20 Pricey Choices That Can Bankrupt The Wealthy

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Fortune disappears faster than it builds. The wealthiest among us indulge in luxuries that make a significant dent in their accounts; mansions collect dust, and jets rust. All these bad investments sink fortunes overnight. What are the financial missteps that turn riches into regrets? Let’s explore the habits that cost even the ultra-rich everything. 

Owning A Private Jet 

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A private jet isn’t just an asset; it’s a commitment to never-ending expenses. Fuel, maintenance, storage, and crew salaries drain millions yearly. Even minor repairs cost more than luxury cars. That’s why many billionaires prefer chartering; because owning one? That’s a financial sinkhole few can sustain. 

Superyachts That Sink Fortunes 

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Many yacht owners spend more time searching for their floating palace than enjoying it. Fuel and maintenance drain six figures, turning a yacht into a bottomless expense. It sails less and swallows money more. The ocean is vast, but the financial losses run even more profound.

Collecting Rare Cars Without Limits 

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Vintage Ferraris and Bugattis look great in a showroom, but collecting them without strategy leads to financial disaster. Values fluctuate, insurance is exorbitant, maintenance costs pile up, and storage isn’t free. Some collections appreciate, but others rust away, taking chunks of wealth with them.

Lavish Weddings With No Expense Spared 

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A $5,000 cake. A million-dollar venue. A dress worth more than a car. Extravagant weddings burn through fortunes in a single night. Guests forget the details, but bank accounts don’t. When the final bill arrives, some newlyweds start their future deep in financial regret. 

Owning Too Many Mansions 

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More homes mean more expenses. Market downturns turn grand estates into liabilities. And property taxes, maintenance, staff salaries, and security costs never stop. Even multimillionaires struggle to offload unnecessary homes when upkeep alone drains six figures a year. 

Failing Business Ventures 

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Money doesn’t guarantee business success. Celebrities and executives have lost fortunes chasing doomed startups. Even with deep pockets, bad investments quickly turn profitable empires into cautionary tales. Sometimes, restaurants flop, clothing lines fade, luxury brands struggle, and tech ideas just fail to launch.

Exotic Pet Obsessions

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Lions, tigers, rare reptiles, and chimpanzees—oh my, what a bill. Exotic animals require specialized care and massive enclosures—even the super-rich struggle with the costs of running private zoos. Many abandon the fantasy when they realize they’re funding a money pit that requires constant feeding and exorbitant veterinary expenses.

Unchecked Gambling Addictions 

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Some bet on Wall Street, others bet in Vegas, but the house always wins. High-stakes poker, private sports betting, high-risk day trading, and impulsive wagers drain accounts faster than a market crash. Celebrities and billionaires alike have watched fortunes vanish with the roll of the dice.

Buying Sports Teams On A Whim 

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Owning a team sounds like a dream until reality hits. Payrolls, stadium upkeep, operations, sponsorship struggles, and player contract disputes cost far more than anticipated. Inadequate investments in franchises have left even billionaires scrambling to sell. Without strategic management, a sports team becomes a luxury few can afford.

Costly Legal Battles 

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One lawsuit can cost more than a lifetime of luxury. Legal fees spiral fast when facing corporate fraud claims, defamation suits, intellectual property disputes, and bitter business disputes. Even those who win in court often lose millions fighting to prove their point. 

Trusting The Wrong People With Money 

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One bad financial advisor can do more damage than a stock market crash. Fraudulent accountants and unchecked spending habits have drained billionaire bank accounts more times than you’d imagine. The wrong inner circle turns fortune into failure before the victim realizes it. 

Luxury Fashion Addiction 

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$10,000 handbags, diamond-studded sneakers, and custom-tailored suits depreciate instantly. In fact, the moment you use it. Unlike real estate, high fashion rarely holds value. Some millionaires spend more on clothes than investments until they realize their wardrobe is worth nothing in resale. 

Expensive Hobbies That Don’t Pay Off 

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Rich people hobbies like racecar driving and space tourism offer thrills but at extreme costs. Private lessons, equipment, insurance, and membership fees add up fast. Many ultra-rich people spend millions on hobbies that provide excitement but zero return on investment. 

Owning An Island (And Everything That Comes With It) 

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A private island is only paradise until the bills arrive. Freshwater supply, security, infrastructure, and other logistical details make ownership a nightmare. Many realize too late that maintaining an island is far more expensive than just visiting one. So, pick wisely.

Funding An Entourage’s Lifestyle 

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The bigger the entourage, the faster the fortune fades. And when the money stops, so do the “friends.” Private chefs, assistants, and stylists all expect millionaire perks. Some celebrities learn the hard way that generosity without limits leads to bankruptcy. 

Bidding Wars At Art Auctions 

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Auction houses thrive on emotion-driven spending. Ultra-wealthy buyers compete for status pieces, often overpaying for art that doesn’t appreciate. When market tastes shift, those $10 million paintings sometimes sell for half, worse, or maybe never. 

Insatiable Jewelry Obsessions 

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Diamonds might last forever, but bank accounts don’t. Watches, necklaces, and ring collections often lose value over time. Unlike stocks or real estate, jewelry offers little financial return, which makes it one of the most overpriced indulgences of the wealthy. 

Unnecessary Private Security Details 

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High-tech armored cars and 24/7 bodyguards cost millions annually. Some billionaires need protection, but others fund excessive paranoia. Security expenses pile up, leaving many paying for safety they don’t need. Yes, safety is important, but the line between precaution and excess can blur.

Chasing Unrealistic Investments 

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Hyped-up stocks failed tech startups, and crypto crashes have drained fortunes overnight. Even seasoned investors make emotional decisions, pouring millions into ideas that never disappear. One wrong bet can erase decades of financial success. Fast. 

Divorce Settlements That Shatter Bank Accounts 

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A single signature can cost billions. High-profile divorces see fortunes sliced in half, with legal fees reaching millions. Property divisions and bitter courtroom battles leave even the wealthiest gasping. Some recover, others don’t, but in the end, money fades faster than love.

Written by Devin J