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[Building a Compounding Machine: Kyle Grieve’s Investing Philosophy]-[TIP755: My Process for Finding Great Investments w/ Kyle Grieve]

We Study Billionaires - The Investor’s Podcast Network · B2 · 2025-09-21

Business
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📋 Summary

Building a Compounding Machine: Kyle Grieve’s Investing Philosophy

In this deep dive, Kyle Grieve pulls back the curtain on his investment strategy, which has generated an annualized return of 187% since 2020. Moving beyond mere performance metrics, Grieve emphasizes the development of a "consistent, repeatable philosophy" that prioritizes long-term capital compounding over short-term market noise.

The Crucible of Experience: From Speculation to Discipline

Grieve’s journey began with a painful lesson in 2017 when he "eviscerated about 97%" of his cryptocurrency assets. This formative failure taught him five critical lessons: be wary of technical indicators, avoid leverage, only buy what you understand, recognize that every action has a downside, and avoid shorting. These experiences shifted his focus toward value investing, where he learned the vital distinction between "price and value."

The Core Framework: Business Ownership Mentality

Grieve operates with the mindset of a business owner rather than a trader. He believes that "investing is the intersection of economics and psychology," striving to emulate successful investors who do very few things but do them well. His portfolio is divided into two primary categories:

  1. Quality Businesses (approx. 63% of portfolio): These are the long-term compounders. He evaluates them based on a "spectrum of quality," seeking competitive advantages (moats), high returns on invested capital (ROIC) exceeding 15%, and management integrity that he deems "unquestionable."
  2. Microcap Inflection Point Businesses: These are smaller, high-growth plays where he looks for two quarters of revenue and earnings growth above 25%. He utilizes a PEG ratio approach here, often seeking a forward PEG below 0.5 to provide a "significant margin of safety."

The Art of Selling and Portfolio Management

Grieve’s sell criteria are strictly limited to three scenarios: finding a better opportunity, the stock price running five to 10 years ahead of itself, or a broken thesis. He explicitly warns against the "sunk cost fallacy" and confirmation bias, noting that his biggest losses, such as "Cannabis Capital, Bosch Health, and Alibaba," resulted from being too slow to admit his thesis was flawed.

His approach to portfolio management has evolved to include "averaging up" on winners—a departure from traditional value investing. He maintains a concentrated portfolio of 8 to 13 positions, allowing his best ideas to grow, with some positions reaching up to 28% of his portfolio value.

Behavioral Edge and Environment

Grieve emphasizes that he does not have an "above average IQ," attributing his success instead to a "behavioral edge." To maintain this edge, he:

  • Engineers Inaction: He avoids financial news and constant market alerts, which he views as noise that prompts unnecessary activity.
  • Audits Thinking: He uses "Bayesian updating" every quarter to re-evaluate his bull, base, and bear case theses for his holdings.
  • Reduces Stupidity: He follows Charlie Munger’s approach of observing his own shortcomings and avoiding the mistakes of others.

Conclusion: The Long Game

Reflecting on "mistakes of omission," Grieve acknowledges that he has passed on winners like Kraken Robotics and Hims & Hers. However, he remains focused on the process rather than regret. By refining his ability to identify businesses that leverage technology—such as John Deere’s move into autonomous tractors—and maintaining a disciplined, long-term perspective, Grieve continues to refine his process for compounding capital over decades.

🎯Key Sentences

1
I'm also going to pull back the curtains on some of my biggest failures.
2
I'm sure glad I did.
3
I learned a hell of a lot.
4
I might as well try to build it myself.
5
I'm trying to reverse that thinking as much as I can.
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📝Key Phrases

1
pull back the curtains
2
long story short
3
be wary of
4
put two and two together
5
shift gears
Expand All

📖 Transcript

You're listening to TIP.
Since 2020, my portfolio has generated an annualized return of 187, compared to 178 for the SP 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.
In today's episode, I'm going to share exactly how I invest.
I'm not just going to focus on the highlights.

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