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. Why Your 30-Year Retirement Plan Report Feels Underwhelming

    3d ago ·  Video

    Why Your 30-Year Retirement Plan Report Feels Underwhelming

    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. 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 Timestamps:00:00 Welcome to Retirement Tax Matters & Summer Catch-Up01:28 The Trap of the 30-Year Retirement Binder02:30 Why Retirees Crave a Step-by-Step Plan03:13 The Evolution (and Failure) of 60-Page Financial Reports04:51 Long-Term Plans vs. Real-Life Changes05:51 Balancing the Long-Term Vision with Annual Tax Strategy06:41 Using Financial Software For Trajectory, Not Exact Predictions07:44 Tax Return Driven Financial Planning Defined09:23 The Year-End Tax Planning Checklist & Working with Adam and Garrett10:47 Real Case Example: Early Retirement, RMDs, and the 24% Bracket11:34 Navigating Roth Conversions and Medicare IRMAA Limits13:24 The Disney World Analogy: Staying Flexible on the Road to Retirement14:48 Final Thoughts: Real Planning Happens in the Annual Adjustments 👉 Visit us online at retirementtaxmatters.comDisclosure Statement: https://www.retirementtaxmatters.com/disclosures

    16 min
  2. $6M Retirement Case Study: IRA Drawdown vs Deferring Pension & Social Security to 70

    Jul 1 ·  Video

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

    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. 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 Welcome to Retirement Tax Matters & Studio Updates00:46 What Does Tax Return Driven Financial Planning Actually Look Like?01:05 Case Study Introduction: Tim & Ann's Retirement Dilemma03:18 Establishing the Case Assumptions: Assets, Income, and Bracket Goals04:54 Financial Planning: Calculator vs. Psychology06:15 Diving into Holistiplan: Analyzing the 2026 Working Year Income08:18 Understanding Phantom Income: Interest, Ordinary, and Qualified Dividends11:13 Navigating the 24% Tax Bracket Summary12:08 Fast-Forwarding to 2028: The Beans and Rice Early Retirement Scenario14:31 The Six-Figure RMD Trap: Projections at Age 75 and Beyond16:44 The Strategy: Delaying Fixed Income vs. Drawing Down the Traditional IRA18:41 Utilizing the Range Calculator & Navigating Medicare IRMAA Penalties20:36 Modeling a $300,000 Strategic Roth Conversion23:11 Shifting Perspectives: Younger Accumulators vs. Older Decumulators24:51 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

    37 min
  3. How Charitable Retirees Neutralize Capital Gains and NIIT with a DAF

    Jun 24 ·  Video

    How Charitable Retirees Neutralize Capital Gains and NIIT with a DAF

    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

    22 min
  4. Why Your Stomach and Your Calculator Disagree on Retirement Risk

    Jun 17 ·  Video

    Why Your Stomach and Your Calculator Disagree on Retirement Risk

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

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

    Jun 10 ·  Video

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

    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

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

    Jun 3

    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
  7. 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
  8. 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
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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.

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