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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Episode 37 of Retirement Tax Matters breaks down why high-net-worth married retirees with portfolios in the $2M–$8M range often look past critical elements of their Social Security filing strategy by prioritizing ROI instead of incorporating the risk-reducing benefits of the program.

Avoid the April 15th tax surprise. Today’s conversation centers on three areas we see where high-net-worth retirees can get tripped up and experience a larger-than-expected tax bill come tax filing day.

Episode 35 addresses why using AI for retirement planning effectively requires an existing level of proficiency and why a recent string of hallucinations regarding the OBBBA is concerning. As good and helpful AI can be in your own retirement planning, it’s important to remember that bad actors are also trying to leverage AI for high-stakes financial scams and elder abuse targeting high-net-worth retirees.

Episode 34 addresses the high-net-worth Single Filer Retiree navigating the 32% tax bracket Roth Conversion decision. Learn why the $201,776 threshold in 2026 is an interesting crosshair for advanced tax planning, where the 32% bracket, NIIT surcharges, and IRMAA cliffs create a unexpected collision of taxes for successful Single Filers.

Episode 33 of Retirement Tax Matters uses a reverse-engineering framework to reframe the six-figure RMD from a problem into a solvable puzzle. Learn how to levelize your lifetime tax liability and your heirs through proactive tax-return driven planning.

Having enough money for a surviving spouse only half the battle. In this week’s episode we explain how some surviving spouses can default to being over-conservative and how it might be worth your time thinking through how your spouse will generate enough income to live the life you always imagined for them.