In this episode, Phillip "Felipe" Toews, author of The Behavioral Portfolio and a long-time advocate for risk-aware investing, joins Jim Worden and Paisley Nardini for a deep, historically grounded conversation on why conventional portfolio construction often fails investors when it matters most. Drawing on decades of market history, Phillip explains how long-duration bear markets, not short-term volatility, create the greatest behavioral and financial risk for investors and advisors alike.

From the Great Depression to multi-decade bond bear markets, Phillip challenges recency bias, questions the foundations of the 60/40 portfolio, and outlines why advisors must think like chief risk officers first. The discussion explores behavioral finance, portfolio design, hedged equity strategies, adaptive fixed income, and why proactive communication, not reactive reassurance is critical to long-term client success.

What you’ll learn

• Why the 60/40 portfolio is a historical accident not a true design framework

• How long-duration bear markets reshape investor behavior and decision-making

• Why recency bias causes advisors and clients to underestimate real risk

• How rebalancing can increase drawdowns in severe market regimes

• What “left-tail risk” really means for real-world portfolios

• Why advisors must proactively discuss worst-case scenarios before they happen

• How hedged equity strategies can preserve upside while limiting catastrophic loss

• Why behavioral risk often matters more than market risk

Chapters

03:00 — Phillip's journey: from Kansas to asset management and risk mitigation

08:00 — Why investor timing destroys returns, even in good strategies

13:00 — The Great Depression, bond bear markets, and what history really shows

19:00 — Why the 60/40 portfolio fails during long-duration drawdowns

25:00 — Rebalancing myths and behavioral breakdowns in severe markets

31:00 — Rethinking portfolio design: cutting the left tail without killing upside

37:00 — Hedged equity, adaptive fixed income, and managing uncertainty

43:00 — Why advisors must act as chief risk officers

49:00 — Communicating risk before markets fall, not after

Guest

Phillip "Filipe" Toews, Founder & CEO, Toews Asset Management and Author of The Behavioral Portfolio

Hosts

Jim Worden, Chief Investment Officer, WCG

Paisley Nardini, Portfolio Manager, Simplify

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