We Study Billionaires - The Investor’s Podcast Network

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

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Sep 21, 2025

Kyle Grieve shares how early mistakes in crypto paved the way for a disciplined investing strategy focused on microcaps and quality businesses. He emphasizes the importance of a business-owner mindset, capital efficiency, and management integrity. Discover his unique approach to investing, including why he rejects benchmarks and employs averaging up. Grieve also discusses key factors that trigger his decisions to sell stocks and how to combat biases that can hinder investment success.

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ANECDOTE

Painful Crypto Losses Shaped His Approach

Kyle lost ~97% of his crypto holdings by using leverage and technical indicators in 2017.
That experience forced him to stop using leverage and focus on assets he understands.

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ADVICE

Use A Clear Return Target

Set a clear numeric return goal to guide your investment selection and sizing.
Use the goal to be picky and only buy ideas that can plausibly meet your hurdle.

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From Crypto Losses to a Business-Owner Mindset

Management, Microcaps, Quality Stocks, and Selling Rules

Concentration, Circle of Competence, Geography, Metrics

47:29 • 9min

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Engineering Inaction, Temperament, and Avoiding Mistakes

• Mentioned in 8 episodes

The Warren Buffett portfolio

Mastering the Power of the Focus Investment Strategy

Robert G Hagstrom

This book introduces the concept of focus investing, a strategy that has historically outperformed the market. Hagstrom explains how to build and manage a concentrated portfolio, similar to Warren Buffett's approach. He demonstrates how to select a few outstanding companies with high probability of continued strong performance and how to allocate investment funds proportionately. The book also delves into the intellectual framework for managing such a portfolio, including understanding price volatility, market psychology, and the importance of intellectual fortitude. It serves as a companion to Hagstrom's earlier work, 'The Warren Buffett Way', by providing tools for organizing and managing a focus portfolio.

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.

IN THIS EPISODE YOU’LL LEARN:

00:00 - Intro 02:16 - Lessons learned from the early days as a pure speculator. 08:40 - Kyle’s simple investing goal and the pros and cons of pursuing it. 09:16 - Why benchmarks are irrelevant to his approach. 14:00 - How adopting a business-owner mindset helps compound capital. 17:29 - The two categories of investments that form the foundation of his investing strategy. 18:21 - Why quality lies on a spectrum and why the highest quality business isn’t always the best investment choice. 19:33 - The importance of skilled and aligned management. 32:21 - The three main reasons Kyle sells a stock. 36:10 - How to combat confirmation bias and the sunk cost fallacy. 38:24 - Why averaging up has been more effective than averaging down.

Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences.

BOOKS AND RESOURCES

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Related ⁠books⁠ mentioned in the podcast.
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