You’ve Saved Enough, but Will Your Surviving Spouse Continue to Spend? | Episode 32

$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 utilize the lower tax brackets during their early retirement years to execute a more aggressive drawdown or strategic Roth conversions from their pre-tax retirement accounts. We have developed a 5-step framework for what tax planning looks like for High-Net-Worth Retirees between $2M-$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients. Request a free resource using this link: https://www.retirementtaxmatters.com/checklist 00:00 Welcome to Retirement Tax Matters & Studio Updates 00:46 What Does Tax Return Driven Financial Planning Actually Look Like? 01:05 Case Study Introduction: Tim & Ann's Retirement Dilemma 03:18 Establishing the Case Assumptions: Assets, Income, and Bracket Goals 04:54 Financial Planning: Calculator vs. Psychology 06:15 Diving into Holistiplan: Analyzing the 2026 Working Year Income 08:18 Understanding Phantom Income: Interest, Ordinary, and Qualified Dividends 11:13 Navigating the 24% Tax Bracket Summary 12:08 Fast-Forwarding to 2028: The Beans and Rice Early Retirement Scenario 14:31 The Six-Figure RMD Trap: Projections at Age 75 and Beyond 16:44 The Strategy: Delaying Fixed Income vs. Drawing Down the Traditional IRA 18:41 Utilizing the Range Calculator & Navigating Medicare IRMAA Penalties 20:36 Modeling a $300,000 Strategic Roth Conversion 23:11 Shifting Perspectives: Younger Accumulators vs. Older Decumulators 24:51 Real-Time Collaboration: Why Financial Planning is Dynamic Visit us online at: https://www.retirementtaxmatters.com Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures

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 High-Net-Worth Retirees between $2M-$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients. Request a free resource using this link: https://www.retirementtaxmatters.com/checklist [https://www.google.com/search?q=https://www.retirementtaxmatters.com/checklist&authuser=1] Chapters: (00:00) – Introduction to Donor-Advised Funds (DAFs) (01:35) – The Year-End Tax Planning Checklist (02:45) – DAFs vs. Qualified Charitable Distributions (QCDs) (04:30) – What is a Donor-Advised Fund and How Does it Work? (05:55) – The Primary Benefits: Value, Capital Gains, and Control (07:15) – Privacy and Giving Anonymously (08:45) – Who is a DAF the Best Fit For? (11:35) – Neutralizing Capital Gains with Cash (11:50) – Understanding the Net Investment Income Tax (NIIT) (13:45) – Navigating AGI Limitations & Five-Year Carryovers (15:15) – How to Set Up and Implement a DAF (17:05) – The Return on Hassle (ROH) and Platform Fees (19:00) – Keeping the True Heart Behind Charitable Giving (20:10) – Summer Projections and Scannable Year-End Planning Visit us online at: https://www.retirementtaxmatters.com [https://www.retirementtaxmatters.com] Review our required industry disclosures here: https://www.retirementtaxmatters.com/disclosures [https://www.retirementtaxmatters.com/disclosures]

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 understanding your risk metrics allows you to safely evaluate speculative market opportunities without jeopardizing the retirement lifestyle you envision for your family.  Chapters: * (00:00) - The History of the 1040 Tax Return * (03:23) - The SpaceX IPO and Swinging for the Fences * (05:10) - The Evolution of the Risk Tolerance Questionnaire * (10:05) - Understanding Risk Capacity vs. Risk Tolerance * (14:44) - Earmarking Risk Across Different Asset Buckets * (20:38) - How We Evaluate Client Risk Dynamics * (26:21) - The Zero-Turn Lawnmower Analogy for Portfolio Risk We have developed a 5-step framework for what tax planning looks like for High-Net-Worth Retirees between $2M–$8M. It walks you through each season of the calendar year and explains how we implement tax-return driven financial planning for our clients. Request a free copy of this resource using this link: https://www.retirementtaxmatters.com/checklist For comprehensive firm disclosures, please visit our website: https://www.retirementtaxmatters.com/disclosures

Why Gifting Wealth From a $2M–$8M Portfolio May Be Simpler Than You Think | Episode 38

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 majority of affluent families. While the 2026 annual exclusion limit is capped at $19,000 per recipient, some retirees find filing a Form 709 gift tax return with their tax preparer is all that may be required to report the excess transfer and reduce their lifetime exemption footprint. Free Resource: We have developed a 5-step framework for what tax planning looks like for High-Net-Worth Retirees between $2M–$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients. Request a free resource using this link: https://www.retirementtaxmatters.com/checklist [https://www.retirementtaxmatters.com/checklist] Review our disclosures at https://www.retirementtaxmatters.com/disclosures [https://www.retirementtaxmatters.com/disclosures]

The Two Most Underrated Social Security Features for High-Net-Worth Married Retirees | Episode 37

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 inflation cycles. We have developed a 5 step framework for what tax planning looks like for High-Net-Worth Retirees between $2M-$8M. It walks you through each season of the calendar year and how we implement tax-return driven financial planning for clients. Request a free resource using this link: https://www.retirementtaxmatters.com/checklist [https://www.retirementtaxmatters.com/checklist] Time Stamps: (00:00) – Intro & Welcome Back from Vacation (01:05) – Topic Introduction: Social Security (01:40) – Garrett's History with Social Security Workshops (03:05) – Social Security for the $2M to $8M+ High-Net-Worth Crowd (04:00) – Underrated Feature #1: The Survivor Benefit Rule (06:25) – Investment ROI vs. Insurance Components (09:05) – Tying Social Security into Proactive Roth Conversion Planning (10:50) – Underrated Feature #2: Cost of Living Adjustments (12:45) – The Historical Blueprint of COLA and Modeling Inflation (15:00) – The Impact of Recent Inflation Waves On Your Capital (17:10) – Why Social Security is a Unicorn Asset (Not Just Bank Cash) (20:05) – Is Social Security Going Bankrupt? (21:55) – Wrap-Up & The Year-End Tax Planning Checklist Challenge Read our full legal disclosures here: https://www.retirementtaxmatters.com/disclosures [https://www.retirementtaxmatters.com/disclosures]