When Aggressive Roth Conversions Make Sense

Today, I'm speaking with David McKnight. David is a best-selling author, world-renowned tax strategist, and financial educator who challenges some of the most popular (and misleading) retirement gurus and influencers in the financial advice space. He's also a great friend, and beloved guest on the show and I'm excited to welcome him back for a 3rd time on the podcast.

David is well known as the author of The Power of Zero which was made into a full-length documentary film. In his latest book, The Guru Gap, he exposes why one-size-fits-all financial guidance from so-called experts often leaves retirees underprepared and overexposed to risk.

We discussed the psychological appeal of "guru" advice and how to identify when those blanket statements—like "annuities are bad" or "the 4% rule always works,"—do more harm than good. One of the things that I love about David is that he shares math-based insights into retirement income planning. We're talking about the true cost of longevity risk, and why annuities can often create more liquidity and peace of mind than traditional withdrawal strategies.

David also shares his perspective on the newly extended tax cuts, how to time Roth conversions in light of the One Big Beautiful Bill, and the three critical questions everyone needs to answer before moving money from tax-deferred to tax-free accounts.

Whether you're skeptical about annuities, curious about LIRPs, or confused by conflicting advice online, this episode will help you cut through the noise and design a retirement plan that's truly tailored to you—not to the masses.

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In this podcast interview, you'll learn:

• Why "one-size-fits-all" financial advice can be dangerous in retirement planning.
• The psychological reason Americans follow gurus—and how it can derail your goals.
• The real math behind annuities, the 4% rule, and the illusion of liquidity.
• How life insurance can serve as a volatility buffer and long-term care resource.
• The truth about Roth conversions and the importance of your "drop-dead date."
• What the new One Big Beautiful Bill means for future tax rates.
• Why simplicity—not complexity—is the hallmark of truly successful investors.

Show Notes: HowardBailey.com/532

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