Position sizing and guardrails

This discussion took place live on March 19th, 2026, on the MicroCapClub Community. Join MicroCapClub and unlock the ability to listen and participate live in these discussions - https://microcapclub.com/#join 

In this insightful interview, co-authors Lee Freeman-Shor and Clare Flynn Levy talk about their new book, Stock Market Maestros and the winning habits, strategies, and mindsets of the world's best investors. They explore how data analytics, behavioral metrics, and disciplined processes can distinguish skill from luck among top fund managers, offering practical tools and frameworks to improve investment performance. 

Useful Links

Lee’s LinkedIn - https://www.linkedin.com/in/l-f-s/ 

Clare’s LinkedIn - https://www.linkedin.com/in/clareflynnlevy/ 

Stock Market Maestros (not sponsored) - https://www.amazon.com/dp/1804091464/?bestFormat=true&k=stock%20market%20maestros%20lee%20freeman-shor%2C%20clare%20flynn%20levy&ref_=nb_sb_ss_w_scx-ent-bk-ww_k1_1_17_de&crid=2C68NH42ZH57K&sprefix=stock%20market%20maes 

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✉️ David’s X (Twitter) -https://x.com/Valuehunte

Chapters

00:00 Introduction and Backgrounds

12:53 Luck vs. Skill in Investing

26:17 Understanding the Behavioral Alpha Score

37:03 The Emotional Challenge of Cutting Losses

37:30 The Importance of Running Winners

38:37 Strategies for Selling: The 15-Month Rule

39:50 Decision-Making: Should I Stay or Should I Go?

43:06 Position Sizing: The Key to Managing Losses

47:53 John Barr: The Lumberjack Investor

55:21 Guardrails for Investment Decisions

01:05:24 Measuring Skill vs. Luck in Fund Management

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