In this episode, we kick off our book project, The Most Important Investing Lesson: What the World’s Best Investors Would Teach You, with a deep dive into the ideas of Michael Mauboussin. We explore his most enduring lessons—concepts that have reshaped how we think about investing, decision making, and life. From base rates to expectations investing, we unpack how Mauboussin’s frameworks can help investors build better models of the world and make more rational, probabilistic decisions.

Main topics covered:

• Why base rates are the most underused yet powerful tool in investing and life

• How to apply expectations investing and reverse engineer stock prices

• Why multiples are not valuation and how to earn the right to use shortcuts

• Understanding the paradox of skill and why luck matters more when everyone is good

• Lessons investors can apply across fields like business, sports, and personal decision making

• How humility, reference classes, and feedback loops improve judgment

• Reflections on learning, writing, and how AI tools are changing the creative process