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.

Episode 31 of Retirement Tax Matters analyzes the strategic logic of maximizing the 24% federal tax bracket for high-net-worth retirees who naturally fall into the 22% range due to modest spending.

Episode 30 of Retirement Tax Matters reframes the April 15th filing deadline as the Opening Day for a retiree’s 2026 tax planning strategy. For high-net-worth retirees and their families in the $2M–$8M range, Garrett Crawford, CFP® explains why the tax return is not a historical receipt but a roadmap that leads the upcoming year’s proactive planning .

Could staying at your desk for just six extra months be worth 30 years of previous savings? Discover an interesting math discussion behind a 2018 NBER study called The Power of Working Longer and why it’s important for high-net-worth retirees to take note. In this episode of Retirement Tax Matters, Garrett Crawford, CFP® breaks down the three levers of One More Year Syndrome and the proactive tax-return-driven strategies you might consider if you encounter this.

Episode 28 evaluates why high-net-worth retirees in the $2M–$8M range typically favor brokerage accounts for early income while choosing to defer Roth IRAs. Discover the advantages of brokerage flexibility and the technical rules of penalty-free Roth withdrawals before age 59 1/2.

Episode 27 of Retirement Tax Matters analyzes technical strategies for high-net-worth retirees to access pre-tax retirement funds before age 59 1/2 without incurring the 10% IRS penalty. Learn how to navigate the rigidity of SEPP (72t) and the Rule of 55.

Discover why health insurance is the #1 roadblock for early retirement. Learn how HNW retirees can bridge the gap to Medicare age 65 without letting sticker shock premiums steal their best years of retirement.