TIP778: HOW MY THINKING ABOUT INVESTING EVOLVED IN 2025

W/ KYLE GRIEVE

TIP778: HOW MY THINKING ABOUT INVESTING EVOLVED IN 2025 W/ KYLE GRIEVE

25 December 2025

On today’s episode, Kyle Grieve discusses the most important investing lessons he learned in 2025 after spending thousands of hours studying great investors, businesses, and mental models. He explores why conviction must be flexible, how customer loyalty, culture, incentives, and founder DNA shape long-term compounding, and why emotions and fragility are often the biggest risks investors face. Kyle also explains why intentional inactivity, incomplete information, and a relentless focus on downside protection are essential to surviving and thriving as a long-term investor.

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IN THIS EPISODE, YOU’LL LEARN:

  • Why “strong convictions, weakly held” is one of the most powerful default frameworks for better investing decisions
  • Why customer loyalty is an underappreciated signal of long-term business quality
  • How sleuthing a business can dramatically deepen your understanding beyond financial statements
  • Why reflecting on your own emotions is essential to improving investment outcomes
  • Why intelligent investing always involves incomplete information, and why that is not a flaw
  • Why intentional inactivity is one of the most profitable actions an investor can take
  • How understanding company culture helps identify true long-term compounders
  • Why founders matter and the overlooked reason their impact often outlives them
  • Why focusing on fragility and downside risk matters more than upside potential
  • Why incentive structures are one of the most critical and misunderstood drivers of business performance
  • And so much more!

Disclosure: This episode and the resources on this page are for informational and educational purposes only and do not constitute financial, investment, tax, or legal advice. For full disclosures, see link.

TRANSCRIPT

Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

[00:00:00] Kyle Grieve: 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 evolve the most in 2025.

[00:00:19] Kyle Grieve: 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.

[00:00:37] Kyle Grieve: 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.

[00:01:00] Kyle Grieve: A more uncomfortable realization was the biggest threat to my portfolio is in 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.

[00:01:16] Kyle Grieve: 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 studying daily. I’ll walk you through updates to my strategy around things like position sizing, how I wait for investments to play out and how I say no.

[00:01:36] Kyle Grieve: 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 invest. Let’s jump right in to what I learned in 2025.

[00:01:57] Intro: Since 2014, and through more than 180 million downloads, we’ve studied the financial markets and read the books that influenced self-made billionaires the most. We keep you informed and prepared for the unexpected. Now for your host, Kyle Grieve.

[00:02:21] 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, you know, it’s a job where I get to share these incredible lessons with you every episode.

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