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

With the release of new IRS guidance on Trump Accounts (Section 530A), the landscape for gifting to grandchildren hasn't just gotten bigger—it’s gotten better.

For years, high-net-worth grandparents have felt forced to choose between the educational tax benefits of a 529 Plan and the flexibility they actually want. In this episode, Adam and Garrett explain all these options finally allows you to align your wealth with your values without compromise.

We move past the headlines about the government's $1,000 seed match to build a framework for your giving to your next generation:

• For Education: Why the 529 Plan (with its new $35,000 Roth rollover buffer) is still best account for those that are education-oriented.

• For Flexibility: How the taxable Custodial Account (UTMA) may allow your grandchildren to pay for a wedding, first home, or maybe start their own business—and enjoy seeing your grandchild use it during your lifetime.

• For Retirement: How the new Trump Account removes the earned income requirement, allowing you to jumpstart a tax-deferred retirement nest egg for a newborn starting at day one.

Listen in to learn how to structure a giving plan that allows you to give to every grandchild equitably while honoring their unique path in life.

Key Topics Discussed:

(00:00) – Intro

(01:35) – 30,000 Foot View

(05:45) – Trump Accounts

(10:06) – No Earned Income Needed

(13:12) – The Roth Conversion Strategy

(16:46) – Trump Accounts vs. 529 Plans

(20:16) – Custodial Accounts

(22:33) – Conclusion

(26:04) – Outro

Links:

Disclosures

Just like shedding holiday weight, your portfolio might need to go on a diet in the New Year—a tax diet.

In this Season One finale of Retirement Tax Matters, Adam and Garrett discuss the concept of Tax Drag and how it can silently erodes the returns of high-net-worth retirees. We dive into the specific strategy of Asset Location (not to be confused with Asset Allocation) as a primary method for reducing this drag.

We explore why holding bonds in your Traditional IRA and growth stocks in your Roth IRA may be an efficient move you could make in 2026. Join us for this lighthearted holiday special as we ring in the New Year with smarter tax planning.

Key Topics:

• What is "Tax Drag" and how does it hurt your returns?

• The difference between Asset Allocation and Asset Location.

• Why High-Net-Worth retirees need to be careful with taxable brokerage accounts.

Timestamps

(00:00) - Intro

(01:15) - New Year's Resolutions

(02:30) - Reducing Tax Drag in 2026

(05:50) - Asset Location

(07:39) - What to do in 2026

(09:50) - Tax Return Driven Financial Planning for HNW Retirees

(10:10) - Outro

(10:44) - Disclosure

Merry Christmas from the team at Retirement Tax Matters!In this special holiday episode, Garrett Crawford, CFP® and Adam Reed step away from the technical world of tax brackets, RMDs, and Roth Conversions to reflect on the season. They share personal Christmas memories—including the story of how they first met during the holidays—and discuss the deeper why behind financial planning.While we spend most weeks focused on tax efficiency, today we focus on the efficiency of the heart. Garrett and Adam discuss why the happiest retirees they work with are often the most generous and connected, and how the spirit of giving can shape a legacy far more than a portfolio return.We hope you enjoy this lighter, reflective episode. We are grateful for you tuning in this year.

Resources:

• Review our Disclosures

• Free Guide: 6 Things High-Net-Worth Retirees Should Know For Retirement:

Timestamps

(00:00) – Merry Christmas from RTM

(01:12) – Garrett’s Favorite Christmas Memories

(04:18) – Adam’s Fender Stratocaster Story

(06:15) – The Role of Generosity in Retirement

(10:02) – Generosity and Connectivity: Two key ingredients in Retirement

(12:22) – Merry Christmas & Luke 2:10

Episode 16 of Retirement Tax Matters tackles the financial psychology of tax aversion—the emotional resistance high-net-worth retirees often feel toward paying taxes, even when it might be the most strategic move. We explore why successful savers, who built wealth by minimizing costs, often struggle to execute strategies like Roth conversions or selling highly appreciated stock because they view paying tax dollars as a loss of capital. | Disclosures

(00:00) Intro

(00:35) Financial Psychology

(02:10) Tax Aversion

(06:30) Personal Experience with Views on Tax

(10:30) Taxes in Non Qualified Accounts

(15:34) Outro

(16:17 ) Disclosure

Resources:

• Join the Weekly Newsletter: Get these tax strategies delivered to your inbox every Thursday: https://www.retirementtaxmatters.com

Is your retirement income triggering an extra 3.8% surtax?

The Net Investment Income Tax (NIIT) is a stealth tax that catches many high-net-worth retirees by surprise. Because its income thresholds haven't been adjusted for inflation since 2013, more retirees are tripping over this wire every year.

In this episode, Garrett and Adam demystify the NIIT. They break down exactly how the "lesser of" calculation works, why your Roth conversions might be inadvertently triggering this penalty, and why you shouldn't necessarily let a 3.8% tax wag the dog of your entire financial plan.

Key Topics Covered:

00:00 Intro01:08 Net Investment Income Tax (NIIT)03:15 What is it?05:01 How it works?07:05 Examples08:57 A Growing Problem11:42 NIIT and Roth conversions14:45 Scared of NIIT?18:25 Outro19:15 NEWSLETTER19:58 Disclosure

Resources:

• Join the Weekly Newsletter: Get these tax strategies delivered to your inbox every Thursday: https://www.retirementtaxmatters.com

Disclaimer:The information provided in this episode is for educational purposes only and does not constitute specific tax, legal, or investment advice. Garrett Crawford and Adam Reed are not promoting any specific security. Please consult with a qualified tax professional or financial advisor before making decisions based on your specific situation.