Living Large: 50 Wild Stories From People Who Serve The Super Rich

So, this wealthy couple toted up the perfect family by adopting a little girl. They spent ages dressing her up and having fun, then - plot twist - the mom decided she didn’t want a girl after all and returned her like a pair of shoes. Yep, said "keep the clothes," but the kid? Nah.

Okay, here’s a rich-life flex: a friend's wife doesn’t medicate for headaches, she *flies* to Aspen just to breathe the 'better air.' Meanwhile, the rest of us are low-key crawling under blankets with ice packs. Fancy, huh?

Imagine spending serious cash - like over $100k - on a gorgeous outdoor party barn, only for the wife to take one look, hate it, and order a full teardown. And the family only uses it a few weeks a year. Talk about royal-level extravagance wasted!

I fly private jets and honestly, the crazy stuff I see is next level. $50k worth of dishes that just sit there, $450k vacations, a $40 million plane, flying dogs an hour away just for a fancy groomer, $34,000/month satellite Wi-Fi, and even a same-day Maui day trip just to get a passport. It’s bananas!

One yacht had a fish tank running the whole height of the staircase. Sounds epic, right? Except there was a shark in there who devoured the other fish weekly. So every week, they’d spend $50k buying more fish to feed the shark’s appetite. Now that’s one ridiculous underwater drama.

A friend’s relatives owned a fancy hotel chain and decided their yard wasn’t big enough. So, they bought the neighbor’s $15 million mansion and knocked it down. Because who needs a house when you can have more grass, right?
On a lighter note, Harrison Ford was apparently a super down-to-earth guy who traded acting talk for carpentry and threw epic parties with surprise tabs. Talk about a mix!

At a private school near a yacht club, a parent casually mentioned they were heading to the Keys to check out a property they forgot they even owned. Happens when your real estate empire has *a lot* of spots.

Worked as a nanny for a billionaire family living in a mansion of loneliness. Mom was busy pretending life was hard while ignoring the kid; dad was hardly around. The kid, left mostly on his own, acted out like a kid from a sad orphanage. After planning an epic Christmas trip, the wife suddenly changed plans two days before and blamed me. Best fired ever.

My girlfriend groomed dogs in SF’s Billionaire’s Row, and guess who managed the dog groomer’s schedule? Not the owner, not even the butler - the hired "dog butler." This guy coordinated dog walkers and groomers and reported to the butler. This world has levels, folks.

Aunt retired from high-end realty tells us Saudis flying in for F1 races don't settle for just one mansion. Nah, they rent 6-8 next door to each other. Airports rented out, helicopter pads built and removed, jets swooping in - all for a weekend escape. Excess really has no limits.

Worked for a Dubai bank’s elite squad. When someone yells “I need $500k in New York,” the team scrambles, preps paperwork, grabs the cash, and heads out via private jet to hand-deliver it. It’s like VIP FedEx, but for piles of cash.

One woman flew herself and her dog to Aspen just to visit a favorite dog groomer - only to find them sick. So, back home she goes... then flies back days later when the groomer’s back. All told, about $75,000 spent for doggy spa days. If only my cat could tell me to do that!
Another flew cross-country to Beverly Hills to shop because she was annoyed at her husband. Spent $100,000 on last-minute flights and armloads of designer bags. She even bragged about using his credit card. Talk about making a statement!

I helped with a $3 million wedding where $480k (yes, nearly half a million) was spent on flowers alone. The venue? A sprawling 600-acre private estate with a barn so fancy it’s worth $1.5 million, a polo field, and massive tents you could theoretically park two circuses inside. And the dad? Super nice and humble, which is the real plot twist.

Worked summer cleaning yachts and learned a super rich pharmaceutical family employed someone whose only job was baking cookies and brownies, nothing else. Warm treats on tap? Yep. They had separate chefs for everything else. Cookie duty sounds like a sweet gig, literally.

A Saudi princess stayed a month at a Paris hotel and paid to merge an entire floor into a palace-sized apartment with private kitchen and entrance - all remodeled to her taste. After her trip, she'd pay to restore everything to how it was. Talk about temporary yet super fancy!

Knew a billionaire who was really down-to-earth and lucky with business deals. People started idolizing him, and he fell for it - surrounded by yes-men and shut out critics. Then he got into some darker stuff trying to "hack" his own body and sadly passed away. Fame and fortune can’t fix everything.

Installed tiles in a 45,000 sq ft mansion with two satellite dishes just for TV (because one wasn’t enough). Mid-build, the wife decided to tack on a million-dollar infinity pool. Also ordered a $50k wood countertop from Africa, but then sent it back because she didn't like the lighting. Bonus: They flew in a private barber to cut their hair. Insane, right?

Nannied for a family where mom’s closet alone was massive - bigger than the first floor of a normal house. She’d shop 8-10 hours a day, carry in loads of designer stuff, but ignored her four boys. Asked for a raise from $9 to $11 an hour, mom said no, and boom - I quit on the spot.

Attorney wife handles clients who treat cars like disposable goods. One dude swaps his ride for a brand new one every 10,000 miles instead of bothering with service appointments. Can't argue with that level of “new car, who dis?” energy.

The ultra-rich don’t do math on prices; they just say, "I want it," and poof - it’s theirs. From grabbing random apartments to ignoring last-minute travel plans, their view of money and time is basically "I got this!"

Managed properties for a mega-rich guy who wanted to copy a garden he saw in San Antonio. When he couldn't describe it, he got on his phone and an hour later, me and the gardener were jetting from Idaho to check it out. No lunch break. Fuel for that flight cost two months of our salaries. Just another day in billionaire land.

My megarich clients mostly grew up on farms or oil rigs. No flashy stuff - not shabby, but no bling either. Nice but not showy cars, vacation homes all-cash. Guess money talks but true wealth whispers!

Worked for a bank CEO with a nanny barely paying attention to their kid, who acted way younger than her age. One day kid runs to hug their parent after a week apart, but the CEO says, "I have to go, my driver’s waiting." Door shut in the kid’s face. Sad vibes all around.

Years with billionaires brought gems like grinding 30 lbs of filet mignon to make hamburgers for a Super Bowl bash (ouch, butcher!). And sneak-attack balloon party setups with 500 helium balloons to wow birthday kids. Oh, and collecting dog diarrhea twice for vet samples, because one vet’s opinion just won’t cut it. Plus, spending half a million on empty hotel rooms just in case they needed them (spoiler: mostly didn't).
Also bribed polar bear researchers to delay trips so a princely client could photo bomb Norway... until he got bored and bailed.

Married a billionaire's daughter and threw separate bachelor/bachelorette parties at family estates. When the groom complained about lack of good pizza in Vail, the bride sent her assistant to charter Boston’s best pizza place, shut the place down, and shipped the cooks and pies over for the party. Cost? $100k+ in 90s dollars. Talk about making dough!

Worked rental at a ski spot where a rich fam dropped $1,500 just for an hour of skis (plus pricey lift passes). One lady even asked me to tie her shoes - nope, husband had to do it. Wealth and cluelessness sometimes go hand in hand.

I’ve seen more than a few private Ferrari showrooms inside billionaires’ homes, not just a car or two, but full blown garages decked out just for Ferraris. Met billionaires both as stuck-up as you’d expect and as chill as your coolest neighbor. One took me camping talk over burgers in his penthouse with a Pollock painting nearby. Surprise hospitality score!

I train fancy horses and lived in guest homes that make homeless shelters look tiny. Billionaire living sure isn't subtle!

I write content for the ultra-rich, and trust me, a lot of their success comes wrapped in a cloak of shady moves. Just saying.

One billionaire insists his pet parrot’s caviar has gold flakes because it makes the bird "sing better." Meanwhile, I’m still trying to get my cat to notice her cheap tuna. Talk about living in different (and sparkly) worlds.

Niece went to a fancy uni on scholarship and roomed with some wealthy girls who just handed her Prada and Gucci stuff like it was nothing. One bag was worth more than her car! They’d say, “Don’t worry, I have a backup in another color.” Can't imagine that kind of generosity or casual splurge.

Stepdad works as head of security for a billionaire hedge fund boss and regularly flies private to run errands. Once, they flew my family to NYC for my brother’s 30th birthday to see Billy Joel at Madison Square Garden, stayed in swanky hotels, ate fancy dinners - and flew home private. So casually dropping $50k on a birthday like it’s no big deal. Wild.

Girlfriend’s friend catered for the Ambani family in London. She noticed the teens would stop and wait for someone to open doors for them, because honestly, they might never have done it themselves. The pampering level is next-level.

Friend stayed at the beach and decided to buy a nearby house on the spot, only to realize it was the seller's actual home full of family photos and toys. He felt so bad because he never thought to ask. Oops, mansion buyer moment.

CEO so busy they don’t recycle themselves but pay someone to go through their trash and do it. Recycling royal style.

My uber-rich boss still hunts for 10% coupons and stays in budget hotels on company time. Then drops a million himself for authentic experiences. Smart with cash but knows when to splurge.

Friend’s billionaire dad won’t sell his $10-15 million Cape Cod beach house because the dogsitter watches the pooch there when they travel. Doggo’s kingdom is sacred.

Cleaned Steve Harvey’s golf clubs once. He walked off without tipping, then tossed me a random crumpled $5 bill from the balcony. Thanks, Steve, kind of?

As a chauffeur, saw a 10-year-old throw his iPad like a tantrum boss. Without drama, nanny popped out a brand new boxed one. No punishment, no chat. No wonder super rich kids act how they do.

Worked for billionaires on construction. Tossed out brand-new toilets ($5k each), top mirrors ($12k each), and quarter-million-dollar marble simply because they didn’t like the color combo. The trash pit was the ultimate waste dump. Not rare in billionaire world!

My brother’s a tech billionaire who basically treats money like Monopoly money. Spends $100k fixing tiny niggles just for peace of mind because the decision’s easy. Has a spa on his massive compound open 365 days but goes twice a week. Living life large and stress-free!

At a fancy restaurant, one super-rich woman spilled $1200 wine on her $10,000 dress and $7,000 purse. Instead of freaking, she laughed and said she’d soak the dress in more wine to match and buy a new purse the next day. Husband just chuckled. Now that’s billionaire confidence.

Did tech gigs for rich folks including a guy who’d pay $1,200/hour to plug in a TV, pulling in an all-Asian team to listen to his racist rantings for hours. The job was less about tech and more about nodding and taking the cash. Weird flex, but okay.
Also installed underwater AV systems in pools not even dug yet, then got paid to look busy while cameras rolled. Rich life has weird perks.

Art galleries sometimes spend thousands installing paintings in homes for clients to “test drive.” If the client doesn’t love it? They pack it up, take it back, and eat the costs. One boss had a $100k piece arrive in a $3k crate - then tossed the crate like garbage. Ouch.

Buddy’s electrician gig: wired a $100k patio with grills, TVs, outlets, and all. Then years later, the owner had it all torn down to build a guest house that dwarfed my own home. Mansions giving birth to baby mansions.

Worked around wealthy seasonal homeowners who spent millions but only picked the priciest options for glass, mirrors, etc... Without considering if it actually looked good. Result? Some mega mansions that are gloriously hideous.

Tax time for one client: $10 million due. But banks have daily max pay limits ($500k/day), so he had to send a half-million each day for 20 days straight. Taxes ain’t small potatoes when you’re THAT rich.

Painted in Malibu for a guy who was CEO of a huge company. One day he asked me my thoughts on a clerk who worked crazy hours for peanuts. I said maybe a future VP? He laughed and said anyone working those hours for low pay is dumb. Maybe harsh, but hey, that’s CEO logic.

Installed glass in a mega mansion with a pool house that wasn’t finished even after seven years. They ripped out the old shower glass and replaced it even though it was never used! Trends wait for no billionaire.

Ran a cake shop near Microsoft campus back in the day. The amount some parents would drop for one-year-olds’ birthday cakes (we’re talking mind-blowing prices) was nuts. Sometimes the cost for a single cake was more than I made in a week. Life lessons: When billionaires throw parties, even cakes make history.