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.