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:
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:
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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.
Episode 14 of Retirement Tax Matters explores the critical difference between being sold an insurance policy and actively engaging in comprehensive insurance planning, specifically tailored for high-net-worth retirees. We discuss why simply buying a product from an agent can leave you with policies you don't understand, versus working with a financial planner who integrates insurance into your broader tax and legacy goals. The conversation covers when life insurance is still necessary (such as for estate tax planning or special needs), why many retirees might not need it, and the importance of conducting a full inventory of your existing policies to identify redundancy. We also introduce advanced strategies like 1035 exchanges to repurpose old, inefficient policies into better-suited products like long-term care coverage. Finally, we highlight the often-overlooked necessity of an umbrella policy for asset protection and discuss how partially self-insuring risk can sometimes be the smartest move for HNW families. | Disclosures
Episode 12 of Retirement Tax Matters provides a financial planner's 101-level orientation to Medicare, breaking down the alphabet soup of Parts A (Hospital), B (Medical), and D (Drug). We explain the general concepts and common paths retirees consider, such as using a Medicare Supplement to create more predictable fixed monthly costs versus the 20% coinsurance. From a financial planning perspective, we then detail the significant impact of IRMAA (Income-Related Monthly Adjustment Amounts), showing how a high income (ex. $325,000) can trigger premium surcharges for married couples. The key insight, however, is that while these fixed Medicare costs are manageable for most HNW Retirees, the real financial risk is the one Medicare does not cover: The cost of Extended Care (Long-Term Care). We call this "Part E" and provide third-party cost projections that show how this risk, which can exceed $15,000/month in the future, is the more critical component of your long-term financial plan. | Disclosures
00:00 Intro
02:50 Disclaimers
06:10 Part A and B Overview
10:00 Supplement and Advantage Plan
12:29 Part D
13:42 Financial Planning with Medicare
15:50 Costs
22:00 Part E
24:30 Cost of Long Term Care
29:25 Conclusion
30:25 Outro
Disclaimer: The information provided in this video is for general informational and educational purposes only and does not constitute specific Medicare or insurance advice. All examples of costs and premiums are illustrative. When you are ready to enroll in Medicare, we strongly recommend you speak with a qualified, independent, and AHIP-certified Medicare specialist who can provide specific recommendations based on your personal health situation, prescription drug needs, and up-to-date state-specific plan rules.
Episode 12 of Retirement Tax Matters focuses on Social Security optimization for Hign-Net-Worth retirees, framing it as a critical spousal protection and legacy tool rather than a simple break-even calculation. We explain why the higher-earning spouse delaying their benefit to age 70 is often the most critical decision, as it maximizes the guaranteed, inflation-adjusted survivor benefit for their partner. We then cover the key 2026 updates, including the 2.8% Cost of Living Adjustment (COLA) and the new maximum monthly benefit of $4,152 for a worker filing at Full Retirement Age. We also discuss how the Social Security payroll tax wage base has increased to $184,500. Finally, we connect this high-benefit strategy to your long-term tax plan, discussing how this large, guaranteed income stream interacts with RMDs and can contribute to the surviving spouse tax shock making proactive planning essential. | Disclosures
In Episode 11 of Retirement Tax Matters we discuss cash dilemmas for high-net-worth retirees: finding the right balance between necessary liquidity and optimizing your returns. While having readily accessible cash for emergencies is important, we explore the potential drawbacks of holding excessive amounts in multiple low-yielding bank accounts, which can add unnecessary complexity. Discover how recent T+1 settlement changes allow funds in conservative brokerage investments like money markets (sometimes yielding more) to be accessed typically by the next business day, challenging the need for overly large bank balances. Furthermore, we examine the tax inefficiency of earning substantial bank interest, taxed at high ordinary income rates, compared to potentially investing a portion of that excess cash to prioritize lower long-term capital gains rates (15-20%). This conversation provides a framework for simplifying your overall cash strategy, balancing peace of mind with potential growth and tax efficiency. | Disclosures
In Episode 10 of Retirement Tax Matters we tackle one of the most significant change to legacy planning in decades: the elimination of the Stretch IRA by the SECURE Act. Although this legislation took effect in 2020, its importance may have been easily missed in our fast-moving world, and new retirees are being reminded of its consequences. The new law replaces the old lifetime stretch RMD provision with a strict 10-year payout rule, forcing most non-spouse beneficiaries to withdraw an entire inherited Traditional IRA—and pay the associated taxes—within a decade. We break down how a multi-million dollar IRA, which was once a straightforward inheritance, could possibly become a complex, decade-long tax challenge for your children during their own peak earning years. The conversation then pivots to the primary solution: proactive Roth conversions, which allow you to pay the taxes now and leave a simple, tax-free inheritance. We also explore the powerful non-financial benefits of this strategy, such as providing your heirs with flexibility and peace of mind, which many of our clients find to be more valuable than purely optimizing for the lowest possible tax bill. Ultimately, we discuss how to frame this decision not just with a calculator, but by aligning your plan with your deepest values and goals for your family. | Disclosures
In Episode 9 of Retirement Tax Matters we delve into the growing challenge of Required Minimum Distributions (RMDs) for high-net-worth retirees with substantial Traditional IRA balances, particularly those in the $2M-$8M range. We establish that a six-figure RMD (beginning at just $2.65 million in an IRA for a 73-year-old in 2025) is a realistic scenario that continues to grow, often exceeding actual spending needs. Our conversation centers on the core dilemma: taking out money you don't need, which becomes fully taxable and can push you into higher tax brackets. | Disclosures
In Episode 8 of Retirement Tax Matters we dive into optimizing your charitable giving, revealing why writing a check from you checking account is likely costing high-net-worth retirees significant tax dollars. You'll learn about Qualified Charitable Distributions (QCDs) from Traditional IRAs, which allow you to donate up to $108,000 tax-free directly from your IRA (bypassing RMD taxes), versus utilizing Donor-Advised Funds (DAFs) for highly appreciated assets like stocks. We illustrate how donating appreciated securities to a DAF can help you avoid up to a 23.8% capital gains tax on your gains, simultaneously providing a charitable deduction and offering flexible timing for your charitable giving. Discover how to strategically use DAFs to create additional Roth conversion space, potentially dropping from a 32% to a 24% tax bracket in a given year, and even leverage DAFs for anonymous giving. We also break down key updates from OBBBA starting in 2026, including the 0.5% AGI floor for itemized deductions and the new $1,000 Individual / $2,000 Married Filing Jointly deduction for non-itemizers, ensuring your giving strategy remains tax-efficient in 2026 and beyond. This is essential listening for maximizing impact and minimizing your tax burden. | Disclosure
In Episode 7, Garrett Crawford, CFP®, and Adam Reed tackle a critical HNW retirement challenge: the tax shock a surviving spouse can face.
It's possible for a married couple's ~24% tax bracket can jump to 35% for a single survivor due to filing changes, growing RMDs & higher Medicare premiums. This creates an increased financial burden during an already difficult time.
Learn how proactive Roth conversions in your 60s or 70s could strategically lower lifetime tax burdens, protect a surviving spouse, and create a tax-efficient legacy. | Disclosure
Explore All Our Resources: https://www.retirementtaxmatters.com/links
Disclosure
The #1 mistake High-Net-Worth retirees make is treating their tax return as a rearview mirror. In this crucial episode of Retirement Tax Matters, we dive deep into the costly disconnect between your tax return, investment plan, and long-term legacy goals.
Discover:
Why overlooking unused tax bracket space each year is costing you significant wealth.
How proactive, intra-year tax projections are the key to unlocking powerful strategies like Roth conversions.
The critical questions to ask your financial advisor about your tax return to ensure your entire financial plan is aligned and working for you.
Don't let valuable opportunities slip away.
🔗 Get our FREE High-Net-Worth Retirement Checklist:
https://www.retirementtaxmatters.com/hnw-checklist
In Episode 5 of Retirement Tax Matters, we define the Golden Window — the critical years of temporary low income after you retire but before RMDs and Social Security begin. For high-net-worth retirees with large pre-tax IRA balances, this is an ideal time to manage what is likely your largest future tax liability. We explore how to leverage this period by executing strategic Roth conversions, transforming a future tax problem into possible lower aggregate lifetime taxes and/or a tax-free legacy for your heirs. Most importantly, we discuss how to balance this powerful strategy with your non-financial life goals by incorporating intra-year tax projections to find the remaining "room" for conversions after you've funded your other spending needs first. | Disclosures
In Episode 4 of Retirement Tax Matters we explore the permanent extension of the higher standard deduction under the new "One Big Beautiful Bill Act" (OBBBA). We'll cover the new 2025 standard deduction amount for married couples ($31,500) and explain how the new law, while beneficial, adds layers of complexity with income-based phase-outs for deductions like the new Enhanced Senior Deduction. Learn why this new tax landscape makes end-of-year projections more critical than ever and how the now-permanent lower tax brackets create a longer "runway" for powerful, long-term Roth conversion strategies. | Disclosures
In Episode 3 of Retirement Tax Matters, we dive into one of the most significant parts of the new "One Big Beautiful Bill Act" (OBBBA): the permanent extension of the lower tax brackets originally established by the Tax Cut and Jobs Act of 2017. We’ll provide a clear refresher on how today's tax rates (12%, 22%, 24%) are historically low compared to prior years and break down a common misunderstanding of how marginal tax brackets work. Most importantly, we discuss what this newfound "runway" means for HNW retirees and how a long-term, strategic approach to Roth conversions can now be even more powerful for managing your lifetime tax bill and creating a simpler legacy for your beneficiaries. | Disclosures
The passage of the recent tax legislation, One Big Beautiful Bill Act (OBBBA), has created significant confusion around how Social Security will be taxed. Many retirees are asking if their benefits will now be tax-free. In this episode, Garrett Crawford breaks down the reality of the new law, explaining that the primary change is not to Social Security taxation itself, but the introduction of a new, substantial "Senior Deduction." We'll cover who qualifies for this deduction, the specific income phase-outs that could affect HNW retirees, and the critical planning dilemma it creates when considering strategic Roth conversions. | Disclosures
In our inaugural episode, Garrett Crawford, CFP® and Adam Reed introduce the mission behind Retirement Tax Matters. Discover our focus on providing advanced tax planning strategies for high-net-worth retirees and learn what to expect from future conversations. | Disclosures