November 30, 2025
TIP773: How Systems and Simple Math Shape Better Investing w/ Kyle Grieve
We Study Billionaires - The Investor’s Podcast NetworkAbout this episode
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. BOOKS AND RESOURCES Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, Kyle, and the other community members. Buy Thinking in Systems here . Buy The Great Mental Models Vol 3: Systems and Mathematics here . Buy Quit here . Listen to my interview with Annie Duke here . Follow Kyle on X and LinkedIn . Related books mentioned in the podcast. Ad-free episodes on our Premium Feed . NEW TO THE SHOW? Get smarter about valuing businesses in just a few minutes each week through our newsletter, The Intrinsic Value Newsletter . Check out our We Study Billionaires Starter Packs . Follow our official social media accounts: X (Twitter) | LinkedIn | Instagram | Facebook | TikTok . Browse through all our episodes (complete with transcripts) here . Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool . Enjoy exclusive perks from our favorite Apps and Services . Learn how to better start, manage, and grow your business with the best business podcasts . SPONSORS Support our free podcast by supporting our sponsors : Simple Mining Human Rights Foundation Unchained Onramp HardBlock Amazon Ads reMarkable Alexa+ Linkedin Talent Solutions Public.com Vanta Netsuite Shopify Abundant Mines Horizon Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm