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 Strategy
02:18 The Pre-Retiree Challenge: High Income & Large Portfolios ($2M-$8M)
03:32 The #1 Tax Mistake: Waiting Until April to Calculate Final Income
04:58 Safe Harbor Traps with Q3 & Q4 Quarterly Estimated Taxes
06:15 Why Your Pay Stub May Be Another Overlooked Tax Planning Document
09:44 Managing Brokerage Accounts, Dividend Reinvestments & Phantom Income
12:44 Bracket Creep vs. Scaling Back: Strategic Roth Conversions While Working
13:54 Implementing a "Season of Pause" in November & December
16:58 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 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

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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

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

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 Conversation
01:43 The National Debt & The Future of Tax Brackets
05:54 Inheritance Strategy: Parents in Lower Tax Brackets Than Kids
10:48 Inheritance Strategy: Parents in Higher Tax Brackets Than Kids
13:59 The Hidden Impact of State Income Taxes
14:55 Garrett's Epiphany: Family Dynamics & Lifetime Giving
21:00 Why Inheriting a Roth IRA is Simpler
22:04 Closing Thoughts & Free Year-End Tax Planning Checklist

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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 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

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 Planning
01:08 Can You Earn $500,000 and Stay in the 12% Tax Bracket?
03:40 Ordinary Income vs. Preferential Capital Gains Brackets
05:27 Case Study: Baseline Income for Tim & Ann
07:08 Scenario 1: Generating $500k Entirely from IRA Distributions
09:07 Scenario 2: $500k Income Utilizing Low-Basis Brokerage Capital Gains
12:15 Scenario 3: Realized Capital Gains vs. Account Cost Basis
15:00 Tactical Roth Conversions & Range Calculator Analysis
17:44 Navigating Medicare IRMAA Tiers & Tax Brackets
20:18 Year-to-Year Tax Minimization vs. Lifetime Tax Liability

Visit us online at: https://www.retirementtaxmatters.com
Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures