TIP755: MY PROCESS FOR FINDING GREAT INVESTMENTS

W/ KYLE GRIEVE

TIP755: MY PROCESS FOR FINDING GREAT INVESTMENTS W/ KYLE GRIEVE

20 September 2025

On today’s episode, Kyle Grieve discusses the lessons that shaped his investing philosophy, from painful early mistakes in crypto to building a disciplined framework focused on quality businesses and high-potential, undervalued microcaps. He shares how goals, temperament, and a business-owner mindset guide his decisions, and why compounding, capital efficiency, and management integrity are the cornerstones of his strategy.

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IN THIS EPISODE, YOU’LL LEARN:

  • Lessons learned from the early days as a pure speculator.
  • Kyle’s simple investing goal and the pros and cons of pursuing it.
  • Why benchmarks are irrelevant to his approach.
  • How adopting a business-owner mindset helps compound capital.
  • The two categories of investments that form the foundation of his investing strategy.
  • Why quality lies on a spectrum and why the highest quality business isn’t always the best investment choice.
  • The importance of skilled and aligned management.
  • The three main reasons Kyle sells a stock.
  • How to combat confirmation bias and the sunk cost fallacy.\
  • Why averaging up has been more effective than averaging down.
  • And so much more!

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: Since 2020, my portfolio has generated an annualized return of 18.7% compared to 17.8% for the S&P 500 over the same timeframe. But what matters even more than the performance is just that I’ve developed a consistent, repeatable philosophy that I believe will allow me to compound capital at attractive rates for many, many years and decades to come, and that process continues to evolve and improve over time.

[00:00:24] Kyle Grieve: In today’s episode, I’m going to share exactly how I invest. I’m not just going to focus on the highlights. I’m also going to pull back the curtains on some of my biggest failures. I’ll start with a painful lesson from my early days as a pure speculator and how those experiences ultimately pushed me to adopt a much more disciplined approach.

[00:00:40] Kyle Grieve: From there, I’ll explain the simple goals that guide my decisions, the pros and cons of aiming so high, and why I don’t spend time worrying about benchmarks like the S&P 500. From there, we’ll dive into the framework that I use today. I’ll walk you through why I think like a business owner rather than a trader.

[00:00:56] Kyle Grieve: The two distinct categories of investments that I focus on and how I evaluate quality as a spectrum rather than as an absolute. You’ll also hear why I place such importance on management integrity, the three main reasons that I sell a stock and the methods that I use to help guard against dangerous biases.

[00:01:11] Kyle Grieve: If you’re an investor who wants to strengthen your mindset, sharpen your process for identifying winners, and build an environment that rewards patients rather than just, you know, constant activity, this episode will help give you the exact tools and perspectives to improve at that. Now, let’s get into this week’s episode, on my investing philosophy.

[00:01:33] Intro: Since 2014 and through more than 180 million 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.

[00:01:57] Kyle Grieve: Welcome to The Investor’s Podcast. I’m your host, Kyle Grieve, and today I’m going to share my investing philosophy with you. I have had the opportunity to learn from some of the industry’s top investors, whether that’s chatting with incredible outperformers as guests on the show, or sharing lessons from outperformers from some of the best investing books that have ever been written.

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