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.

Episode 17 takes a break from tax brackets to celebrate Christmas. Garrett and Adam discuss their favorite holiday memories and why generosity and connectivity are often the secret sauce for a joyful retirement.

Episode 16 of Retirement Tax Matters tackles the financial psychology of tax aversion—the emotional resistance high-net-worth retirees often feel toward paying taxes, even when it might be the most strategic move. We explore why successful savers, who built wealth by minimizing costs, often struggle to execute strategies like Roth conversions or selling highly appreciated stock because they view paying tax dollars as a loss of capital.

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.

Episode 14 of Retirement Tax Matters explores the critical difference between being sold an insurance policy and actively engaging in comprehensive insurance planning, specifically tailored for high-net-worth retirees. We discuss why simply buying a product from an agent can leave you with policies you don't understand, versus working with a financial planner who integrates insurance into your broader tax and legacy goals. The conversation covers when life insurance is still necessary (such as for estate tax planning or special needs), why many retirees might not need it, and the importance of conducting a full inventory of your existing policies to identify redundancy.

Episode 13 of Retirement Tax Matters provides a financial planner's 101-level orientation to Medicare, breaking down the alphabet soup of Parts A (Hospital), B (Medical), and D (Drug). We explain the general concepts and common paths retirees consider, such as using a Medicare Supplement to create more predictable fixed monthly costs versus the 20% coinsurance.

Episode 12 of Retirement Tax Matters focuses on Social Security optimization for Hign-Net-Worth retirees, framing it as a critical spousal protection and legacy tool rather than a simple break-even calculation…

In Episode 11 of Retirement Tax Matters we discuss cash dilemmas for high-net-worth retirees: finding the right balance between necessary liquidity and optimizing your returns. While having readily accessible cash for emergencies is important, we explore the potential drawbacks of holding excessive amounts in multiple low-yielding bank accounts, which can add unnecessary complexity. Discover how recent T+1 settlement changes allow funds in conservative brokerage investments like money markets (sometimes yielding more) to be accessed typically by the next business day, challenging the need for overly large bank balances.

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 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.