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

High-net-worth retirees often reach a point where DIY tax software like TurboTax no longer offers the peace of mind their $2M–$8M portfolio requires. In this episode we pull back the curtain on the referral conversation we have with clients and prospects.

We discuss the increasing prices of tax preparer professionals and the shift that many retirees make from saving money to buying freedom, and why your tax preparer and financial planner must be on the same page to avoid tax inefficiencies.

Resources:

Year-End Tax Planning Checklist for HNW Retirees

Timestamps:

(00:00) – Intro

(01:20) – Mindset Shift

(06:45) – The Cost of Tax Prep

(11:01) – Spectrum of Price

(15:55) – What does more expensive tax prep get me?

(18:00) – Expectations are Key

(24:12) – Conclusions

Disclosures Direct Link:

www.retirementtaxmatters.com/disclosures

Are you tired of playing the middle man between your CPA and your financial planner? (Or all the roles yourself!)

For many high-net-worth retirees, tax season feels like a burden not because of the cost, but because of the coordination. You have a CPA looking in the rear-view mirror to file your forms, and a financial planner already looking into the new year to strategize your future. But if they aren't talking to each other, you are the one stuck in the middle carrying the weight of complex decisions.

In Episode 20, Garrett and Adam kick off a special two-part series on building your ideal tax team. They break down the critical difference between Tax Preparation (compliance) and Tax Planning (strategy) and explain why relying on just one often leads to missed opportunities .

This episode is about relieving the pressure, buying back your mental RAM and developing our thesis that there is space at the tax table for you, your tax preparer, and your financial planner.

Key Topics Discussed:

(00:00) – Introduction: Kicking Off the 2-Part Tax Team Series

(01:45) – Tax Prep vs Tax Planning

(06:45) – Short Term vs Long Term Efficiency

(09:20) – Why Financial Planners are best for Planning

(12:20) – Contribution Decisions

(17:10) – Lighten Your Load

(18:05) – Conclusion

Resources:

Disclosures