Retirement Tax Matters | Advanced Tax Planning for $2M-$8M Retirees

Garrett Crawford, CFP® and Adam Reed
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  • Investing
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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.

  1. 9h ago ·  Video

    A High-Net-Worth Retiree's Walkthrough of the New 3.6% Social Security Increase for 2027

    Episode 58 of Retirement Tax Matters breaks down the 2027 Social Security cost-of-living adjustment and what the 3.6% increase means for retirees and pre-retirees with $2M to $8M. Garrett Crawford, CFP® and Adam Reed review the official fact sheet, explaining why the maximum monthly benefit at full retirement age only moved up by $36 to $4,188 while current beneficiaries receive the full percentage adjustment. The conversation covers the jump in the taxable wage base to $192,300 for high earners, how COLAs credit to your record starting at age 62, and how rising guaranteed income impacts fall tax projections and Medicare IRMAA brackets. 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 01:19 Tracking the Annual Social Security COLA04:30 The 3.6% COLA Announcement for 202705:20 Payroll Taxes and Rising Wage Limits07:05 Maximum and Average Social Security Benefits11:40 How COLA Impacts High-Net-Worth Retirees14:04 Social Security Strategies: Spousal Benefits & Bend Points16:47 Navigating Medicare IRMAA Thresholds18:13 Proactive Year-End Tax Planning21:04 Will Social Security Go Bankrupt? Visit us online at: https://www.retirementtaxmatters.com  Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

    A High-Net-Worth Retiree's Walkthrough of the New 3.6% Social Security Increase for 2027

  2. Oct 28 ·  Video

    IRMAA: The Scariest Part of Retirement Planning

    Episode 57 of Retirement Tax Matters unpacks why Medicare IRMAA surcharges are often considered the scariest part of retirement planning for high-net-worth retirees. Garrett Crawford, CFP® professional and Adam Reed break down how the two-year lookback period and cliff penalty structure create unexpected costs for families with portfolios between $2M and $8M. The conversation reframes these surcharges by looking at the actual numbers, showing that IRMAA typically adds only one to three percent to a household's effective tax rate. Discover why intentionally crossing an IRMAA threshold to execute a strategic Roth conversion can protect a surviving spouse and future beneficiaries from much higher tax brackets down the road. 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 & A Spooky Halloween Episode03:10 Medicare IRMAA 101: The Basics08:10 Why Do People Feel IRMAA is a Trick?10:40 The Frustration of the Two-Year Lookback Period13:40 The Danger of Medicare Penalty Cliffs15:35 The Treat: Reframing How You View IRMAA Surcharges19:00 Don't Miss the Forest for the Trees: Roth Conversions vs. IRMAA22:48 Bonus: Our Favorite Halloween Candies! Visit us online at: https://www.retirementtaxmatters.comReview our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

    IRMAA: The Scariest Part of Retirement Planning

  3. Oct 21 ·  Video

    CPA vs. Enrolled Agent: Which Do $2M to $8M Retirees Actually Need?

    How should retirees with $2M to $8M evaluate a Certified Public Accountant (CPA) versus an Enrolled Agent (EA) for annual tax preparation? In this episode, Garrett Crawford, CFP® professional and Adam Reed break down the distinct difference between forward-looking tax planning and spring tax preparation. They examine state accountancy licensing versus federal IRS credentials, why conversations with a CPA or EA do not carry attorney-client privilege, and how to determine which professional fits your state tax situation and business exit 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 Tax Preparation vs. Tax Projections02:20 Defining CPAs and Enrolled Agents (EAs)06:40 When Do You Need a Tax Attorney?11:43 Which Tax Professional is Right for You?18:50 The Importance of Year-End Tax Planning Visit us online at: https://www.retirementtaxmatters.com Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

    CPA vs. Enrolled Agent: Which Do $2M to $8M Retirees Actually Need?

  4. Oct 7 ·  Video

    Ready To Admit You've Outgrown the 24% Tax Bracket?

    Episode 54 of Retirement Tax Matters explores why high net worth retirees in the $2M to $8M asset range often outgrow the 24% tax bracket. Garrett Crawford, CFP®  and Adam Reed break down the psychological impact of holding onto lower tax brackets and explain how staying in 24% out of habit can lead to larger tax bills when required minimum distributions, inherited IRAs, or single survivor filing status take effect. The conversation outlines how accelerating income into the 32% bracket today can possibly protect your family from 35% or 37% tax rates later in life while avoiding multi-year Medicare IRMAA surcharges. 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 & The Fear of the 32% Tax Bracket01:07 The Pant Size Analogy: Mental Games in Tax Planning03:00 Why Paying 32% Tax Can Save You Money Long Term04:19 Overcoming "Rules of Thumb" for High-Net-Worth Retirees07:42 CPA vs. Financial Planner: Annual vs. Lifetime Tax Planning09:36 Practical Strategies: Roth Conversions & Taxable Brokerage Accounts14:14 Summary & Football Predictions Visit us online at: https://www.retirementtaxmatters.comReview our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

    Ready To Admit You've Outgrown the 24% Tax Bracket?

  5. Sep 30 ·  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

  6. 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

  7. 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

  8. 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?
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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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