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

Garrett Crawford, CFP® and Adam Reed
  • 4.3 (6)
  • 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. 1d ago ·  Video

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

    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 Planning01:18 The Shoebox Method vs. Return on Hassle07:08 Integrating HSAs with Long-Term Care Planning13:28 IRS Limits for HSA Long-Term Care Premium Payments15:35 Rules and Pitfalls of Inheriting an HSA18:20 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

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

  2. Sep 2 ·  Video

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

    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. 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 Timestamps00:00 Introduction & Social Security Unease02:26 Breaking Down the 2025 Social Security Trust Fund Report05:19 Depletion in 2032 & The 78% Benefit Reality07:31 Potential Fixes: Tax Hikes vs. Benefit Cuts08:52 What Social Security Depletion Means for $2M–$8M Retirees12:57 Why Planning for $0 in Social Security Is a Mistake14:26 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

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

  3. Aug 26 ·  Video

    Multi-Year Roth Conversion Planning Explained

    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. 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) - 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

    Multi-Year Roth Conversion Planning Explained

  4. Aug 19 ·  Video

    Roth vs. Traditional: The Better Inheritance?

    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. 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 Introduction: The Inheritance Conversation01:43 The National Debt & The Future of Tax Brackets05:54 Inheritance Strategy: Parents in Lower Tax Brackets Than Kids10:48 Inheritance Strategy: Parents in Higher Tax Brackets Than Kids13:59 The Hidden Impact of State Income Taxes14:55 Garrett's Epiphany: Family Dynamics & Lifetime Giving21:00 Why Inheriting a Roth IRA is Simpler22:04 Closing Thoughts & Free Year-End Tax Planning Checklist Review our disclosures here: https://www.retirementtaxmatters.com/disclosures

    Roth vs. Traditional: The Better Inheritance?

  5. Aug 12 ·  Video

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

    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. 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 & 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

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

  6. Aug 5 ·  Video

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

    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 Brackets05:22 Reason 1: The Surviving Spouse Tax Trap06:58 Reason 2: RMDs & SECURE Act 10-Year Rule08:42 Reason 3: Tax Arbitrage via Brokerage Accounts09:47 Reason 4: Managing Medicare IRMAA & NIIT Limits11:34 Reasons to Pump the Brakes on Roth Conversions17:14 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

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

  7. Jul 29 ·  Video

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

    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. 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 Back to the Basics: Tax Return Driven Financial Planning01:08 Can You Earn $500,000 and Stay in the 12% Tax Bracket?03:40 Ordinary Income vs. Preferential Capital Gains Brackets05:27 Case Study: Baseline Income for Tim & Ann07:08 Scenario 1: Generating $500k Entirely from IRA Distributions09:07 Scenario 2: $500k Income Utilizing Low-Basis Brokerage Capital Gains12:15 Scenario 3: Realized Capital Gains vs. Account Cost Basis15:00 Tactical Roth Conversions & Range Calculator Analysis17:44 Navigating Medicare IRMAA Tiers & Tax Brackets20:18 Year-to-Year Tax Minimization vs. Lifetime Tax Liability Visit us online at: https://www.retirementtaxmatters.comReview 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

  8. Jul 22 ·  Video

    Year One Reflections + Why Great Retirement Planning Takes a Team

    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. 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 & One-Year Anniversary Celebration01:54 Podcast Growth & Community Milestones03:12 Parallels Between Podcasting and Financial Planning04:56 Behind the Scenes: Why We Started the Podcast06:59 Discovering the Power of Tax-Driven Financial Planning08:08 Steve Jobs, Teamwork, and Leaving the Echo Chamber10:43 The Challenges of the Decumulation Phase13:00 Do You Need to Hire a Financial Advisor?14:24 Why Your Spouse or Friend is Your Most Important Teammate17:19 The Value of a Second Opinion19:07 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

    Year One Reflections + Why Great Retirement Planning Takes a Team
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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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