About this episode

The episode discusses key life moments to consult a financial advisor and explores financial insecurity among retirees.

On this episode of Simply Money, Bob and Brian break down the key life moments when calling your financial advisor can make—or cost—you thousands. They also tackle a surprising trend: why retirees with millions saved still feel financially insecure, and how shifting from pension-style income to managing a “pile of money” has changed everything. Plus, insights from CIO Andy Stout on how tax-efficient investing strategies like tax loss harvesting and direct indexing can add real after-tax returns, and practical advice on gifting strategies, insurance gaps, and why not having a power of attorney could create major problems for your family.

People in this episode

Hosts: Bob, Brian

Topics covered

• financial advisor
• retirement
• financial insecurity
• tax-efficient investing
• gifting strategies
• insurance gaps

Keywords

• financial advisor
• retirement
• tax loss harvesting
• direct indexing
• gifting strategies
• insurance gaps
• power of attorney

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• The One Thing That Can Wreck Your Retirement—Even With Millions Saved · May 29, 2026 · 39 min
• How to Turn Financial Success Into Personal Freedom · May 22, 2026 · 38 min

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