Stroke Of Luck: People Who Got Unexpected Windfalls Share Their Unbelievable Stories

October 9, 2020 | Mathew Burke

Stroke Of Luck: People Who Got Unexpected Windfalls Share Their Unbelievable Stories

Who among us hasn’t dreamed of finding a winning lottery ticket, or inheriting a fortune from a long-lost relative? The things a person could do with that kind of money could change their lives forever—whether it’s starting their own business or just making rent that month. It sure would be sweet to hit the jackpot, but despite the odds, that’s just what happened to these lucky folks. Remember that money doesn’t always buy happiness, and not all of these stories have a happy ending. Still, try not to get too jealous.

1. He Won It All on the Ponies

My grandfather was a big animal veterinarian out in the country. He was driving home one night and noticed a guy on the side of the road. The guy was trying to calm down his horse and not doing well. My grandfather stopped to help the man, and found that the horse was having a medical issue that he helped take care of.

After everything was done, my grandfather put the horse in a trailer which, luckily, he had connected to the truck. Then he gave the man, Joe, a ride home. Joe wanted to pay my grandfather for his work, but he refused, so Joe took the money he was going to pay and invested it. My grandfather passively agreed and moved on.

About 15 years later, a young man came by my grandfather's house. My grandfather was confused, but as the guy explained, it all came together. The young man was Joe’s son and he had come by to let my grandfather know that Joe had passed on and he was closing all his father’s accounts. Joe had invested $200 for 15 years on behalf of my grandfather, and turned it into $1.2 the 1960s.

My grandfather kept working until he was 62 years old, but he payed off all his bills, expanded his farm, and sent his children to college. He even gave the five oldest grandchildren (the ones he met, including me) $5k each for our 21st birthdays. My grandfather eventually retired and fulfilled his dream of moving to Alaska.


2. Won’t You Be My Neighbor?

My neighbor had friends or family and left everything in her will to us. Everyone always asks if we were great neighbors to her. I’d say no, we were just neighbors and treated her as we would want to be treated. We cleared her driveway when it snowed, took care of her cats when she went to the beach, said hello to her.

She could be a tough cookie. She hated if I played basketball in the driveway and when we were cleaning out her garage after she passed, we found three of my old basketballs. But she was also the type of person who, if she wanted an apple pie, would bake an apple pie, take out her slice, then bring the rest over to us.


3. It Was All in the Cards

Playing blackjack in Reno. I had $300 to waste at the $5 table. Got lots of free watered-down drinks while I was playing, so I wasn’t paying attention. I have a rule whenever I play blackjack: I keep two piles of cash—one is the pile of cash I can waste, and the other, the pile of money I won. I try not to mix the two.

I had been playing for about three hours before I realized I wasn’t out of betting money. By then, the dealer had changed at least four times. I won $4,000 at that table, which was enough to pay for the trip and still have a bit leftover. I haven’t been to a casino since, but I doubt I’d have that kind of luck again.


4. Veteran’s Benefits

I worked with a guy who was in his late 20s, an ex-serviceman. When he got out, a friend he served with told him to buy Bitcoin. He bought several thousand dollars' worth when it was nothing and forgot about it. When it started spiking and getting attention on the news, he went looking for the drive because he thought he had some.

He did and he had a lot of it. Sold it all well before the peak and made millions. He had an $800,000 house, multiple high-end cars. He still came to work at our manual labor job “because he was bored.” Needless to say, he didn't stay here long and all he did was show off his money and clock hours not actually working.


5. The Great Aunt

My wife’s aunt had been institutionalized her whole life and neither of us had ever even met her. We all kind of forgot about her until my wife’s uncle—the aunt’s husband—emailed her and said that we were going to get some money in her aunt’s will. We thought “Oh, okay, that's kind of weird,” but we weren’t complaining.

Then my wife got a phone call from the uncle one evening that changed everything. I heard a lot of “ums,” and “OKs,” and, finally, a “wow.” We’d been grinding away making $15 an hour, barely making rent every month, and then boom, out of nowhere, we were getting over $300,000. That meant the difference between owning a home versus getting evicted.


6. Tales from the Cryptocurrency

I went to a nerdy high school and one of my friends was really into blockchain and cryptocurrency way before it was even a thing. After high school, he scrounged up some money (a couple thousand) and used it ALL to buy bitcoins. This was around 2010-2011. We all thought. he was insane, but he was a real believer in it.

Fast forward to today and the dude is worth millions. He took out most of the money and used it to buy real estate, and now he has a small real estate empire. As I said, I went to a nerdy school, so he was already really smart and had gone to NYU Stern undergrad for business, but I don’t think he finished his degree.


7. Ask and Ye Shall Receive

I didn’t get any money, exactly, but I was given a brand new $1,200 laptop for free once, just because I posted about needing a new one on a forum. There can be a lot of trolls and creeps on the internet, but this showed me that there are still a lot of really generous people out there, too. So thank you, kind stranger!


8. Paid Back…with Interest

Back in the early 2000s, I loaned a friend $12,000 to buy inventory to sell flea and tick medications for pets online. He did really well and went on to make a ton of money. He paid me back, in full, within six months. After that, he started sending me checks for $1,000 a month as a thank you for supporting him early on.

I have been getting these checks for going on 15 years now. $1,000, every month, for 15 years, plus my initial $12,000 loan. Just recently, I finally had to ask him to stop. I don’t need the money now, and it’s a pain trying to account for it on my taxes.  And besides, he’s paid me back like 10 times over for the loan.


9. A Very Nice Retirement Gift

I had a boss who was single, childless, and making around $250k a year. He was set to retire around age 56, but the company begged him to stay for one more year, so he did. During that year, the parent company suddenly offered a buyout to eliminate senior positions, offering a month for every year they had worked there.

Well, by that point, my boss had been with that company for 30 years. Because of the buyout, he ended up walking away with an additional $600k beyond what he would have if he had left when he first planned to. Everything just worked out perfectly for him. The last I heard, he was traveling the world in luxury.


10. Cash To Go

I once found $3,600 in a food takeout box in the middle of a giant field. I live in a rich neighborhood and supposedly a lot of suspicious deals happen near here, so it seems very possible I accidentally took thousands of dollars from a crook. But no bad guys ever came looking for me, so I guess I’m in the clear.


11. Easy Come, Easy Go

When I was 10 years old, me and my two friends found a paper bag in a shopping cart outside the local grocery store. It was stuffed with money. We counted and there was just over $600. We split the $600 three ways and went home. Not a load of money, but for three 10-year-old kids—man, we were proper rich for a minute!

Of course, eventually one of my friends later crumbled under the pressure and told their moms who told our moms. Turns out the money belonged to one of the suppliers to the grocery who accidentally left it in his cart on the way out. We had to return it, and I only got the chance to spend like 10 bucks. I felt cheated.


12. Daddy’s Money

When I was about to turn 18, my mom told me to open a bank account because I was going to get some money from my dad. I opened the account, signed the papers, and got a whopping $15,400 deposited into my account. Four years later, I find out he got a huge settlement for a car accident; I get another $15k over 2.5 years.


13. Enough Is Enough

My wife and I got some stock options when the part of the company we worked for spun off from a much larger corporation. They weren't worth much when we got them, but it was the 90s and every tech stock was going up. Eventually, we jokingly decided that we'd sell when the stock price got high enough to pay off the house.

One day, just as we were about to leave on vacation, it got there. We did consider holding out for more but nope, we cashed out and left. Thank god. In the two weeks we were gone, the stock price surged up, then crashed, never to see those levels again. In fact, the stock crashed below $1 and the company did a 10:1 reverse split.

The stock eventually went below $1 again and got de-listed. Funny thing is that a lot of our friends told us we were crazy to sell. One friend even exercised his options when we did, but put the proceeds into the stock market. We did really well on the deal, but it was a combination of luck and our conservative nature.


14. Home Sweet Home

I lost my parents when I was in my 20s and inherited a small buttload of money. The real kicker was the house I grew up in, a three-bedroom single-family with an attached business in Boston. I was a landlord for a while, but it was too much of a pain, so I sold it. Look up what a three-bedroom house goes for in Boston.


15. Thanks a Slot

I was on a business trip that passed through Lake Tahoe. Three people in one hotel room, so I went down to the casino to get some space. I couldn’t find a table to lose my $100 at, so I sat down at a slot machine instead. Ten minutes later I’m absent-mindedly pressing the spin max bet and hit the jackpot. $1.1 million.

It’s the sort of thing you assume never happens. I took a lump payment of $690k, which, after I pay taxes, will end up being about $390k. I got a financial advisor, bought a car and some investment properties, and got my now-wife her ring. Everything else is the exact same, except I have an epic story to tell strangers.


16. The Goodbye Gift

My partner suffered a sudden and unexpectedly massive seizure. He had had smaller seizures before, but nothing this serious. He hadn’t even turned 40, and he was gone. Three months later, I received a notice. I came to find out that he had taken out a sizeable life insurance policy, and that he had named me as his primary beneficiary.

The life insurance policy left me with enough money to buy a house, donate to a few of his favorite charities, and still have enough of a nest egg left to start saving up for my retirement. I miss him every single day…but I guess his last act of love was setting me up for the future, even without him being here with me.


17. Just Being Neighborly

I cut my elderly neighbor’s yard growing up, helped him with random things around the house. I came home one weekend to find a letter. It was my neighbor’s lawyer: he left me his house, money, and cars. We were close, but I never knew he had no family. I sold the cars, rented the house out, and invested 50% of the money.


18. Nowhere to Hide

I was super young when the falling out happened, maybe four or five, but I had an aunt that was basically excommunicated from my family for reasons that still are unclear to me. I never really got to see her after that. I remember how she used to play hide and seek with me when I was little, but literally nothing else.

My aunt was married to some super old guy who made a lot of money in the oil industry, and she inherited his fortune after he passed. She passed when I was 23, and as it turns out, crazily enough, I was her favorite family member. She apparently really liked me, and left me a letter saying I was the son she never had.

She left me $2.4 million. It was exciting, of course, but it makes me sad to think about how she was kicked out of the family, how she seemed to have really thought a lot of young me. In the back of my mind, I’ve always tried to make her proud of me because she was the cool hide and seek aunt I never really knew.


19. Beginner’s Luck

I decided to celebrate my 20th birthday at this nice casino an hour away from campus with my then-boyfriend. We played bingo because that was all we could afford and it occupied some time, but we lost. After bingo, I called my dad. He loves casinos (when he has the money to go) and he suggested I try three-card poker.

I’d seen him play before, but I didn't know how to play and was on the last $20 to my name. He said that would be enough for a hand or two and to just give it a shot, the dealer would explain the rules. I sat at the table to play one hand. I was pretty clueless, but the dealer got really excited: I had a straight flush.

I just kept on winning. People would take the seat in front of me, they would lose, I would win. It didn't matter. I got two more straight flushes that night and lots of other good hands. I kept betting the minimum, but wish I had been putting down more. I turned $20 into $3k that night. My dad still doesn't believe me.


20. Splitsville

I always loved my grandfather's old desk. I spent tons of time drawing and working on it, and after my grandparents passed, they left the desk and all its contents to me. I was cleaning it out when I found it. Stuffed into the back of a drawer, buried in a folder, was a stock certificate for a big company from the 70s.

At first glance, the stock was worth a few thousand dollars. Awesome, but, overall, it’s a disappointing return for stock purchased more than 40 years ago. I looked into it, however, and it turns out the stock had split since times! Let’s just say it’s worth more than a few thousand dollars. Thanks, Grandpa.


21. Everybody Wins!

I used to play low limit poker at a local casino. I was usually pretty decent at it, but one night I played for a couple of hours and didn't win a single hand. I wasn’t winning, but I was still playing pretty well, and I still had a decent amount of my buy-in. Eventually, I ended up in a hand where I had a full house.

The guy sitting next to me was betting into me, and from the table and his actions I knew that he had a four of a kind. While I was debating, the guy whispered “raise.” I figured he was trying to psych me out, so I said to heck with it and called. Sure enough, when the cards were revealed, the guy had a four of a kind.

He did beat me, but the night didn’t end there. It turns out there’s this thing called a “bad beat jackpot.” You can win a lot of money if you have a full house and get beaten by a four of a kind, but only if the pot is over a certain amount—that’s why he told me to raise. Luckily, the pot was $3 over the amount. I won three grand because of that.


22. The Art of the Deal

My friend’s father was gifted an oil pencil drawing in the late 70s. His family always assumed it was pretty much worthless, and I always joked that it looked like my friend had drawn it as a child. This silly, angry stick figure drawing turned out to be an unsigned piece by a famous artist called Jean-Michel Basquiat.

His family did some digging and eventually had it authenticated by the JMB estate; they sold it at an auction for an amazing sum of money. I was blown away. My friend and his family were far from wealthy, so to realize they had this unknown treasure just sitting out in the living room for so many years was mind-blowing.


23. Sweet Dreams

Around my 20th birthday, I inherited enough money that ensured I would never have to work again as long I lived (assuming, of course, I didn’t blow it all on stupid junk). I ended up buying a three-bedroom house in a safe neighborhood, filled it with furniture and whatnot, and bought a used car. Nothing too extravagant.

I never have to work so most of my days are spent doing whatever I feel like doing that day—gardening, volunteering, playing with my dog, brewing, or watching all three Harold & Kumar movies in one sitting. The biggest problem I had was, the first year I had the money, I slept far too much and probably gained 40 pounds.


24. Lucky Seven

A girl I went to school with had this old painting in the garage. In grade 12 English class, there was a conversation about the Canadian art scene. She said some of the paintings looked like the one they had in the garage. Turns out her grandma dated one of the Group of Seven. Her family sold the painting for a lot of money.


25. A Winning Smile

I got a random message from a guy who I hadn’t seen since kindergarten. This guy offered me $65 for each picture I sent him of my braces, so I sent two. We haven’t talked since and to this day I have no idea what those pics were used for. It’s probably best not to think about it, but hey, at least I got $130 out of it.


26. Three Chairs for You!

It all started because I needed a new chair. I needed a new chair for my dorm room so I did what any sensible 18-year-old would do: I called up my grandmother to go garage sale-ing together. We found a nice one in an interesting part of town, paid all of $10 bucks for it, and joked about finding a $20 bill in the chair.

When we got it home and started cleaning it out, and lo and behold! My grandmother pulled out a $20 bill. And then another. And another. And another. One bill after another until we had almost $500 in total. Based on where I picked the chair up from, I decided to give it back, but I got to keep a $20 so my wish came true!


27. Stay-at-Home Dad

After my divorce, I ended up with the kids. They still saw their mom, but they lived with me. I hadn’t done my taxes in years, but the IRS owed me money so didn’t worry. When I finally did do my taxes, I got back a couple of grand. But what happened next was a surprise. Since I did my taxes, I was eligible to get child tax.

Once I got in touch with the government regarding child tax, they said that after mine and my wife’s bank account had closed down, the payments stopped because they didn’t know where to send the money. After some documents back and forth they said it was all good and that I should start getting child tax payments again.

Some time goes by. I’m near broke and still not working fulltime, but I go to 7-11 to get my dad $20 for gas I’d borrowed. The ATM spits out a receipt and I think it must be the guy before me, but the time and date are from when I used the machine. I had gotten backpay for all the missed child tax over almost two years.

I crapped myself when I realized I had over $20,000 deposited overnight. The amount of stress that left my body is hard to describe. The happy ending to this story is my kids are healthy, I have a good relationship with their mom, and I split the child tax with her so the kids have a good quality of life at both houses.


28. Internet Famous

My site went viral. Within 14 days of creating the site, we were on Buzzfeed and blogs all over the internet. It even started popping up on news stations around the world. On the best day, the site ended up doing $78,000 in sales. I wasn’t prepared for that and sold the whole thing for six figures by the end of the month.

Friends thought it was funny. Strangers recognized me from a VICE article and wanted to play 20 questions. Nobody harassed me for money or anything, but I’m still introduced to people as “that guy.” It’s weird, but I made enough money to start a business I’m actually passionate about and should be launching it this month.


29. Always Look Both Ways

I got into an accident on my way home from dropping my son off to his mom. I'm grateful that it happened then and not while he was with me. A dude in a company truck blew a stop sign and creamed me. He broke my arm and gave me a concussion. A few months later, after I had almost entirely healed, I got a check for $70,000.


30. And Bingo Was His Name-O

I won $5,000 playing bingo while on a cruise. It was my first time having gone on a cruise, and it was the only time I have ever played bingo in my life. I decided to go out on top, to quit while I was ahead, and I have since retired from both.


31. They Shoot, They Score!

My husband and I won $60K at a hockey game on the 50/50. We bought one $20 ticket and lost our minds when we won. We were less than a year out of university and my husband had been out of work for the prior few months. He had only just recently started a new job. It was a blessing and helped us purchase our first home.


32. The Early Bird

I saved up $1,000 as a kid by keeping every cent that came my way. When I was 12, I learned about stocks. A family member was starting a business so I asked if I could buy a share. They said sure, I’d be a 2% owner. Great! Cut to 15 years later: they sell the company for $130 million and suddenly I’m a millionaire. Also great!

I invested it all in a risky portfolio and the next thing I know it’s up 50%. At the end of January 2020, I’m thinking things are going too well, so I put the money in safe investments and convert a lot to cash. Boom, March hits and everything goes to pot. I wish I could say this was prudence and careful planning, but the truth is I got extremely lucky. I don’t really need to work if I don’t want to, but I do because otherwise, I’d be super bored.


33. Compensating for Something

I was hurt on the job. I felt like I went back too soon, and I kept informing my boss I wasn’t ready and still having a lot of problems (like severe insomnia, among other things). My boss did nothing and kept me working. I got the feeling I was being targeted to get fired because of all the sick leave, so I lawyered up.

I documented everything and recorded all meetings. The company realized that I was being smart about handling the situation, spoke to labor relations, and opted to buy me out instead. Ended up with about $40k severance package, enough to ride out my recovery at least. Kinda wished they were stupid and fired me instead.


34. For Love or Money

I married into mine. I grew up lower-middle class, served in the Navy, and was a plumber for 20 years. I met my wife a few years ago when I was 44 and we got married a year later. Turns out she’s from a very well-known company that makes household products. We are millionaires several times over. It’s weird saying that.

We live modestly, more so than the others in the family. I retired and neither of us works. She volunteers at animal shelters, I putter around the house, and pursue my hobbies. I splurge on things I like to collect and dining out, but I don’t blow money on stupid stuff. We’ve set up a few trusts for children of friends.


35. Auntie Kitty

My great-aunt, who was also my godmother, was a lesbian. Her partner—who I called Auntie Kitty—had been with her since the 1950s, after my godmother moved to New York City to work as a magazine photographer. Auntie Kitty was disowned by her family when the truth came out that she and my godmother were partners.

When I was 12, my great-aunt passed and left my Auntie Kitty everything in her will. Things were a little strained with my family, though my dad and one of his brothers still talked to her. When I was 18, I wound up moving to New York to go to university. I didn’t know anyone else in the city, and she and I became close.

She was thrilled that I wanted to have a relationship and spend time with her. I didn't hesitate to think of her as my aunt, even if, technically, she wasn't. We spent holidays together and she would come to things I worked on. I knew all her friends and she knew mine. For a whole decade, like another grandmother to me.

As she got older, she began to constantly remind me that I was going to be the executor of her will, and that I was to follow her instructions to the T. No one from her own family was to get anything of hers. I would get the bulk, my dad and uncle would get some, and my sister and my nieces would get a little as well.

I knew that Auntie Kitty had money—she owned a vacation home in the Carolinas and a brownstone in NYC—but since they were both bought in the 70s, I figured, outside of real estate values, there wasn't much. How wrong I was. I inherited enough that potentially I wouldn't have to work ever again if I didn't feel like it.


36. The Accidental Millionaire

I was in a car accident when I was five. After about $250,000 in medical bills, my parents’ insurance company and my grandfather (who is a lawyer) went after the other dude’s insurance company. We also got awarded punitive damages to the tune of 3:1 of medical bills. I have gotten a payment every year now since I was 18.

The actual value when I was 18 was about $560,000. I am now 23. I have paid for my college and I should have the remainder of the money by the time I turn 27. I can effectively contribute nothing towards my retirement, and because it’s a court-ordered settlement, in my particular state, I don’t have to pay taxes on it.

It’s very likely that I’ll retire a millionaire. At the time it was terrible. I was near the end for about 18 hours, and in surgery, but now I am perfectly healthy and have only minor scarring on my face. All things considered, I count myself very fortunate, not only for surviving, but also for having this nice nest egg.


37. Repo-ing What You Sow

My ex-husband is a bad dude. He currently owes me over $26k in back child support. When we were together, all the bills were in my name. He left me for another woman three weeks after I gave birth to our second child and defaulted on all our bills. Both our cars got repossessed, and I ended up having to file for bankruptcy.

Last year, I got a notice in the mail from the lender of one of the two repo-ed cars. Apparently, there was a class-action lawsuit against them for hidden fees. Since the cars were in my name, I was getting a refund of a few thousand dollars. I was able to use that money to help move out of my mom’s and get my own place.


38. A Private Fortune

I grew up extremely privileged. After I suddenly lost my father, I inherited millions of pounds and property. I don't tell anybody. I keep my fortune a secret from everyone around me. The truth of the matter is, I would give it all away for another hour with my father.


39. Flip A Coin

When I was younger, a friend of my brother’s asked me to buy him some drinks. He said he would throw me a couple of bucks for my trouble, so I said no problem. I met up with him at the store and he handed me this strange $20 gold coin. My coin knowledge is still pretty minimal, but something about this coin made me curious.

I decided to buy the stuff with my own money. He threw me $10, and we were all good. When I got home, I went online to find out the value of the coin. The low end was around $1,000. I took the coin to a collector who basically gave me the value in gold weight—at that time it was about $1,250.00. Easiest $1,260 I ever made.


40. Very Cool

My friend’s dad’s friend decided to open an ice business. Everyone needs ice, right? He bought an old warehouse because it was cheap. Then the government decided to redo the on-ramps and needed one-third of his parking lot, maybe 20 parking spots worth. He didn't care, he had a staff of four, and never used more than that.

Well, apparently the government is willing to pay more than a fair price when they need to buy someone’s private property. I don’t know the exact number, but my friend says his dad was paid more for those 20 parking spots than he paid for the entire parking lot and the warehouse. It didn’t even affect his business.


41. Spare Parts

I built a motorcycle back in 2011. Built all the parts on it. I took it to a few rallies and it made its way around the internet, some magazines. A ton of people ask if I sold this part or that part—I sold 10,000 parts out of my garage in my first two years. Eventually, I bought a shop and started automating my process.

One day, a friend came by. He owns a business that supplies stuff to practically every nuclear plant in the world, and he asked me to design a connector for a surveillance system that he sells. Took a day, had the prototype done. That part cut out 20 minutes on each individual camera installation and required no tools.

I sold a ton of them, then jumped into radiation shielding. Big money in that. It's been nearly 10 years now. I sell thousands upon thousands of bike parts that I designed and build every year. Travel to motorcycle events all over. Generally, I have a blast. I'm 31 and have the financial freedom to do whatever I want.


42. No Happy Ending Here

One of the smartest people I know convinced me to buy a Bitcoin miner back in 2013. I mined a few before the power bills made it seem like it wasn’t worth the money. When Bitcoin started going crazy in late 2017, I looked into trading. I saw a one-liner online somewhere that said something like, “xrb about to explode.”

I was able to buy around 25k xrb (now Nano). Within a few weeks, I was a millionaire. xrb was only sold at Kucoin and Bitgrail. I chose the latter. Big mistake. Sadly, I didn't cash out due to greed. Bitgrail went belly up and now I'm in some international lawsuit that will never pay out. 2018 was a tough year, but I got through it.


43. Far Out, Man!

Back in 1999, I was living in a school bus with eight of my closest friends, traveling down the California coast. The bus was starting to smell pretty funky, so we stopped to collect eucalyptus nuts to make it smell better. We found a huge roll of cash under a tree. When we brought it back to the bus, there was $3,050.


44. I Scream, You Scream

When I was eight years old, my family was in Toronto to celebrate Passover with my Canadian cousins. One rainy day, we walked out of our hotel and saw a big Canadian grocery store chain was having a big event in the field across the street. They were giving away all kinds of free food and drinks to anyone who showed up.

It turns out they were launching their new product and filming a TV commercial. The product was this new ice cream sandwich where the outside is cookies. All you had to do was sign a form and then you would get to try the product. Maybe you would be in the commercial. I tried it and said to the camera, “It’s delicious!”

They used my footage in the commercial and made $1,200. If you can find the commercial on YouTube, I am the cute little girl at the end. I know it may not seem like a ton of money now, but to an eight-year-old girl, $1,200 was basically enough to buy the entire world. Or at least a lifetime supply of ice cream sandwiches.


45. A Lesson Learned

I work in poker rooms. An elderly man once came in and asked me to teach him how to play. I did and about 20 minutes in he won the grand jackpot of around $9,000 AUD (or about $6,500 American). I was overjoyed for him and we both got really excited. But then, there was a dark twist. For months after that, I watched him come in and just lose, lose, lose.

I felt so bad that I had taught him how to play and that he won so big to start with because his bar was then set so high that he could never live up to it again. He just kept playing, trying to recapture that feeling. Maybe if he’d lost, things would be different. Instead, the poor man won himself a gambling addiction.


46. You Can’t Pick Your Family

While I was at university, I befriended one of my lecturers. I had majorly abusive parents and this lecturer acted more like both a father and a mother to me than my real parents ever had. He also happened to own a lot of property. He and I were very close. A terminal illness took his life. I was heartbroken—but soon after, I received jaw-dropping news.

He left everything to me. Without going into details, I'm young and the assets left to me mean I'll never have to work. They grow faster than my lifestyle can go through them. I may never have to work, but I do find plenty to do with my time. I strained at the bit to spend, I but reigned it in with the fear of my parents taking that security from me.

What made me keep my cool was paranoia and distancing myself from my parents’ mistreatment. I knew if they had even the slightest hint I had something that could benefit them, they'd be all over me, so I bought an average-looking small house and pretended I rented it, went into further study, and sat on everything else.

Years later I think my mother knows, but I purposely keep no contact with her for any reason whatsoever. I still live in the little house because I realized I like it, and my first-reaction dreams of a large ostentatious property weren’t what I wanted or needed. I owe it all to one lecturer that was like a parent to me.


47. You Lucky Dog

In the 90s I fostered a dog for some friends who were leaving town and left the dog with me. This dog immediately made an impression upon me, and even though I really didn't want a pet at that time, but he was such an amazing dog that he quickly convinced me otherwise. He was super smart, half black lab, half pit bull.

Later, I used him as a mascot for a recording studio I set up, and I used his name as the domain name for my website. My dog passed several years later and I was heartbroken for years. I maintained the domain name, even though I didn't really have any projects associated with it—it was just an homage to my best friend.

I originally secured the domain name for nothing. In the early days of the Internet, it didn't cost you any money to register a domain name, you just had to fill out the right forms. I never even would have had to pay a renewal fee if not for a sysadmin that made changes to the domain and accepted new terms of service.

Then in 2000 with the dot-com boom, there was new interest in domains and IPOs. A few groups started bugging me for the domain name and kept increasing their offers. Eventually, the numbers got into life-changing amounts, and I couldn't ignore them. Besides a few hundred dollars in fees, I made $475,000, cash, in profit.

I continue to be in awe that my little dog had the ability to bestow such an amazing gift upon me so many years later; I'm determined to use that gift to help others. I took the money to create a maker space for a community of wonderful people. It was my dog, and this significant windfall, that gave me that opportunity.


48. The Self-Made Millionaire

I became ridiculously wealthy at two years old when my father passed. My mother never touched his money; instead, she opted to struggle through medical school while taking care of me, all by her own means. She was scared to touch it because she knew his family would try to take the money from me if they ever found out.

Heck, after he passed, they took his car, our house, the insurance money, everything they could get their hands on. They thought they had taken everything, but the judge didn't let them see a penny of what I got. My mom didn't let me see that money either, until I discovered one of the accounts by myself when I was 12.

When I turned 18, I found out that the inheritance didn’t stop at six figures. It was well into the sevens! My mom and stepdad only told me when I was deciding on colleges. They didn’t want me to feel like I had to give up my dream of going to UChicago because of the price. But then I looked at my hardworking parents.

Looking at my mom and stepdad, I realized then that the money didn’t matter. I wanted to forge my own way in this world, like my mother did and my biological father did. I didn’t want his fortune to be my story. My parents told me they wanted to forget the money and pay for college for me as they had always planned.

I ended up very happily going to a state school. I won a scholarship, so I didn’t have to use my parents’ money or my inheritance and I haven’t regretted a thing. I used to think that I would buy flashy things and live a rich lifestyle with my inheritance, but that money has humbled me and made me more aware of my luck.

My parents wanted me to save my money for “the right things,” that I would know in my heart what those things were. I haven't touched that money for myself. Instead, I gave $30K so the bank wouldn’t foreclose on my aunt's house and another $5k to help some young girls in India pay for their education and rehabilitation.


49. Justice Served

I was the victim of housing discrimination and the landlords put it in writing. They literally sent me an email explaining they wouldn't rent to me because of…well, the reason was discrimination. Had they never sent me that email, they would have been just fine—nobody would have known why they'd rejected my application.

It’s normal to reject applications for a wide variety of reasons. If they had made up some reason, or even given no explanation at all, they wouldn't have found themselves in so much trouble. I filed a complaint with my state and the state assigned me a free lawyer to handle the case. I didn't even know they'd do that.

Anyway, these landlords continued to lie and say I was making things up. They insulted my character in a wide variety of ways which went way beyond the issue at hand. Think stuff like claiming I was faking the reason they discriminated in the first place, so how could they discriminate against something I was faking?

It was really ridiculous, but in the end, I wound up with a decent-sized check. Again, when I reported them, I thought I’d never learn the result of what the state would decide to do—I was just reporting a broken law. But that wasn’t the best part. When I won, my lawyer asked me if I wanted them to take an anti-discrimination course.

The state included the course in the landlords’ punitive measures. The course was two hours away from their place, in the constant traffic of our area, and I liked imagining them having to sit there in some ugly, depressing room while being educated about why they were terrible people and needed to stop being terrible.


50. Down in the Valley

I will never, ever forget this. Sometimes I Google it just to see why it happened, but no luck. When I was a kid, we used to drive from our Southern California home to Vegas for family vacations. We stopped at Zzyzx Road in Death Valley every time because my dad loved the name. We would get out just to stretch our legs.

One year when I was 10-ish I walked around there and started finding bills...some tens, some twenties, and lots of hundreds. Under rocks, by trees where the wind had blown them...we collected around $8,000. My parents let me keep it. My dad thinks maybe someone hit it big in Vegas and got crazy in the desert or something.


Sources: Reddit,

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