Borrow for Boring
Debt amplifies everything. Not just the upside.
I have a friend who mortgaged everything on one bet. A decade of all-in. It paid off in a company sale that most people only dream about. I was genuinely happy for him. Still am.
I have another friend who keeps going. One risky bet after another. No retirement account. Lost his house in a prior startup. Got divorced. Been working sixty-plus hours a week for the better part of a decade. And honestly? I think he might hit it big eventually.
But a broken family. Overweight. Blood pressure through the roof.
I’m not saying he’s wrong. I’m saying I couldn’t do it. Not because I’m unwilling to work hard. Because if I loaded myself up with that much pressure and leverage, I wouldn’t sleep. I know this about myself.
That’s the thing about leverage. It doesn’t just amplify returns. It amplifies everything. The uncertainty. The pressure. The cost of being wrong.
When I bought commercial real estate, I used a mortgage. Predictable asset, long-term lease, reliable tenant. The leverage amplified a boring bet into a good return. I sleep fine.
A long while ago, I started buying Bitcoin. Insanely risky bet for me. I wouldn’t recommend it to most. With those kinds of investments, you only want to use money you’re comfortable losing. So I set up a fund I’d be comfortable losing. It exists because I drive a car that’s now a couple of decades old. No car payment. I took what the average American spends on a car payment at that time, around $500 a month, and put it into that fund. I call it my house money fund. If it all went to zero, I’d still have my car. Red as it is.
Many people do it backward.
They borrow to gamble and pay cash for the safe things.
Exciting bets have the widest range of outcomes. When you add debt to one, you’re not just risking the money. You’re risking your ability to keep playing.
My buddy who lost his house kept playing. That takes a different kind of person than I am.
Cash for the bets that keep you up at night. Borrow for boring.