There’s an old saying that luck is what happens when preparation meets opportunity. I used to think that was just a nice thing people said to make hard work sound more romantic. Now I think it might be the most accurate description of my husband Carl’s investment portfolio that exists.
Carl and I have a portfolio made up of individual stocks and index funds. The individual stocks are a wildly outsized chunk of the current value, even though they started out as a tiny sliver of what we actually put in. In other words, we experimented with a handful of individual companies, and we got very, very lucky. Preparation-plus-opportunity lucky. Almost lottery-ticket lucky.
Here’s the thing though. Luck like that doesn’t usually fall out of the sky. It grows out of paying attention to something long before anyone else thinks it matters.
The Man Who Saw a Phone Coming
Carl worked in tech. He reads tech news every single day, not because he has to, but because he genuinely finds it fascinating. He’s also had a lifelong obsession with space, which tells you a lot about the kind of person who gets excited about things most of us walk right past.
In January 2007, when the iPhone was announced, most people saw a phone with a fancy touchscreen. Carl saw something else entirely. He’d point out that it wasn’t just a phone. It was a phone, a music player, and a computer, all rolled into one device that fit in your pocket. Fewer gadgets to carry, fewer things to charge, fewer things to lose. To him, that wasn’t a neat trick. That was a fundamental shift in how people would live.
So we bought our first shares of Apple stock. We didn’t know what an index fund was back then. If you wanted a piece of the stock market in 2007, you bought individual companies, full stop. (Turns out, index funds did exist back then, we just didn’t know about them.)
The timing turned out to be rough in the short term, since the iPhone launch landed right before the Great Recession chewed through the market. But once the recovery kicked in around 2009, Apple took off. (I asked Claude to fact check the exact numbers for this article, and the real figure is a lot wilder than I remembered.) Since the market bottomed out in March 2009, Apple’s split adjusted share price has climbed more than 9,000%. That’s not a typo. A $1,000 investment made right at that low would be worth well into six figures today. I had it in my head that it was up around 500%, which honestly shows you how easy it is to underestimate what patience and a good thesis can do over almost two decades.
The Coworker Who Said “Just Google It”
Carl’s Apple story is impressive, but it’s not even his best one. Let’s travel back further, to the late 1990s.
Carl was at work, programming, and he grabbed a reference book to figure out how to solve a coding problem. A coworker glanced over and said something that sounds completely unremarkable today: “just Google it.” Except at the time, that phrase didn’t exist yet. Google was brand new. It wasn’t a verb. It wasn’t even really a noun most people had heard of.
Carl went to google.com, typed in his question, and got an answer instantly. All that searching, done in the blink of an eye.
Most people’s reaction to that moment would have been something like, “oh nice, that saved me twenty minutes.” Carl’s reaction was different. His first thought was, “how do I invest in this company?”
That’s the preparation part of the luck equation. He started following Google closely, reading everything he could find about it, long before it was a household name. When the company finally went public in 2004, it did something unusual for the time. Instead of a traditional IPO, where getting shares often depends on knowing the right banker or broker, Google used a Dutch auction. That structure opened the door to regular investors instead of just insiders. That’s the opportunity part. Carl was ready, and the door happened to open in a way he could actually walk through.
The Big One
Facebook is another one of Carl’s long term winners, and it came together a little differently. The IPO itself was very much a “know a guy” situation, and we didn’t know a guy, so that door just wasn’t open to us. That’s fine. There was nothing to chase there. We simply waited for our own opportunity, and it showed up once the stock was trading on the open market like everything else we buy. We bought 1,000 shares at $42 a share. That single purchase was the largest dollar amount we’d ever put into one stock at one time (until SpaceX in 2023) and it’s paid off handsomely since.
Meanwhile, My Method Was a Lot Less Nerdy
I’ll be honest, I don’t read tech news for fun. It just isn’t my thing. But I do pay attention to the world around me, and it turns out that counts as research, too.
Have you ever walked into a Costco on a Saturday? It’s chaos. The lines stretch back past the rotisserie chickens, the carts are piled so high you can barely see over them, and people are buying paper towels in quantities that suggest they’re preparing for a very long winter. I didn’t need an earnings call to tell me something was working. I just needed to stand in that line for twenty minutes. We bought Costco at $162 a share. It’s trading around $950 now.
Chipotle worked the same way for me. Go to any Chipotle at lunch or dinner and you’ll find a line out the door. It’s fast, it’s fresh, and it’s a genuinely good amount of food for a fair price. Plenty of restaurants can claim one or two of those things. Chipotle seemed to nail all three at once, consistently, which is rarer than it sounds. Maybe it also helps that I have a soft spot for a good burrito bowl. If In-N-Out ever goes public, I will be first in line, figuratively and probably also literally. (We ended up selling Chipotle to be able to invest in SpaceX in 2024. I probably need to go have another burrito and get back into that stock…)
This Isn’t Magic, It’s Just Noticing
Here’s what I want to be really clear about. Carl and I didn’t have some secret formula. We didn’t have insider information, and neither of us can predict the market. What we had was preparation. Carl’s preparation looked like years of reading, following companies, and understanding an industry inside and out. Mine looked like standing in a checkout line and thinking, “huh, everyone here seems to really love this place.”
Both of those are forms of research. They just don’t look like research in the traditional sense, and that’s exactly why they’re accessible to basically anyone. You don’t need a finance degree to notice that a store is always packed, or that a product has become something people genuinely can’t live without. You just need to be paying attention, and you need to be willing to act on what you notice.
The Part Where I Tell You to Be Careful
Now, before you go dump your emergency fund into whatever restaurant had a long line last Tuesday, let’s talk about the downside of all this, because there is one.
Our individual stock portfolio has grown into an outsized portion of our total net worth. That’s the flip side of picking a few big winners. When something like Apple goes up 9,000%, it doesn’t just make you money, it also quietly takes over your portfolio. What started as a small, diversified slice can turn into a concentrated position without you ever making an active decision to concentrate it. Our cost basis for that slice of the portfolio is laughably small compared to what it’s worth today, which is a wonderful problem to have and also a real risk to manage.
Concentration cuts both ways. It’s how you end up with life changing gains, and it’s also how you end up overly dependent on the fortunes of a handful of companies. If Carl’s read on any one of these had been wrong, or if the market had simply decided to punish that stock instead of reward it, we’d be telling a very different story right now.
Experimenting with individual stocks isn’t automatically reckless, but it does require an honest look at your own risk tolerance, and it requires never betting money you can’t afford to lose. Preparation reduces risk. It doesn’t eliminate it.
So What Have You Noticed?
I keep coming back to this question, because I think it’s the real takeaway here. What companies stick out to you? Not because a headline told you to care, but because you’ve actually experienced something firsthand. Maybe it’s a grocery chain that’s always slammed. Maybe it’s a piece of software your entire team suddenly can’t stop using. Maybe it’s a product that solved a problem you didn’t even realize you had until it was gone.
You don’t need Carl’s decades of tech obsession to have an edge. You need your own version of it. Preparation can be reading company filings for fun, or it can be the accumulated knowledge you’ve built just by living your life, working your job, and shopping at the same stores everyone else does. The opportunity part still has to show up, and you still have to be paying close enough attention to recognize it when it does.
If you’ve got the risk tolerance for it, throwing a small, deliberate amount of money at a company you genuinely believe in isn’t a bad way to test your own instincts. Keep it small. Keep your foundation in diversified index funds. And treat it as an experiment, not a strategy for your whole portfolio.
Carl’s preparation was years of tech news and a genuine love of space and computers. Mine was standing in a Costco line getting mildly annoyed at how popular rotisserie chicken is. Neither of those things sounds like sophisticated investing advice, and yet here we are. So look around. What do you keep noticing? That might be your opportunity waiting for its preparation to catch up.
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