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

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On today’s episode, Kyle Grieve discusses powerful mental models from systems thinking and mathematics and applies them directly to investing and life. He breaks down concepts like feedback loops, kill criteria, scale, compounding, randomness, and regression to the mean to show how they shape real-world outcomes. He'll also share practical frameworks for improving decision-making, managing uncertainty, and positioning your portfolio to benefit from long-term compounding.




IN THIS EPISODE YOU’LL LEARN:


00:00:00 - Intro


00:03:23 - How feedback loops stabilize or reinforce outcomes in investing


00:10:11 - How kill criteria help you make predetermined decisions in a noisy world


00:14:09 - Why the cone of uncertainty is useful for evaluating conviction and position sizing


00:17:33 - How scale changes the behavior, costs, and risks of a growing business


00:25:06 - How algorithms clarify which inputs drive the conclusions you rely on


00:30:20 - How to evaluate a company’s ability to reach critical mass and become self-sustaining


00:35:35 - The hidden forms of compounding that are just as powerful as the visible ones


00:40:02 - Why power laws should influence your portfolio concentration


00:43:12 - How randomness shapes investing outcomes, and how to take advantage of it


00:51:24 - Why regression to the mean matters during periods of strong or weak performance




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




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