In the Company of Mavericks

Simple But Not Easy

– The Investment Wisdom of Richard Oldfield

Richard Oldfield, Founder of Oldfield Partners and author of Simple But Not Easy. 

We discuss the psychology of value investing, the structural flaws of modern asset management, and the challenges of navigating the bifurcated markets of the mid-2020s.

Episode Overview

In this episode, veteran investor Richard Oldfield debunks myths about the finance industry, arguing that successful investing is "simple but not easy." Drawing on decades of experience—from the 1970s inflation era to the AI boom of 2025—Oldfield explains why value investing is a character trait rather than a learned skill, why "doing nothing" is often the best strategy in a crisis, and why investors should treat the stock market like a casino where the odds vary wildly depending on which "table" you sit at.

Key Takeaways

Value Investing is In the Blood. Oldfield argues that true value investors are born, not made. It requires a contrarian temperament that naturally gravitates toward unloved assets—a trait that is "simple" to understand but psychologically challenging ("not easy") to execute.

Growth vs. Value. Oldfield believes value provides a "margin of safety" that prevents the ground from opening up beneath you, as it does with growth stocks. He discusses his view of an exciting future for value versus growth. 

Index Hugging. Oldfield is a fierce critic of large asset management firms, arguing they inevitably drift toward mediocrity and "index hugging" (mimicking the market to avoid being fired). He advocates small, independent firms that can maintain "distance" from the noise of Wall Street and the City, enabling independent thought.

A Checklist for Selecting Managers: When choosing a fund manager, Oldfield warns against relying on past performance, calling it a "trap". 

Brought to you by Progressive Equity.