Position Sizing and Kelly Principles

Buy Toby's Bookhttps://amzn.to/478SMBfIn this episode of Excess Returns, we sit down with Tobias Carlisle, founder and portfolio manager at the Acquirers Fund, and author of the new book “Soldier of Fortune: Warren Buffett’s Sun Tzu and the Ancient Art of Risk Taking.” Tobias joins Matt Zeigler and Bogumil Baranowski to explore how timeless strategic principles from The Art of War apply to investing and how Warren Buffett embodies many of those ideas—from invincibility and victory without conflict to the disciplined avoidance of ruin. The conversation connects Buffett’s real-world decisions—from Apple to General Re to Japan’s trading houses—to broader lessons on temperament, risk, and wisdom in markets.

Main topics covered:
• The three key ideas from The Art of War that define Buffett’s approach: invincibility, victory without conflict, and unassailable strength
• Why Buffett’s General Re acquisition was a misunderstood masterstroke in defensive investing
• How Buffett achieved “victory without conflict” through his massive Apple investment
• The principle of via negativa — succeeding by avoiding mistakes and ruin
• Temperament vs. intellect and the psychology of avoiding self-defeat
• Circle of competence and why simplicity often beats complexity
• Sins of omission vs. sins of commission in investing decisions
• How Buffett applies wu wei (effortless action) through patience and alignment with natural forces
• Lessons from Buffett’s Japanese trading house investments and moral law in business
• The role of reputation, intuition (coup d’œil), and character in long-term investing
• Charlie Munger’s blueprint and the strategic architecture of Berkshire Hathaway

Timestamps:
00:00 Introduction and overview of Tobias Carlisle’s key ideas
02:00 Applying Sun Tzu’s “invincibility, victory without conflict, and unassailable strength” to Buffett
06:00 The General Re acquisition as a defensive masterpiece
12:00 Victory without conflict — Buffett’s Apple investment
19:00 The principle of via negativa and avoiding ruin
22:00 Survival, temperament, and controlling emotion in investing
25:00 Circle of competence and the power of simplicity
28:00 Sins of omission vs. sins of commission
32:00 Temperament, intellect, and avoiding self-defeat
40:00 Wu wei and investing with effortless alignment
49:00 Position sizing, concentration, and the Kelly Criterion
50:00 Buffett’s investments in Japan’s trading houses
56:00 Reputation, intuition, and the power of pattern recognition
61:00 Charlie Munger’s blueprint and Buffett’s strategic genius
64:00 Closing thoughts and where to find Tobias online