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People Share Stories Of How They Got Rich By Sheer Randomness

Trista Smith December 19, 2022

Some people get to live the ultimate dream: making a considerable amount of money through pure randomness. Hard work and dedication are fabulous and far more reliable, but who doesn’t want to believe they’ll one day stumble upon a massive windfall through sheer luck? Until we strike it rich on our own, we can at least live vicariously through the financial adventures of Redditors who shared their stories in an /r/AskReddit thread about random financial windfalls.

So read ahead for 20 of the wildest stories of unexpected financial gain. If you like these crazy stories from Redditors, read about real-life people who wasted tons of money.

One Redditor made a killing from a Cisco board buyout. Credit: Pixabay

20. Cisco Board Buyout

Many of the stories Redditors shared of sudden financial gain were from dumb luck like slot machines or other gambling forms, but at least a few stories were about people who were working hard in their chosen profession and just happened to strike gold at the right time and cashed out. One Redditor shared their flipping experience. The user said, “I was maybe 20 years old and bought stuff at auctions and resold it full time, working for myself. One of the other regular auction attendees told me he found “some boards” in a pallet he bought and wondered if I wanted them.”

They continued, “I looked at them, and they were new Cisco boards, but this was over 20 years ago, so smartphones weren’t a thing, and I had no idea what they were worth. I offered him $50, and he was very happy. I ended up selling those boards for $18,000. No joke. I split the sale between two different resellers because I was uncomfortable selling them all to one company.” An $18,000 return on a $50 investment is wild by any measure. Too bad for the poor seller who had no idea what he had.

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Slot machine dreams came true for one Redditor. Credit: Pixabay

19. Slot Machine Jackpot

Who among us hasn’t dreamed of trying out a slot machine and hitting a jackpot. It’s the ultimate gambling fantasy. You don’t have to be clever or count cards; you simply pull the arm of the machine. For one Redditor, the dream came true. They said, “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 blackjack table to lose my $100 at, so I sat down at a Wheel of Fortune slot machine instead.”

They continued their incredible story, “Ten minutes later, I’m absent-mindedly pressing the max bet and hit the progressive jackpot. $1.1 million. It’s the sort of thing you assume never happens, but it did. I took a lump payment of $690k, which after I pay taxes next week will end up being about $390k. I quickly got a financial advisor, bought my car, now own a couple of investment properties, and bought my now-wife her ring! Everything else is quite literally the exact same, except I have an epic story to tell to strangers on Reddit.” Well done on the investments!

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One lucky Redditor got paid for a beer run with a real gold coin. Credit: Pixabay

18. Beer Buy

While none of the items on this list involve explicitly illegal activity, this one is the closest. While we certainly don’t condone buying beer for underage connoisseurs, the illegal trade worked out well for one Redditor. They said, “When I was younger, a friend of my brothers asked me to buy him a beer. He said he would throw me a couple of bucks for my time, so I said sure. I meet up with him at the store, and he hands me a $20 gold coin. With my coin knowledge being very low, something about the coin made me curious.”

They continued their incredible beer buying caper, “I bought the beer with my own money. He threw me $10, and we were all good. When I got home, I went online to see the value of the coin. The low end was around $1000. I took the coin to a collector who basically gave me the value in gold weight at the time, about $1250.00. Easiest $1260 I’ve ever made.” It’s incredible that someone with a $1,000+ gold coin would even need a beer helper. Who keeps solid gold coins on hand?

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A kind neighbor left one helpful Redditor their entire home. Credit: Pixabay

17. Neighborly Love

There is something extraordinary about having a neighbor who becomes a close friend. Who didn’t dream about having their best friend live next door to them as a child? Whether it’s visiting an older neighbor to take them cookies or watching out for a young neighbor, it can be a special relationship. For /u/Rotoscope8, the dream was a reality with an older neighbor they had been helping since childhood. The neighbor returned their care and attention after death, with a surprising result for the young Redditor.

They shared their story, “I cut my elder neighbors yard growing up and helped him with random things around the house. He passed away while I was in college. I came home one weekend, and I have a letter in the mail. It was from my old neighbor’s attorney advising me he left me his house, money, and two cars. I was fairly close with the guy but never knew he had no family at all. Immediately sold the cars, I rent the house out, and I invested 50% of the money.” While it’s sad that he had no family, the Redditor became like family to them.

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One man ensured their partner would be protected with life insurance. Credit: Pixabay

16. Tragic Windfall

Sadly, many Redditor’s stories of random windfalls did stem from tragedy by losing a loved one who left an inheritance. Many shared stories of grandparents, aunts, uncles, or even neighbors or family friends left them estates. However, unless the deceased was a genuinely mean person who made life difficult, no one wants to receive money in place of a person since people are irreplaceable and no amount of money can bring them back. That is embodied in truly tragic fashion in a story from Redditor /u/bullet5000, who received their windfall from a truly unthinkable loss.

They said, “Dunno if it’s really sheer random. My partner passed away suddenly and unexpectedly from a massive seizure. He had seizures before, but nothing that would indicate he’d die from one. He hadn’t even turned 40. About three months later, I find he had a life insurance policy I didn’t know about. He made me the primary beneficiary. It gave me enough to buy a house, donate to a few causes he cared about, and still have a nest egg to start a real retirement savings off of. I miss him every day. However, I guess his last act of love was setting me up for the future, even without him being there.”

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One Redditor’s unique algorithm netted them seven figures so far. Credit: Pixabay

15. Algorithm Randomness

Sometimes, some persistence winds up paying off through an unexpected windfall. One Redditor discovered this when they went back to an old pet project and dusted it off. They said, “I quit a job at a startup that was a mess, and I just wanted to do something relaxing, so I took some time cleaning up an old algorithm I wrote ten years ago. I told a friend of mine, who told some industry people about it. They contacted me, and I got invited to talk about it at a conference, and then large companies started getting in touch.”

They continued their incredible entrepreneurial tale, “So far, I have signed one 7 figure deal to license it. It’s not random, but it feels very random. I’m making more in interest now than I ever have earned holding down a job. The world is not fair.” While it may not seem fair to them, it’s clear their intelligence and cleverness in creating a unique algorithm led to their success. The clear takeaway here is if you have a passion project sitting on the backburner, show it some love, and you may be handsomely rewarded with some big gains.

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A loan to buy flea and tick medicine for pets turned into a huge return. Credit: Pixabay

14. Friendly Loan

For a very long time now, the common wisdom has been never to let money enter into the bonds of a friendship. Loaning money to a friend can cause long-term grievances. That is true especially if the money isn’t paid back. Alternatively, if the borrower holds the loan over the other friend’s head, and so on. However, for these Redditors, borrowing their friend a large sum of money only strengthened the friendship. Furthermore, it also resulted in an unexpected increase in fortunes. Redditor /u/drewbiez shared their story of loaning a friend money for their business and the unexpectedly large windfall that resulted.

They said, “I loaned a friend 12k to buy the inventory to sell flea and tick meds for pets online in the early 2000s. He did really well and went on to make tons of money doing it. He paid me back in like six months and sent me checks for 1k a month as a thank you for going on 15 years now. I made him stop recently because I don’t need it, it’s a pain to account for on my taxes, and he’s paid me like 10x back for the loan, lol.” Not only did they help their friend, but they made quite a profit on the loan.

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Housing discrimination resulted in a major payout for one Redditor. Credit: Pixabay

13. Discrimination

A couple of entries on this list stem from sinister circumstances. None are more so than for Redditor /u/InvincibleSummer1066, who experienced severe illegal housing discrimination. They shared their story, “I was the victim of housing discrimination, and the morons put it in writing. They literally sent me an email explaining they wouldn’t rent to me because of [illegal discrimination reason]. Had they just not sent the email, they would have been fine — nobody would have known they’d rejected my application for a bad reason. It’s okay to reject applications for a wide variety of reasons.”

They continued, “If they’d chosen a fake one, or even given no explanation at all, they wouldn’t have found themselves in legal trouble. I made a complaint to my state, and the state assigned a free lawyer to handle it. I didn’t even know they’d do that. Anyway, the people kept lying and saying I was making shit up. They insulted my character in a wide variety of ways that went way beyond the issue at hand. (Think stuff like claiming I was faking [reason they discriminated] in the first place, so how could they discriminate against something I was faking?) It was just ridiculous. In the end, I wound up with a decent-sized check.”

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One family received a museum-quality art gift worth millions. Credit: Pixabay

12. Accidental Art

How many of us have received a random gift of art or at least a print of art from a friend or family member and simply hung it on the wall without considering how much it might be worth? While in the vast majority of cases, the answer will be approximately nothing, one Redditor’s family had quite the opposite experience. They said, “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.”

They continued, “This stilly angry stick figure drawing ended up being an unsigned piece of art by Jean-Michel Basquiat. His family did some digging and eventually had it authenticated by the JMB estate before selling it at Christie’s auction house for an amazing sum of money. I was absolutely blown away when I learned this. 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.” For some context, an original Jean-Michael Basquiat painting just sold last week for $41 million dollars.

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An open field yielded thousands of dollars for one commenter. Credit: Pixabay

11. Field Money Randomness

One of the most sinister encounters with a windfall on this list literally took place in an open field. Reading like something out of a Narcos plotline, a Redditor found money in the middle of a field. Redditor /u/Hingadowshow said, “I found 3600 dollars in a food takeout box in the middle of a giant field; I live in a rich area, and a lot of drug deals happen, so it’s possible I stole multiple thousands of dollars from a drug dealer on accident.” While this windfall is quite wild in and of itself, it was the replies from other Redditors that made it into a genuinely sinister story.

One Redditor simply stated, “Someone is probably dead because of this.” Another confirmed the idea saying, “You got someone killed. Guaranteed!” While there was a great deal of bickering back and forth over whether $3,600 was enough to cost someone’s life in the drug trade and how likely revenge or punishment would be, everyone agreed that someone likely had a very bad day when that money was discovered to be missing. It certainly is a good thing no one saw /u/Hingadowshow taking it, or we may have had a sequel to ‘No Country for Old Men’ on our hands.

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A mean dog led to a significant payout for one Redditor. Credit: Pixabay

10. Dog Bite

One ‘lucky’ Redditor’s unexpected windfall was due to a dog bite. Redditor /u/Br1nkley explained, “The summer after my freshman year in college, I was walking my little 20lb dog on a street near my house. A neighbor lady was walking her two dogs, who were a husky and some other similar sized dog. The husky attacked my dog, and in the process, I got some teeth marks on my wrist.”

They continued their canine caper, “Since the neighbor’s dog started it and the owner obviously couldn’t control it, I wanted them to pay the vet fees for my dog, which was under 500. The guy ended up being an [expletive] about it, and my roommate’s dad was a lawyer, so about a year and a half later, I ended up with about 20k.” This story contains several vital lessons; one of which is that sometimes there’s a golden lining to even something as unpleasant as a dog bite. The other is not to be a jerk if your dog bites a person through sheer randomness.

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A lost job led to a cushy existence for one commenter. Credit: Pixabay

9. Severance Pay

Losing a job can be an incredibly traumatic life experience. In addition to the loss of income and possible loss of housing, medical insurance, etc., you also have to deal with a somewhat crushing blow to your self-esteem, especially if the job loss was due to being fired. However, for some, a job loss ends up being a blessing in disguise as it was for one Redditor who shared their experience of an incredibly fortunate job loss. Redditor /u/paranoid, who likely isn’t American given the quality of severance pay which is quite rare in the States, shared their tale.

They said, “My previous employer eliminated my position, our whole department actually. I got a severance of 1 week/year which worked out to be 22 weeks of salary. Not only that, I got paid a bonus to stay on for the last three months. After that was over, I got a job with a competitor company making the exact same salary and doing mostly the same job. It started the very next Monday! I actually even like working for the new company better. I don’t know how ‘random’ that really was, but it sure felt like a real fortunate way to lose a job!”

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Selling private label goods on Amazon made one Redditor thousands. Credit: Pixabay

8. Amazon Money Randomness

When Amazon was first coming into its full prominence as a massive international retailer, there was a lot of money to be made in starting your own private label business to sell bulk manufactured goods. One Redditor shared their story of making a massive windfall from a private label business. They said, “I started an Amazon private label business on a whim in 2015. I made about 25% of the sale in profit after product, shipping, and advertising costs. Sales doubled every month for six months June $4k, July $8k, August $18k, September $40k, October $84k, November $175k, December $362k.”

They continued, “I didn’t know what to do. I quit my job in January to focus on growing the business. However, my time was spent mostly trying to fend off competition, copying my listing and posting fraudulent reviews, and then lowering my price in the Reece to the bottom. It went well for a few years, but I never made as much as I made that first December.” It may seem complicated to believe now since many manufacturers now sell directly on Amazon themselves. However, this type of private labeling business made many people quite wealthy in Amazon’s earlier days.

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Blackjack is a challenging game, but one Redditor won big. Credit: Pixabay

7. Blackjack Wealth Through Randomness

Is there any more iconic casino game than Blackjack? Any movie that wants to make gambling look fun and exotic will always show the hero at the Blackjack table poised to strike it rich with the perfectly timed “hit me.” While Blackjack isn’t that easy of a game to win, at least one Redditor made a significant cash-in at a Blackjack table. They shared their story with their fellow Redditors in a thread.

/u/zaise_chsa said, “Playing Blackjack while drunk 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; two piles: one of cash I can waste and another of money I won. I was there for about three hours before I realized I wasn’t out of betting money, and the dealer had changed four times. Won $4k at that table. Paid for the trip and a bit leftover. I haven’t been to a casino since, but I doubt I’d have that kind of luck again.”

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Workplace injuries handled badly netted several Redditors big money. Credit: Pixabay

6. Workplace Woes

Along with the housing discrimination earlier on this list, perhaps the nastiest source of a windfall on this list came from the Redditors mistreated by their jobs after workplace injuries. Redditor /u/confused3366 said, “Worked a job for a long time. Got hurt on the job. They, instead of helping me, terminated me. I got a lawyer. A year later got 260k for the whole fiasco.” While some of it went to the worker’s comp lawyer fees, they still thankfully got a good chunk of change out of their employers for that terrible mistreatment. Another Redditor chimed in to confirm that their employer committed similar behavior.

They said, “I was hurt off the job. I went back too soon and kept informing my boss I wasn’t ready and still have a lot of problems (bad, bad, severe insomnia, among others). My boss did nothing and kept me working. I got the feeling I was being targeted to be fired because of the sick leave, so I lawyered up, documented everything, and recorded all meetings. The company got wise. I was being smart about handling the situation, spoke to labor relations, and decided to buy me out instead. Ended up with about a 40k severance package. Enough to ride out my recovery at least.”

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Several Redditors have been able to yell “Bingo!” Credit: Pixabay

5. Bingo Cash and Randomness

Many Redditors had first-time success stories of gambling and winning incredible amounts. Beginner’s luck has long been a concept in many things, including gambling, and one Redditor’s tale of bingo success gave ample evidence to the massive power of beginner’s luck. /u/frivus said, “I won $5,000 playing bingo on a cruise. I have only been on one cruise, and it was the only time I have played bingo in my life. I have retired from both.”/u/frivus demonstrated true wisdom by striking it rich with their beginner’s luck and then knowing when to walk away from the table and enjoy their winnings.

One incredulous Redditor chimed in with an eerily similar story saying, “Are you freaking kidding me, the exact same scenario I’m in! I went on a Carnival Cruise back in April, right before the world went to shit. I played bingo for the first time and won $5,000! Wtf? I’m freaking out.” Apparently, lightning can strike twice, at least the randomness of bingo on Carnival Cruise ships.

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Redditors are striking it big thanks to bitcoin. Credit: Pixabay

4. Bitcoin Randomness

Do you pay any attention to stocks or cryptocurrencies? Redditors know that Bitcoin, one of the earliest cryptocurrencies, is BIG money. One bitcoin is currently worth over fifty thousand dollars. There is a truly tragic tale of a man using 10,000 bitcoins in the early days of the currency to order a single pizza. That means he wasted what is now $500,000,000 on two ordinary pizzas. Redditors agree that it was perhaps the worst investment in all of human history. However, at least one Redditor shared a story of a coworker who wisely worked with Bitcoin and walked away quite loaded.

Redditor /u/uoYredruM said, “I briefly worked with a guy who was in his late 20s, ex-military. When he got out, a friend of his he served with told him to buy Bitcoin. He bought several thousand worth when it was nothing and forgot about it. When it first started spiking and getting attention on the news, he started looking for the drive because he thought he had some. He did, and he had a lot of it. Sold well before the peak. Dude made millions.”

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The family was a huge source of windfalls for many Redditors. Credit: Pixabay

3. Distant Relative

A common theme in many Redditors’ financial gains stories was the gaining of an unexpected windfall from a distant relative. In some cases, Redditors hadn’t even thought about in years. /u/TomBergerr said, “I had an aunt that was basically excommunicated from my family for reasons that still are unclear to me. I was super young when the falling out happened (4 or 5). She was married to some super old guy who was oil wealthy. She inherited his fortune when he passed. When I was 23, she passed, and crazily enough, I was her favorite.

They continued, “She liked me, and in her letter left to me, I was the son she never had. (I remember the way she used to play hide and seek with me but nothing else). It makes me sad that she was kicked out of the family. She seemed to have really thought a lot of young me. She left me 2.4 million dollars. I’ve always in the back of my mind tried to make her proud of me cause she was the cool hide and seek aunt I never really knew.” Whatever the family rift, at least she loved her nephew.

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In the early days of the internet, you could strike it rich with domain names. Credit: Pixabay

2. Domain Name

Back in the ‘Wild West’ days of the internet, when it was still new technology, many people purchased obscure or random domain names that ended up being worth fortunes. One Redditor lived this exact experience and shared, “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 the time, he was such an amazing dog. He convinced me otherwise. He was super smart, half black lab, half pit bull. I called him “wisdom” because he was so smart.”

They continued, “Fast forward a few years I used him as a mascot for a recording studio I set up. I registered the domain name wisdom.com. My dog passed away several years later, and I was heartbroken and depressed for many years. I maintained the domain name even though I didn’t really have any projects associated with it. Over the years, people made offers on the domain name, but I always passed. The domain was a homage to my long-lost best friend.” They admitted that the domain name’s sale made them over $400,000. That is quite the payout for a loving tribute to an old doggy friend.

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Going viral on YouTube made one Redditor a hefty sum. Credit: Pixabay

1. Viral Video Randomness

Is there anything that applies to outright randomness than what content becomes viral? Likely, millions of advertising people have tried to figure out how things become viral to capitalize on it, and yet it remains a mystery. One Redditor managed to tap into the viral craze and made much money in the process. They said, “I bought a waterproof camera back in 2010 and thought it would be cool to try it out at the new water park that just opened. One year later, the video blew up, making me tons of money monthly. I still make some during the summer months but not much. Now I’m sitting at just over 100,000,000 views.”

Another Redditor chimed in to confirm how truly random going viral can be, reflecting on the OP’s video. The user said, “Holy moly, it’s only like 27 seconds long. I thought you were riding the water slides using it as a GoPro showing your point of view….You are so randomly lucky, as there’s nothing amazing about it, yet it went viral….” The OP confirmed, “Yes, it was pure luck. I just uploaded it and forgot about it. It didn’t blow up until about a year later. I think being the first video of that water park helped get it rolling but to blow up like that was just algorithm luck.”

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