Retirement Tax Matters | Advanced Tax Planning for High-Net-Worth Retirees

If you have decided that 2026 is the year to execute a large Roth conversion, you might be wondering about the mechanics of the tax bill. In Episode 22, Garrett Crawford, CFP® professional, and Adam Reed break down the three primary ways to pay the IRS: the simple way, the efficient way, and the strategic way. We explain why high-net-worth retirees with assets between $2M and $8M should typically avoid federal withholding to keep their tax-free growth engine at full capacity.Free Resource for High-Net-Worth Retirees:Year-End Tax Planning Checklist for HNW RetireesTimestamps:(00:00) - Intro(01:30) - Roth Conversions How To(03:50) -Withholding vs Estimated Payment(08:50) - 59 1/2 Penalty(09:45) - Utilize the Brokerage Account(17:05) - Concerns with Estimated Payments(22:15) - Conclusion(24:46) - OutroDisclosures:www.retirementtaxmatters.com/disclosures

Show Notes

If you have decided that 2026 is the year to execute a large Roth conversion, you might be wondering about the mechanics of the tax bill. In Episode 22, Garrett Crawford, CFP® professional, and Adam Reed break down the three primary ways to pay the IRS: the simple way, the efficient way, and the strategic way. We explain why high-net-worth retirees with assets between $2M and $8M should typically avoid federal withholding to keep their tax-free growth engine at full capacity.


Free Resource for High-Net-Worth Retirees:

Year-End Tax Planning Checklist for HNW Retirees


Timestamps:

(00:00) - Intro

(01:30) - Roth Conversions How To

(03:50) -Withholding vs Estimated Payment

(08:50) - 59 1/2 Penalty

(09:45) - Utilize the Brokerage Account

(17:05) - Concerns with Estimated Payments

(22:15) - Conclusion

(24:46) - Outro


Disclosures:

www.retirementtaxmatters.com/disclosures

What is Retirement Tax Matters | Advanced Tax Planning for High-Net-Worth Retirees?

An educational podcast from financial advisors Garrett Crawford, CFP® and Adam Reed, dedicated to helping retirees between $2M-$8M with tax-return driven financial planning. At this level of wealth an integrated strategy for your tax return, investments, and long-term goals is critical. We explore advanced topics like Roth conversions, RMDs, and charitable giving to help you ensure your family remains your biggest beneficiary.