Episodes

If you have a specific subject on your mind, you can use our complete episode index, organized by topic, to find the conversation you're looking for.

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Tax-Efficient Income Strategies Garrett Crawford, CFP® Tax-Efficient Income Strategies Garrett Crawford, CFP®

The 3.8% Net Investment Income Tax: The Inflation Trap for Retirees

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.

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Insurance Strategies in Retirement Garrett Crawford, CFP® Insurance Strategies in Retirement Garrett Crawford, CFP®

Insurance Planning vs. Sales: A HNW Retiree's Guide

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.

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Medicare & IRMAA Planning Garrett Crawford, CFP® Medicare & IRMAA Planning Garrett Crawford, CFP®

A HNW Retiree's Introduction to Medicare's Alphabet Soup

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.

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Tax-Smart Investing Garrett Crawford, CFP® Tax-Smart Investing Garrett Crawford, CFP®

The HNW Cash Dilemma: How to Balance Liquidity and Growth

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.

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Estate & Legacy Planning Garrett Crawford, CFP® Estate & Legacy Planning Garrett Crawford, CFP®

Align Your Legacy with the SECURE Act's 10-Year Rule

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.

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RMDs (Required Minimum Distributions) Garrett Crawford, CFP® RMDs (Required Minimum Distributions) Garrett Crawford, CFP®

A HNW Retiree's Guide To Navigating RMDs from Large IRA Accounts

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.

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Strategic Charitable Giving Garrett Crawford, CFP® Strategic Charitable Giving Garrett Crawford, CFP®

High-Net-Worth Charitable Giving: Maximize Impact, Minimize Taxes

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.

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Estate & Legacy Planning Garrett Crawford, CFP® Estate & Legacy Planning Garrett Crawford, CFP®

Surviving Spouse Tax Planning: Avoid Post-Death Tax Bracket Jumps

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.

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Working With A Financial Professional Garrett Crawford, CFP® Working With A Financial Professional Garrett Crawford, CFP®

The #1 Financial Mistake HNW Retirees Make

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.

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Roth IRA & Conversions Garrett Crawford, CFP® Roth IRA & Conversions Garrett Crawford, CFP®

The Golden Window: Roth Conversions Before Social Security & RMDs

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.

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Tax Legislation & Policy Garrett Crawford, CFP® Tax Legislation & Policy Garrett Crawford, CFP®

Permanent Tax Brackets? How to Plan for Your HNW Retirement

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.

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Social Security Optimization Garrett Crawford, CFP® Social Security Optimization Garrett Crawford, CFP®

Will My Social Security Benefit Be Taxed Moving Forward?

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.

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Garrett Crawford, CFP® Garrett Crawford, CFP®

Welcome To Retirement Tax Matters

In our inaugural episode, Garrett Crawford, CFP®, and Adam Reed introduce the mission behind Retirement Tax Matters and our focus on providing advanced tax planning strategies for high-net-worth retirees.

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