25 People Share How An Ordinary High-school Classmate Became Rich

Published 8 months ago

During our high school years, we imagined that conquering the world would be a piece of cake. However, while we may have all wanted to make it big and be rich, not everyone could manage to achieve it. 

One Redditor recently inspired a retrospective look back at our high school years once more but this time around the topic of discussion was how that one kid from high school became rich. Scroll below for some interesting stories of people who were capable of more than others imagined, teaching us to never judge a book by its cover. 

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Image source: MW240z, CBS

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 source: maru_badaque, Anna Nekrashevich

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 source: UOLATSC, Pixabay

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 source: alwaysmyfault, wikipedia.org

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 source: the_original_Retro, Lukas

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 source: centaurquestions, fanpop.com

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


Image source: tekhed303, Zachary DeBottis

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


Image source: garlicroastedpotato, energepic.com

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 source: mcgato, Alexey Demidov

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 source: oxide-NL, Sippakorn Yamkasikorn

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


Image source: dma1965, wikipedia.org

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


Image source: Snoo_18863, wikipedia.org

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 source: Ausramm, DJI Official YouTube Channel

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.


Image source: ReflectionsGo2Ways, wikipedia.org

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 source: thekickassduke, Kindel Media

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


Image source: Sploshta, Worldspectrum

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 source: MrsRobertshaw, Wonderlane

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 source: DrteethDDS, imdb.com

He wrote Hamilton.


Image source: anon, Valeria Boltneva

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 source: Kurainuz, Sebastian Coman Photography

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 source: AnotherDrunkCanadian, ladygaga.fandom.com

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 source: waltwalt, Nothing Ahead

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


Image source: Henry__Every, wikipedia.org

They Imagine(d) Dragons…


Image source: cuppa_tea_4_me, Leah Kelley

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


Image source: Savings-Delay-1075

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.

Shanilou Perera

Shanilou has always loved reading and learning about the world we live in. While she enjoys fictional books and stories just as much, since childhood she was especially fascinated by encyclopaedias and strangely enough, self-help books. As a kid, she spent most of her time consuming as much knowledge as she could get her hands on and could always be found at the library. Now, she still enjoys finding out about all the amazing things that surround us in our day-to-day lives and is blessed to be able to write about them to share with the whole world as a profession.

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become rich, classmates, high school, money, people, rich
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