Do you ever find yourself wondering, whatever happened to that classmate that was a little odd back in school? Or to the science whiz, or the one gifted in athletics? Well, some of them might be millionaires by now. Whether it’s their hard work and determination or pure luck that got them there, they often have quite a story to tell. Or, at least their classmates do.

Members of the ‘Ask Reddit’ community recently discussed such stories after one of them asked how that person in redditors’ class became rich. The answers cover all sorts of scenarios, ranging from difficult to believe, to heartwarming, to somewhat upsetting even, so scroll down to find them and see for yourself.

#1

She started working for a little company called Microsoft in the mid-1980s. She retired at 40. 

Image credits: dma1965

#2

Smart guy. A little socially awkward but was a swimmer and in top classes.

Went to UCLA, became a doctor (maybe a surgeon). Started to play the stock market for fun. Ran a bulletin board to talk stocks.

Turns out he had Asperger and was able to read the stock market signs really well.

Made $300M when the market crashed as he bet against it. Christian Bale played him in the movie about him, the Big Short.

Mike Burry. Class of 1989. We knew each other. Not friends but acquainted. Couldn’t be happier for the guy. Truly, happy he’s done well. Not seen him since we graduated. If I did I’d totally (and jokingly) ask him for some cash. I’d try to make him laugh. He’d probably still be awkward.

Image credits: MW240z

#3

Started online gambling sites back in the 90s, dropped out of high-school, millionaire by 20, Overdosed by 25. 

Image credits: waltwalt

#4

He started studying solar technology in ’88 and now owns a solar installation company in Texas and one in California. He employs close to 200 people. I don’t know how rich he is but I’m really familiar with where he came from and what he overcame to do it all. The guy was constantly reading and tinkering with anything solar related, even when we were in high school. 

Image credits: Savings-Delay-1075

#5

A girl from my hometown won an island on a Mr. Beast video. It was worth millions. She’s in the process of selling it currently. Until that money comes through she’s just living life like normal. I imagine that must be a great place to be in, knowing most of your problems are about to disappear but not yet overly intoxicated by money.

Image credits: Snoo_18863

#6

Lecturer of mine rode the IT wave at exactly the right time and had a damn fine head for business. He was a workaholic at age 30, started a business offering remote tech support which was a new idea at the time, signed on some super big clients who were enamored of the idea, and built a giganto house from the proceeds that pissed everyone off.

Sold the business and then died of a heart attack at 45 or so though. So, yeah. There can be complications.

Image credits: the_original_Retro

#7

There’s a lot of them that became rich. For most of them they graduated as engineers or medical doctors and simply did their jobs and were reward handsomely.

But **that friend** became rich through trades. He took his student loan and bought a piece of very inexpensive land just outside of his city limits. Just by an absolute fluke the city announced shortly after that it planned to expand city limits to include his vacant land…. and suddenly it skyrocketed in value. This was at a time before any real internet and before everyone had a cell phone. And there’s all these property developers trying to figure out who owns this land so they can buy it.

Eventually his mom opens his mail and finds a past due property tax notice and an offer for about 20x what he paid for it.

He took the first offer he got (and regretted it) and went to a bank and directed them to invest entirely in dividend stocks and for the dividends to be deposited directly into his bank account.

He used that money to stay a student for life and basically never worked a day in his life. There was one point where it got close to him needing to get a job… but then one of the companies announced increasing their dividend.

I have rich friends, and then there’s him… just living off of his wealth. He doesn’t have a great life, but he also doesn’t work.

Image credits: garlicroastedpotato

#8

I went to school and was friends with the guy who founded Uber. He offered to take my SATs for me for $500 as we looked alike and he is very smart. He was always “that guy”.

Image credits: ReflectionsGo2Ways

#9

I’ve got two: one guy was *extremely* gifted in music. I remember my dad going to the talent show and said this guy is going to be the next Jimi Hendrix. Well, not quite, but he has performed plenty of times with Lady Gaga. His name is Ricky Tillo

The other guy did voices in high-school all the time. He would hop on the PA system and do cartoon voices. He was recently in the Mario movie as Toad General and is literally the new voice of Bugs Bunny and a ton of other popular cartoon guys. Eric Bauza.

Image credits: AnotherDrunkCanadian

#10

Big-time stoner who I always thought was a lazy scumbag who would never amount to anything. He went on to start one of America’s most successful edible companies. Classy billboard ads in multiple cities. My mom bought their CBD gummies for awhile. Every year he donates millions of dollars of his company’s profits to bail funds for people of color who’ve been arrested for m*******a possession. He is more successful and has done more objective good for the world than I ever have or will. Turns out I was a bitter judgmental loser in high school!

Image credits: UOLATSC

#11

Guy’s parents told him in middle school, we’re giving you $20k right now and that’s all you’ll get from us. He was told he can use it for college if he pleased or a car when he was old enough to drive. He started studying stocks like a madman, invested most of that money, and now he’s a millionaire

Image credits: maru_badaque

#12

Not my close friend but a kid in my English class, really f*****g smart kid. He entered a coding/robotics competition and got third place. He was pretty bummed out for a while. First prize was a scholarship for a pretty big university. And third place got a lousy 500 bitcoin. He kept the 500 bitcoin despite people telling him to cash it and get the $100 or whatever it was worth. Anyway he cashed it at the peak of bitcoin and is now living pretty f*****g well with his $30mil.

Image credits: Sploshta

#13

Robbed banks that he worked at twice to the tune of $160K. He got caught because he was never a street kid, just a spoiled prick who thought he was above the rules. I knew he’d be a criminal when I was a kid because he stole my church offering money during church and used his to buy a soda after the service.

Image credits: DuckFlat

#14

He got in extremely early on Bitcoin. Like, within the first few days.

At one point he had 300 Bitcoin. He sold a good chunk of it in like 2013 when it was like $300/coin, but he kept 60 or 70, which he still has to this day.

He also invested a bunch of money in Tesla on day 1, and Nvidia about 10 years ago too.

In other words, he’s just made super good/lucky financial decisions.

Image credits: alwaysmyfault

#15

He dropped out of high school at 15 to be a pro skateboarder. People laughed, he’s now worth 50 mil.

Image credits: tekhed303

#16

Hot girl. She married a ridiculously rich guy. Had 2 kids with him, then left him and took half his money plus child support. Married another ridiculously rich guy, left him and took half his money.

Currently gets alimony and child support from two different guys. Constantly changes her name on her Facebook profile “to try a new one on” even though she’s pushing 50 now.

#17

Knew people who had servers running in their dorm rooms, just mining bitcoin 24/7 since 2014 or earlier. Some of them are probably very comfortable now. Some are probably kicking themselves for cashing out early and buying a few pizzas. I didn’t get rich on it, but I did pay my senior spring tuition.

#18

Lucky guy won the lottery, lived lavishly for a few years, lost most of it partying, gambling, being a dumb**s, but the 2 ex wives took him for most of it. He dropped off the radar for a few years. I Wasn’t shocked when I heard he passed.

#19

A guy in the grade above me was one of the founders of Dogecoin.

#20

They Imagine(d) Dragons…

#21

Selling life insurance policies then selling their soul to Github.

#22

His parents were super smart and very artsy. He and his father built their own computer when he was maybe 10 in 1976 from a kit.

He was an appealing outgoing guy, but also super smart. He went to an Ivy League college in New England, his brother followed a year later.

We lost touch, but he moved to the West Coast, founded a couple of super tech software companies, sold them. Did that a few times.

He’s not rich, he is wealthy. Knows Gavin Newsom personally level.

#23

She double-majored in math and accounting. Accepted a job offer at an accounting company for like $75k/year the day she graduated. She never really worked over 40 hours a week, said the job was easy and relaxing, and really lived her best life the other 128 hours of the week.

#24

Weird kid, he was obsessively into insects.

Now a days he runs the largest worm farm
in my country. Also believe other insects like maggots and such

Apparently there is good money to be made with worms and maggots

Fishing bait? I assume why else would you buy them

#25

Sold fake Magic The Gathering Cards. Then sold Duped Items on Diablo. Sold his Star Wars Galaxies Account when he was one of the first to get Jedi Status. Then he opened a Legit Hard Apple Cider Company. Also Parents money and married well.

#26

Nepotism or luck. Other than the nepotism babies, everyone I went to college with ended up getting out and making 80k+ a year in programming or consulting positions.

The best I could do was 45k in IT.

#27

I have a mate who just started a job installing kitchen cabinets. He has obscene standards for the quality of his work. Which evidently is uncommon.
Then, he started buying lower class property in regional areas. He could fix them up himself. And he is more concerned with having good tenants than he is with the amount of rent they pay.
It’s worked well for him.

#28

He wrote a popular comic book that got optioned for a movie, though the movie never materialized. He really didn’t seem like he’d be the one to get out of our hometown, but he really made it.

#29

He started buying and selling used cars, moved to higher end cars, then buying and selling limos, started a limo rental company while still selling limos, sold the rental company. Sells high end limos and sprinter vans and exotic cars now.

The other friend started in car sales in highschool, stayed with the company during and after college, is now a sales manager for said company at one of their higher end stores. Invested wisely and loans his own money out at 15% as well as some real estate investing.

Friends with both of them still.

#30

He got hit by a garbage truck. The driver was on drugs, so the settlement was in the millions.

#31

One of my friends made an AI that changes the stadium advertisment boards to whatever the TV company wants on the fly. Basically those advertisements will be different for one Stream VS another. They also have another software that can show the game footage from perspective of the players (a rendering).

Another friend has made a company that makes hip joint implants.

#32

Guy went to Phillips Exeter academy, then MIT. Started his own power train company, sold a patent to the department of defense, retired at 34 living in San Fran. 

Image credits: mathaiser

#33

Scammed medicare through his company over 2 billion. Awaiting trial now.

Image credits: thekickassduke

#34

She got into a relationship with someone who played soccer and he happend to get scouted all the way to the best soccer clubs in the world.

Image credits: Taxfraud777

#35

Opened a small p**n shop with private booths to do your business. Then after he made a fortune, he sold it and went into welding, then became a huge christian. He saids everybody pretends that his p**n money didnt help rebuild the church.

Image credits: anon

#36

The best wealth story I ever heard was a nerdy computer guy – early internet adopter – realised things like Vancouver.com or Paris.com would be valuable.

So he bought up all the city.com websites he could and just had a landing page that said “page for sale – contact me”.

Badabing badaboom

Image credits: MrsRobertshaw

#37

Got salmonella from Wendy’s chili.

Image credits: stubgoats

#38

High fashion male modeling. He was always jetting off to Europe for fashion shows during the school year. He’s now instagram famous. It must pay well cuz he lives a lavish lifestyle. He is conventionally attractive but did nothing for me (think “beautiful landscape painting”). His average height, non male-model best friend, on the other hand was the most popular/desirable guy at our school. That guy had so much charisma. It’s no surprise that he went on to be an actor. There was another male model classmate (really hot, definitely not a painting). He recently just got released from prison for dealing drugs. Never would’ve guessed it, dude was so soft spoken and vanilla. Then again, I’m reminded of how he wanted to live large and “be a baller.” He got his wish, for a few years that is. His mugshot was wild, he totally got high on his own supply. My school was by the sea in a city where everyone is obsessed with looks and having a beachbody year round. The rich and famous flock there, so it’s not unusual to see insanely good looking people on the daily.

Image credits: ladeeedada

#39

He wrote Hamilton.

Image credits: DrteethDDS

#40

A higschool mate of me went to college and left college at first year, did a cooking course and found his passion, he is now the best cheff in the city an will probably get a michelin star next year

Image credits: Kurainuz

#41

She oopsy got pregnant by a guy whose family is worth $800 million.

Image credits: cuppa_tea_4_me

#42

Guy that I grew up hit big with Crocs. His family moved away when I was about 6th grade, but my older brother remains friends with his older brother. I guess the guy worked selling insurance and was offered an opportunity to invest in Crocs (the weird shoes). He went for it and got a few checks back in the $5 to 10 million range. I learned this through my brother, and I think it is true.

Image credits: mcgato

#43

There were two of them: they both starred on the American version of *The Office.*

Image credits: centaurquestions

#44

Married a drug dealer con artist. Now he’s dead and she owns a few houses worth several million

Image credits: Teledoink

#45

A good friend worked at an early Subway and they helped him buy a franchise. He ended up with a dozen, sold the group and retired.

Image credits: mekonsrevenge

#46

Born to a multibillionaire family company, now ‘works’ at a satellite office in a different region (to be kept out of the way; he wasn’t very bright), takes half the year off to vacation.

Image credits: Early_Yesterday_6819

#47

Most people I went to school with who got rich started rich.

#48

They became a lawyer and married another lawyer.

#49

Not me but my bf went to school with the guy who made Snapchat lol

#50

“Daddy’s Money”

#51

Grew up in Silicon Valley, went to good schools studying computers, started a company, sold it a few years later. Started another company, sold it later for more millions.

#52

Gave birth to someone who became one of Hollywood’s best young directors and producers.

#53

Best friend, dating a beast of a woman, who just happened to be the daughter of a cfo of ups or something.

#54

NBA All Star.

He was a pretty OK guy, but we ran in different circles.

#55

I graduated with Halsey