Why More Money Doesn’t Always Mean More Security

Why More Money Doesn’t Always Mean More Security

August 28, 2026 · 38 min · Episode 360

About this episode

Bob and Brian discuss the complexities of financial security, tax implications, and retirement planning.

On this episode of Simply Money, Bob and Brian explain why having more money doesn’t always mean feeling more financially secure, reveal the overlooked portfolio number that could trigger a major tax bill, and discuss why some retirees may be waiting too long to enjoy the wealth they’ve built. Plus, how to navigate wealth differences with friends, plan for valuable collectibles, and recognize three phrases that should immediately put you on alert for a scam.

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Hosts: Bob, Brian

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Organizations: Simply Money, Allworth Financial

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