Episodes
If you have a specific subject on your mind, you can use our complete episode index, organized by topic, to find the conversation you're looking for.
IRMAA: The Scariest Part of Retirement Planning
Medicare IRMAA surcharges create significant frustration for retirees due to two year lookback rules and cliff penalties. Garrett Crawford, CFP® and Adam Reed explain why reframing these costs as a small effective tax percentage allows $2M to $8M households to execute strategic Roth conversions before December 31st without missing the forest for the trees.
CPA vs. Enrolled Agent: Which Do $2M to $8M Retirees Actually Need?
Retirees with $2M to $8M often assume every tax professional does the same job. Garrett Crawford, CFP® and Adam Reed break down the distinct roles of a state-licensed CPA, an IRS-credentialed Enrolled Agent, and a Tax Attorney. Learn how to evaluate which tax preparer fits your retirement portfolio, state tax liabilities, and year-end planning goals.
Ready To Admit You've Outgrown the 24% Tax Bracket?
Many high-net-worth retirees in the $2M to $8M asset range work hard to stay inside the 24% tax bracket. This episode explores why intentionally moving into the 32% tax bracket today can protect your family from hitting 35% or 37% tax rates later in retirement.
Managing Dual Inherited and Personal Six-Figure RMDs
Managing both personal and inherited traditional IRAs creates overlapping required minimum distributions that complicate year-end tax planning. This episode breaks down IRS account aggregation rules and tax-efficient positioning strategies for retirees in the $2M to $8M asset range.
Helping Retirees Tackle Year-End Tax Planning: Easiest to Hardest
Ranking the year-end tax data-gathering process for $2M to $8M retirees from easiest to hardest to build an accurate fall income tax projection before December 31st.
Fall Tax Planning Checklist for Pre-Retirees Between $2M-$8M
A fall income tax projection is one of the most essential planning step high-earning W-2 pre-retirees miss each year. Learn how a mid-year paystub review helps high-earning W-2 wage workers in the $2M to $8M range make better financial planning decisions before the December 31st deadline.
What Should You Actually Do With a $150K HSA in Retirement?
Garrett Crawford, CFP® and Adam Reed discuss how high-net-worth retirees in the $2M to $8M range should manage a six-figure Health Savings Account. Discover why hoarding an HSA into your 80s can create administrative friction and estate tax pitfalls for adult children, and how to build a drawdown plan.
Social Security Trust Fund Depletion: What It Means for $2M to $8M Retirees
Episode 50 of Retirement Tax Matters reviews the numbers behind the latest Social Security Trust Fund report and what the possible projected 2032 reserve depletion means for retirees between $2M and $8M. Garrett Crawford, CFP® and Adam Reed walk through the report details, noting that while trust fund reserves are projected to run out in the fourth quarter of 2032, ongoing payroll tax revenues may still cover approximately 78% of scheduled benefits.
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.
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 families 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, which often makes proactive parent-level Roth conversions at lower rates the superior decision for the family balance sheet.
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 and Adam discuss how to identify NUA opportunities you may have in your employer retirement plan and to help you know if it might be a tax planning strategy you should learn more about.
Tax Planning When You Don't Drop Tax Brackets in Retirement
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.
How a $534K Income Can Still Leave You in the 12% Ordinary MFJ Tax Bracket
A live Holistiplan tax planning case study showing how a married couple with $534,200 in total income stays in the 12% ordinary marginal tax bracket. Garrett Crawford, CFP® and Adam Reed break down Form 1040 tax stacking, long-term capital gains, Net Investment Income Tax (NIIT), and multi-year Roth conversion strategies for high-net-worth retirees.
Why Great Retirement Planning Takes a Team
Episode 44 of Retirement Tax Matters marks the one-year anniversary of the podcast. Garrett and Adam explore how consistently showing up to produce a weekly show shares a surprising number of parallels with navigating a successful retirement, highlighting why a team approach is a powerful ingredient for better retirement planning.
How To Move Appreciated Brokerage Accounts Without Huge Taxes
Episode 43 of Retirement Tax Matters addresses the technical and psychological hurdles that high-net-worth retirees between $2M-$8M face when managing highly appreciated, taxable brokerage accounts. Learn how to think through a systematic, multi-year transition strategy to diversify away from concentrated stock risk without triggering a tax surprise the following April.
Why Your 30-Year Retirement Plan Report Feels Underwhelming
Long-term retirement planning is a necessity, but it must be balanced with yearly execution. Episode 42 explores why a static 30-year trajectory feels underwhelming without proactive tax planning, and how tactical adjustments to your tax return provide real-world confidence as the future unfolds.
$6M Retirement Case Study: IRA Drawdown vs Deferring Pension & Social Security to 70
Episode 41 of Retirement Tax Matters reviews a screen-share case study of a married couple at age 63 navigating a $6 million portfolio. This scenario highlights the critical planning decision between taking a combined $85,000 pension and Social Security stream immediately or deferring those guaranteed streams until age 70.
How Charitable Retirees Neutralize Capital Gains and NIIT with a DAF
Episode 40 of Retirement Tax Matters breaks down the mechanics of using a Donor-Advised Fund to help lessen capital gains taxes and the 3.8% Net Investment Income Tax on highly appreciated brokerage assets. Transferring low-basis stock directly into a DAF allows savers within the $2M–$8M range to claim a charitable deduction while legally erasing some of the embedded tax debt.
Why Your Stomach and Your Calculator Disagree on Retirement Risk
Episode 39 of Retirement Tax Matters breaks down the difference between emotional risk tolerance and risk capacity for high-net-worth retirees in the $2M–$8M range. Garrett and Adam explore how an individual's psychological response to market volatility differs fundamentally from a retirement capacity to absorb downturns safely.
Why Gifting Wealth From a $2M–$8M Portfolio May Be Simpler Than You Think
Gifting money to your adult children is sometimes simpler than many high-net-worth retirees realize. In 2026, the federal lifetime gift and estate tax exemption sits at 15 million dollars per individual, meaning the annual 19,000 dollar exclusion threshold usually just involves whether you need to file Form 709 with your tax return using up some of your $15M limit.