Brian D. O'Leary

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Wednesday, April 22, 2026

The Market Doesn’t Care About Feelings

In his final career game for the Czech National Team, Ondřej Satoria threw 4 2⁄3 scoreless innings against the defending champs and was treated to a standing ovation by the Tokyo Dome fans.
Meanwhile, the umpires blew calls as usual. Unfortunate, but to be expected.

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Abstract Philosophy Doesn’t Raise Kids

The adult in the libertarian room I recently joined Adam Haman for the 200th episode of his podcast. The room was full of serious thinkers—Scott Horton, Stephan Kinsella, and others. It was a milestone. I was honored. But I wasn’t there to nod along with ideological reflexes. If you want to know what I’m building …

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A Different Kind of Defense Budget

Geopolitcs & Your Bank Account A few days ago, the Ron Paul Institute republished my column about “Uncle Bibi’s War.” The premise is simple. Washington continues to write blank checks for foreign conflicts while the domestic economy slowly bleeds out. You can get mad about it. You can argue with strangers on the internet. Or you …

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Renting Land From Billionaires

The Insurance Policy We need to talk about the danger of renting land. Substack is an excellent tool. I use it. I teach others how to use it. But relying on it as your sole connection to your audience is a fool’s errand. You are building a house on property owned by Silicon Valley billionaires. …

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Why I fired my “IT Department” (Me)

The Value of a Team Yesterday, I sent out my first dispatch in months that wasn’t from my Substack. The response was telling. It turns out, while I was “screaming into the void,” a lot of you were actually listening. One of the biggest reasons for my silence was a trap most entrepreneurs fall into. I …

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