I had a chat with a friend the other day about investing. He’s a day trader and dividend kind of guy. I, on the other hand, am a passive investor.

So far, my simple, boring strategy has worked out pretty well. I’ve saved a ton of time by not watching prices or reading financial reports. Nope—just a couple of clicks a year, and that’s that.

My friend brought up venture capitalists. Venture capitalists make wild bets, hoping that one investment out of hundreds delivers an enormous return. We both agreed it’s kind of BS that VCs get early access to potential unicorns before they IPO, while we retail investors get the crumbs. Okay, maybe that’s a little dramatic—but if you’re into the stock market, you probably know what I mean.

Anyways, I told him I’d like to take a shot at finding the next unicorn, even if it has already IPO’d. So, I’ve decided to slowly (emphasis on slowly) introduce what I call moonshots into my portfolio.

Right now, I’m buying JOBY. It seems like a cool project—one that could disrupt how humans move around. They’re a major player in the air taxi space. I mean, that alone sounds pretty nutty.

Thinking back to my first year at university—more than a decade ago—a classmate and I were talking about stocks. I was loading up on BlackBerry, hoping for the company to comeback. He, on the other hand, was buying shares of some electric car company… Tesla.

If I had bought 100 shares of Tesla back then at $9 (pre-split), those shares would be worth about $500,000 today.

It’s an illustrative example—not of missed opportunity per se, but of the enormous upside occasionally available to the early believer.

Today, JOBY trades between $5 and $9.

I’ve bought a few hundred dollars’ worth, thinking: my downside is limited—at worst, I lose a few hundred bucks. But my upside? That’s essentially unlimited. It’s a much better bet than blowing the same money at a casino. Right?

Maybe I’m not thinking straight—but this is something I want to explore. Add some moonshots to my portfolio for the long run. Good idea? Bad idea? Who knows. But over a 10+ year horizon, a well-considered asymmetrical bet—even if only occasionally successful—can shift outcomes in unexpected ways.

P.S. This is not investment advice.