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 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.

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 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 15 of Retirement Tax Matters demystifies the 3.8% Net Investment Income Tax (NIIT), a surtax that is increasingly trapping high-net-worth retirees due to income thresholds ($200,000 for singles, $250,000 for married couples) that have not been adjusted for inflation since 2013. We explain the specific “Lesser of" calculation used by the IRS, illustrating how this tax applies to your dividends, interest, and capital gains once your Modified Adjusted Gross Income (MAGI) exceeds those fixed limits.