January 29, 2024

Why I Train with a Hall of Famer

As you are reading this, I'll be knee-deep in fresh powder with 40 of my closest friends. This weekend is the legendary Maple Summit trip - hosted by my dear friend...
January 22, 2024

Understanding the Distribution of Outcomes

The fear in his voice was unmistakable. It was the weekend that Silicon Valley Bank failed. My friend called me to help him brainstorm a way out. He was in...
January 8, 2024

The Scorpion and the Toad

The greatest minds in investing all seem to have the same advice: invest in the indices, and don’t try to beat the market yourself. Buffett, Dalio, even Morgan Housel, author of The Psychology...
January 1, 2024

The Unbreakable Year in Review

I love this time of year. While New Year's resolutions have become cliche (and most people don't stick with them anyway), I find value in taking stock of the past year and...
December 27, 2023

Ten More Lessons from Ten Years

Last week, I shared 10 things I wish I knew when I became a millionaire at 33. One of our sayings in the fighter squadron was, "Criticism keeps us alive."...
December 18, 2023

Ten Lessons from Ten Years

I became a millionaire at 33. Now reflecting back at 43, here are 10 things I’ve learned that I wish I knew ten years ago. 1. Cash is king. It’s...