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 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.

n Episode 10 of Retirement Tax Matters we tackle one of the most significant change to legacy planning in decades: the elimination of the Stretch IRA by the SECURE Act. Although this legislation took effect in 2020, its importance may have been easily missed in our fast-moving world, and new retirees are being reminded of its consequences.

n Episode 9 of Retirement Tax Matters we delve into the growing challenge of Required Minimum Distributions (RMDs) for high-net-worth retirees with substantial Traditional IRA balances, particularly those in the $2M-$8M range. We establish that a six-figure RMD (beginning at just $2.65 million in an IRA for a 73-year-old in 2025) is a realistic scenario that continues to grow, often exceeding actual spending needs. Our conversation centers on the core dilemma: taking out money you don't need, which becomes fully taxable and can push you into higher tax brackets.

In Episode 7 of Retirement Tax Matters we tackle a critical, yet often emotionally challenging, aspect of HNW retirement planning: the significant tax bracket shock a surviving spouse can face. We reveal how a married couple's ~$250,000 taxable income, typically in the 24% bracket, can jump to a 35% bracket for a surviving spouse due to the shift from married filing jointly to individual rates, compounded by growing RMDs and even higher Medicare premiums.

In Episode 6 of Retirement Tax Matters, we reveal what we believe is the #1 mistake most high-net-worth retirees make: treating your tax return as a once-a-year, historical document instead of a forward-looking tool to guide their investment and long-term financial plan. This podcast conversation explores why this reactive approach causes retirees to miss out on valuable, unused tax bracket space each year.

In Episode 5 of Retirement Tax Matters, we define the Golden Window — the critical years of temporary low income after you retire but before RMDs and Social Security begin. For high-net-worth retirees with large pre-tax IRA balances, this is an ideal time to manage what is likely your largest future tax liability.

The passage of the recent tax legislation, One Big Beautiful Bill Act (OBBBA), has created significant confusion around how Social Security will be taxed. Many retirees are asking if their benefits will now be tax-free. In this episode, Garrett Crawford breaks down the reality of the new law, explaining that the primary change is not to Social Security taxation itself, but the introduction of a new, substantial "Senior Deduction." We'll cover who qualifies for this deduction, the specific income phase-outs that could affect HNW retirees, and the critical planning dilemma it creates when considering strategic Roth conversions.

The passage of the recent tax legislation, One Big Beautiful Bill Act (OBBBA), has created significant confusion around how Social Security will be taxed. Many retirees are asking if their benefits will now be tax-free. In this episode, Garrett Crawford breaks down the reality of the new law, explaining that the primary change is not to Social Security taxation itself, but the introduction of a new, substantial "Senior Deduction." We'll cover who qualifies for this deduction, the specific income phase-outs that could affect HNW retirees, and the critical planning dilemma it creates when considering strategic Roth conversions.