Evaluating NUA for Highly Appreciated Employer Stock In Your 401(k)
Episode 47 of Retirement Tax Matters breaks down Net Unrealized Appreciation (NUA) for employer stock held inside a 401(k) plan. Garrett Crawford, CFP® and Adam Reed explain how transferring appreciated company shares in-kind to a taxable brokerage account allows retirees to pay ordinary income tax on the original cost basis while securing long-term capital gains tax rates on the growth. The episode examines how cost basis ratios dictate whether NUA outperforms a traditional IRA rollover, while…
Tax Planning When You Don't Drop Tax Brackets in Retirement
Episode 46 of Retirement Tax Matters addresses the common assumption that retirees always drop into lower tax brackets once they stop working. For savers in the $2M to $8M range, pension income, Social Security, taxable yield, and future required distributions often keep taxable income in the 24% or 32% brackets throughout retirement. Garrett and Adam walk through why converting at the same tax rate can still make sense by protecting a surviving spouse from bracket compression, managing the 10-year…
How a $534K Income Can Still Leave You in the 12% Ordinary MFJ Tax Bracket
Episode 45 of Retirement Tax Matters walks through a live Holistiplan tax planning case study for a married couple reporting $534,200 in total Adjusted Gross Income who remain inside the 12% ordinary marginal tax bracket. Garrett Crawford, CFP® and Adam Reed demonstrate how $100,000 in Social Security and Pension paired with $400,000 in realized long-term capital gains keeps ordinary income at lower rates. Learn how evaluating cost basis versus realized gains inside taxable brokerage accounts may…
Year One Reflections + Why Great Retirement Planning Takes a Team
Episode 44 of Retirement Tax Matters marks the one-year anniversary of the podcast, opening with a look behind the scenes at the growth of the community. Garrett and Adam explore how consistently showing up to produce a weekly podcast shares a surprising number of parallels with navigating a successful retirement. The central focus of the conversation highlights how a collaborative team framework is a powerful ingredient that helps high-net-worth retirees balance their financial planning with real-life…
How To Move Appreciated Brokerage Accounts Without Huge Taxes
Episode 43 of Retirement Tax Matters addresses the unique tax challenges and psychological hurdles of managing large, highly appreciated taxable brokerage accounts. For retirees in the $2M–$8M range, holding concentrated stock positions or outdated, expensive mutual funds can feel like wearing financial handcuffs due to the threat of a massive capital gains tax bill. Garrett and Adam break down the all-or-nothing trap, outlining how a structured, multi-year transition plan can help you diversify your…
Why Your 30-Year Retirement Plan Report Feels Underwhelming
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 made every fall to manage tax brackets and track Medicare IRMAA limits. Real retirement planning happens in…
$6M Retirement Case Study: IRA Drawdown vs Deferring Pension & Social Security to 70
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 deferring those guaranteed streams until age 70. Delaying the fixed income benefits may allow the couple to…
How Charitable Retirees Neutralize Capital Gains and NIIT with a DAF
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 portfolio control. We have developed a 5 step framework for what tax planning looks like for…
Why Your Stomach and Your Calculator Disagree on Retirement Risk
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 tax-free Roth IRAs while reducing risk inside traditional pre-tax accounts. The discussion outlines how…