Shows
Retirement Tax MattersWhy Converting Your Traditional IRA to Roth Might Feel Like Paying Off Your Home Mortgage | Episode 24Just 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 Traditional IRA could end up a little better this approach misses the psychological benefits of value of simplicity and control. (00:00) – Intro(01:10) – Tax Free Scream(03:57) – Roth Conversions and Mortgages(07:00) – Debt to the IRS and why to Conve...
2026-02-2519 min
Retirement Tax MattersHow to Handle Your 1099-R Code 7 to Ensure Your QCD Stays 100% Tax-Free | Episode 23It'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 custodians are still using the generic Code 7 (Normal Distribution) in for tax year 2025. Unless you remember to tell your tax preparer about these distributions, your tax return will likely treat your tax-free gift as fully taxable in...
2026-02-1815 min
Retirement Tax MattersHow to Determine the Best Way to Pay Federal Taxes on Large Roth ConversionsIf 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 avoid federal withholding to keep their tax-free growth engine at full capacity.Free Resource for High-Net-Worth Retirees:Year-End Tax Planning Checklist for HNW Retirees
2026-02-1125 min
Retirement Tax MattersThe Tax Preparer Referral Conversation For High-Net-Worth RetireesHigh-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 why your tax preparer and financial planner must be on the same page to avoid tax inefficiencies. Resources: Year-End Tax Planning Checklist fo...
2026-02-0425 min
Retirement Tax MattersTax Preparation vs. Tax Planning: Why High-Net-Worth Retirees Need Both - EP 20Are 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 aren't talking to each other, you are the one stuck in the middle carrying the weight of complex decisions.In Episode 20, Garrett and Adam kick...
2026-01-2821 min
Retirement Tax MattersNavigating Gifting To Grandchildren in 2026: Trump Accounts, 529s vs Custodial AccountsWith 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 align your wealth with your values without compromise.We move past the headlines about the government's $1,000 seed match to build a framework for your giving to your next generation:
2026-01-2126 min
Retirement Tax MattersHow Better Tax Planning Can Help You Drop the Extra Weight of Tax Drag in 2026Just 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 reducing this drag.We explore why holding bonds in your Traditional IRA and growth stocks in your Roth IRA may be an efficient move yo...
2025-12-3111 min
Retirement Tax MattersMerry Christmas! Reflecting on the Gift of GivingMerry 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 spend most weeks focused on tax efficiency, today we focus on the efficiency of the heart. Garrett and Adam discuss why the happiest retirees they work with are often the most generous and connected, and how t...
2025-12-2414 min
Retirement Tax MattersThe Downside of Tax Minimization: Why Paying Taxes Can Be a Winning StrategyEpisode 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 paying tax dollars as a loss of capital. | Disclosures(00:00) Intro(00:35) Financial Psychology(02:10) Tax Aversion(06:30) Personal Experience with Views on Tax(10:30) Taxes in Non Qualified Accounts(15:34) Outro...
2025-12-1716 min
Retirement Tax MattersThe 3.8% Net Investment Income Tax: The Inflation Trap for RetireesIs 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" calculation works, why your Roth conversions might be inadvertently triggering this penalty, and why you shouldn't necessarily let a 3.8% tax wag the dog of your entire financial plan.Key Topics Covered:
2025-12-1020 min
Retirement Tax MattersInsurance Planning vs. Sales: A HNW Retiree's GuideEpisode 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...
2025-11-2619 min
VSiN College Football Betting PodcastIs Notre Dame a Lock for the CFP? ACC & G5 Madness and Overreaction or Market CorrectionTim Murray and Adam Burke are back to recap another wild weekend of college football and lookahead to Week 13. Tim & Adam open up the show discussing the improbable Oklahoma win over Alabama this Saturday. With the Sooners likely jumping over Notre Dame, is there a scenario where the Irish get left out of the College Football Playoff? South Florida got knocked off at Navy this weekend... is there a bet to be made for the Group of 5 representative in the College Football Playoff? North Texas? Tulane? James Madison? With Al...
2025-11-171h 10
Retirement Tax MattersA HNW Retiree's Introduction to Medicare's Alphabet SoupEpisode 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 perspective, we then detail the significant impact of IRMAA (Income-Related Monthly Adjustment Amounts), showing how a high income (ex. $325,000) can trigger premium surcharges for married couples. The key insight, however, is that while these fixed Medicare costs are manageable for most HNW...
2025-11-1230 min
Retirement Tax MattersSocial Security Optimization for HNW Retirees (2026 Update)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 partner. We then cover the key 2026 updates, including the 2.8% Cost of Living Adjustment (COLA) and the new maximum monthly benefit of $4,152 for a worker filing at Full Retirement Age. We also discuss how the Social Security payroll tax wage base has increased to $184,500...
2025-11-0516 min
Retirement Tax MattersThe HNW Cash Dilemma: How to Balance Liquidity and GrowthIn 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. Furthermore, we examine the tax inefficiency of earning substantial bank interest, taxed...
2025-10-2922 min
Retirement Tax MattersAlign Your Legacy with the SECURE Act's 10-Year RuleIn 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 provision with a strict 10-year payout rule, forcing most non-spouse beneficiaries to withdraw an entire inherited Traditional IRA—and pay the associated taxes—within a decade. We break down how a multi-million dollar IRA, which was...
2025-10-1521 min
Retirement Tax MattersA HNW Retiree's Guide To Navigating RMDs from Large IRA AccountsIn 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. | Disclosures
2025-10-0818 min
Retirement Tax MattersHigh-Net-Worth Charitable Giving: Maximize Impact, Minimize TaxesIn 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 utilizing Donor-Advised Funds (DAFs) for highly appreciated assets like stocks. We illustrate how donating appreciated securities to a DAF can help you avoid up to a 23.8% capital gains tax on your gains, simultaneously providing a charitable deduction and offering flexible timing for your...
2025-10-0126 min
Retirement Tax MattersSurviving Spouse Tax Planning: Avoid Post-Death Tax Bracket JumpsIn 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 conversions in your 60s or 70s could strategically lower lifetime tax burdens, protect a surviving spouse, and create a tax-efficient legacy. | DisclosureExplore All Our Resources: https://www.retirementtaxmatters.c...
2025-09-1720 min
Retirement Tax MattersThe #1 Financial Mistake HNW Retirees MakeThe #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 the key to unlocking powerful strategies like Roth conversions.The critical questions to ask your financial advisor about your tax return to ensure your entire financial plan is aligned and working for...
2025-09-1021 min
Retirement Tax MattersThe Golden Window: Roth Conversions Before Social Security & RMDsIn 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, transforming a future tax problem into possible lower aggregate lifetime taxes and/or a tax-free legacy for your heirs. Most importantly, we discuss how to balance this powerful strategy with your non-financial life goals by incorporating in...
2025-09-0319 min
Retirement Tax MattersUnderstanding the New Standard Deduction Under OBBBA | Retirement Tax Matters Ep 04In 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. Learn why this new tax landscape makes end-of-year projections more critical than ever and how the now-permanent lower tax brackets create a longer "runway" for powerful, long-term Roth conversion strategies. | Disclosures
2025-08-2615 min
Retirement Tax MattersPermanent Tax Brackets? How to Plan for Your HNW Retirement | Retirement Tax Matters Ep 03In 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 misunderstanding of how marginal tax brackets work. Most importantly, we discuss what this newfound "runway" means for HNW retirees and how a long-term, strategic approach to Roth conversions can now be even more powerful fo...
2025-08-2615 min
Retirement Tax MattersWill My Social Security Benefit Be Taxed Moving Forward? | Retirement Tax Matters Ep 02The 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. | Disclosures
2025-08-2611 min
Retirement Tax MattersWelcome To Retirement Tax Matters | Retirement Tax Matters Ep 01In 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
2025-08-2614 min