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 wringer. 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 evolve 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 continue working. This episode is packed with how I've turned this thinking into usable tools to help me improve as an investor. And the reason I think these tools work is that nearly all of them have been cloned from the legendary investors I get the privilege of studying daily. I'll walk you through updates of my strategy around things like position sizing, how I wait for investments to play out, and how I say no. So if you've ever felt the urge to act when nothing needed to be done or felt extreme confidence right before proven wrong, this episode is just for you because I feel your pain. This episode will help you learn from my mistakes and give you a few ways to think differently about your own investing. Let's jump right in to what I learned in 2025. Since 2014 and through more than 180,000,000 downloads, we've studied the financial markets and read the books that influence self made billionaires the most. We keep you informed and prepared for the unexpected. Now for your host, Kyle Grieve. Welcome to The Investor's Podcast. I'm your host, Kyle Grieve. And today, I'm happy to discuss my nine biggest learnings from my last year, specifically from this podcast. So the podcast game is just super interesting for me because it's a job where I get to share these incredible lessons with you every episode, but then I can also pick and choose which of these strategies and meta models that …