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) – The "Tax Guy" Confusion: Can Financial Planners File Your Taxes?

(02:30) – Rear-View vs. Windshield: Defining Tax Prep vs. Tax Planning

(05:10) – The Core Conflict: Saving Taxes Now vs. Saving Over a Lifetime

(06:15) – The "Gap" Story: When the CPA Doesn't Have the Investment Data

(08:00) – The Hidden Value: Why Your Advisor Must Talk to Your CPA Before Dec 31st

(09:40) – Removing the "Brick in Your Backpack": The Value of Delegation

(10:20) – Teaser for Part 2: Who Should You Hire? (CPA vs. EA vs. DIY)

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