Retirement Tax Matters | Advanced Tax Planning for High-Net-Worth Retirees

Episode 42 of Retirement Tax Matters looks at the difference between a long-term retirement trajectory and proactive annual tax planning. For retirees with portfolios between $2M and $8M, relying entirely on a static 60-page financial report often leaves families feeling unprepared when real-world changes occur. Garrett and Adam discuss how to balance a 30-year vision with tactical adjustments mad...

Episode 41 of Retirement Tax Matters reviews a screen-share case study of a married couple at age 63 navigating a $6 million portfolio. With $5 million concentrated in pre-tax traditional IRAs and 401(k) plans alongside $1 million in brokerage and savings accounts, this scenario highlights the critical decision between taking a combined $85,000 pension and Social Security stream immediately or def...

Episode 40 of Retirement Tax Matters examines the use of Donor-Advised Funds for high-net-worth retirees evaluating their year-end charitable strategies. Garrett and Adam break down how to properly navigate the 30% adjusted gross income limitation for gifting long-term appreciated securities, allowing families to neutralize capital gains and Net Investment Income Tax surcharges without sacrificing...

This episode explores the disconnect between your psychology and the calculator when evaluating portfolio risk capacity in the $2M–$8M range, using recent client inquiries about the SpaceX IPO as a real-world backdrop. Garrett and Adam break down how to segment a retirement portfolio into separate asset buckets based on their purpose, explaining why can make sense to maximize equity growth inside...

Episode 38 of Retirement Tax Matters examines the common misunderstandings and anxieties high-net-worth parents face when gifting money to adult children. For retirees with a portfolio in the $2M–$8M range, the federal gift tax framework under the One Big Beautiful Bill Act provides an individual lifetime exemption of $15 million, removing the tax penalty from early wealth transfers for the vast m...

In this episode, Garrett and Adam explore why high-net-worth married retirees often overlook the risk-reducing power of Social Security by focusing strictly on an investment ROI calculator. Discover how maximizing your baseline benefit maximizes the compounding strength of both the household survivor benefit and annual cost-of-living adjustments to shield your total portfolio from unexpected infla...

For many high-net-worth retiree between $2M-$8M, a successful financial life isn't just about how much you grow; it’s about how much you actually get to keep. Yet, many retirees find themselves blindsided on April 15th by an unwelcomed tax surprise. It's not the fact that paying owed tax is bad, but having to pay significantly more than planned can bother anyone. Tax return-driven financial planni...

Episode 35 analyzes the limitations of artificial intelligence in high-net-worth retirement planning and why retirees must distinguish between raw data processing and fiduciary human judgment. We explore the specific risks of AI hallucinations regarding 2026 tax law and the critical steps needed to protect your resources from sophisticated AI-driven financial scams. We have developed a 5 step fram...

Single filers often feel overlooked when discussing Roth Conversions. Most content is geared towards Married households, yet Single Retirees face pretty tight tax brackets, especially for the $2M-$8M single Retiree. In this episode, Garrett and Adam dive into why the income range between $200,000 and $250,000 represents a challenging income range for individual retirees considering a Roth Conversi...

What if RMDs didn't exist for pre-tax 401(k)s or Traditional IRAs? In this episode we discuss why even if you don't like RMDs, even if they didn't exist, you might still not want to let your pre-tax accounts grown untouched. Garrett Crawford, CFP® discusses the benefits of reverse-engineering an RMD plan. High-net-worth retirees between $2M-$8M might be playing a different RMD game than their peer...

In many high-net-worth households, one spouse naturally takes the lead as the primary financial quarterback. While this works well during the accumulation years, it often creates a significant challenges later in retirement. On this episode of Retirement Tax Matters , Garrett Crawford, CFP® and Adam Reed discuss the psychological gap between having a multi-million dollar portfolio and having the a...

Episode 31 analyzes why high-net-worth retirees should consider intentionally filling the 24% tax bracket to protect against future 32% RMD spikes and surviving spouses tax rates increasing when going from Married Filing Jointly to Individual Filing. Garrett Crawford, CFP® details the math behind the 2% decision and how to identify these opportunities before the December 31st deadline. Request a 5...

For many retirees, tax season feels like the finish line. In reality, it is the starting point for smarter retirement tax planning. In this episode, Garrett Crawford, CFP® and Adam Reed explain why reviewing your tax return in the spring can help you make better decisions for the rest of the year. They walk through their tax return driven financial planning framework, including why an early income...

Discover why working just six months longer can be a bigger retirement planning boost than most near-retirees realize. But while working longer almost always works out, for retirees in the $2M-$8M range sometimes this question comes back to defining enough and knowing when continuing to wait one more year might not be the best path to take. We have developed a 5 step framework for what tax plannin...

Episode 28 of Retirement Tax Matters discusses the different types of investment accounts high-net-worth retirees can use to bridge the income gap when retiring in their 50s. While technical workarounds like SEPP 72(t) exist for pre-tax funds, Garrett and Adam address the access and wisdom of using Roth IRAs and taxable brokerage accounts to fund an early lifestyle. The conversation dives deeper r...

Episode 27 of Retirement Tax Matters examines a couple bridge strategies for retirees in the $2M–$8M range who have a large amount of pre-tax funds but restricted by the age 59 ½ milestone. Garrett Crawford, CFP® and Adam Reed break down Substantially Equal Periodic Payment (SEPP) method and the Rule of 55 for 401(k) plans. (00:00) – Intro (01:45) – Accessing Retirement Funds Before 59½ (06:15) –...

In this episode of Retirement Tax Matters, Garrett Crawford, CFP® and Adam Reed tackle one of the largest roadblocks for high-net-worth retirees considering early retirement: health insurance costs before Medicare age 65. For retirees in the $2M–$8M range, the decision to retire early often hinges on a psychological standoff. Is it wise to pay $2,000 or more a month for private insurance after yea...

If you are planning to stop work before age 60, your Social Security statement estimate for age 67 or 70 likely contains misleading benefit amounts. Standard benefit projections assume you will continue earning your current salary until the year you file—an assumption that is incorrect for early retirees who have gap years before filing with $0 in earnings . In the kickoff of our Early Retirement...

Just as individuals rarely regret paying off their primary home, retirees rarely regret the peace of mind that comes from settling their tax debt and ensuring their family has more control over their finances. This episode explores the psychological parallels between a strategic Roth conversion and the Debt-Free Scream made famous by Dave Ramsey. While a calculator might suggest keeping a Traditio...

It's tax document season, and for retirees over age 70½, a common tax filing mistake could be costing you thousands in unnecessary taxes. In this episode, Garrett Crawford, CFP® and Adam Reed discuss an important and commonly missed reporting issue with Qualified Charitable Distributions (QCDs). While the IRS recently introduced Code Y to explicitly label these gifts on Form 1099-R, many major cus...

If you have decided that 2026 is the year to execute a large Roth conversion , you might be wondering about the mechanics of the tax bill. In Episode 22, Garrett Crawford, CFP® professional, and Adam Reed break down the three primary ways to pay the IRS: the simple way, the efficient way, and the strategic way. We explain why high-net-worth retirees with assets between $2M and $8M should typically...

High-net-worth retirees often reach a point where DIY tax software like TurboTax no longer offers the peace of mind their $2M–$8M portfolio requires. In this episode we pull back the curtain on the referral conversation we have with clients and prospects. We discuss the increasing prices of tax preparer professionals and the shift that many retirees make from saving money to buying freedom, and wh...

Are you tired of playing the middle man between your CPA and your financial planner? (Or all the roles yourself!) For many high-net-worth retirees, tax season feels like a burden not because of the cost, but because of the coordination. You have a CPA looking in the rear-view mirror to file your forms, and a financial planner already looking into the new year to strategize your future. But if they...

With the release of new IRS guidance on Trump Accounts (Section 530A), the landscape for gifting to grandchildren hasn't just gotten bigger—it’s gotten better. For years, high-net-worth grandparents have felt forced to choose between the educational tax benefits of a 529 Plan and the flexibility they actually want. In this episode, Adam and Garrett explain all these options finally allows you to a...

Just like shedding holiday weight, your portfolio might need to go on a diet in the New Year—a tax diet. In this Season One finale of Retirement Tax Matters, Adam and Garrett discuss the concept of Tax Drag and how it can silently erodes the returns of high-net-worth retirees. We dive into the specific strategy of Asset Location (not to be confused with Asset Allocation ) as a primary method for r...