556: Investing in Movies?

556: Investing in Movies?

April 26, 2026 · 38 min

About this episode

The episode discusses the balance between boring investments and those that are more exciting, particularly in the context of investing in movies.

When it comes to investing, boring is good. In fact, in most cases, boring is exactly what you want. The fewer moving parts an investment has, the fewer ways it can break. You're not relying on perfect timing, you're not depending on some heroic execution, and you're not sitting there hoping everything lines up just right. It just… works. That's why a lot of the stuff I like—cash-flowing real estate, simple structures, things with predictable outcomes—tends to look pretty unexciting on the surface. But over time, that's where wealth is built. But… boring rarely creates outsized wealth. The biggest wins almost always come from things that are the opposite of boring. If you bought Bitcoin ten years ago and held it, that wasn't a conservative decision. That was a bet. A bet on something with massive uncertainty that most people didn't understand. Same thing in Silicon Valley. Most startups fail. Everybody knows it. But the ones that work? They don't just work—they hit so big that they make up for everything else. And then there's this other category of investments. Investments that you make not just because of the potential return—but because they're interesting. Because they give…

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