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

Garrett Crawford, CFP® and Adam Reed
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  • 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. 4d ago ·  Video

    Managing Dual Inherited and Personal Six-Figure RMDs

    Episode 54 of Retirement Tax Matters examines the challenges high-net-worth households face when coordinating required minimum distributions across multiple accounts. For retirees in the $2M to $8M asset tier, receiving an inherited IRA alongside personal pre-tax retirement accounts creates a multi-RMD scenario requiring separate distributions. Garrett Crawford, CFP® and Adam Reed break down IRS aggregation rules, highlighting why personal traditional IRAs can be combined for single-account withdrawals while inherited IRAs must be handled separately. They cover spousal RMDs, annuity income rider nuances, and three common ways to handle RMDs, including direct spending, reinvestment into taxable brokerage accounts, and Qualified Charitable Distributions at age 70.5. 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 RMD Blindspots Retirees Miss02:30 Current RMD Rules03:35 RMD Tunnel Vision 04:55 Dual Threat RMD Issue06:58 RMD Aggregation Rules & Annuities14:02 3 Ways to Handle Your RMDs17:26 Why Not All RMDs Are Bad for Your Retirement Plan19:12 Year-End Tax Planning Checklist & Closing Remarks Visit us online at: https://www.retirementtaxmatters.comReview our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

    Managing Dual Inherited and Personal Six-Figure RMDs

  2. Sep 24 ·  Video

    Helping Retirees Tackle Year-End Tax Planning: Easiest to Hardest

    Episode 53 of Retirement Tax Matters ranks the year-end tax data-gathering steps for $2M to $8M retirees from easiest to hardest. Garrett Crawford, CFP® and Adam Reed break down how to collect Social Security, pension, brokerage dividend, Schedule E, and Roth conversion numbers to build an accurate fall income tax projection. Estimating your December 31st taxable income before year-end gives you the opportunity to make informed financial choices rather than waiting for spring tax filing when planning windows have closed. 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 & Year-End Tax Planning Checklist01:24 Power Ranking Retirement Tax Numbers03:00 Tier 1: The Easiest Numbers to Estimate (Social Security, IRAs & Pensions)07:50 Tier 2: Medium Difficulty Estimates (Dividends, Interest & Itemized Deductions)09:43 Tier 3: The Hardest Tax Levers (Schedule E, DAFs & Roth Conversions)13:58 Managing Estimated Tax Payments to Avoid Tax Season Surprises14:51 How to Explore Episode Topics & Wrap Up Visit us online at: https://www.retirementtaxmatters.com Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

    Helping Retirees Tackle Year-End Tax Planning: Easiest to Hardest

  3. Sep 16 ·  Video

    Fall Tax Planning Checklist for Pre-Retirees Between $2M-$8M

    Episode 52 of Retirement Tax Matters launches a two-part autumn series focused on year-end tax planning for high-net-worth pre-retirees in the $2M to $8M space. Garrett Crawford, CFP® professional, and Adam Reed discuss why running a fall income tax projection is the most essential step working pre-retirees fail to complete each year. They break down how auditing a mid-year W-2 paystub helps verify federal tax withholding, catch bonus timing shifts, and prevent IRS estimated tax underpayment penalties before the December 31st deadline. 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 Year-End Tax Planning & Pre-Retiree Strategy02:18 The Pre-Retiree Challenge: High Income & Large Portfolios ($2M-$8M)03:32 The #1 Tax Mistake: Waiting Until April to Calculate Final Income04:58 Safe Harbor Traps with Q3 & Q4 Quarterly Estimated Taxes06:15 Why Your Pay Stub May Be Another Overlooked Tax Planning Document09:44 Managing Brokerage Accounts, Dividend Reinvestments & Phantom Income12:44 Bracket Creep vs. Scaling Back: Strategic Roth Conversions While Working13:54 Implementing a "Season of Pause" in November & December16:58 Action Steps: DIY Tax Planning vs. Delegating to a CFP® Visit us online at: https://www.retirementtaxmatters.com  Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

    Fall Tax Planning Checklist for Pre-Retirees Between $2M-$8M

  4. Sep 9 ·  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?

  5. 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

  6. 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

  7. 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?

  8. 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)
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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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