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

What Should You Actually Do With a $150K HSA in Retirement?

Garrett Crawford, CFP® and Adam Reed — Wed, 09 Sep 2026 08:14:54 -0400

Episode 51 of Retirement Tax Matters addresses how high-net-worth retirees in the $2M to $8M range should evaluate managing a six-figure Health Savings Account during retirement. Garrett Crawford, CFP® professional and Adam Reed break down the trade-off between saving an HSA for late-in-life tax-free compounding versus spending those funds earlier to pay qualified health expenses. The conversation examines the administrative hassle of maintaining decades of medical receipts, highlighting why trying to over-optimize account mechanics into your 80s can create unnecessary friction for adult children and healthcare powers of attorney.

We have developed a 5-step framework for what tax planning looks like for High-Net-Worth Retirees between $2M-$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients. Request a free resource using this link: https://www.retirementtaxmatters.com/checklist

00:00 Introduction to HSAs in Retirement Planning
01:18 The Shoebox Method vs. Return on Hassle
07:08 Integrating HSAs with Long-Term Care Planning
13:28 IRS Limits for HSA Long-Term Care Premium Payments
15:35 Rules and Pitfalls of Inheriting an HSA
18:20 Itemized Medical Deductions (7.5% AGI) vs. Saving Your HSA

Visit us online at: https://www.retirementtaxmatters.com or https://www.providenceadvisors.com

Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

Social Security Trust Fund Depletion: What It Means for $2M to $8M Retirees

Garrett Crawford, CFP® and Adam Reed — Wed, 02 Sep 2026 08:30:00 -0400

In Episode 50 of Retirement Tax Matters, Garrett Crawford, CFP® professional, and Adam Reed review the latest numbers from the Social Security Trust Fund report and what projected 2032 reserve depletion means for retirees with $2M to $8M portfolios. They break down why ongoing payroll tax collections still cover approximately 78% of scheduled benefits even if reserve funds run out, and why modeling Social Security at zero creates an artificial gap that can lead retirees to trade valuable time by working longer than needed. Garrett also shares his perspective on potential Congressional fixes and explains how an annual tax-return-driven process helps high-net-worth families keep headlines in perspective and protect their multi-year drawdown plan.

Timestamps
00:00 Introduction & Social Security Unease
02:26 Breaking Down the 2025 Social Security Trust Fund Report
05:19 Depletion in 2032 & The 78% Benefit Reality
07:31 Potential Fixes: Tax Hikes vs. Benefit Cuts
08:52 What Social Security Depletion Means for $2M–$8M Retirees
12:57 Why Planning for $0 in Social Security Is a Mistake
14:26 Will Congress Cut Benefits? Predictions & Tax Return-Driven Planning

Visit us online at: https://www.retirementtaxmatters.com
Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

Multi-Year Roth Conversion Planning Explained

Garrett Crawford, CFP® and Adam Reed — Wed, 26 Aug 2026 08:30:00 -0400

Episode 49 of Retirement Tax Matters breaks down why multi-year Roth conversion planning must be treated as an annual process rather than a static five-year document. Garrett and Adam address the common desire among retirees in the $2M to $8M range to establish a fixed conversion schedule, explaining how shifting tax laws, market movements, and income adjustments render long-term predictions unreliable. The show details a repeatable seasonal framework that moves from spring tax return reviews to fall income projections, helping retirees systematically fill lower tax brackets while maintaining flexibility year after year.

(00:00) - Multi-Year Roth Conversions
(02:00) - Escaping the Financial Advisor Bubble
(04:35) - Lump-Sum vs. Annual Conversions
(06:00) - Tax Return Driven Financial Planning & The Year-End Checklist
(08:35) - The Flaw of Static Conversion Numbers
(11:58) - Avoiding IRMAA Surcharges & Net Investment Tax Pitfalls
(12:20) - Small Incremental Changes
(14:20) - Building Your Repeatable Annual Conversion Process

Visit us online at: https://www.retirementtaxmatters.com

Review our disclosures here: https://www.retirementtaxmatters.com/disclosures

Roth vs. Traditional: The Better Inheritance?

Garrett Crawford, CFP® and Adam Reed — Wed, 19 Aug 2026 08:30:00 -0400

Episode 48 of Retirement Tax Matters evaluates the financial trade-offs of inheriting a Roth IRA versus a Traditional pre-tax IRA for high-net-worth retirees in the $2M to $8M range. Garrett and Adam break down why adult children in their peak earning years face compressed 10-year distribution windows under the SECURE Act, making proactive parent-level Roth conversions at lower tax rates a strong consideration for the family balance sheet. The conversation also explores scenarios where leaving pre-tax balances intact makes sense, factoring in state income tax disparities and lifetime giving strategies.

Timestamps:
00:00 Introduction: The Inheritance Conversation
01:43 The National Debt & The Future of Tax Brackets
05:54 Inheritance Strategy: Parents in Lower Tax Brackets Than Kids
10:48 Inheritance Strategy: Parents in Higher Tax Brackets Than Kids
13:59 The Hidden Impact of State Income Taxes
14:55 Garrett's Epiphany: Family Dynamics & Lifetime Giving
21:00 Why Inheriting a Roth IRA is Simpler
22:04 Closing Thoughts & Free Year-End Tax Planning Checklist

Review our disclosures here:
https://www.retirementtaxmatters.com/disclosures

Evaluating NUA for Highly Appreciated Employer Stock In Your 401(k)

Garrett Crawford, CFP® and Adam Reed — Wed, 12 Aug 2026 08:30:00 -0400

Episode 47 of Retirement Tax Matters breaks down Net Unrealized Appreciation (NUA) for employer stock held inside a 401(k) plan. Garrett Crawford, CFP® and Adam Reed explain how transferring appreciated company shares in-kind to a taxable brokerage account allows retirees to pay ordinary income tax on the original cost basis while securing long-term capital gains tax rates on the growth. The episode examines how cost basis ratios dictate whether NUA outperforms a traditional IRA rollover, while outlining rules like single calendar year distributions and trade-offs like single-stock concentration risk.

00:00 Introduction & High-Saver Net Worth Profiles

01:45 What is Net Unrealized Appreciation (NUA)?

04:15 What Accounts & Stock Types Qualify?

05:40 Cost Basis vs. Appreciated Growth Explained

07:10 Example: How NUA Tax Savings Actually Work

08:50 The Calendar Year Rule & 4 Qualifying Events

10:15 Ideal Candidates & The 50/50 Basis Dilemma

13:30 Key NUA Trade-Offs: Step-Up in Basis & Upfront Taxes

15:25 Concentration Risk & Psychological Challenges

17:00 Taking Action: Multi-Year Tax Projections

19:10 Employer Rules & Basis Tracking Gotchas

Visit us online at: https://www.retirementtaxmatters.com

Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

Tax Planning When You Don't Drop Tax Brackets in Retirement

Garrett Crawford, CFP® and Adam Reed — Wed, 05 Aug 2026 08:30:00 -0400

Episode 46 of Retirement Tax Matters addresses the common assumption that retirees always drop into lower tax brackets once they stop working. For savers in the $2M to $8M range, pension income, Social Security, taxable yield, and future required distributions often keep taxable income in the 24% or 32% brackets throughout retirement. Garrett and Adam walk through why converting at the same tax rate can still make sense by protecting a surviving spouse from bracket compression, managing the 10-year SECURE Act rule for adult children, and suppressing age-75 RMDs to avoid Medicare IRMAA surcharges and Net Investment Income Tax. The conversation also outlines scenarios where keeping money in a pre-tax IRA is the better choice, such as planning for charitable gifts, leaving assets to heirs in lower tax brackets, or relocating to a state with no state income tax. Ultimately, by using a tax-return-driven process to project income in the fall, retirees can evaluate their whole balance sheet and decide whether a Roth conversion fits their family's long-term plan before the December 31st deadline.

Request a free resource using this link: https://www.retirementtaxmatters.com/checklist

00:00 Feeling Stuck in High-Net-Worth Tax Brackets
05:22 Reason 1: The Surviving Spouse Tax Trap
06:58 Reason 2: RMDs & SECURE Act 10-Year Rule
08:42 Reason 3: Tax Arbitrage via Brokerage Accounts
09:47 Reason 4: Managing Medicare IRMAA & NIIT Limits
11:34 Reasons to Pump the Brakes on Roth Conversions
17:14 Tax Return-Driven Financial Planning & Strategic Timing

Visit us online at: https://www.retirementtaxmatters.com

Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

How a $534K Income Can Still Leave You in the 12% Ordinary MFJ Tax Bracket

Garrett Crawford, CFP® and Adam Reed — Wed, 29 Jul 2026 08:30:00 -0400

Episode 45 of Retirement Tax Matters walks through a live Holistiplan tax planning case study for a married couple reporting $534,200 in total Adjusted Gross Income who remain inside the 12% ordinary marginal tax bracket. Garrett Crawford, CFP® and Adam Reed demonstrate how $100,000 in Social Security and Pension paired with $400,000 in realized long-term capital gains keeps ordinary income at lower rates. Learn how evaluating cost basis versus realized gains inside taxable brokerage accounts may reveal more room than you think to execute strategic Roth conversions before December 31st.

00:00 Back to the Basics: Tax Return Driven Financial Planning
01:08 Can You Earn $500,000 and Stay in the 12% Tax Bracket?
03:40 Ordinary Income vs. Preferential Capital Gains Brackets
05:27 Case Study: Baseline Income for Tim & Ann
07:08 Scenario 1: Generating $500k Entirely from IRA Distributions
09:07 Scenario 2: $500k Income Utilizing Low-Basis Brokerage Capital Gains
12:15 Scenario 3: Realized Capital Gains vs. Account Cost Basis
15:00 Tactical Roth Conversions & Range Calculator Analysis
17:44 Navigating Medicare IRMAA Tiers & Tax Brackets
20:18 Year-to-Year Tax Minimization vs. Lifetime Tax Liability

Visit us online at: https://www.retirementtaxmatters.com
Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

Year One Reflections + Why Great Retirement Planning Takes a Team

Garrett Crawford, CFP® and Adam Reed — Wed, 22 Jul 2026 08:30:00 -0400

Episode 44 of Retirement Tax Matters marks the one-year anniversary of the podcast, opening with a look behind the scenes at the growth of the community. Garrett and Adam explore how consistently showing up to produce a weekly podcast shares a surprising number of parallels with navigating a successful retirement. The central focus of the conversation highlights how a collaborative team framework is a powerful ingredient that helps high-net-worth retirees balance their financial planning with real-life family goals.

00:00 Welcome & One-Year Anniversary Celebration
01:54 Podcast Growth & Community Milestones
03:12 Parallels Between Podcasting and Financial Planning
04:56 Behind the Scenes: Why We Started the Podcast
06:59 Discovering the Power of Tax-Driven Financial Planning
08:08 Steve Jobs, Teamwork, and Leaving the Echo Chamber
10:43 The Challenges of the Decumulation Phase
13:00 Do You Need to Hire a Financial Advisor?
14:24 Why Your Spouse or Friend is Your Most Important Teammate
17:19 The Value of a Second Opinion
19:07 Final Thoughts & Looking Ahead to Season Two

Visit us online at: https://www.retirementtaxmatters.com

Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

How To Move Appreciated Brokerage Accounts Without Huge Taxes

Garrett Crawford, CFP® and Adam Reed — Wed, 15 Jul 2026 08:30:00 -0400

Episode 43 of Retirement Tax Matters addresses the unique tax challenges and psychological hurdles of managing large, highly appreciated taxable brokerage accounts. For retirees in the $2M–$8M range, holding concentrated stock positions or outdated, expensive mutual funds can feel like wearing financial handcuffs due to the threat of a massive capital gains tax bill. Garrett and Adam break down the all-or-nothing trap, outlining how a structured, multi-year transition plan can help you diversify your portfolio safely without triggering an avoidable single-year tax shock.

00:00 - Introduction & The $2M-$8M Brokerage Account Problem
01:03 - The Psychology of Tax Aversion & Embedded Capital Gains
02:04 - Why Old Mutual Funds are Creating Tax Friction (ETFs vs. Mutual Funds)
05:05 - The "All or Nothing" Trap vs. A Balanced Game Plan
06:22 - The "Nasty Divorce" of Concentrated Stock Positions (Amazon, Apple, Tesla)
08:51 - Understanding the 23.8% Capital Gains Tax & Net Investment Income Tax (NIIT)
10:41 - How Providence Wealth Management Navigates a Multi-Year Transition Plan
12:15 - Forced Mutual Fund Capital Gain Distributions & The Medicare IRMAA Charge
15:00 - Unlocking Your Brokerage Account for Roth Conversions & Major Purchases
16:07 - Retirement Strategy: Why You Need Singles and Doubles, Not Strikeouts
17:28 - Utilizing the Summer for Your Year-End Tax Planning Checklist

Visit us online at: https://www.retirementtaxmatters.com

Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

Why Your 30-Year Retirement Plan Report Feels Underwhelming

Garrett Crawford, CFP® and Adam Reed — Wed, 08 Jul 2026 08:30:00 -0400

Episode 42 of Retirement Tax Matters looks at the difference between a long-term retirement trajectory and proactive annual tax planning. For retirees with portfolios between $2M and $8M, relying entirely on a static 60-page financial report often leaves families feeling unprepared when real-world changes occur. Garrett and Adam discuss how to balance a 30-year vision with tactical adjustments made every fall to manage tax brackets and track Medicare IRMAA limits. Real retirement planning happens in these annual course corrections, ensuring your portfolio stays optimized as your story unfolds.

Timestamps:
00:00 Welcome to Retirement Tax Matters & Summer Catch-Up
01:28 The Trap of the 30-Year Retirement Binder
02:30 Why Retirees Crave a Step-by-Step Plan
03:13 The Evolution (and Failure) of 60-Page Financial Reports
04:51 Long-Term Plans vs. Real-Life Changes
05:51 Balancing the Long-Term Vision with Annual Tax Strategy
06:41 Using Financial Software For Trajectory, Not Exact Predictions
07:44 Tax Return Driven Financial Planning Defined
09:23 The Year-End Tax Planning Checklist & Working with Adam and Garrett
10:47 Real Case Example: Early Retirement, RMDs, and the 24% Bracket
11:34 Navigating Roth Conversions and Medicare IRMAA Limits
13:24 The Disney World Analogy: Staying Flexible on the Road to Retirement
14:48 Final Thoughts: Real Planning Happens in the Annual Adjustments

👉 Visit us online at retirementtaxmatters.com
Disclosure Statement: https://www.retirementtaxmatters.com/disclosures

$6M Retirement Case Study: IRA Drawdown vs Deferring Pension & Social Security to 70

Garrett Crawford, CFP® and Adam Reed — Wed, 01 Jul 2026 09:27:48 -0400

Episode 41 of Retirement Tax Matters reviews a screen-share case study of a married couple at age 63 navigating a $6 million portfolio. With $5 million concentrated in pre-tax traditional IRAs and 401(k) plans alongside $1 million in brokerage and savings accounts, this scenario highlights the critical decision between taking a combined $85,000 pension and Social Security stream immediately or deferring those guaranteed streams until age 70. Delaying the fixed income benefits may allow the couple to utilize the lower tax brackets during their early retirement years to execute a more aggressive drawdown or strategic Roth conversions from their pre-tax retirement accounts.

00:00 Welcome to Retirement Tax Matters & Studio Updates
00:46 What Does Tax Return Driven Financial Planning Actually Look Like?
01:05 Case Study Introduction: Tim & Ann's Retirement Dilemma
03:18 Establishing the Case Assumptions: Assets, Income, and Bracket Goals
04:54 Financial Planning: Calculator vs. Psychology
06:15 Diving into Holistiplan: Analyzing the 2026 Working Year Income
08:18 Understanding Phantom Income: Interest, Ordinary, and Qualified Dividends
11:13 Navigating the 24% Tax Bracket Summary
12:08 Fast-Forwarding to 2028: The Beans and Rice Early Retirement Scenario
14:31 The Six-Figure RMD Trap: Projections at Age 75 and Beyond
16:44 The Strategy: Delaying Fixed Income vs. Drawing Down the Traditional IRA
18:41 Utilizing the Range Calculator & Navigating Medicare IRMAA Penalties
20:36 Modeling a $300,000 Strategic Roth Conversion
23:11 Shifting Perspectives: Younger Accumulators vs. Older Decumulators
24:51 Real-Time Collaboration: Why Financial Planning is Dynamic

Visit us online at: https://www.retirementtaxmatters.com

Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

How Charitable Retirees Neutralize Capital Gains and NIIT with a DAF

Garrett Crawford, CFP® and Adam Reed — Wed, 24 Jun 2026 08:30:00 -0400

Episode 40 of Retirement Tax Matters examines the use of Donor-Advised Funds for high-net-worth retirees evaluating their year-end charitable strategies. Garrett and Adam break down how to properly navigate the 30% adjusted gross income limitation for gifting long-term appreciated securities, allowing families to neutralize capital gains and Net Investment Income Tax surcharges without sacrificing portfolio control.

We have developed a 5 step framework for what tax planning looks like for High-Net-Worth Retirees between $2M-$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients. Request a free resource using this link:

https://www.retirementtaxmatters.com/checklist

Chapters:

(00:00) – Introduction to Donor-Advised Funds (DAFs)

(01:35) – The Year-End Tax Planning Checklist

(02:45) – DAFs vs. Qualified Charitable Distributions (QCDs)

(04:30) – What is a Donor-Advised Fund and How Does it Work?

(05:55) – The Primary Benefits: Value, Capital Gains, and Control

(07:15) – Privacy and Giving Anonymously

(08:45) – Who is a DAF the Best Fit For?

(11:35) – Neutralizing Capital Gains with Cash

(11:50) – Understanding the Net Investment Income Tax (NIIT)

(13:45) – Navigating AGI Limitations & Five-Year Carryovers

(15:15) – How to Set Up and Implement a DAF

(17:05) – The Return on Hassle (ROH) and Platform Fees

(19:00) – Keeping the True Heart Behind Charitable Giving

(20:10) – Summer Projections and Scannable Year-End Planning

Visit us online at:

https://www.retirementtaxmatters.com

Review our required industry disclosures here:

https://www.retirementtaxmatters.com/disclosures

Why Your Stomach and Your Calculator Disagree on Retirement Risk

Garrett Crawford, CFP® and Adam Reed — Wed, 17 Jun 2026 08:30:00 -0400

This episode explores the disconnect between your psychology and the calculator when evaluating portfolio risk capacity in the $2M–$8M range, using recent client inquiries about the SpaceX IPO as a real-world backdrop. Garrett and Adam break down how to segment a retirement portfolio into separate asset buckets based on their purpose, explaining why can make sense to maximize equity growth inside tax-free Roth IRAs while reducing risk inside traditional pre-tax accounts. The discussion outlines how understanding your risk metrics allows you to safely evaluate speculative market opportunities without jeopardizing the retirement lifestyle you envision for your family.

Chapters:

(00:00) - The History of the 1040 Tax Return
(03:23) - The SpaceX IPO and Swinging for the Fences
(05:10) - The Evolution of the Risk Tolerance Questionnaire
(10:05) - Understanding Risk Capacity vs. Risk Tolerance
(14:44) - Earmarking Risk Across Different Asset Buckets
(20:38) - How We Evaluate Client Risk Dynamics
(26:21) - The Zero-Turn Lawnmower Analogy for Portfolio Risk

We have developed a 5-step framework for what tax planning looks like for High-Net-Worth Retirees between $2M–$8M. It walks you through each season of the calendar year and explains how we implement tax-return driven financial planning for our clients. Request a free copy of this resource using this link: https://www.retirementtaxmatters.com/checklist

For comprehensive firm disclosures, please visit our website: https://www.retirementtaxmatters.com/disclosures

Why Gifting Wealth From a $2M–$8M Portfolio May Be Simpler Than You Think | Episode 38

Garrett Crawford, CFP® and Adam Reed — Wed, 10 Jun 2026 08:30:00 -0400

Episode 38 of Retirement Tax Matters examines the common misunderstandings and anxieties high-net-worth parents face when gifting money to adult children. For retirees with a portfolio in the $2M–$8M range, the federal gift tax framework under the One Big Beautiful Bill Act provides an individual lifetime exemption of $15 million, removing the tax penalty from early wealth transfers for the vast majority of affluent families. While the 2026 annual exclusion limit is capped at $19,000 per recipient, some retirees find filing a Form 709 gift tax return with their tax preparer is all that may be required to report the excess transfer and reduce their lifetime exemption footprint.

Free Resource: We have developed a 5-step framework for what tax planning looks like for High-Net-Worth Retirees between $2M–$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients. Request a free resource using this link: https://www.retirementtaxmatters.com/checklist

Review our disclosures at https://www.retirementtaxmatters.com/disclosures

The Two Most Underrated Social Security Features for High-Net-Worth Married Retirees | Episode 37

Garrett Crawford, CFP® and Adam Reed — Wed, 03 Jun 2026 08:30:00 -0400

In this episode, Garrett and Adam explore why high-net-worth married retirees often overlook the risk-reducing power of Social Security by focusing strictly on an investment ROI calculator. Discover how maximizing your baseline benefit maximizes the compounding strength of both the household survivor benefit and annual cost-of-living adjustments to shield your total portfolio from unexpected inflation cycles.

Request a free resource using this link: https://www.retirementtaxmatters.com/checklist

Time Stamps:

(00:00) – Intro & Welcome Back from Vacation

(01:05) – Topic Introduction: Social Security

(01:40) – Garrett's History with Social Security Workshops

(03:05) – Social Security for the $2M to $8M+ High-Net-Worth Crowd

(04:00) – Underrated Feature #1: The Survivor Benefit Rule

(06:25) – Investment ROI vs. Insurance Components

(09:05) – Tying Social Security into Proactive Roth Conversion Planning

(10:50) – Underrated Feature #2: Cost of Living Adjustments

(12:45) – The Historical Blueprint of COLA and Modeling Inflation

(15:00) – The Impact of Recent Inflation Waves On Your Capital

(17:10) – Why Social Security is a Unicorn Asset (Not Just Bank Cash)

(20:05) – Is Social Security Going Bankrupt?

(21:55) – Wrap-Up & The Year-End Tax Planning Checklist Challenge

Read our full legal disclosures here: https://www.retirementtaxmatters.com/disclosures

3 Common Tax Return Surprises for High-Net-Worth Retirees | Episode 36

Garrett Crawford, CFP® and Adam Reed — Wed, 20 May 2026 08:30:00 -0400

For many high-net-worth retiree between $2M-$8M, a successful financial life isn't just about how much you grow; it’s about how much you actually get to keep. Yet, many retirees find themselves blindsided on April 15th by an unwelcomed tax surprise. It's not the fact that paying owed tax is bad, but having to pay significantly more than planned can bother anyone. Tax return-driven financial planning is a proactive financial planning throughout the year to help minimize lifetime taxes, but it also helps decrease the amount of tax surprises you experience on April 15th each year.

This week, Adam and Garrett dive into three common tax landmines: the Social Security withholding trap, the complexities of reporting Roth conversion estimated payments, and the invisible income generated by large brokerage accounts. When your tax preparer and financial planner work together, they transform a reactive tax bill into a proactive wealth strategy that protects your hard-earned nest egg from unnecessary IRS erosion.

Time Stamps:

(00:00) - Tax Surprises in Retirement

(01:45) - The Value of Tax Return Driven Financial Planning

(03:15) - Social Security Tax Withholding

(07:00) - Roth Conversions Estimated Taxes

(11:15) - Invisible Income of Brokerage Accounts

(14:30) - Why 1099-Bs are so long

(17:45) - How to Use the Year-End Tax Planning Checklist

(19:15) - Communicating with Your Advisor about Capital Gains

📈Do you want to be more tax efficient? Do you want a guide to making sure you are on track and on schedule?

Check out our free Tax Planning Checklist:

https://www.retirementtaxmatters.com/free

Disclosure Statement: https://www.retirementtaxmatters.com/disclosures

AI & Retirement Planning in 2026: A Financial Planner’s Perspective | Episode 35

Garrett Crawford, CFP® and Adam Reed — Wed, 13 May 2026 08:30:00 -0400

Episode 35 analyzes the limitations of artificial intelligence in high-net-worth retirement planning and why retirees must distinguish between raw data processing and fiduciary human judgment. We explore the specific risks of AI hallucinations regarding 2026 tax law and the critical steps needed to protect your resources from sophisticated AI-driven financial scams.

Request a free resource using this link: https://www.retirementtaxmatters.com/checklist

(00:00) – The AI Era

(02:15) – WSJ: Can AI Manage Your Portfolio?

(04:00) – Windows 95 to ChatGPT

(07:30) – Is AI Going To Replace the Financial Advisor?

(09:45) – The Tax Planning Software Paradox

(11:15) – When AI Gets the Law Wrong

(13:30) – Elder Abuse Rising with AI

(16:45) – Why Fiduciary Advice is Being Valued More

(19:00) – Free Year-End Checklist Request

Disclosure Statement: https://www.retirementtaxmatters.com/disclosures

Roth Conversions for Single Retirees Feeling the Painful 32% Bracket Jump | Episode 34

Garrett Crawford, CFP® and Adam Reed — Wed, 06 May 2026 08:30:00 -0400

Single filers often feel overlooked when discussing Roth Conversions. Most content is geared towards Married households, yet Single Retirees face pretty tight tax brackets, especially for the $2M-$8M single Retiree. In this episode, Garrett and Adam dive into why the income range between $200,000 and $250,000 represents a challenging income range for individual retirees considering a Roth Conversion in 2026. Between the 32% federal bracket jump, the 3.8% Net Investment Income Tax (NIIT), and the Tier 4 Medicare IRMAA surcharge....there's a lot of ditches to watch out for! Whether you are single by choice, divorce, or the loss of a spouse, this episode provides a better path forward to navigate retirement taxes.

(00:00) – The Single Filer Dilemma

(08:30) – Navigating $200k & the 32% Bracket

(11:28) – Net Investment Income Tax & IRMAA Surcharges

(15:47) – The RMD Threat & Roth Conversions

(18:14) – Beneficiary Considerations

(24:30) – Adapting After the Loss of a Spouse

(29:20) – Tax Return Driven Financial Planning for Singles

View our full disclosures here: https://www.retirementtaxmatters.com/disclosures

Reverse-Engineering The Six-Figure RMD Problem | Episode 33

Garrett Crawford, CFP® and Adam Reed — Wed, 29 Apr 2026 08:30:00 -0400

What if RMDs didn't exist for pre-tax 401(k)s or Traditional IRAs? In this episode we discuss why even if you don't like RMDs, even if they didn't exist, you might still not want to let your pre-tax accounts grown untouched. Garrett Crawford, CFP® discusses the benefits of reverse-engineering an RMD plan. High-net-worth retirees between $2M-$8M might be playing a different RMD game than their peers and this episode will help you think through a better game plan for getting RMDs under control during your retirement.

Download a Free Tax Planning Resource - Click Here

Timestamps

(00:00) – Intro
(02:25) – Reverse Engineering Financial Planning
(05:03) – What if RMDs Didn't Exist?
(09:59) – Somebody Will Pay Taxes
(12:09) – Required MAXIMUM Distribution Mindset
(17:55) – How To Estimate Your Future RMDs
(21:45) – Free Resources

Disclosures

You’ve Saved Enough, but Will Your Surviving Spouse Continue to Spend? | Episode 32

Garrett Crawford, CFP® and Adam Reed — Wed, 22 Apr 2026 08:30:00 -0400

In many high-net-worth households, one spouse naturally takes the lead as the primary financial quarterback. While this works well during the accumulation years, it often creates a significant challenges later in retirement. On this episode of Retirement Tax Matters, Garrett Crawford, CFP® and Adam Reed discuss the psychological gap between having a multi-million dollar portfolio and having the actual confidence to spend it, especially for a surviving spouse who has been less involved in the family finances.

Click Here to get our FREE 5 step tax planning framework for High-Net-Worth Retirees between $2M-$8M

Timestamps:

(00:00) - Introduction and Guilty Spending Habits(02:55) - Helping Your Spouse Spend in Retirement(06:15) - The Scarcity Mindset in Surviving Spouses(09:10) - Addressing Annuities(13:10) - Simple vs. Complicated Financial Products(15:20) - Forced Income for Surviving Spouse(19:35) - MFJ vs Single Filer(24:10) - Finding the Right Advice(28:15) - Next Steps: Tax Planning Checklists and Projections

Disclosures Here

Evaluating the 22% to 24% Tax Bracket Jump for Strategic Roth Conversions for High-Net-Worth Retirees | Episode 31

Garrett Crawford, CFP® and Adam Reed — Wed, 15 Apr 2026 08:30:00 -0400

Episode 31 analyzes why high-net-worth retirees should consider intentionally filling the 24% tax bracket to protect against future 32% RMD spikes and surviving spouses tax rates increasing when going from Married Filing Jointly to Individual Filing. Garrett Crawford, CFP® details the math behind the 2% decision and how to identify these opportunities before the December 31st deadline.

Request a 5 step framework for annual tax planning for High-Net Worth Retirees between $2M-$8M:

https://www.retirementtaxmatters.com/checklist

(00:00) – Intro: Masters Weekend & CPA Nose to the Grindstone Season

(02:21) – The $2M-$8M Niche: Why High Net Worth Doesn't Mean High Spending

(05:10) – Understanding No Man's Land: The 22% vs. 24% Tax Brackets

(06:55) – The Psychology of Saving vs. The Reality of RMDs

(10:15) – The Six-Figure RMD: How Compound Interest Becomes a Tax Liability

(11:55) – Navigating Medicare IRMAA Surcharges and Roth Conversions

(14:15) – The Age 65 Window: Converting Without IRMAA Penalties

(16:10) – Opportunity Identification: Using the Year-End Tax Planning Checklist

(18:45) – Why Rule of Thumb Doesn't Replace Personalized Tax Planning

Read our full disclosures here: https://www.retirementtaxmatters.com/disclosures

Why April 16th is Opening Day of Tax Planning: Using Your 1040 as a Roadmap | Episode 30

Garrett Crawford, CFP® and Adam Reed — Wed, 08 Apr 2026 08:30:00 -0400

For many retirees, tax season feels like the finish line. In reality, it is the starting point for smarter retirement tax planning. In this episode, Garrett Crawford, CFP® and Adam Reed explain why reviewing your tax return in the spring can help you make better decisions for the rest of the year.They walk through their tax return driven financial planning framework, including why an early income projection matters, how Roth conversion planning can start months before execution, and what a tax return review should actually uncover. You will also hear how market downturns can create Roth conversion opportunities, why communication gaps often cause tax issues, and how retirees can use this season to prepare instead of react. Like, subscribe, and check the links below for more retirement tax planning resources.

📈Do you want to be more tax efficient? Do you want a guide to making sure you are on track and on schedule? Check out our free Tax Planning Checklist: https://www.retirementtaxmatters.com/checklist

(00:00) Starting 2026 retirement tax planning

(02:28) Why April 15 is the strategic launch pad

(06:09) - Building an early income projection

(08:25) - Roth conversion planning in the spring

(10:56) - Pre-planning during market volatility

(15:41) - What a professional tax review does

(18:19) - Tax issues vs. communication issues

(20:01) - Tax returns drive better decisions

(22:20) - DIY retirement tax planning resources

Click Here For Disclosures

One More Year Syndrome: Why Proactive Tax Planning is the Cure for High-Net-Worth Retirees| Episode 29

Garrett Crawford, CFP® and Adam Reed — Wed, 01 Apr 2026 08:30:00 -0400

Discover why working just six months longer can be a bigger retirement planning boost than most near-retirees realize. But while working longer almost always works out, for retirees in the $2M-$8M range sometimes this question comes back to defining enough and knowing when continuing to wait one more year might not be the best path to take.

(00:00) – Welcome & Spring Allergies

(01:51) – The One More Year Syndrome

(03:27) – The Power of Working Longer Study

(06:21) – The Retirement Boost of Working Longer

(08:44) – The Role of Social Security & Portfolio Preservation

(12:47) – Tax Implications & Roth Conversion Windows

(17:34) – The Identity Crisis of a High Achiever

(21:14) – Practical Tax Planning Steps for This Year

(24:02) – Finding Peace of Mind in Retirement

Disclosures: https://www.retirementtaxmatters.com/disclosures

Getting To Age 59 1/2 for High-Net-Worth Retirees: Why Brokerage Accounts Typically Win and Roth IRAs Often Deferred | EP 28

Garrett Crawford, CFP® and Adam Reed — Wed, 25 Mar 2026 08:30:00 -0400

Episode 28 of Retirement Tax Matters discusses the different types of investment accounts high-net-worth retirees can use to bridge the income gap when retiring in their 50s. While technical workarounds like SEPP 72(t) exist for pre-tax funds, Garrett and Adam address the access and wisdom of using Roth IRAs and taxable brokerage accounts to fund an early lifestyle.

The conversation dives deeper regarding the specific order of operations for Roth IRA withdrawals, highlighting that while original contributions can be accessed penalty-free at any time, earnings remain restricted until retirement. Garrett explains why the taxable brokerage account is often the favored vehicle for early retirees due to its ultimate liquidity and the ability to realize income at preferred long-term capital gains rates.

For those in the $2M–$8M range, prioritizing these taxable assets first may protect the high-value growth of pre-tax IRAs and the permanent tax-free status of Roth IRAs for future legacy goals. The episode underscores that making these tactical funding decisions requires annual intra-year tax projections to monitor for Medicare IRMAA thresholds and avoid unnecessary penalties .

(00:00) – March Madness & The Start of Tax Planning Season

(01:45) – Can You Access a Roth IRA Before Age 59½?

(04:00) – Order of Operations for Roth Withdrawals

(06:20) – Why Roth May Not Be Best for Early Retirement

(08:50) – The Ultimate Early Retirement Tool: Brokerage Accounts

(11:00) – Understanding Preferred Long-Term Capital Gains Rates

(14:00) – Why Tax Return-Driven Planning is Important

(15:15) – Avoiding Traps (Like Medicare IRMAA)

(16:40) – Free Year-End Tax Checklist

Here is a 5 step tax-return driven financial planning framework for making better tax planning decisions for Retirees between $2M-$8M https://www.retirementtaxmatters.com/checklist

Disclosures: https://www.retirementtaxmatters.com/disclosures

Getting To Age 59 1/2 for High-Net-Worth Retirees: Utilizing SEPP (72t) and The Rule of 55 for Pre-Tax Accounts | Episode 27

Garrett Crawford, CFP® and Adam Reed — Wed, 18 Mar 2026 08:30:00 -0400

Episode 27 of Retirement Tax Matters examines a couple bridge strategies for retirees in the $2M–$8M range who have a large amount of pre-tax funds but restricted by the age 59 ½ milestone. Garrett Crawford, CFP® and Adam Reed break down Substantially Equal Periodic Payment (SEPP) method and the Rule of 55 for 401(k) plans.

(00:00) – Intro

(01:45) – Accessing Retirement Funds Before 59½

(06:15) – Why the IRS Penalizes Early Withdrawals

(08:40) – Strategy 1: SEPP for IRAs Explained

(12:20) – The Risks, Formulas, and Strict Rules of SEPPs

(16:30) – Partitioning Your IRA

(19:10) – Strategy 2: The Rule of 55 for 401(k) Accounts

(21:45) – The Danger of Rolling Your 401(k) to an IRA Too Soon

(25:00) – The Roth 401(k) Pro-Rata Landmine

(28:00) – Our Tax Return-Driven Planning Process & Free Checklist

Download a FREE Year-End Tax Planning Checklist for HNW Retirees: https://www.retirementtaxmatters.com/checklist

Read the full disclosures here: https://www.retirementtaxmatters.com/disclosures

Early Retirement & Health Insurance: Deciding When Your Time is Worth More Than the Premium | Episode 26

Garrett Crawford, CFP® and Adam Reed — Wed, 11 Mar 2026 08:30:00 -0400

In this episode of Retirement Tax Matters, Garrett Crawford, CFP® and Adam Reed tackle one of the largest roadblocks for high-net-worth retirees considering early retirement: health insurance costs before Medicare age 65.

For retirees in the $2M–$8M range, the decision to retire early often hinges on a psychological standoff. Is it wise to pay $2,000 or more a month for private insurance after years of employer-subsidized coverage? We explore the primary paths to bridging the gap—including spousal plans, the ACA Marketplace, and sharing ministries—while reframing the premium not as an expense, but as the purchase price for your most valuable asset: your time.

Discover how tax-return driven financial planning provides the tactical clarity needed to handle high-cost prescriptions and volatile premium landscapes without delaying your best years of freedom.

Timestamps:

(00:00) – Introduction: The Healthcare Boogeyman

(02:25) – The Psychological Friction of Paying for Health Insurance

(06:45) – Option 1: The Spousal Plan Advantage

(08:40) – Option 2: Healthcare.gov, High Premiums & Expired Subsidies

(12:25) – The Value of Pre-Existing Condition Coverage

(13:50) – Option 3: Health Share Ministries (Medi-Share & CHM)

(18:25) – Math vs. Psychology: Don't Let Fear Keep You Working

(21:20) – The Power of Tax Return-Driven Financial Planning

(23:45) – Closing Thoughts & Free Year-End Tax Checklist

Resources:

Year-End Tax Planning Checklist for HNW Retirees ($2M-$8M)

Disclosures:

⁠https://www.retirementtaxmatters.com/disclosures⁠

Early Retirement & Social Security: Is Your Statement Estimate Accurate? | Episode 25

Garrett Crawford, CFP® and Adam Reed — Wed, 04 Mar 2026 08:30:00 -0500

If you are planning to stop work before age 60, your Social Security statement estimate for age 67 or 70 likely contains misleading benefit amounts. Standard benefit projections assume you will continue earning your current salary until the year you file—an assumption that is incorrect for early retirees who have gap years before filing with $0 in earnings .

In the kickoff of our Early Retirement series, Garrett Crawford, CFP® professional, explains why your statement estimate is misleading and how to fix it. We discuss how to use the online estimator tool to model $0 income years and why bridging the pre-60 gap requires a strategic focus on taxable brokerage accounts to avoid early withdrawal penalties .

Finally, we examine the survivor benefit as a critical piece of longevity insurance, emphasizing that optimizing for a higher check is often about protecting a surviving spouse from a future tax shock.

(00:00) – Intro

(01:15) – Announcing the New Early Retirement Series

(03:00) – The Big Mistake Early Retirees Make with Social Security

(05:30) – How to Calculate Your Actual Early Retirement Benefit

(07:45) – Bridging the Gap: Income Strategies Before Age 59 ½

(09:20) – The Secret Weapon for Early Retirement: Brokerage Accounts

(11:00) – Spousal & Survivor Benefits Explained

(13:30) – Math vs. Happiness: When Should the Higher Earner Claim?

(15:00) – Key Takeaways & Free Retirement Checklist

(19:54) – Outro

Free Tax Planning Framework Resource for HNW Retirees:

https://www.retirementtaxmatters.com/checklist

Disclosures:

https://www.retirementtaxmatters.com/disclosures

Why Converting Your Traditional IRA to Roth Might Feel Like Paying Off Your Home Mortgage | Episode 24

Garrett Crawford, CFP® and Adam Reed — Wed, 25 Feb 2026 08:30:00 -0500

Just as individuals rarely regret paying off their primary home, retirees rarely regret the peace of mind that comes from settling their tax debt and ensuring their family has more control over their finances.

This episode explores the psychological parallels between a strategic Roth conversion and the Debt-Free Scream made famous by Dave Ramsey. While a calculator might suggest keeping a Traditional IRA could end up a little better this approach misses the psychological benefits of value of simplicity and control.

(00:00) – Intro(01:10) – Tax Free Scream(03:57) – Roth Conversions and Mortgages(07:00) – Debt to the IRS and why to Convert(09:44) – Psychology of Conversions(16:08) – Tax Return Driven Financial Planning(17:15) – Conclusion(18:48) – Outro

Disclosures

Free Resource: Year-End Tax Planning Checklist for HNW Retirees ($2M-$8M):

How to Handle Your 1099-R Code 7 to Ensure Your QCD Stays 100% Tax-Free | Episode 23

Garrett Crawford, CFP® and Adam Reed — Wed, 18 Feb 2026 08:30:00 -0500

It's tax document season, and for retirees over age 70½, a common tax filing mistake could be costing you thousands in unnecessary taxes. In this episode, Garrett Crawford, CFP® and Adam Reed discuss an important and commonly missed reporting issue with Qualified Charitable Distributions (QCDs). While the IRS recently introduced Code Y to explicitly label these gifts on Form 1099-R, many major custodians are still using the generic Code 7 (Normal Distribution) in for tax year 2025.

Unless you remember to tell your tax preparer about these distributions, your tax return will likely treat your tax-free gift as fully taxable income, potentially triggering higher tax bills and potentially unexpected Medicare IRMAA surcharges. We break down how to review your tax return and what to look for in Box 7 of your 1099-R, and how to fix prior-year errors through the amendment process.

Timestamps:

(00:00) – Intro

(01:02) – Tax Documents

(02:25) – QCD Mistake

(04:40) – 1099-R discussion

(07:31) – Code 7 and Code Y

(09:50) – Can it be Fixed?

(13:10) – Conclusion

(15:05) – Outro

Year-End Tax Planning Checklist for HNW Retirees: https://www.retirementtaxmatters.com/checklist

Disclosures:

www.retirementtaxmatters.com/disclosures

How to Determine the Best Way to Pay Federal Taxes on Large Roth Conversions | Episode 22

Garrett Crawford, CFP® and Adam Reed — Wed, 11 Feb 2026 08:30:00 -0500

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

The Tax Preparer Referral Conversation For High-Net-Worth Retirees

Garrett Crawford, CFP® and Adam Reed — Wed, 04 Feb 2026 08:30:00 -0500

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

Tax Preparation vs. Tax Planning: Why High-Net-Worth Retirees Need Both - EP 20

Garrett Crawford, CFP® and Adam Reed — Wed, 28 Jan 2026 08:30:00 -0500

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

Navigating Gifting To Grandchildren in 2026: Trump Accounts, 529s vs Custodial Accounts

Garrett Crawford, CFP® and Adam Reed — Wed, 21 Jan 2026 08:00:00 -0500

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

How Better Tax Planning Can Help You Drop the Extra Weight of Tax Drag in 2026

Garrett Crawford, CFP® and Adam Reed — Wed, 31 Dec 2025 08:30:00 -0500

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! Reflecting on the Gift of Giving

Garrett Crawford, CFP® and Adam Reed — Wed, 24 Dec 2025 08:30:00 -0500

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

The Downside of Tax Minimization: Why Paying Taxes Can Be a Winning Strategy

Garrett Crawford, CFP® and Adam Reed — Wed, 17 Dec 2025 08:30:01 -0500

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

The 3.8% Net Investment Income Tax: The Inflation Trap for Retirees

Garrett Crawford, CFP® and Adam Reed — Wed, 10 Dec 2025 08:30:00 -0500

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.

Insurance Planning vs. Sales: A HNW Retiree's Guide

Garrett Crawford, CFP® and Adam Reed — Wed, 26 Nov 2025 08:00:00 -0500

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

A HNW Retiree's Introduction to Medicare's Alphabet Soup

Garrett Crawford, CFP® and Adam Reed — Wed, 12 Nov 2025 08:30:00 -0500

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.

Social Security Optimization for HNW Retirees (2026 Update)

Garrett Crawford, CFP® and Adam Reed — Wed, 05 Nov 2025 08:00:00 -0500

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

The HNW Cash Dilemma: How to Balance Liquidity and Growth

Garrett Crawford, CFP® and Adam Reed — Wed, 29 Oct 2025 08:00:00 -0400

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

Align Your Legacy with the SECURE Act's 10-Year Rule

Garrett Crawford, CFP® and Adam Reed — Wed, 15 Oct 2025 08:00:00 -0400

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

A HNW Retiree's Guide To Navigating RMDs from Large IRA Accounts

Garrett Crawford, CFP® and Adam Reed — Wed, 08 Oct 2025 08:00:00 -0400

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

High-Net-Worth Charitable Giving: Maximize Impact, Minimize Taxes

Garrett Crawford, CFP® and Adam Reed — Wed, 01 Oct 2025 08:00:00 -0400

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

Surviving Spouse Tax Planning: Avoid Post-Death Tax Bracket Jumps

Garrett Crawford, CFP® and Adam Reed — Wed, 17 Sep 2025 08:00:00 -0400

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

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The #1 Financial Mistake HNW Retirees Make

Garrett Crawford, CFP® and Adam Reed — Tue, 09 Sep 2025 20:42:41 -0400

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

The Golden Window: Roth Conversions Before Social Security & RMDs

Garrett Crawford, CFP® and Adam Reed — Wed, 03 Sep 2025 14:10:14 -0400

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

Understanding the New Standard Deduction Under OBBBA | Retirement Tax Matters Ep 04

Garrett Crawford, CFP® and Adam Reed — Tue, 26 Aug 2025 11:14:00 -0400

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

Permanent Tax Brackets? How to Plan for Your HNW Retirement | Retirement Tax Matters Ep 03

Garrett Crawford, CFP® and Adam Reed — Tue, 26 Aug 2025 11:04:39 -0400

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

Will My Social Security Benefit Be Taxed Moving Forward? | Retirement Tax Matters Ep 02

Garrett Crawford, CFP® and Adam Reed — Tue, 26 Aug 2025 11:00:04 -0400

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

Welcome To Retirement Tax Matters | Retirement Tax Matters Ep 01

Garrett Crawford, CFP® and Adam Reed — Tue, 26 Aug 2025 10:17:37 -0400

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