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We Study Billionaires

TIP773: How Systems and Simple Math Shape Better Investing w/ Kyle Grieve

64 min episode · 2 min read

Episode

64 min

Read time

2 min

Topics

Productivity, Investing, Startups

AI-Generated Summary

Key Takeaways

  • Feedback Loops & Compounding: Reinforcing feedback loops create exponential growth when interest compounds without interruption. A 15% annual return doubles capital every five years. Investors sabotage compounding by selling winners prematurely, withdrawing funds unnecessarily, or failing to maintain consistent deposits into their portfolios over extended periods.
  • Kill Criteria Framework: Combine state and date into pre-commitment contracts: "If margins aren't 8% by year three, sell." This forces action despite noise. Grieve sold Thermal Energy International after it missed three specific KPIs (37-40 development agreements, $35-37M order intake, $22-24M backlog) rather than waiting indefinitely for improvement.
  • Power Law Returns: Portfolio returns follow extreme distributions where 80% of gains come from 20% of positions. Grieve's top four holdings generated 53% of year-to-date returns from 19 positions. This asymmetry means investors can be wrong 50% of the time and still achieve strong overall performance if winners compound sufficiently.
  • Cone of Uncertainty: Businesses with predictable futures deserve larger position sizes. Costco's customer-focused model creates a narrow cone versus speculative microcaps with wider uncertainty. Start positions at 1.5% for high-uncertainty ideas, then average up as the cone narrows and conviction increases through validated KPIs and demonstrated execution.
  • Scale Challenges: Revenue growth creates non-linear problems that destroy value without proper planning. WeWork spent $1.9B to generate $1.8B revenue growth by scaling without sustainable unit economics. Monitor whether R&D and SG&A expenses as percentage of revenue shrink (economies of scale) or grow (diseconomies) as companies expand operations.

What It Covers

Kyle Grieve explores mental models from systems thinking and mathematics that shape better investing decisions, including feedback loops, kill criteria, power laws, and compounding asymmetry, demonstrating how understanding these forces improves portfolio construction and long-term performance.

Key Questions Answered

  • Feedback Loops & Compounding: Reinforcing feedback loops create exponential growth when interest compounds without interruption. A 15% annual return doubles capital every five years. Investors sabotage compounding by selling winners prematurely, withdrawing funds unnecessarily, or failing to maintain consistent deposits into their portfolios over extended periods.
  • Kill Criteria Framework: Combine state and date into pre-commitment contracts: "If margins aren't 8% by year three, sell." This forces action despite noise. Grieve sold Thermal Energy International after it missed three specific KPIs (37-40 development agreements, $35-37M order intake, $22-24M backlog) rather than waiting indefinitely for improvement.
  • Power Law Returns: Portfolio returns follow extreme distributions where 80% of gains come from 20% of positions. Grieve's top four holdings generated 53% of year-to-date returns from 19 positions. This asymmetry means investors can be wrong 50% of the time and still achieve strong overall performance if winners compound sufficiently.
  • Cone of Uncertainty: Businesses with predictable futures deserve larger position sizes. Costco's customer-focused model creates a narrow cone versus speculative microcaps with wider uncertainty. Start positions at 1.5% for high-uncertainty ideas, then average up as the cone narrows and conviction increases through validated KPIs and demonstrated execution.
  • Scale Challenges: Revenue growth creates non-linear problems that destroy value without proper planning. WeWork spent $1.9B to generate $1.8B revenue growth by scaling without sustainable unit economics. Monitor whether R&D and SG&A expenses as percentage of revenue shrink (economies of scale) or grow (diseconomies) as companies expand operations.

Notable Moment

Scott Barbee's Aegis Fund dropped 72% during 2007-2009, yet he maintained his strategy knowing extreme negative events regress to mean. The fund rebounded 91% in 2009, landing him on the Wall Street Journal front page by trusting his process through volatility.

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Episode Transcript

You're listening to TIP. Did you know that over long periods, just a handful of stocks will account for the vast majority of a portfolio's return? And that's even if half of your investments fail. The winners can still make up for the losses and then some. Now that asymmetry results from power laws and convex compounding. And once you truly understand how these mathematical forces work inside of real world systems, it will completely change the way that you think about investing. In today's episode, we're exploring the mental models from systems thinking and mathematics that have had the biggest impact on my own personal investing approach. We'll look at things such as feedback loops, kill criteria, and the cone of uncertainty, and how these systems can be used to improve your thinking process. We'll examine how scale changes a business as it grows, how algorithms help you make more certain decisions, and how critical mass can propel a company into beneficial self sustaining mode. Then we'll shift over to the mathematical side of things, and don't worry. You won't need to pull out a calculator to follow along. We'll look at concepts like hidden compounding, power laws, randomness, and regression to the mean, and then we'll tie them all together so you can really understand just how these forces quietly shape your portfolio's long term performance. This episode is for investors who wanna think more clearly, whether you're trying to expand your mental toolbox, aiming to avoid common pitfalls, or looking for new ways to stress test your own reasoning. If you're someone who really values long term thinking, likes understanding just why things work the way they do, and wants an edge that isn't based on things like predictions or noise, then this episode is for you. Let's get right into it. 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, we're gonna discuss mental models from two very distinct areas, systems and mathematics. So my first introduction to systems was by reading Thinking in Systems, a Primer by Donella Meadows. That book really helped me develop a basic understanding of just how systems work. My biggest takeaway was just, you know, how these systems tend to work together and how small changes to one part of the system could cause a very massive change to outputs in other part of the system. And obviously, this could be a desirable or undesirable outcome. As I began to think more and more about systems, I came across another excellent book which was the great mental models volume three, Systems of Mathematics by Farnam Street. This book compiles numerous great mental models from these two broad areas of learning. While preparing for this episode, I also couldn't …

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