How My Views on Roth Conversions Evolved

Today, I’m speaking with Edward McQuarrie. Ed is the Professor Emeritus at Santa Clara University, where he taught in the marketing department for more than three decades before retiring in 2016. After stepping away from teaching, Ed pursued a new passion in researching financial market history and retirement income planning. 

His work has been featured in the Wall Street Journal, MarketWatch, and Barron’s, and he frequently contributes to our Weekend Reading for Retirees series. He was introduced to us by past guest William Bernstein, who insisted Ed would be a must-hear voice on the show.

In this conversation, Ed challenges decades of conventional wisdom around investing. He explains why “stocks for the long run” isn’t always the safest bet, how cherry-picked data can mislead investors, and why separating risk-free assets from growth assets may be more important than diversification alone. Ed also shares the insights from his extensive historical research, covering stock and bond returns going back to the 1700s, and how it relates to retirement planning today.

We also dig into the evolving conversation around Roth conversions, the limitations of relying solely on stocks and bonds, and why tools like TIPS ladders or annuities can help secure baseline retirement income. Ed’s clear-eyed, historically grounded perspective will challenge the assumptions you’ve been taught and help you build a more resilient, reality-based plan for the future.

In this podcast interview, you’ll learn:

• Why “stocks always outperform bonds” is a myth—and what 200 years of history actually reveal.
• The risks of relying on cherry-picked data in financial planning.
• How economic “regimes” shape investment returns across decades and centuries.
• Why risk separation, not just diversification, is key to retirement planning.
• The pros and cons of Roth conversions—and why sometimes doing nothing may be the smartest move.
• How to use TIPS ladders, annuities, and other tools to secure your baseline retirement income.

Show Notes: HowardBailey.com/527

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