Three times I saved twenty thousand dollars. Three times I watched it disappear.
And nobody — not one person — sat me down and told me what I'm about to tell you.
This isn't a formula. It's my actual history, including the parts that make me look stupid. I'm writing it because there's a decent chance you're standing where I was standing, you think you're behind, and you're about to make the same call I made. Three times.
There's also one boring habit that finally stopped the cycle. It took me until my forties to find it. It's at the bottom.
Quick housekeeping first: I'm not a financial advisor. I'm a guy who bought three vehicles at once in his twenties and then had to call his grandmother for mortgage money. Take it for what it's worth. Full disclaimer at the end.
Why I write this stuff
When I was in my twenties, there was nothing. The internet was brand new. No podcasts. No YouTube University. Nobody on your phone breaking down what an index fund is while you eat lunch.
And in my family, nobody had ever made it. I don't say that to be dramatic. I say it because it means I had never seen what success looked like up close. I didn't know what I was aiming at. I just knew I was supposed to want it.
So I did what you do when nobody teaches you. I guessed. And I guessed wrong for about fifteen years.
I know who's reading this, too. There's three of you.
You're twenty-five with twenty grand saved and you think you're behind. You're not — that's more than most of this country has. You're ahead and you don't know it.
Or you're thirty, same job for fifteen years, and there's a business in your head you're too scared to start. I lived in that one.
Or you're forty with nothing saved, doing the math in your head at two in the morning. I get messages like that constantly. Here's what I tell every single one of you: most people don't really make it until their forties. I didn't. Same boat. It's okay.
Round one: three vehicles, one person
Early two-thousands. I'm in my twenties. I'd been grinding and I'd finally stacked up about twenty thousand dollars.
Then I decided I was going to be cool.
A 1993 Mazda RX-7 for fifteen thousand. A CBR F4 motorcycle for eight grand. A Jeep Wrangler for about five.
Do the math with me. Three vehicles. For one person. Who can only drive one at a time.
And that's just the sticker. I was paying hundreds a month in insurance alone, in the early two-thousands, when hundreds of dollars a month meant something. Every month, money leaving my account for the privilege of owning things that sat in my driveway.
The cars aren't the lesson, though. The lesson is what was happening in my head.
I had worked so hard to save that money that spending it felt earned. That's the trap. It wasn't recklessness. It was that having twenty grand gave me a false sense of security. I looked at the number and thought, I made it. I'm good. And the second you think you're good, you stop building.
Twenty grand isn't made it. Twenty grand is barely started. But nobody told me that, so I bought a sports car.
Here's the part that stings. That twenty-eight thousand dollars in vehicles, if I'd put it in an S&P 500 index fund instead and never touched it, would be worth somewhere around a quarter of a million dollars today at the market's long-run average return of about 10% a year. A quarter of a million dollars, for three vehicles I don't own anymore. I don't even remember what the RX-7 sounded like.
The penny stock that made me feel like a genius
I have to tell you where some of that money came from, because it's the most important story I've got.
Somewhere in there I put two thousand dollars into a penny stock. I don't want to make this sound smart, because it wasn't. I heard about it, I liked it, I bought it.
And it went up. Two thousand dollars became thirty thousand dollars.
Thirty grand on a two thousand dollar bet. I thought I had cracked something.
Then it started falling. And I watched it fall, because that's what you do when you don't know anything — you watch. By the time I sold, it was down to ten thousand.
So I took the ten grand and bought a motorcycle.
Here's the punchline: that stock eventually went to zero. Nothing. So buying that motorcycle, one of the dumbest financial decisions of my twenties, is the only reason I got anything out of that trade at all.
That's a funny story at a dinner table. But I want to be careful here, because a lot of guys tell that story like it's a flex.
It's not a flex. I didn't do anything. I got lucky, then unlucky, then lucky again in the dumbest possible way. There was no skill in any of it. I had no idea what I owned, no idea why it went up, no idea when to sell, and no plan for the money when I got it.
That's what happens when you have money but no education. You're not investing. You're gambling and calling it investing. I've written about what that looks like at a much bigger scale in the Stanley Druckenmiller FOMO story — it happens to legends too, it just costs them more.
Luck is not a plan. You can't build a life on the hope that your next dumb decision accidentally saves you.
Round two: the responsible mistake
I climbed back up. Twenty grand again.
This time I did something everybody would have called smart. I bought a house. A fixer-upper. Buying it wiped out the savings, which is what a down payment does. That part's fine. That's the part I'd do again.
Here's the part I wouldn't.
I wasn't making enough to renovate that house fast, so I renovated it slow. And when I say slow, I mean I lived in an active construction site for the better part of a decade. Fifteen years in that house total. Ten of them, something was torn open.
I have a very clear memory of standing on a ladder hanging sheetrock on a ceiling at eleven at night, arms burning, thinking: what am I doing with my life. Not planning my empire. Not visualizing anything. Just holding drywall over my head wondering if any of it was going to be worth it.
Both halves of the honest ending:
It worked. Fifteen years in that house was one of the best financial moves I ever made. The equity, the stability, staying put while everything else in my life was chaos — that house carried me.
And I would never do it again.
Because nobody tells you what living in a renovation costs that isn't money. A decade of not being comfortable in your own home. A decade of every spare dollar and every spare Saturday going into a ceiling. You can win the trade and still not want to make it twice.
But it taught me the thing this whole article is built on. The long game is the best game. In real estate, in stocks, in business. The stuff that made me money is the stuff I held for ten and fifteen years. Everything I flipped, sold early, or got cute with is the stuff that cost me.
Round three: the business that died
I started a company. We made one of the first packaged Thai curry sauces sold in America. I'm not exaggerating when I say I was early — there are videos of me on YouTube from 2006. That's twenty years ago.
It could have worked. It really could have. But it was my first business, I didn't know what I was doing, and I didn't have access to capital.
Then the currency moved. The dollar went from about forty baht down into the high twenties. If you've never run a business that buys in one currency and sells in another, that sentence sounds boring. Let me translate it: overnight, everything I bought got dramatically more expensive, and I couldn't raise prices fast enough to survive it.
That was the end. No cash. Plenty of debt.
I'm not going to spend a thousand words on it, because it's tuition, not tragedy. I paid for an education. It was expensive.
The phone call
When it all came apart, I called my grandmother to borrow money to make my mortgage payment.
My grandmother. Who's almost ninety-three now, God bless her. I called her because I could not pay for my own house.
I didn't sleep for three days. Not "slept badly." Did not sleep. I laid there doing math that didn't work no matter how many times I ran it.
I paid her back. Every dollar. That mattered to me more than almost anything I've ever done.
I bring it up for one reason. People comment on my videos and say, Mikey, you don't understand, I'm broke.
I understand. I've been broke more than once. I've had the bank account with nothing in it and the bills that don't care. I've made the phone call you never want to make. It was not fun and I'm not romanticizing it.
I'm telling you because I got out. Not fast, not gracefully, but I got out, and I'm not going back.
If nothing changes, nothing changes
Late thirties. I'm sitting there with the wreckage of a failed business and a house I'm still renovating.
And I said the thing that finally stuck: if nothing changes, nothing changes.
That's the whole revelation. It's not clever and it's not on a poster in my office. But I meant it that time in a way I had never meant anything before.
So I started the beauty business I still own today. Everything went in. No toys — I mean actually none.
I've become a minimalist over the years, and I didn't read a book about it. It came from getting older and finally noticing the pattern: you want the thing, you get the thing, and about a week later you don't care about the thing. Once you see that a few times you stop buying things. Not out of discipline. Out of boredom.
Within a few years I went from negative — actual debt, not zero — to positive. And then I kept going.
I crossed $100,000 at 41
2017. I crossed a hundred thousand dollars invested. I was forty-one years old.
Say that back to yourself if you're sitting there thinking you missed your shot. Forty-one. After three failed runs at twenty grand. After a business that died. After borrowing money from my grandmother.
And I want to be honest about what that moment felt like, because everybody expects a scene.
There wasn't one. No confetti. Nobody called me. I didn't take a screenshot. I looked up one day, the number had a one and five zeros in it, and I thought, huh. Okay.
That's how it happens. The first hundred grand doesn't arrive. It accumulates while you're busy. Which is exactly why so many people quit before it — there's no applause anywhere along the way, and the middle of it feels like nothing is happening.
Here's what's actually happening in that stretch, and this is what I wish somebody had told twenty-five-year-old me. At the beginning, your contributions do basically all the work. The market's doing almost nothing for you. You put in a thousand, you go up a thousand. It feels like saving, not investing, and it feels pointless.
Then somewhere around six figures, it flips. The money starts pulling its own weight. You start having months where the market moves more than you contributed. Once you feel that, you never want to stop.
But you have to get there first. And getting there is boring, and boring is what makes people quit.
What I did right after — and the part I got wrong
Right after I crossed it, I stopped contributing.
In 2017 I bought our first investment property, an acre and a half of land. That land has since five-x'd in value. Then another property in 2019. Another in 2020. One in 2021. Two more in 2022.
Was that a mistake? No. Buying that real estate was one of the best decisions I've made and I still love real estate. Long-term hold, tax advantages, appreciation, control. It's a real wealth builder.
The mistake was going to zero in my brokerage accounts while I did it.
Because real estate is not liquid. That money is locked. Unless you want to take on more debt and borrow against the property, you can't touch it. It's not there when you need it. It's there in twenty years, which is great — but life happens in between, and I've already told you what life happening does to me.
So I started doubling down on the accounts again. Not instead of real estate. Alongside it. One of them buys me the long game, and the other one I can actually get to.
The boring habit that ended the cycle
If you take one thing out of this, take this.
Every Friday, I put a thousand dollars into my brokerage account. Every Friday. It doesn't matter what the market's doing. Doesn't matter if we're green, red, if there's a headline, if somebody on TV says a crash is coming. Friday, the money goes in.
I'll make other trades during the week if something makes sense. But that Friday buy is not a decision. It's a habit. I removed it from the list of things I'm allowed to have an opinion about.
Underneath it, the dividends reinvest. The money I put in makes money, that money buys more, and I never touch any of it. If you want to see exactly where it goes, I broke my whole portfolio down in the 3-bucket portfolio post — the exact buckets, the exact funds, the exact split.
Now, I know what some of you are thinking. Mikey, I don't have a thousand dollars a week.
Neither did I. For twenty years, neither did I.
The number is not the point. If it's fifty dollars, it's fifty dollars. If it's twenty, it's twenty. The point is the Friday.
Because here's what actually killed my first twenty grand, and my second, and my third. It wasn't the amount. It was that investing was something I did when I felt like it, when there was money left over, when things were going well.
And things are never going well for long enough. Life happens. That's not a personal failing. That's just what life does.
The only thing that survives life happening is a habit you stopped negotiating with.
Pick a day. Pick a number small enough that you'll still do it in a bad month. Automate it if you can. Then let it be boring for ten years.
So, look
I lost twenty thousand dollars three times because I bought things I didn't need. Because I had a false sense of security. Because I had no plan, no education, and nobody in my life who'd been there.
I don't say any of that with regret. I've had a great life. I've worked way more than the average person and that's fine — nobody ever said it was going to be easy and it wasn't supposed to be.
But that's exactly why I make this stuff.
I mentor people in my industry. I wrote a book, Fearless Beauty, because I thought it might help somebody. And I pour all of this out here with the information I wish somebody had handed me at twenty-five, when I had twenty grand and a really bad idea about what to do with it.
If one person reads this and doesn't lose their third twenty grand — if one person picks a Friday and just doesn't stop — it was worth writing.
I've been broke. Many times. I'm not going back. And you don't have to go there at all.
Next read: Once you get past that first hundred thousand, the question becomes where you actually put it. Start with the 3-bucket portfolio, then my honest take on QQQI if the income bucket is where your head is at.
The content in this article is for educational and entertainment purposes only and reflects my personal opinions and where my own investing mindset is today, which may change at any time. I am not a financial advisor, broker, or tax professional, and nothing here is financial, investment, or tax advice or a recommendation to buy or sell any security. Investing involves risk, including the possible loss of principal. Past performance does not guarantee future results, and any historical return figures referenced are illustrative averages, not projections. Always do your own research and consult a licensed professional before making any investment decision.