It's incredible how people can lose staggeringly huge amounts of money simply out of stupidity, love gone wrong, and sometimes, bad luck. So how do you go from driving luxury sports cars and yachts to working minimum wage? Sometimes, it's easier than you might think. People share the true stories of how they (or a loved one) lost everything. Stories slightly edited for clarity.
The Power Of The Postal Service
“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.
He was so successful at one point, he shipped the pot to 9 different states (7 of which weed is still illegal) using USPS.”
Squandered Millions With A Twist
“So a little backstory. My great grandparents owned a luxury fur coat business and made an absolute ton of money. When my grandma and her brother, my great uncle, had moved out from their parents’ house, they were given a sizable amount of money (not millions, but far more than the average person might get in such a situation) to fund their adulthood.
Great uncle ended up opening two businesses using this money – a gas station and a used car lot. He made pretty good money running these two businesses. We’ll get back to him a little bit later in the story.
Grandma however took this money that was given to her and blew a lot of it on fancy clothes, vacations, etc. She then got married to my grandpa and had three kids, and then he ended up cheating on her and took a bunch of her remaining money in the divorce.
Meanwhile, great uncle was furthering his business ventures, opening a payphone business, helicopter tours, and all kinds of other lucrative stuff. He was rolling in money at this point.
Some time later, my great grandparents died, within months of each other. They then split their inheritance two ways – 1/3 of it going to my great uncle, and 2/3 going to my grandma. The argument was that he was a wealthy bachelor with no kids, and she was struggling to get by with a secretary job while raising three kids by herself.
This ticked off my great uncle quite a bit, since he knew what she had done with her previous huge handout. He was mad about the inheritance not being 50/50, but not something that he’d quit talking to my grandma over. Not yet, anyway.
So, what do you think my grandma did with her huge windfall of money? Did she open a business? No. Did she invest it in some way? Nah. Did she do absolutely anything productive whatsoever? Of course not.
The first thing she did was buy a great big house in a nice neighborhood. Actually, no wait, that was the second thing she did. The first thing she did was quit her job.
Then, she bought a luxury car. Then came luxury clothes for my mom, aunt and uncle. Then she hired a full-time live-in maid. Then came the vacations to all the hottest vacation spots of the day. Gourmet meals every day. All the toys and gadgets that they could possibly want. You name it, she bought it.
So it should come as no surprise that she burned through the entire inheritance in less than a year.
Two-thirds of the money that her parents had worked their whole lives for, more money than anyone should reasonably ever be able to spend, she blew through in under 12 months. But she kept spending, driving herself into debt. They lost the house, lost the luxury car, and even had to sell all their fancy clothes and toys, just to pay the enormous debt she had gained.
And then she came to my great uncle’s office and asked him for money.
She was promptly thrown out by security, and was told that he would never speak with her again. And he never did.
Imagine my surprise when I grew up in what was basically the borderline of total poverty, and my family tells me that they used to be filthy stinkin’ rich.
Because of what my grandma did, my great uncle more-or-less cut off contact with her side of the family for YEARS. It wasn’t until I was a teenager that I ever met the man. I think later on in his life, he felt bad about punishing the rest of the family when all of the fault lied on my grandma, and he started to talk with us every so often… but we knew to never ask him for anything, even though we were all struggling.
When my grandma was on her death bed, she begged for us to have my great uncle come to the hospital so she could apologize to him. When told about this, his response was basically “I don’t give a care.”
And then, in an almost ironic twist, he married an obvious gold digger, 30ish years his junior, who had already survived two other dead old rich guys. And then when he died, she got everything, disconnected their phone line, and disappeared like an absolute bandit. His actual family got nothing.”
Multi-Millionaire At Age 18
“I dated a guy who unexpectedly inherited six million dollars. His parents had been killed in a bad accident with an inebriated driver 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. He 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. 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.”
He Would Be Making $600k/Month
“My dad, not me.
When he was young in the 70s he wrangled other people into investing with him and bought a bunch of duplexes and four-plexes in San Francisco, renovated them, and mostly sold for a profit. However, he kept some. I think my mom estimated at one point (this was over a decade ago too) that if he had just sat on the properties he owned he’d be taking in about $600k/mo. in rent.
Instead he invested with his brother in a home gym company and kept selling off property to fund it, and then got nailed by the IRS for failing to pay taxes.
When I was a kid he lived on a 30 foot sail boat because he’d lost it all.”
There’s A Lesson Here
“I built a business worth about $3 million, had a house worth $1.4 million, Investments worth more than $2 million, and 4 nice cars.
I got divorced. The divorce laid me low. An ex-wife, a lawyer, and a judge stripped me of at least 3/4 of that. It left me with a Miata race car, a bit of money, and 51% of my company. On top of that, I 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 got off the grid.
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.
The moral of the story? 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.”
He Owned Oil Fields And Still Went Broke
“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 gave any cares about the businesses. He was just partying and squandering everything. Like he bought basically a new luxury car every week. And boats. And 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.
After some years it all collapsed, and he had to sell everything to a big US corporation when hitting insolvency. Everyone in the family hates him now. Well, he was always an entitled brat.
But guess what: Despite being an unproductive loser he managed to marry a bank director. She is rich as all else and continues to sponsor his stupid lifestyle. Basically his sugar mommy.
For some people, consequences just don’t seem to exist. I mean how can you go broke owning oil fields? It boggles my mind.
And every time we are visiting family in Turkey and drive from Istanbul to the city where my family is from, we pass like 20 gas stations that used to have our family’s name on them.”
Lesson #1: Diversify
“My dad made some really shrewd stock market investments after he retired. They were options on an oil refiner 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 PhD in mathematics and was a highly respected big-brain professional all the way 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:
2. You aren’t an investment genius after your first blockbuster win. You need a track record.”
Only In America
“My poor first husband. He 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 a dog for three years. The last two years were very expensive (because we live in America). 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 we could have tried. His millions bought his kids two more years of time with their dad. And I’m glad for him that he enjoyed his life while he could.”
The E Word
“Not me, but a close friend’s parents worked at a well-renowned American company in Houston in the early 2000s. They were really 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 friends parents were also very good in 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 2000’s or so), they have had invested close to $5-6M and was 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.”
It’s Always Karen
“My grandfather was a thrifty man. Always was a DIY guy, hated hiring contract workers (except for my father, whom he introduced to my mother), and worked for nearly 40 years at our local GM plant.
His savings, myriad cash deposits, and investments over the years netted him a net worth of about $2 or 3 million. After walking off the job at GM after a scuffle with the plant management, he went into business for himself and became a landscaper and evergreen farmer at 64 years old, earning government contracts with county and local agencies, which netted him another sizable chunk of money.
His sister’s husband did the same thing essentially, and this is where my aunt comes in, we will call her Karen. Karen worms her way into my great aunt’s life and as my great aunt approached her 80’s started becoming more frail, and Karen “took care of her” which means she had my great aunt sign over power of attorney and immediately signs everything over to herself. Brand new house, all three cars, RV, everything. Consigns my great aunt to a convalescent home where she died, the will having been officially amended to award everything not already taken by Karen to Karen.
My other great aunt died suddenly and left my mother as her executor of her modest will, which was basically the stuff in her house, as she was in the process of selling the house. I was very young, but I remember Mom loading me and my two brothers into the car and flying down the highway to beat Karen to the house before “anything turned up missing.” We were successful and Mom got to inventory and disperse everything properly. We ended up with, of all things, her turn-of-the-century pasta crank and her big box of recipes.
Grandpa by this point had developed cancer, and slowed down his business. Now 75 years old, he had a nice, modest house on a nice chunk of extremely valuable land thanks to the explosive development there. Mom takes time off work to help Grandma care for him, until he too passes away, leaving everything to Grandma. At this point, we move into Grandma’s house to help her around the house and to help her close and liquidate the business assets. After about a year, Karen worms her way in like a tick and things start disappearing, like…farm equipment, and other things. Her daughter’s husband also had gone into the storage barn and “trashed out” a lot of family heirlooms (which also was where we kept a lot of our furniture from our home) which all ended up in a fire pit behind the barn. It wasn’t long after this that Karen convinced Grandma to let her “handle” her finances and Karen evicts us. Within two years, they sold the family home and land, liquidated all of Grandpa’s stocks and bonds, and fled to Florida. Karen had once again gained power of attorney and legally stole all of Grandma’s remaining assets. Grandma died ignominiously when she was given an insulin shot 20 times her supposed dose, and she went into DKA and died slowly and horribly in brain death.
Out of an estimated $4 million dollar inheritance, Mom and her two sisters were given an “equal” inheritance of twelve thousand dollars. Karen kept the house, the cars, and ended up burning through everything. Obviously this ended up shattering the family, and now none of us speak to the other.”
A Couple Million Down The Drain
“My grandfather died and left everything to my mom.
My father died and left everything to my mom.
Mom always thought she was a smart gambler that would win – and as proof she won something like $25,000 in the lottery once and went out and bought a car. That just got her hooked… good.
When dad was alive, he didn’t let her gamble – he kept it under control.
After dad died, mom found a boyfriend. A former bookie who was a professional gambler. They used to like going to the Indian casinos where they subsequently squandered every single penny and more as my sister told me that mom, after selling the big house for another half million bucks and buying a small little condo – has now taken out a home improvement loan against the condo for $50,000.00 – no improvements were ever made.
Casinos and lottery tickets. A cool million or two gone.”
A Government Mistake
“My dad had over $20 million dollars in a business with 12 locations and 3 more opening on the way. An employee who was caught selling pot fabricated an elaborate story that he got the pot 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. Absolutely 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 nothing. 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.”
“My great grandfather started a candy company that serviced most of the Wyoming Valley in Pennsylvania. 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 cutting out of the will) 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 afterwards from her lawyer that the will was never changed. 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.”
Lifestyles Of The Rich And Famous… And Then Not-So-Rich
“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 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
Took my sister and I traveling all around the world.
My life growing up was literally 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 high-end bottles 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.
They now 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.”
Great Farmers, But…
“My great grandparents were farmers and lived in North Dakota. In their prime, their team and them were absolutely great farmers. This along with some other factors made them suuuuper rich. For an example, they owned multiple planes and even had a hangar built to store them. They also had a really nice house (not a mansion, but a really nice and large one).
Well, it turns out they were really great at farming but not so much at paying taxes.”
I Could Have Been Someone
“Technically not me, but rather my family; my great grandfather was born to a long line of priests 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 FRIGGIN CHURCH. Land, property and titles all, and lived of his priest’s salary. Obviously it was never mine to lose, but the knowledge that I could have been a Lord with a horse and an affordable illegal substance addiction really stings.”