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

Garrett Crawford, CFP® and Adam Reed
  • 5.0 (4)
  • Investing
  • Updated Weekly

An educational podcast from financial advisors Garrett Crawford, CFP® and Adam Reed, dedicated to helping retirees between $2M-$8M with tax-return driven financial planning. At this level of wealth an integrated strategy for your tax return, investments, and long-term goals is critical. We explore advanced topics like Roth conversions, RMDs, and charitable giving to help you ensure your family remains your biggest beneficiary.

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

    2d ago

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

    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. 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 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

    24 min
  2. 3 Common Tax Return Surprises for High-Net-Worth Retirees | Episode 36

    May 20

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

    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

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

    May 13

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

    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. 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) – 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

    21 min
  4. Roth Conversions for Single Retirees Feeling the Painful 32% Bracket Jump | Episode 34

    May 6

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

    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. 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) – 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

    32 min
  5. Reverse-Engineering The Six-Figure RMD Problem | Episode 33

    Apr 29

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

    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

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

    Apr 22

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

    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

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

    Apr 15

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

    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

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

    Apr 8

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

    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

    24 min
See All (37)

Ratings & Reviews

5
out of 5
4 Ratings

About

An educational podcast from financial advisors Garrett Crawford, CFP® and Adam Reed, dedicated to helping retirees between $2M-$8M with tax-return driven financial planning. At this level of wealth an integrated strategy for your tax return, investments, and long-term goals is critical. We explore advanced topics like Roth conversions, RMDs, and charitable giving to help you ensure your family remains your biggest beneficiary.

Information

You Might Also Like