Episodes

If you have a specific subject on your mind, you can use our complete episode index, organized by topic, to find the conversation you're looking for.

Working With A Financial Professional Garrett Crawford, CFP® Working With A Financial Professional Garrett Crawford, CFP®

Why April 16th is Opening Day of Tax Planning: Using Your 1040 as a Roadmap

Episode 30 of Retirement Tax Matters reframes the April 15th filing deadline as the Opening Day for a retiree’s 2026 tax planning strategy. For high-net-worth retirees and their families in the $2M–$8M range, Garrett Crawford, CFP® explains why the tax return is not a historical receipt but a roadmap that leads the upcoming year’s proactive planning .

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Working With A Financial Professional Garrett Crawford, CFP® Working With A Financial Professional Garrett Crawford, CFP®

The Tax Preparer Referral Conversation For High-Net-Worth Retirees

Episode 21 of Retirement Tax Matters is Part 2 of our series exploring the shift high-net-worth retirees face when moving from DIY tax filing to using a professional tax preparer. Garrett Crawford, CFP® provides an anecdotal look at the 2026 pricing landscape and how to set the right expectations for your tax team.

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Working With A Financial Professional Garrett Crawford, CFP® Working With A Financial Professional Garrett Crawford, CFP®

The #1 Financial Mistake HNW Retirees Make

In Episode 6 of Retirement Tax Matters, we reveal what we believe is the #1 mistake most high-net-worth retirees make: treating your tax return as a once-a-year, historical document instead of a forward-looking tool to guide their investment and long-term financial plan. This podcast conversation explores why this reactive approach causes retirees to miss out on valuable, unused tax bracket space each year.

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