that supposedly differentiate those rolling in dough from us mere mortals scraping pennies for a cup of coffee. From morning routines stranger than alien rituals to beliefs about money so peculiar you'd think they're trading in Monopoly cash, these insights are like studying a species from a distant galaxy. People dive into these posts quicker than the realization that money can't buy happiness, because, let's face it, there's a twisted fascination with dissecting how the other, presumably more lavishly adorned, half lives. So, buckle up for a crash course in the peculiarities that supposedly come with a bulging bank account.

To people who have also worked with multimillionaires or billionaires, what is something different they do from ordinary people?

Years ago a friend of mine's dad was trying to sell his start-up company and picked-up an investor at the airport. He was proud of his classic Rolls Royce and noticed the investor looking around, playing with the air vents. So he said "Is this your first time in a Rolls Royce?" The guy said no, but it was his first time in the front seat.

Well the owner of my small company is incredibly wealthy but also rad as f and he drives a tank on property all the time just for the fuck of it. He also owns a very old, gorgeous estate from an extremely influential family (think Vanderbilts) and we throw parties there. But on top of it - he lets his employeees rent it out for events. So my husband and I are throwing an anniversary party (never had a reception) in 2024. We have the entire estate and all 10 bedrooms for a whole weekend and it isn't costing us a single dime. If I didn't work for the company, the cost of the venue would be upwards of $25k for the day. I never expected someone so incredibly wealthy to be so down to earth and generous. It's exactly who I would strive to be at that level of wealth.

He managed time very differently than anyone I was used to. E.g., our meeting with him began precisely on schedule, lasted 30 minutes, and there was no chit chat. Before this meeting we had a pre-meeting with his admin to discuss expectations. The admin explained that we had to be on time, no introductions/titles just name, no small talk, no marketing, be prepared to answer technical and financial questions quickly and succintly. For this latter, if there were numbers we had to know precisely which page of the material had the information. When the meeting took place we were brought in exactly -- to the second -- at the start time. Sat down and within 30 seconds he was asking us all manner of questions. I had to field technical questions that appear to be asked not so much for whether my answer was right, but that I didn't hesitate. I also gained a healthy respect for my manager as he was SHARP and answered quickly and accurately.

I work for a major corporation. One of my colleagues started talking to a director as they were leaving once. They were both walking towards the train station and she assumed he was also getting a train. As they got there a limo pulled up and he nonchalantly said "bye" and left.

Hire a private chef for a casual Tuesday lunch with her girlfriends… $2k, just like that.

My son's friend when in elementary school dad was one of the 2 founders of Capital One . Mom had a secretary for play dates. Dad would fly to London to watch Tottenham. Had a permanent seat. Their London house was next to J.K. Rowling's. You couldn't tell by the way they dressed or their cars. But their vacations were the big difference. The strange thing is that their son loved a mango juice sold maybe 10-15min from their house. I always made sure we had some for mine. I send it to him via Amazon occasionally.

One old money rich person treated me to a fancy meal and she was super polite and nice and tipped well, what struck me was the decisiveness and confidence that everyone there would cater to her, and they did. She wanted x dish that they didn't make that day and they made it. The one that sticks with me was at the end she said "I want a cappuccino with (something) I want them to put a design on it" like I've gotten cute cappuccinos in my life, it doesn't even cost extra, it never occurred to me to just ask for everything I want all the time. This was the same person that on a business trip hugged me after the flight "I did it, (womanthorned)!" Me: "oh was this your first time in economy" and she goes "no, flying commercial" just so we all understand how rich.

Have no fear when addressing anyone, no social barriers

My aunt and uncle are self made multimillionaires. If you met them, you'd think they were well off, but nothing spectacular. In general, they're both very frugal. However, the two areas where they completely detach from ordinary life are: 1 - Vet bills for their animals. The example that most stands out in my mind is their last dog. He needed dialysis and no vet where we live could provide it. So they did their research and discovered that the best treatment in the country was available in London. A flat in Kew (I think, somewhere fairly central anyway) was rented for the six months the dog would need treatment for and my uncle would stay in it for one week a month while the dog had his treatment, then travel back home for the other three weeks.

My friend was a pilot for a very large aluminum business, think aluminum foil. The brothers would fly for business meetings and my friend would make all the arrangements, including car rentals. These guys would drive off and go to meetings, dinner, etc. Sometimes they would just leave the rental car behind and ride with others to change venues or whatever. He tried to tell them the rental doesn't stop unless the car gets returned. They didn't really care. If it was any level of inconvenience they just moved on. It was more than once he had to go back and find a car based on their recollection and get it returned.

I was working on securing a large gift for a hospital with naming rights from a very generous donor and commented on his beautiful Patek Philippe watch. He took it off and gave it to me. I could not accept it, despite the watch being worth more than my annual salary a few years over. Later when I changed jobs he took me out to lunch with my former boss and presented it to me. Far too generous a gift, but he liked me.

My experiences: 1) CEO of large company. Didn't come from huge wealth so fairly self made. As others said, a literal workaholic. 24/7, 365 days a year. Zero boundaries between work and personal (and expected the same of his direct reports unfortunately). Endless energy. Perfectionist. Edited to add: his wife was a bltch and his adult kids hated him. 2) Billionaire who inherited wealth. Was on his ranch in the West and this cow poke guy went with us on a horseback ride. He also cooked breakfast. I literally thought he was a hired hand, ends up he was the owner of the ranch. Was kind, friendly, could rope a steer like the "true" hired hands and make some mean breakfast tacos. Of course he flew to the ranch on his PJ while we got there dragging ass in economy class with 12 hours of delays.

I worked for a billionaire for a year. At first, it was great, because he made us feel he was in the trenches with us. I came to find out that he made fun of us (there was only 8 employees) for the salary he was paying us and tended to throw people under the bus. It was one of the very few jobs that I gave less than 2 weeks notice and never looked back. I am so glad to be out of there.

They view life through the lense of time, over essentially anything else. Time is their most valuable resource, and anything that saves them time or unnecessary effort is worth whatever the price.

In those 35 revelations, it's a bizarro journey through the rabbit hole of behaviors that define the affluent, where morning rituals involve more than just hitting the snooze button multiple times. Online, these insights trigger discussions on the psyche of wealth and the eternal pursuit of the elusive dollar sign. Eager for more peeks into the lives of the moneyed elite and their oddball behaviors? Dive deeper into the rabbit hole of wealthy lifestyle musings that'll make you wonder if you're doing breakfast all wrong, the psychology of success that's more perplexing than advanced calculus, and explorations of the millionaire mindset that might just leave you feeling financially inferior. Because let's be honest, the world of the well-off is a potent mix of bizarre habits and lifestyles that make you question if you're even playing the same game.

Roy

Roy R., Chief Meme Curator Roy founded Thunder Dungeon in 2012 and has since guided its growth into a 2.5 million‑strong community of meme enthusiasts. With over a decade of digital‑media experience and a nose for viral humor, Roy oversees content strategy, ensuring every post is both hilarious and high‑quality