Home Money Consciousness Former Millionaires Share Sad Stories Of How They Lost It All

Former Millionaires Share Sad Stories Of How They Lost It All

Trista Smith January 1, 2023

What would you do with a million dollars? Perhaps you’d pay off debt, buy houses and cars, or put it into the stock market. Regardless of what you do, there’s always that chance that you’ll either spend it too quickly — or lose it. People who stay millionaires understand that it’s always a smart choice to only spend what’s necessary for your circumstances, but that doesn’t always work for everyone. The thrill of having that much money can often go to people’s heads.

You’re so excited to finally be able to buy whatever is needed for a happy life, so I can imagine how quickly that money could be spent. One Reddit user decided to ask millionaires around the world how they lost all their money, and the answers don’t disappoint. Keep reading for an in-depth look at how former millionaires decided to spend their money and what finally broke the camel’s back and caused them to lose everything. Afterward, check out these real-life stories from people who share what everday items made them rich.

20. You Need To Diversify

Reddit User KlownPuree had an interesting story to share about his father. “My dad, not me. He made some shrewd stock market investments after he retired. They were options on an oil refinery at a time when the USA had a real shortage of them. My dad had done a lot of research on this and studied the situation carefully. He got rich to the tune of maybe $2 million. He could have been set for life. My dad was already a really smart guy. He has a Ph.D. in mathematics and was a highly respected big-brain professional back into the 1960s.

“However, he thought this took him to the next level. He bought a lot of newer options in the same company. I suggested to him that he diversify, put a bunch of money into something closer to an annuity or another conservative investment that would give him plenty of income forever. I told him if he did that, he would always be rich. Well, he is pretty far from that now. I haven’t said a thing about that to him since he lost everything. I did what I could, at the time, to save him from himself. But who was I? It pains me to see how it played out for him. He did a lot of things right in life. He deserved better, but there’s no “deserve” in securities investing. Morals of this story: You aren’t an investment genius after your first blockbuster win. You need a track record. Diversify.”

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19. Crime Doesn’t Pay

SeattleSushiGirl shared, “I have a relative who is a self-made millionaire many times over. He was the hardest working person I’ve ever known. As soon as he graduated from high school, he got his real estate license and became a successful realtor. Within 30 years he opened a successful construction company, a store that sold kitchen cabinets, and owned over 20 rental properties. This wasn’t enough for him, and he started renting out his properties to people that would pay him more to grow pot in. His granite company was used to ship the pot across state lines, and now he’s sitting in jail facing a minimum of 10 years.

“The government is coming after all his rentals and money. Edit: I should add he shipped the pot to 9 different states (7 of which weed is still illegal) using USPS.” This Reddit user’s family member decided to ship marijuana to numerous states without thinking of the repercussions. Had he decided to run a legitimate business, things could have ended differently. Now with the government seizing all of his properties and money, he’ll likely lose everything while sitting in jail for the next ten years. It just makes you realize that crime doesn’t pay and is not worth it ruining your life over money.

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18. A Sad Story for Most Millionaires

Lowhangingfruitcake shared the story of her first husband and how he lost millions. “My first husband was making a million a year. He was enjoying life- spending frivolously, but bringing in enough that it didn’t matter. We divorced, but amicably (no alimony, no child support), he just paid for whatever the kids needed. Then he got leukemia. He fought like heck for three years. The last two years were very expensive. It was worth it. Money won’t make you happy, but the lack of it can destroy you. The kids and I can take comfort in knowing that truly, there was nothing else possible.”

“His millions bought his kids two more years of dad. And I’m glad for him that he enjoyed his life while he could.” This is truly a sad story. This woman’s first husband received a devastating diagnosis and fought back for three years before passing away. He didn’t lose his money to greed or other factors. It was simply paying for all of his treatments that made this family lose everything. Even though they split up, this couple was able to give their children more time with their dad by paying for treatments until the end.

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17. Stocks Don’t Always Pan Out

Queen_Serenity I shared the story of her best friend and how he lost millions. “My best friend was a National Sales Manager for a big tech company. His team invented the bomb-sniffing tech now used at airports, designed the computer network for a baseball stadium, added a monitor to the Apache attack helicopter, and sold a lot of storage equipment to the Intelligence Community. He was making a quarter of a million a year and had a million in company stocks. Then the tech bubble burst. His company froze his stocks, refusing to let him sell them.

“He watched them dwindle to pennies. Then, when he was about to make a sales trip to London, he was laid off. He got in his limo and asked his driver for a job. He’s been driving limos for over a decade now. He didn’t downsize quickly enough, still lived like a millionaire for a while, and went through his savings. He’s afraid that after driving limos for so long, he’ll never get another high-paying job again. He’s embarrassed to put “limo driver” on his resume even though he loves the job. He doesn’t want to go back to corporate anyways.”

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16. The Casino

Plasmac9 witnessed an interesting interaction at a well-known casino with a friend. He claimed, “I was at the Borgata a few years back with my buddy. He had never been in a casino or gambled before. I’m showing him the ropes at blackjack. We’re at a $25 min table with a $3k max. My friend was maybe up a few hundred bucks and have a great time. This other guy sits down and starts betting max bet hands. The dealer gets 2 blackjacks in a row then four 20s in a row. The new guy lost $18k in about 4 minutes. My buddy wasn’t paying attention to the guy’s bet.

“In a joking-friendly manner, he just turns to the guy and says, “wow, you’re bad luck.” I swear, I thought the guy was going to punch his lights out. I intervened, and the guy got up and left.” Going to the casino can be fun when you win, but betting at such high stakes can often be dangerous. You can lose your money quickly and leave feeling overwhelmed due to the amount lost. It’s always a safe bet to just take a limited amount of cash with you to the casino. That way you don’t leave feeling stressed out.

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15. Pent-Up Emotions

Cooldart61 talked about a distant relative that lost everything. He said, “Not me but one of my ancestors. It was my 4th great-grandpa Jacob. At the time the family had tons of family and land. Now Jacob was known for keeping to himself and not making a fuss despite all the drama his family would cause. Jacob blamed his father for not taking more control over the behaviors of the other family members. When his father lay dying on his death bed, Jacob decided that was the best time to spill out every emotion and ounce of hatred he ever held back.

“He unleashed everything on his father. Well, from what I understand, his father was not dead yet! So with the last of his energy, he signed a new will. The will takes away everything: money, houses, land, businesses, etc. That father gave it to friends, distant family, and random strangers. Thanks to one emotional outburst, our family lost our entire fortune.” Holding back feelings often leads to outbursts, so, understandably, this happened. This man’s great-grandfather didn’t like what he heard, so he decided to change his will during his last days. It sounds like he would have rather helped strangers than give an ounce of money to his son.

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14. Nearly Six Million Lost

Wishnana told the story of close friends and a recognizable company. “Not me, but a close friend’s parents worked at a well-renowned American company in Houston in the early 2000s. They were high up in the management chain and enjoyed a lot of the perks that came with their position, after sticking through thick and thin, especially during the dot-com bubble. Said friend’s parents were also very good at managing their money, living very frugally, and investing for their future nest egg. Unfortunately, therein lied the rub… All that investment (401Ks, extra cash, etc.) was on a single pot.

“I believed, with all their allocation (back in the 2000s or so), they have had invested close to $5-6M and were due to pull it out so they could finally retire. But a company scandal brought all that to a collapse. The company? Enron. All their money evaporated.” Losing that much had to be devastating. It makes you realize there’s always a chance that something could happen. It’s important to save money when you have a big amount just in case. Even though they were good at money management, they couldn’t change what happened.

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13. Natural Disasters Can Ruin Millionaires

Sushitrash69 told their story. “Not me, but my parents. Both smart people went to the best universities, graduated with BAs and Masters in Architecture. Went on to design very high-end apartments and homes all over Queensland (Australia) – saved up enough to open a Michelin-style restaurant on the water. It was a hit, they became incredibly wealthy, and this is where the money started to take a toll on them. They went all out. Bought two penthouses in the same building and combined them into one. Owned and managed multiple high-end apartments all over the city. Bought multiple sports cars and even a yacht.

“They took my sister and I traveling all around the world. My life growing up was a model’s Instagram page. But then one day a flood came, the restaurant went completely underwater and destroyed close to a million dollars worth of wine and not to mention the write-off on the kitchen. They were ruined. They had to sell everything just to cover the cost of the restaurant. Now, they live in a small apartment and are both still working over 70 to pay off all the loans they still owe. Word of warning, if you come into possession of a large sum of money, don’t be stupid.”

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12. A Sneaky Wife

Nstav13 shared a nefarious yarn of millions lost. ” Not me but my great grandfather. He started a candy company that serviced most of the Wyoming Valley in PA. My grandfather (his son) sold the company for upwards of 100 million. My mother and I are unsure of the full amount. He used the money to buy some land down in Florida, franchised a few radio shacks, and bought a lot of cars. During this time he divorced my grandmother and married another woman with Children. Towards the end of his life, he reconnected with my mother and met me, but then developed brain cancer. He decided to cut his wife out of his will and give all of his money (still around 10 million) to my mother and her brother.

“Because he was bedridden, he had to have his lawyer email and print out the new will, which he would sign and mail out to the lawyer. But he asked his wife (that he was screwing over) to mail the new will, but for some reason, it got “lost”. He died a few days later with my mother unaware the will change hadn’t gone through. She paid for the funeral only to learn afterward from her lawyer that the will was never changed. So, she went to confront her stepmother only to find out that she and her sons had already flown to Florida, taken the money, and moved. She tried for a few years to sue, but due to state laws and lack of written evidence couldn’t get the suit off the ground. And that’s how my mother lost a multi-million dollar inheritance and got stuck with a $50,000 funeral bill.”

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11. Franchise Woe

Reddit user GhostRiders said, “This happened to friends of my parents. They were one the first people in the UK to purchase a Burger King franchise, it was in the ’70s. They were based in Birmingham, the second-largest city in the UK. A Decade later they were running 5 Burger Kings and raking it in. However, they got greedy and started to buy stock from non-approved suppliers. They were doing this for about a year, then one day several men all in suits turned up at each of their restaurants all armed with massive amounts of paperwork.

“The paperwork stated that due to them breaking their contract that they were taking ownership of the restaurants. About a year later, tens of thousands spent on solicitors, courts ruled in favor of Burger King. They lost all of the restaurants and to run salt in the wound Burger King then proceeds to sue them. Fast forward a couple of years, hundreds of thousands more spent on solicitors and the court ruled in favor of Burger King again. They had to sell all their houses, cars, possessions, etc. They were left with next to nothing and left the UK.”

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10. Millionaire Buyer’s Remorse

A Reddit user with a deleted username said, “I have a rich uncle whose father owned a big chain of gas stations and some oil fields in Turkey. When the father died and the uncle took over, he didn’t give any crap about the businesses. He was just partying and squandering everything. Like he bought a new luxury car every week. Plus all of the boats. Every few months he would move into a new luxury home and buy 100% new furniture for it and just threw the old stuff away. He was living a slippery slope that would end quickly.

“After some years, it all collapsed and he had to sell everything to a big US corp when hitting insolvency. Everyone in the family hates him now. Well, he was always an entitled guy… But guess what: Despite being an unproductive loser, he managed to marry a bank director. She is rich as heck and continues to sponsor his stupid lifestyle. His sugar mummy… For some people, consequences just don’t seem to exist…I mean how can you go broke owning oil fields? It boggles my mind…” This man squandered his wealth buying houses, cars, and boats. He had the opportunity to be a multimillionaire in the oil industry but couldn’t stop spending.

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9. Millionaires Who Don’t Want It

I-Euan says, “Technically not me but rather my family; my great grandfather was born to a long line of vicars who had land, properties, and farms. They were loaded. He was the rebel only son and swore that he would break tradition, so he joined the army, and come world war 2 he was shipped off to fight for Britain. While overseas, he was captured and spent a few years in a POW camp where he subsequently found Jesus. After the war, he returned, joined the clergy and, his father having died, gave every single penny to the Gosh darn church.

“All of the land, property, and titles were given up, and he lived off his vicar’s salary. It was never mine to lose, but the knowledge that I could have been a Lord with a horse sting.” It sounds like this great-grandson is a little bitter about his great grandfather’s choices. It sounds like he led a difficult life with being in a POW camp. He deserved to do whatever he wanted with that money. The poor man probably saw more than we’ll ever see in our lifetimes.

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8. A Tale of Embezzlement and Prison Time

Cat9tail shared the story of his dad’s boss. “Not me, but my dad’s boss. He was a corporate executive in the finance world, wealthy, and was very well-liked until they discovered he was embezzling from the company. He lost his job, went to prison for a long time. Shortly after the crime was discovered, my dad was offered his boss’ job, which he took. He was over the top transparent about everything, and I grew up hearing the cautionary tale told over and over again. My dad retired with a large company stock portfolio, worth nearly $2M. Sadly, he never sold the stock (he has other retirement income) and today it is worth about $300K.”

It sounds like this executive made some bad choices. He decided to embezzle from the company and ended up going to prison. It’s never a good idea to take advantage of your position at work. It seems as though he got what he deserved for doing such a thing. The father in the story never made waves at work and ended up with a large stock portfolio involving lots of money. He told his son the tale to ensure he never decided to take advantage of a position at work. If only the father sold his stock to receive the money he deserved.

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7. Greed Changes People

Nonuniqueusername’s mother was married to a millionaire. Their interesting story may just leave you in shock. “My mom’s second husband was a millionaire. Our family and his first family treated everything as one big family. When he got cancer, he set a very intricate and fair system. Then he appointed three people to oversee any emergency changes to his estate. My mom, his first wife, and her second husband. As soon as he died they voted against my mother to throw away his whole plan and just give them themselves the money, 50-50.

This Reddit user’s mother was married to a millionaire, and as soon as he passed away, his ex-wife went above her head to take all of his money. This poor woman was entitled to some of his estate, but lost everything to her husband’s ex. It’s sad to think someone would stoop so low as to take everything for themselves, but it does happen every day. Even if they split the money it was enough for everyone to live comfortably. Being greedy and taking everything for yourself isn’t the way to go. The husband’s wishes should have been kept at the forefront during these discussions.

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6. He Couldn’t Stop Buying

Moonbunnychan dated someone who suddenly came into money and was unable to control it. “I dated a guy who unexpectedly inherited 6 million dollars. His parents had been killed in a drunk driving accident when he was a baby, and so their life insurance plus money from a legal settlement sat in an account collecting interest for 18 years. He got a call from a lawyer on his 18th birthday, and that’s how he found out about it. He went nuts. Every time I saw him he had a new car. This guy bought an extravagant house.

“He started a store that was more just a hang out for him and his friends and bled money. He insisted on taking these extravagant vacations. Then, he would go to our local comic shop and just buy EVERYTHING. Like ever see those statues in a comic store that are thousands of dollars and wonder who buys these? He had several. It was a major factor in why we broke up…it was all just too much, watching him blow through money like that. He didn’t invest any of it. In 5 years he blew through all of it. Last I saw of him on Facebook he was destitute.”

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5. Blew It All With Travel

Reddit User SansCitizen tells the story of their ex’s mom. “She grew up as a trust fund kid in a tremendously rich Jewish family in New York. When she turned 18, she decided to see the world, so she moved to Israel. Then Iraq. Then France. She spent 30 years moving from country to country, burning her money away like it was unlimited, but as it turns out, trust funds are finite, and one day she found herself with just barely enough left to get back to the US and buy a tiny house. Her family had at that point long since disowned her, so she had to get a job.

“Only, what do you do when you have no prior work experience, no credentials beyond high school, and you’re 48 years old? Answer: housekeeping at the local Best Western… Until they fire you for rocking the boat too much (she proposed a bunch of changes within her first couple of months there, most of which being rather expensive and offering no real benefit beyond “I think it would look nice.”) Then, you drive a short bus for senior citizens… Until you turn the wrong way down a one-way street, panic at the sight of oncoming traffic, and steer straight into a fire hydrant… Then flee the scene, abandoning the company vehicle and its several now-injured passengers…”

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4. Lost Everything To Alimony

Reddit user _effed_up stated, “I built a business worth ~3 million, had a house worth 1.4 million, Investments worth more than 2 million, 4 nice cars. Divorce laid me low. An ex-wife, a lawyer, and a judge stripped me of at least 3/4 of that. Left me with a Miata race car, a bit of money, and 51% of my company. Still had to pay alimony. I gave up. I negotiated my way out of alimony by giving up more of the company, liquidated everything else, bought a boat, and fu**** off. 26 months later, I sailed back into my life and started over.

“I’ve earned enough to live a modest retirement, and that’s where I am today. Don’t get married boys, it ain’t worth it. I’ve done it twice, the first time was a disaster, the second time was an annoyance. Just my opinion and experience. I’m way too drunk and shouldn’t have posted. Anyway. There it is.” It sounds like this business owner had a difficult time with his divorce. Hopefully, everything worked out in the end for him after buying his boat. and a fresh perspective made him feel better.

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3. A Traumatic Lie

PianoToonr shared the story of how their father lost millions. “My dad had over 20 million dollars in a business with 12 locations and 3 more openings on the way. An employee who was caught selling drugs fabricated an elaborate story that he got the drugs from my dad’s company, and that the whole company was a front for the Mexican cartels. My dad spent a lot of time in Mexico back in the day and had a criminal record, so that was enough for the DEA to raid him on this story. They stole all the computers, terrorized the employees, and raided every one of the locations on the same day with over 300 SWAT, including a raid on his own home (he wasn’t there, just his young children–they’re traumatized by it). They found nothing. Nothing. All papers in order. No indictments came, no case.

“Regardless, most of the employees and management quit due to the investigation. He had to close most locations and sell after less than a year at a huge loss just to pay for the lawyers to defend his case. The worst part is that they won’t admit they’ve found anything. The DA spent millions on this raid. So–they’ve left the case open indefinitely, making it impossible for him to work in his field. His lawyers said the prosecution has privately asked him (seriously), to find something wrong that he can plea to so they can save face. He won’t lie, so they won’t close the case. The government took my dad’s life’s work, his savings, and ruined hundreds of other’s lives–and we have zero recourse.”

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2. Managing Finances

Reddit user mistmanners and her husband lost their wealth due to a common situation these adays. “Well, I see a lot of stories here, but here’s one that’s a bit different. We moved from the USA to Lebanon after college to be with my husband’s family, they were close. Surprise, his parents died before we could get there, his dad a few months before we left and his mom, unfortunately, passed away during our flight and was buried a few hours before we arrived. This was not a good omen. However, we had moved every last possession with us, and we’re determined to stay nevertheless.

“After 30 years and close to retirement, we had several houses, apartments, good jobs with benefits, and ample pensions. It had been a tough road and we had starved at first. Now, we were looking forward to living where we wanted, whether in the USA or Lebanon and living off of a modest retirement income. All that was wiped away due to the current economic disaster in the country, worsened by covid but mainly due to financial mismanagement of the country and corruption on a grand scale pretty much unparalleled in modern history. Everyone in Lebanon wants to emigrate now. There are no renters with money to inhabit our apartments. The lira is worthless, and our pensions are worth almost nothing. We could have spent those years in the US building up 401ks and buying a home.”

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1. A Dangerous Situation For Millionaires

A Reddit user with the username PabloChickaso shared the story of their family wealth and downfall. “My mother’s family. It was the separation of India and Pakistan. My mother’s family was crazy rich in (now) Pakistan. I’m talking mansions, maids, businesses, and repute. But because of the socio-political unrest between Hindus and Muslims, they had to pack up everything and move in with their relatives in India. Her grandfather sent the family here (India) overnight and stayed back in Pak disguised as a Muslim. He had to stay undercover for 3 months so he could wrap up some financial affairs. His family could have no contact with him because being identified as a Hindu could’ve gotten him killed in that situation. They could only hope he was alive.

“He had to let go of much of their wealth but brought a bunch of big solid gold bricks with him so his family could start a new life here. He first went to Bombay and gave the bricks to a goldsmith telling him to coat them with silver. Traveling to a smaller town with so much gold was risky and silver didn’t cost as much then. When he reached his destination, he gave the bricks to another goldsmith to have the silver coating removed and evaluated for their worth in cash. Turns out his gold bricks were swapped for solid silver bricks.”

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