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

Merry Christmas from the team at Retirement Tax Matters! In this special holiday episode, Garrett Crawford, CFP® and Adam Reed step away from the technical world of tax brackets, RMDs, and Roth Conversions to reflect on the season. They share personal Christmas memories—including the story of how they first met during the holidays—and discuss the deeper why behind financial planning. While we spen...

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 p...

Is your retirement income triggering an extra 3.8% surtax? The Net Investment Income Tax (NIIT) is a stealth tax that catches many high-net-worth retirees by surprise. Because its income thresholds haven't been adjusted for inflation since 2013, more retirees are tripping over this wire every year. In this episode, Garrett and Adam demystify the NIIT. They break down exactly how the "lesser of" ca...

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 bro...

Episode 12 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. From a financial planning perspectiv...

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. We explain why the higher-earning spouse delaying their benefit to age 70 is often the most critical decision, as it maximizes the guaranteed, inflation-adjusted survivor benefit for their...

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 r...

In 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. The new law replaces the old lifetime stretch RMD provisi...

In 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 act...

In Episode 8 of Retirement Tax Matters we dive into optimizing your charitable giving, revealing why writing a check from you checking account is likely costing high-net-worth retirees significant tax dollars. You'll learn about Qualified Charitable Distributions (QCDs) from Traditional IRAs, which allow you to donate up to $108,000 tax-free directly from your IRA (bypassing RMD taxes), versus uti...

In Episode 7, Garrett Crawford, CFP®, and Adam Reed tackle a critical HNW retirement challenge: the tax shock a surviving spouse can face. It's possible for a married couple's ~24% tax bracket can jump to 35% for a single survivor due to filing changes, growing RMDs & higher Medicare premiums. This creates an increased financial burden during an already difficult time. Learn how proactive Roth...

The #1 mistake High-Net-Worth retirees make is treating their tax return as a rearview mirror. In this crucial episode of Retirement Tax Matters, we dive deep into the costly disconnect between your tax return, investment plan, and long-term legacy goals. Discover: Why overlooking unused tax bracket space each year is costing you significant wealth. How proactive, intra-year tax projections are th...

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. We explore how to leverage this period by executing strategic Roth conversions , tr...

In Episode 4 of Retirement Tax Matters we explore the permanent extension of the higher standard deduction under the new "One Big Beautiful Bill Act" (OBBBA) . We'll cover the new 2025 standard deduction amount for married couples ( $31,500 ) and explain how the new law, while beneficial, adds layers of complexity with income-based phase-outs for deductions like the new Enhanced Senior Deduction ....

In Episode 3 of Retirement Tax Matters , we dive into one of the most significant parts of the new "One Big Beautiful Bill Act" (OBBBA): the permanent extension of the lower tax brackets originally established by the Tax Cut and Jobs Act of 2017. We’ll provide a clear refresher on how today's tax rates (12%, 22%, 24%) are historically low compared to prior years and break down a common misundersta...

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 ne...

In our inaugural episode, Garrett Crawford, CFP® and Adam Reed introduce the mission behind Retirement Tax Matters. Discover our focus on providing advanced tax planning strategies for high-net-worth retirees and learn what to expect from future conversations. | Disclosures