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.

Many HNW retirees planning to stop work before age 60 can unexpectedly rely on Social Security statements that have misleading benefit amounts. This episode reveals why your benefit statement may estimate incorrectly by assuming continued earnings and how to use the online estimator tools to confirm your real future benefit before hitting submitting your retirement papers.

Episode 24 of Retirement Tax Matters was inspired by Dave Ramsey’s Debt-Free Scream and the parallels we see when high-net-worth retirees settle their tax liability with the IRS. Learn why the psychological victory of a Roth conversion often outweighs the raw math of a calculator.

Episode 23 of Retirement Tax Matters tackles a critical reporting gap that can cause high-net-worth retirees over age 70½ to be taxed on their charitable giving that was supposed to be tax-free. While the IRS recently introduced Code Y for Box 7 of Form 1099-R to explicitly identify Qualified Charitable Distributions (QCDs), many major custodians are still using Code 7 (Normal Distribution) in 2026. T

Episode 22 focuses on the logistics of executing large Roth conversions for high-net-worth retirees, specifically how to manage your Roth conversion taxes without slowing your tax-free growth. Learn why high-net-worth retirees should use outside funds to keep their Roth growing with a bigger tax-free growth engine.

Episode 21 of Retirement Tax Matters is Part 2 of our series exploring the shift high-net-worth retirees face when moving from DIY tax filing to using a professional tax preparer. Garrett Crawford, CFP® provides an anecdotal look at the 2026 pricing landscape and how to set the right expectations for your tax team.

Episode 20 kicks off a two-part series on why most retirees between $2M-$8M need both a Tax Preparer and a Financial Planner. We explore the difference between filing forms (rear-view) and strategic planning (windshield) to help you stop being the middleman and start building a coordinated tax team.

The government is offering a $1,000 seed deposit for the new Trump Accounts, but is it the best place for your grandchild's inheritance? In Episode 19, we break down the pros and cons of Trump Accounts versus 529 Plans and Custodial Accounts (UTMAs) to help high-net-worth grandparents navigate this new "abundance of choice."

Episode 18 of Retirement Tax Matters explores how Tax Drag can erode investment returns and introduces Asset Location as a key strategy to fix it. Discover why placing bonds in Traditional IRAs and growth stocks in Roth IRAs can act as a diet for your tax bill in 2026.