Advertise on podcast: Retirement Tax Matters | Advanced Tax Planning for High-Net-Worth Retirees

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

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

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

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

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

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

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

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

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

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

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

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

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

Episode 43 of Retirement Tax Matters addresses the unique tax challenges and psychological hurdles of managing large, highly appreciated taxable brokerage accounts. For retirees in the $2M–$8M range, holding concentrated stock positions or outdated, expensive mutual funds can feel like wearing financial handcuffs due to the threat of a massive capital gains tax bill. Garrett and Adam break down the all-or-nothing trap, outlining how a structured, multi-year transition plan can help you diversify your portfolio safely without triggering an avoidable single-year tax shock. 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 $2M-$8M Brokerage Account Problem01:03 - The Psychology of Tax Aversion & Embedded Capital Gains02:04 - Why Old Mutual Funds are Creating Tax Friction (ETFs vs. Mutual Funds)05:05 - The "All or Nothing" Trap vs. A Balanced Game Plan06:22 - The "Nasty Divorce" of Concentrated Stock Positions (Amazon, Apple, Tesla)08:51 - Understanding the 23.8% Capital Gains Tax & Net Investment Income Tax (NIIT)10:41 - How Providence Wealth Management Navigates a Multi-Year Transition Plan12:15 - Forced Mutual Fund Capital Gain Distributions & The Medicare IRMAA Charge15:00 - Unlocking Your Brokerage Account for Roth Conversions & Major Purchases16:07 - Retirement Strategy: Why You Need Singles and Doubles, Not Strikeouts17:28 - Utilizing the Summer for Your Year-End Tax Planning Checklist Visit us online at: https://www.retirementtaxmatters.com  Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

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