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Chief
Family member made millions selling cigarettes online during the 90’s and was able to avoid taxation.
He bought on reservations, in bulk at lower cost then sold online until it got shutdown. He and his partners walked away with 8 figures and now he works in commodities at JP Morgan.
Umm
There trading desk is under criminal investigation for defrauding the precious metals market, no?
Got into the stock market 6 yrs ago. Been holding Tesla, Shopify (since IPO), and FAANG. I’m no longer chasing partnership.
My pay-it-forward contribution: GoodRX. Bought it last week when it debut. Don’t be “that guy” 5 years from now that missed out.
I made about 250k day trading tech stocks in the late 90s while I was an intern in the Bay Area, using my student loans and a margin account.
I was 19 and thought I was pretty awesome. I was just dumb and lucky, as it turns out.
Rising Star
Better to be lucky than good sometimes...
Not exactly a fortune but I had a coworker who was able to quit her corporate job by renting out mismatched vintage China. She had spent years collecting in at garage sales and thrift stores for her own wedding and now rents it for parties, showers, and weddings
Wow cool
My friend worked at his dads thrift shop and started extracting metals from old computers and other electronics. Fast forward 20 years. Guy owns a plant with 200 employees grosses 600M a year and has thousands of oz of gold. Dude pulls in a few million per month. No college education just a blue collar guy.
Pro
Apparently there were millions to be made buying a tractor trailer full of cigarettes in VA and selling untaxed in in NY. The retail spread per pack was like $15
Apparently the government got involved quickly because of terrorism funding concerns. For all we know it was the CIA doing it 😁
A guy I knew (older) had a lot of long standing deals to produce those metal navigational road signs you see on every freeway in America. He owned the business by himself, used the money to purchase or start several other businesses, mostly in the manufacturing space. Did not live a very extravagant life (no crazy houses or watches or anything). Except for one thing: every year he traded in his Bentley for a new one. He died about 10 years ago, his two kids split about $100 million from what I heard.
Friend of mine won $250K on Who Wants to Be a Millionaire. Used the money to set up his own trivia company and now does that for a living
Out of curiosity do you know the $500k question he walked away from?
Buddy of mine started an Amazon store. Made 5K his first month, 100K the second month.
Let’s just say this is INCREDIBLY rare and drop shipping was saturated even back in 2013
Chief
I had a college friend resell bootleg designer jeans way back when $200+ jeans were in trend, it was like selling the fake LV bags but denim edition. That guy made 500k+/year for a while- reinvested into legit businesses and is now doing well for himself.
I also knew a couple that opened a Pilates studio that’s very high end, they never made a ton of income so I assumed some inheritance came their way . It turns out the husband was a professional thief and decided to go legit before inevitably getting caught. You’d never believe it if you met them though.
Advising senior executives rehashing what their reports told me and earning $250k per year
Joking
I once made about $10k in minutes doing commodity arbitrage
Roommate had 300k of Bitcoin at its peak. He started buying small amounts of it in high school as a joke. His stake is still worth north of 160k.
I am in a WhatsApp group with some current and former Deloitte folks from Nigeria. In 2014, one of the guys suggested that we pool some funds together and invest in Bitcoin because it was going to "blow". I had just bought a house so I really didn't have much cash to invest. A couple of those guys are chilling right now.
Bought a place in an up and coming neighborhood in NYC and three years later sold it for a $275k profit. Tax free since we lived there for just over 3 years!
Astoria
Family friend, self employed, makes hundreds of thousands selling rock salt to municipalities in the winter. Buys by the barge load and sells to local governments all over the country.
The American Dream
My father went to school with this guy’s son. Been living on trust disbursements since the 70’s. https://huddleup.substack.com/p/the-greatest-business-deal-in-sports
I sold my Neopets account for about $10k when I was a kid. It was one of the top accounts on the site, and I probably couldn’t get that much now, but I kinda regret it.
My friend is making a fortune by acting as a liaison between organizations that sell PPE and organizations that buy PPE. He makes a couple pennies per unit sold but these transactions include hundreds of thousands, even millions of items (gloves, masks, etc...). He doesn’t own or buy any inventory, literally sets up the exchange between the two parties. He’s made over $500k this year
How did he get started doing this?
Family friend of my parents escaped Vietnam as a kid (literally watched her brother get gunned down while trying to flee) and found a job in the US at a dry cleaner in Newark NJ. Eventually saved up and bought her own dry cleaner in Newark. Had tons of shady business but she would return any “product” or wads of cash she found. Gained a loyal clientele who paid a little extra for her discretion. Eventually bought a series of dry cleaners and then some restaurants she completely turned around into very nice places. She passed away from ALS a couple years ago and her son inherited 8 figures after she sold everything as she got more sick.
I once made a small fortune breeding and racing thoroughbred horses. You know how I did it? I started with a large fortune! ;-)
My uncle sold aluminum siding after he came back from WWII, was really popular in the newly invented suburbs. sold his company before he was 30 and never worked a day after that. Golfed everyday.
I know one of the founders of Wizards of the Coast, and another artist friend in Seattle has a plaque over their gorgeous kitchen that reads “This is the house that Pikachu built.”
Resigned a Tuesday to become the tenth or so employee of an unheard startup, “Facebook”