Friend of mine is a direct decedent of a super rich Spanish noble from Madrid. Essentially, this guy made so much money, nobody in the family needed to work for over a century. But because nobody worked, there was no money added to the family fortune, and it slowly dwindled away. His dad got the last of it and used it to get a degree from a good university and is doing really well for himself.

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 hell 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.

My dad is an Ex-millionaire. He's a f*****g wizard at starting successful businesses... His problem is he can't *let them go*. He's the boss/owner who never hires a manager that's not family because he just doesn't trust anyone else to run it. He drove 3, million dollar companies into the ground because he couldn't keep up with his own success, and refused to hire people to do it for him.

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 form 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.

Not me, my mom. 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.

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 ignomiously 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.

My dad, not me. He 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: 1. You aren't an investment genius after your first blockbuster win. You need a track record. 2. Diversify.

Not me (technically), but my grandma. So a little backstory. My great grandparents owned a luxury fur coat business and made an absolute shitload of money. When my grandma and her brother, my great uncle, had moved out from their parents' house, they were given a sizeable 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 s**t. 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 f*****g 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 f**k." 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 a f*****g bandit. His actual family got nothing.

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 travelling 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 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. 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.

I don't know if this fits, but my ex had a friend who inherited a million dollars in cash and near-cash assets when his only parent died and he was 20 years old. Now, you aren't just going to retire at 20 on a million bucks but it's a great way to pay for college, maybe buy a car and a down payment on a house, and save/invest the rest. Basically, it's a really good way to start your adult life and nearly ensure you'll be quite wealthy in your later years. Did he do any of that? Nope. Bought himself a ridiculous luxury car, bought cars for his friends, bought wardrobes of designer clothes, threw huge parties repeatedly, etc. Ended up broke in two or three years and went back to waiting tables to make rent. Sad to see.

My wifes Aunt used to be rich. Was married to a brain surgeon who was also on the board of directors for all the local hospitals so pulling down two checks. She was a platinum member of a local casino and would send us and other family members coupons for all inclusive weekend visits to the casino. You literally did not need to bring any money for anything. All food, drink, gratuity, ect was all taken care of. Anyway her husband had his medical license revoked for writing too many scripts for pain killers to her and other people and they both now live in Mexico somewhere.

Hypothetical millionaire. I bought $100 worth of bitcoin when they were about $1 each. I sold them when they were about $2.50 each and was so happy I made money from "internet coins". As of the moment I am typing this those coins would be worth $1,855,000.

Not me but my great grandfather 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 bed ridden 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 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

Having children.

it wasn’t me, it was an ex-girlfriend and her family. her dad was a war artifact/art collector and salesman. the kind of job where one sale = $5,000-$100,000. that kind of quick money made him believe he could live rich. so he lived in a big house, had another big house in a different state, a timeshare on an island, he would swap out for the newest Cadillac Escalade every two years. he managed to run life like this, getting into a habit of really bad spending choices, for 20 or so years until it was revealed to everyone he was subsidizing all of it with credit and wasn’t making nearly as much money as he used to or claimed. that was when the IRS and the banks came knocking. he had held onto some artifacts and art and was able to sell those piece by piece to slow down and lessen the blow, but it was an undeniable downward spiral and he ended up declaring bankruptcy. private artifact collectors and art collections just aren’t as hot as they used to be so he’d have to settle on low prices for all the sales. now he frequently moves around in a different state to keep the IRS and banks off his tail, and my ex is just about the only person who has stuck by him through this but there’s only so much she can do.

I have never been rich but my family was well above average when i was a kid. My father was a mechanic and in 1981 he bought a car repair shop that made us money pretty well. Then in 1992 the Bosnian war started and our hometown of Sarajevo was put under a siege that lasted until 1996. In 1994 we were able to escape the city and move into a refugee camp. When the war ended we returned to Sarajevo and my fathers car repair shop as well as our home were in total ruins after all the artillery and mortar fire. We were able to get a new home fairly quickly with the help of some of our relatives but we never got the car repair shop fixed. It was in so bad condition we just demolished it after we had sold all found scrap metal and usable tools.

Not me alone but my family: Both parents got serious illnesses. About $2 million gone in 5 years. I went from really never thinking much about money to everything being gone, wondering how to run up all of my parents debts as far as possible to keep a roof over their head before having them declare bankruptcy.

Divorce. I was a millionaire, got divorced which nearly sent me to insolvency, buckled down and worked my butt off and am re-millionaired. Guys, don't underestimate the pernicious impact on net worth a bad divorce can have.

Crypto millionaire. Still worth a lot, with my accounts about $850,000 today (I have a lot of xrp) But in 2017 I was worth about 3.5 million before the crash. Lowest was $300,000. I’m a hodler so o don’t day trade usually.

Covid. Built a business that was given a valuation of a few million back in January, but the industry is now down 80% and I'm doing all I can to avoid bankruptcy.

We were close, then the great recession hit. Lost 60% in 3 years. Just updated the balance sheet today , we're almost back! Who knows what will happen in the next 24 to 36 months though.

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 f****d 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.

I work in finance and my team and I work with all very affluent clients. I’ve seen so many millionaires lose it all not from investing in the markets, but from: Taxes, Lifestyle and poor business decisions. Once had a client who was making 50k a month, but was spending 60k a month and perpetually dipping into his investments. There were months where payments bounced because he was living a lifestyle and always wanted more. My favorite investment advice: Same car, same house, same spouse

Not a millionaire, but I was super close, hope that counts. Was in my early 20s and had a s**t ton of cash saved up from investing + hard work. Had a rough childhood, so I was kinda empathetic towards others. I regularly volunteered at an orphanage in my city for reference. Used all of my money to buy houses, vehicles, and anything else lifechanging for strangers these past few years. I don't really regret it. I do think back to times where I used to have a really luxurious lifestyle (6 star hotels, concierge, fine dining, sports cars), but when I think about all those times people came to me crying and begging to help them escape their situation I could only shrug and think to myself, "why the hell hasn't anyone else helped them out? what kind of cruel world do we live in to the point where I had to be the 10,000th person they had to ask to help them out? what the f**k is wrong with people? So, I did what I could. I'd like to hope someday, if there is a god or higher-being out there, that they show me at least a gram of mercy when it's my time to be judged after death.

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 in order 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 were 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 really 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.

My dad’s family came from Ukrainian nobility apparently. Then Stalin rolled in and screwed ALL of that up. They barely escaped, my grandparents met in a refugee camp, and we’ve built our lives since then as working class Canadians thankful for what we have.

Obligatory not me but both my grandparents from both sides were extremely wealthy. They lost all their wealth during partition. My paternal grandpa told me how they buried KGs of gold in pakistan to get it back one day. His father was a landowner and moneylender. Basically really wealthy. But they never returned post partition. All wealth lost in a day. Many people have similar stories of burying gold and moving and never went to get it back

My parents had built up a multi million dollar company over a couple decades before and during my early childhood. Around 2006 they separated and ran each other dry in court. Then the crash came and bankrupted both of them and lost everything they put years into. Unknowingly recently after my mother’s parents passed away she was able to take a portion of an investment account that built millions from her fathers stock from working in the railroad industry. My father rebuilt his business from scratch repaired his credit and has grown it bigger than it ever was before. By the age of 21 I’ve witnessed my life go from rich to broke to wealthy. I am in a great position in life now for my age but work,plan,live and learn like everything could be again gone in the blink of an eye.

I watched a guy at a casino somehow get a loan against his house, about 200k and lose it. He looked suicidal. Apparently he was already in almost 50k and thought he could win it back. I got hired there, and I would leave on Friday and Return monday, and see the same people in the same clothes, who pissed and s**t themselves and were still sitting at the blackjack table gambling.

Gambling and spouse terminal illness.

Not me but an acquaintance. He got caught not paying taxes and dealing in stolen goods. He spent time in Federal prison and lost everything, including his wife. Crime does not always pay!

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.

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 swaore 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 GODDAM CHURCH. Land, property and titles all, and lived of his vicar'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 coke addiction really stings.

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.

My ex's mom, not me. 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 actually finite, and one day she found herself with just barely enough left to get back 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 highschool, and you're 48 years old? Answer: housekeeping at the local Best Western, apparently... 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 on-coming traffic, and steer straight into fire hydrant... Then flee the scene, abandoning the company vehicle and it's several now-injured passengers...

Twelve years ago, I was making 95K as a software engineer. I was in an accident, suffered a brain injury, lost everything, and haven't worked as a programmer since then. My injury easily cost me a million dollars.

Not a millionaire, but at 19 I had accumulated about $170,000 USD through hard work and determination, as well as a big ol' stroke of luck regarding the kindest employer I've ever worked for. After seeing all that money, I made a series of frivolous financial decisions, and one good one which has been my saving grace through covid. I bought a car, in cash, paid for 6 months of a townhouse rental in cash, and proceeded to smoke weed and get caught doing it, multiple times, in a state where it isn't legal to do so. Most of my money went to treatment classes, drug testing, court fees and fines, and two lawyers. I'd say smoking pot in a conservative state has cost me roughly $50,000 (That's counting the cost of the pot) and the rest went towards a Roth IRA, two cars, three motorcycles, and three hospital visits. I'd been fortunate enough to recoup some of what was lost through a great employment opportunity, which, unfortunately, didn't last due to covid. I was laid off and didn't work there long enough to qualify for unemployment or severance and so I was stuck dipping into my savings to feed my family. While I was working for my last employer I decided to take a loan out for my dream car, and two weeks later I was laid off, so a good bulk of my IRA has been going to that and I'm now being forced to sell it or give it up for repossession. Luckily I've paid enough on it, with help from my family, to be able to sell it for more than what my loan is, so I'm not exactly screwed, but next month is likely going to be filled with lots of fasting and ketchup sandwiches. Anymore of what I take from my IRA would be heavily penalized since I've used up the initial capital investment so that's no longer an option. It's amazing how quickly a dumb kid can go from saving so well and not really understanding what I was doing, to blowing it all realizing I had the freedom to do whatever I wanted with the money I'd earned. It took some years to get there, and it's taken some years to get back to a rational mind, as well as some dumb financial decisions, but I'm finally able to say that every dime of what I earn is going to be saved, and I no longer do illegal drugs so there's no chance of me getting slapped with fines and court fees anymore. However, I am aware that the job I had in gaining my initial accumulation of funds is a one-in-a-million chance which I blew, and it's really hard to settle for anything less than what I've earned before. It's really quite soul-sucking to see people offering $10/hr or $15/hr like it's some blessing bestowed upon the poor people in this country, knowing just how easily they could offer more. That's something I'd like to see change, everybody deserves the opportunity to earn more than the bare minimum to survive and from my perspective, not everybody gets that chance. I'd say not even half the population of this country gets that chance.

Grandfather and great uncle both went into the US Air Corps as bomber pilots. After the war, they both were offered prestigious high paying job flying for some airlines. Great uncle took the job, made a fortune flying and then got in the car business, becoming VP for a large American car company. Died rich in Jupiter, FL. Grandpa found Jesus during the war, declined cushy jobs to go to the seminary. Preached hell and mayhem as a Southern Baptist minister. As you can imagine I’m shitpoor as my distant cousins grimace about two-year old Maseratis being out of style.

Not me but my late grandpa. He was a navy doctor who was the chief medical officer at the Okanawa base in Japan following the Korean War. After he left the military, he opened his own private practice in the Hudson Valley. He also did high-risk surgeries at local hospitals. He was the richest person in his suburban town and he and my grandma (a minister at the local church) were respected community leaders who oversaw racial and religious integration in the area (he himself was Jewish and singlehandedly convinced the town council that black neighbors would not drive down housing prices). At his wealthiest, he had about $3.5 million. He lost it by having 3 kids, all of whom went on to at least tertiary education. My uncle and aunt both became lawyers (one has a double doctorate in law and psychology, the other has a masters in law) and my mom became a teacher (a masters in education). All on Grandpa’s dime. That’s not to say he died penniless, but he definitely wasn’t the wealthy local mogul he was known as in the 60s and 70s.

The Somali Civil war. My grandfather had a manufacturing company, but the war ruined it. My family used our last half-million to get our relatives out of the country.