You're Selling Your Winners Too Soon | Jerry Parker on the Paradox of Trend Following

Video Description

In this episode of Excess Returns, Jerry Parker joins us for a deep dive into the philosophy and practice of trend following. As one of the original Turtle Traders, Jerry shares lessons from Richard Dennis and Bill Eckhardt, explores how trend following has evolved over the decades, and offers timeless wisdom on markets, psychology, and risk management. From his early days in the Turtle Trading program to running Chesapeake Capital today, Jerry explains what it takes to survive and thrive as a systematic trader in an uncertain world. Topics covered: • The origins of the Turtle Trading program and what Jerry learned from Richard Dennis and Bill Eckhardt • How trend following has evolved from short-term to longer-term systems • Why trading psychology is harder than following the rules • The role of discomfort and doing “hard things” in successful investing • The design and diversification of a robust trading universe • Risk management, drawdowns, and letting profits run • Why trend following belongs alongside a 60/40 portfolio • How ETFs are expanding access to managed futures strategies • Incorporating crypto and new markets into trend following systems • The internal truths of trend following and why smooth returns can be dangerous Timestamps: 00:00 Trading should be hard 02:00 The origins of the Turtle Trading program 08:00 Evolution of trend following systems 12:00 The psychology of following rules 16:00 The famous Turtle Trader true/false test 20:00 Could the Turtle program work today? 23:00 Building a diversified trading universe 28:00 Risk management and position sizing 32:00 How trend following complements 60/40 portfolios 38:00 Managed futures, stocks, and diversification 41:00 The rise of trend-following ETFs 45:00 Incorporating crypto and futures 48:00 Where the strongest trends are now 52:00 AI and systematic investing 53:30 The internal truths of trend following 56:00 The belief Jerry holds that most investors would disagree with