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We Study Billionaires

TIP755: My Process for Finding Great Investments w/ Kyle Grieve

64 min episode · 2 min read

Episode

64 min

Read time

2 min

Topics

Productivity, Personal Finance, Investing

AI-Generated Summary

Key Takeaways

  • Portfolio Structure: Divide holdings into two buckets: quality businesses (63% of portfolio) requiring 15%+ ROIC and competitive moats for long-term compounding, and microcap inflection points (37%) showing two consecutive quarters of 25%+ revenue and earnings growth for faster gains.
  • Position Sizing Strategy: Start quality positions at 2-3% cost basis, allowing growth to 10% maximum, while microcap positions begin at 1% and cap at 5-6%. Never trim winners regardless of absolute portfolio weight, as top performers often reach 20-28% through appreciation without intervention.
  • Three-Part Sell Discipline: Exit positions only when finding better risk-reward opportunities, when price pulls forward five to ten years of expected returns, or when investment thesis breaks. Ignore sunk costs and focus solely on forward-looking fundamentals rather than purchase price when evaluating holds.
  • Management Evaluation Framework: Assess executives across twelve criteria including insider ownership percentage relative to net worth, capital allocation discipline, transparency consistency during downturns, and compensation structure. Management integrity ranks as non-negotiable requirement, warranting immediate exit if any cracks appear in trustworthiness.
  • Performance Measurement Method: Track owner earnings (operating cash flow minus maintenance capex) growth rather than stock price movements to evaluate investment success. Require 15%+ annual owner earnings growth for quality holdings and 25%+ for microcaps, checking quarterly against probability-weighted scenarios using Bayesian updating.

What It Covers

Kyle Grieve shares his complete investing framework that generated 18.7% annualized returns since 2020, covering his evolution from cryptocurrency speculation losses to disciplined value investing through quality businesses and microcap inflection points.

Key Questions Answered

  • Portfolio Structure: Divide holdings into two buckets: quality businesses (63% of portfolio) requiring 15%+ ROIC and competitive moats for long-term compounding, and microcap inflection points (37%) showing two consecutive quarters of 25%+ revenue and earnings growth for faster gains.
  • Position Sizing Strategy: Start quality positions at 2-3% cost basis, allowing growth to 10% maximum, while microcap positions begin at 1% and cap at 5-6%. Never trim winners regardless of absolute portfolio weight, as top performers often reach 20-28% through appreciation without intervention.
  • Three-Part Sell Discipline: Exit positions only when finding better risk-reward opportunities, when price pulls forward five to ten years of expected returns, or when investment thesis breaks. Ignore sunk costs and focus solely on forward-looking fundamentals rather than purchase price when evaluating holds.
  • Management Evaluation Framework: Assess executives across twelve criteria including insider ownership percentage relative to net worth, capital allocation discipline, transparency consistency during downturns, and compensation structure. Management integrity ranks as non-negotiable requirement, warranting immediate exit if any cracks appear in trustworthiness.
  • Performance Measurement Method: Track owner earnings (operating cash flow minus maintenance capex) growth rather than stock price movements to evaluate investment success. Require 15%+ annual owner earnings growth for quality holdings and 25%+ for microcaps, checking quarterly against probability-weighted scenarios using Bayesian updating.

Notable Moment

Grieve reveals losing 97% of his cryptocurrency portfolio in 2017 through leverage trading on one-minute charts using technical indicators, which taught him five critical lessons including avoiding leverage and shorts that shaped his disciplined business-owner approach to stock investing.

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Episode Transcript

You're listening to TIP. Since 2020, my portfolio has generated an annualized return of 18.7% compared to 17.8% for the S and P 500 over the same time frame. But what matters even more than the performance is just that I have 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. In today's episode, I'm gonna share exactly how I invest. I'm not just gonna focus on the highlights, I'm also gonna 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. 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 and 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, 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. If you're an investor who wants to strengthen your mindset, sharpen your process for identifying winners, and build an environment that rewards patience 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. 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 Investors Podcast. I'm your host, Kyle Grieve. And today, I'm gonna 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. I've had the fortunate opportunity to absorb just a ton of incredible information from many of the best investors to ever do it. To understand my investing philosophy today, I don't need to go too far back in time to explain some of the crucial mistakes that I've made and these mistakes have helped shaped me into the investor that I am today. My first risk asset was actually in cryptocurrencies and I won't get into crypto too much as my co host Preston Pysh knows more about crypto than I ever …

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