I have this specific memory of sitting in my bedroom as a tween in the early 90s, staring at a 14.4 baud modem, realizing domains like KMart.com were totally up for grabs. It felt like the biggest opportunity in the world. But alas, I was 12 and didn’t do anything about it. We’ve all had those moments where we saw the open door but didn’t walk through it, right?
But then you hear the stories about the people who did walk through that door, or just happened to stumble through it by accident. It’s wild how often getting rich isn’t about grinding 18 hours a day or reading every self-help book on the shelf. Sometimes, it’s just about being in the right place, at the right time, with the right amount of cash—or just being clueless enough to not know what you’re doing is risky.
Let’s look at some of the craziest ways people ended up loaded without really trying.
Should you have bought Bitcoin in 2013?
Honestly, if you bought Bitcoin in 2013, you were either a genius or a total rebel. There’s a story about a guy who got 10k€ from his grandparents for turning 18 back in 2013. Instead of buying a car or investing in a sensible mutual fund, he dumped it all into Bitcoin when it was around $150 a piece.
His family thought he was nuts. It caused a huge scandal at family reunions. Fast forward to after he graduated university, and he’s living a millionaire lifestyle despite never having worked a day in his life. Then there’s the hazmat driver who had a few grand from his grandparents, did the same thing, and later used that crypto windfall to buy shares in a tiny camera lens company. That company got acquired by a massive phone giant, and suddenly he’s retired at 30, married his college sweetheart, and is funding playgrounds for the local school. It’s almost annoying how well it worked out for them.
Is being an early employee a cheat code?
You hear about the “employee number ten” at companies like Spotify, and it sounds like a fairy tale. One guy was among the first ten employees at a major streaming service and ended up getting “a little rich” off the equity. But you gotta remember, for every Spotify success story, there are thousands of “employee number tens” at companies nobody has ever heard of.
Working for a startup is basically gambling, except the currency you’re betting is years of your life. It’s a high-risk, high-reward game. Sometimes you hit the jackpot and get to retire early, and sometimes you just end up with a lot of useless stock options and a gap in your resume.
Can being “dumb” actually be an asset?
This one is funny. There was a complete moron working for a tech company during the dotcom era. He and the other managers didn’t understand the tech at all but were hyping it up like crazy. Right before their IPO, three big players got into a bidding war to buy them. The company got acquired, and the big winner realized later that this manager didn’t actually have the technology he claimed.
They laid him off, but his golden parachute forced him to exercise tens of thousands of stock options at the absolute peak of the dotcom bubble. He walked away with over 30 million dollars. The company considered fraud charges but realized they couldn’t prove he knew he was lying because he was truly just that ignorant. He was charismatic and likable, which turned out to be more profitable than being smart.
Do simple ideas still work?
Sometimes the best ideas are the ones you see while traveling. Like the guy whose grandpa worked on a boat and stopped in Germany back in the day. He saw a guy with a suitcase that folded down wheels, thought it was brilliant, and filed for a patent when he got back to the US.
Now, he gets a cut every time one of those “baby carriages” for luggage sells. Some people call it patent piracy, others call it genius. Either way, he’s getting paid for a simple observation that nobody else acted on. It’s a reminder that you don’t need to reinvent the wheel; sometimes you just need to put wheels on something else.
Does money change who you are?
You’d think a sudden windfall would ruin a person, but not always. There’s a story about a guy who bought a few Bitcoin in college, despite being, by all accounts, a “dumb ass” addicted to partying. He has two houses, a Lambo, and hasn’t worked a day since. But here’s the thing—he lent a friend 30k to pay off loans and literally forgot about it.
He has a broker who handles his budget, and he just lives his life. He’s not stressing over asset allocation or market trends. He’s just vibing. It makes you wonder if the secret to enjoying wealth is not taking it too seriously. He’s still the same silly guy, just with a better car.
Is real estate just a waiting game?
Timing is everything. Consider the guy who bought derelict, rent-controlled social housing in West Berlin right before the wall came down. He renovated them like domino pieces, using the rent from the first to pay the mortgage on the second, and so on.
For a decade, it looked like a Ponzi scheme from the outside. But once rent control was abolished, the property values skyrocketed. Now he’s sitting on 50 million Euro worth of real estate, drives a 30-year-old Mercedes, and works every day because he enjoys it. He started with a physics degree and a hunch. It took ten years of patience, but the payoff was massive.
Why do we stress so much about strategy?
Reading all these stories, from the hazmat driver to the Bitcoin guy, it becomes pretty clear. Almost all of these wins boil down to either “gambled and got lucky” or “had some cash to start with and worked really hard.” Or, in some cases, you just married well or won the lottery.
The takeaway here isn’t that you need to find the next Bitcoin or patent a rolling suitcase tomorrow. It’s that opportunities are usually weird, unexpected, and look like bad ideas at the time. So maybe relax a little. Keep your eyes open for that KMart.com moment, but if you miss it? No stress. Life’s pretty good either way.