Rules don’t break. They get expensive. For decades, college basketball enforced a curious rule: jersey numbers could only use digits zero through five. The explanation was technical. Referees reported fouls using hand signals, and each digit had to be shown on one hand. The rule made sense once. Then technology changed. Scorekeeping improved. The original reason faded. The rule stayed anyway. That’s how most rules survive—not because they’re especially good, but because they’

I made a small but deliberate change to my portfolio. A week ago, I wrote about how money, incentives, and responsibility don’t disappear just because they’re abstracted through markets. I wanted to offer a practical example of what applying that idea can look like. I sold my U.S. small-cap ETF in my retirement accounts because it owned two companies whose businesses are significantly tied to contracts with Immigration and Customs Enforcement. I replaced it with a very simil

Why owning a company might not mean what you think it does Many of us own companies by owning their stock without ever really thinking about what that means. If you have a retirement account, you almost certainly own tiny pieces of hundreds if not thousands of firms. You may not think about ownership in any concrete way, but I bet you do notice how it feels when the balance goes up, or how uncomfortable it feels when it goes down. There’s something else that feels strange too

Debt shifting is rational on paper. But money is weird. That gap is where most “perfect” financial strategies fail. The term debt shifting originates in corporate finance. It’s got a nice, buzzy ring to it, so naturally it escaped the Arc’teryx finance-bro down jacket and wandered into personal finance. Originally, debt shifting described multinational company strategies for allocating debt across subsidiaries—specifically, moving interest expense into high-tax jurisdictions