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

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.

Retirement Tax Matters | Advanced Tax Planning for High-Net-Worth Retirees is a business podcast hosted by Unknown Host, with 51 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Retirement Tax Matters | Advanced Tax Planning for High-Net-Worth Retirees, a business show with 51 episodes published.

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  Episode #51

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

  Sep 9, 202623 min

  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

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  Episode #50

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

  Sep 2, 202621 min

  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 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

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  Episode #49

  Multi-Year Roth Conversion Planning Explained

  Aug 26, 202616 min

  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

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  Episode #47

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

  Aug 12, 202621 min

  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

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  Episode #46

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

  Aug 5, 202622 min

  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

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