TIP778: How My Thinking About Investing Evolved in 2025 w/ Kyle Grieve

You're listening to TIP. This past year has been a predictably unusual one for me in the markets. Between the tariff tantrum and the AI scare, many of the companies that I own have really been put through the ringer. But after spending hours each day researching investing, I've learned a lot and taken the time to reflect on which of those lessons have really helped me. evolved the most in 2025.

This episode, like all my previous episodes, won't bother at all guessing with what will happen in 2026. It's about what I've learned that has directly impacted how I think and how I strategize. Now when reflecting on some of the biggest mistakes I've ever made in my investing career, I realized that two of them didn't really stem from poor analysis. They came from fairly simple psychological errors. It's easy to learn about investing and assume that we'll all act rationally, but the reality is far from it.

This episode was an excellent exercise for forcing me to confront where my thinking was too rigid, too emotional, or even too optimistic. One of my biggest thinking shifts was realizing that being confident and being flexible can actually coexist. A more uncomfortable realization was the biggest threat to my portfolio isn't interest rates, geopolitical unrest, or AI, but me and my imperfect thinking. I also share my thoughts on fragility of compounding and the steps that I've taken to protect myself, so the compounding engine can just

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