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

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

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: HardBlock Human Rights Foundation Plus500 Shopify Netsuite Vanta Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

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TIP785: My Reflections on Money, Life, and Happiness w/ Stig Brodersen

TIP785: My Reflections on Money, Life, and Happiness w/ Stig Brodersen

In this episode, Stig Brodersen shares personal reflections on money, life, and happiness. He explores how money magnifies who we already are, why lifestyle creep can quietly erode happiness, and how ...

18 Tammi 59min

TIP784: History's Biggest Market Bubbles w/ Clay Finck

TIP784: History's Biggest Market Bubbles w/ Clay Finck

In this episode, Clay reviews Devil Take the Hindmost by Edward Chancellor and explores three of the most infamous market bubbles in financial history: the South Sea Bubble of 1720, the Railway Mania ...

16 Tammi 1h 2min

BTC257: Bitcoin Mastermind Q1 2026 w/ Jeff Ross, Joe Carlasare, and American HODL (Bitcoin Podcast)

BTC257: Bitcoin Mastermind Q1 2026 w/ Jeff Ross, Joe Carlasare, and American HODL (Bitcoin Podcast)

The Bitcoin mastermind group explores geopolitical tensions, including a potential U.S. response to Taiwan's defense and Venezuela’s strategic oil reserves. They analyze the revolutionary impact of AI...

14 Tammi 1h 20min

TIP783: What the Market Missed: Prem Watsa and One of the Greatest Records in Business w/ Kyle Grieve

TIP783: What the Market Missed: Prem Watsa and One of the Greatest Records in Business w/ Kyle Grieve

Kyle Grieve breaks down how Prem Watsa and Fairfax Financial compounded for decades through disciplined value investing, insurance float, and resilient capital allocation. IN THIS EPISODE YOU’LL LEA...

11 Tammi 1h 8min

TIP782: The Search for Mispriced Stocks w/ Clay Finck

TIP782: The Search for Mispriced Stocks w/ Clay Finck

In this episode, Clay reviews the book Hidden Investment Treasures by Daniel Gladiš and explores how the rise of passive investing has created growing inefficiencies in today’s market. IN THIS EPIS...

9 Tammi 1h 1min

TECH012: Monthly Tech Roundup – Data Centers in Space, AI5 Chip, Tesla vs. Waymo w/ Seb Bunney (Tech Podcast)

TECH012: Monthly Tech Roundup – Data Centers in Space, AI5 Chip, Tesla vs. Waymo w/ Seb Bunney (Tech Podcast)

Preston and Seb unpack AI’s implications for safety, governance, and economics. They debate AGI risks, corporate centralization, Bitcoin's regulatory role, and Elon Musk’s ventures in space and autono...

7 Tammi 1h 10min

TIP781: My Portfolio & Current Market Conditions w/ Clay Finck & Stig Brodersen

TIP781: My Portfolio & Current Market Conditions w/ Clay Finck & Stig Brodersen

In this episode, Stig Brodersen sits down with Clay Finck to reflect on Clay’s portfolio decisions, investment philosophy, and personal evolution as an investor. Clay walks through the rationale behin...

4 Tammi 1h 27min

TIP780: Top Stocks for 2026 w/ Shawn O'Malley, Daniel Mahncke, & Clay Finck

TIP780: Top Stocks for 2026 w/ Shawn O'Malley, Daniel Mahncke, & Clay Finck

Clay is joined by Shawn O’Malley and Daniel Mahncke to share their top stock ideas for 2026. Shawn is pitching Exor N.V. ($EXO), Daniel is pitching Mercado Libre ($MELI), and Clay is pitching Meta ($M...

2 Tammi 1h 32min

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