Divorce the IRS

James Miller
  • 5.0 (4)
  • Investing

Welcome to Divorce the IRS, the Retirement Income Planning Podcast—built for people who want to pay the least amount of taxes possible and create retirement income that actually lasts. Inspired by Jimmy Miller’s bestselling book Divorce the IRS, this show takes you behind the scenes of the tax rules, retirement strategies, and planning decisions that can quietly determine how much of your money you keep. The truth is, taxes aren’t just “something you deal with later.” The U.S. tax code is massive, confusing by design, and full of traps that can hit hardest right when you need your money most. From 401(k)s and IRAs to Social Security and Medicare, many common “smart moves” can turn into expensive surprises—like required minimum distributions, Medicare surcharges, the widow’s penalty, and other retirement tax time bombs most people don’t see coming until it’s too late. With 20+ years of experience as a global wealth manager, Jimmy breaks these topics down in a clear, practical way—so you can plan proactively, avoid unnecessary taxes, and build a retirement where your delayed gratification finally pays off. Subscribe so you never miss an episode, and remember: this podcast is for general education only and isn’t legal, tax, or investment advice—always consult a qualified professional for guidance specific to your situation.

  1. 4d ago

    Die Broke, Annuities, and Tax-Free Retirement Income

    In this episode of the Divorce the IRS Podcast, Jimmy Miller discusses a retirement philosophy that has become increasingly popular: die broke, also known as die with zero. The idea behind this strategy is to maximize retirement income and enjoy more of your money during your lifetime, especially when leaving a financial legacy is not a major goal. Jimmy explains why the concept can make sense in theory, but why trying to personally spend your portfolio down to zero without guarantees can create serious risks. Jimmy also explains how the die broke philosophy can work together with the Divorce the IRS framework when lifetime income annuities are used properly, especially inside Roth IRA accounts. In this episode, Jimmy discusses: What the die broke or die with zero philosophy meansWhy the concept appeals to many retirees and future retireesThe danger of becoming too frugal and never enjoying your moneyWhy aiming for exactly zero can be risky without the right structureHow lifetime income annuities can support a die broke strategyWhy guaranteed income may help reduce retirement stressThe risk of running out of money before running out of lifeHow annuities can allow retirees to spend both growth and principalWhy Roth IRA annuities can create tax-free lifetime incomeThe importance of understanding annuity rules before purchasing oneHow fixed index annuities may help address inflation concernsJimmy also shares why dying broke can be a reasonable goal for some people, but only when the plan is built carefully and includes the right guarantees. When structured correctly, the goal is not simply to spend everything. It is to create a retirement income strategy that allows you to enjoy your money with confidence while reducing the risk of outliving it. Visit Divorce-the-IRS.comVisit Baobab WealthVisit Baobab Wealth AbroadBuy a copy of Jimmy's book, Divorce the IRSFollow us on FacebookSubscribe to us on YouTubeConnect with us on LinkedIn

    Die Broke, Annuities, and Tax-Free Retirement Income

  2. Jul 6

    Real Estate, Retirement Income, and the IRS Problem

    In this episode of the Divorce the IRS Podcast, Jimmy Miller continues the conversation from last week’s episode on the FIRE movement by taking a closer look at real estate investing and how it fits into the Divorce the IRS framework. Real estate is one of the most common investment topics Jimmy gets asked about. How does it compare to the stock market? Can it work as a retirement income strategy? Does it help or hurt when the goal is to reduce taxes in retirement? Jimmy gives his honest perspective on the appeal of real estate, including the ability to own something tangible and understandable, while also explaining why he does not view rental properties as an ideal primary investment strategy for retirement. In this episode, Jimmy discusses: How real estate compares to long-term stock market investingWhy home values and investment returns are not always the same thingThe hidden costs of rental properties, including repairs, vacancies, insurance, HOA fees, and managementWhy being a landlord may not fit the retirement lifestyle many people actually wantHow rental income can affect the taxation of Social Security benefitsWhy provisional income matters in the Divorce the IRS frameworkHow depreciation recapture works when a rental property is soldWhy some investors underestimate the tax bill that can come at the endThe difference between owning rental properties directly and investing in REITsHow REITs can offer real estate exposure inside a diversified portfolioJimmy also explains why real estate investment trusts, or REITs, may be a more practical way to include real estate in a retirement portfolio, especially when used inside Roth accounts where income and growth can potentially avoid creating provisional income. In the next episode, Jimmy will discuss another popular retirement philosophy: the desire to die broke. Visit Divorce-the-IRS.comVisit Baobab WealthVisit Baobab Wealth AbroadBuy a copy of Jimmy's book, Divorce the IRSFollow us on FacebookSubscribe to us on YouTubeConnect with us on LinkedIn

    Real Estate, Retirement Income, and the IRS Problem

  3. Jul 1

    F.I.R.E. and Divorce the IRS: Building an Early Retirement Strategy

    In this episode of the Divorce the IRS Podcast, Jimmy Miller breaks down the F.I.R.E. movement, which stands for Financial Independence Retire Early, and explains why the concepts in Divorce the IRS can be especially useful for people who want to retire before the traditional retirement age. Jimmy discusses why Roth accounts can be such a powerful tool for early retirees, including how Roth IRA contribution withdrawals, Roth conversion withdrawals, and Roth growth are treated differently under IRS rules. He also explains why having access to tax-free and penalty-free sources of income can help solve one of the biggest challenges early retirees face: accessing retirement savings before age 59½. This episode also looks at the lifestyle side of F.I.R.E. Jimmy shares why learning to be happy with less, avoiding lifestyle creep, and saving a high percentage of income can dramatically change the retirement planning equation. He also explains why a successful retirement is usually about retiring to something, not just away from something. In this episode, Jimmy discusses: What F.I.R.E. means and why it has grown in popularityWhy Divorce the IRS resonates with people pursuing F.I.R.E.How Roth IRA contributions can be accessed tax and penalty-freeThe order in which money comes out of a Roth IRAWhy Roth conversions may help early retirees create future incomeHow Roth accounts compare to Rule of 55 and 72(t) strategiesWhy lifestyle creep can make retirement harder to achieveThe importance of retiring with purpose, not just escaping workWhy real estate is often part of the F.I.R.E. conversationJimmy also mentioned his short video on the different types of F.I.R.E. You can watch that here: https://www.youtube.com/watch?v=IcKHu8ygKg0 In the next episode, Jimmy will explore how real estate fits into the idea of divorcing the IRS. Disclaimer: This podcast is for educational purposes only and should not be considered tax, legal, or financial advice. Please consult with a qualified professional before making decisions based on your personal situation. Visit Divorce-the-IRS.comVisit Baobab WealthVisit Baobab Wealth AbroadBuy a copy of Jimmy's book, Divorce the IRSFollow us on FacebookSubscribe to us on YouTubeConnect with us on LinkedIn

    F.I.R.E. and Divorce the IRS: Building an Early Retirement Strategy

  4. Jun 25

    The Dividend Detail Your Index Strategy May Be Missing

    Welcome back to The Divorce the IRS Podcast. In this episode, we build on the previous conversation about life insurance retirement plans and take a closer look at one of the most overlooked details in many index-based insurance products: dividends. This is not an anti-IUL or anti-annuity episode. Fixed index annuities and indexed universal life policies can have a place for the right person when they are designed properly, funded properly, and fully understood. But when someone says you can “participate in the S&P 500 without market risk,” it is important to understand what that actually means. Many indexed annuities and IUL policies are linked to the price return of an index, not the total return. That means the dividends paid by the companies inside the index may not be included. Over long periods of time, that difference can be enormous. In this episode, we discuss: The difference between S&P 500 price return and total returnWhy reinvested dividends are one of the quiet engines of long-term wealth creationHow missing dividends can impact compounding over decadesWhy indexed annuities and IULs are not the same as owning an S&P 500 index fundHow caps, participation rates, spreads, and crediting formulas can affect growthWhy tax efficiency alone does not automatically make a strategy betterThe key question to ask before using an index-linked insurance strategyThe goal of divorcing the IRS is not just to pay less in taxes. The goal is to build efficient wealth, grow more, protect more, and understand exactly how your money is working. Before making any decision, review your situation with a qualified tax, legal, and financial professional. And when someone shows you a strategy tied to the S&P 500, don’t just ask about upside and downside. Ask about the dividends. Visit Divorce-the-IRS.comVisit Baobab WealthVisit Baobab Wealth AbroadBuy a copy of Jimmy's book, Divorce the IRSFollow us on FacebookSubscribe to us on YouTubeConnect with us on LinkedIn

    The Dividend Detail Your Index Strategy May Be Missing

  5. Jun 18

    Should You Use Life Insurance for Retirement Income?

    Many retirees and high-income earners are constantly searching for ways to build more tax-free income in retirement. One strategy that often enters the conversation is the Life Insurance Retirement Plan, better known as a LIRP.  Proponents often market LIRPs as a powerful way to create tax-free retirement income while maintaining life insurance protection. But are they really as good as advertised? In this episode of The Divorce the IRS Podcast, we take an objective look at Life Insurance Retirement Plans, including how they work, who they're designed for, and the risks that are often left out of the sales presentation.  We explore the evolution of cash value life insurance from Whole Life to Universal Life, Variable Universal Life (VUL), and Indexed Universal Life (IUL), and discuss why IUL policies have become the most common structure used for modern LIRP strategies.  You'll learn how these policies generate tax-deferred growth, how tax-free policy loans are used to create retirement income, and why proper funding and ongoing management are critical to success. We also cover the potential drawbacks, including policy costs, surrender charges, underwriting requirements, Modified Endowment Contract (MEC) rules, policy lapse risks, and the limitations that come with indexed crediting strategies.  Most importantly, we discuss who should consider a LIRP and why, for many investors, there may be better tax-free options to explore first before turning to life insurance as a retirement planning tool.  If you've ever been pitched a LIRP, IUL, or cash value life insurance policy as a retirement strategy, this episode will help you understand the benefits, the risks, and whether it deserves a place in your financial plan. In This Episode • What a Life Insurance Retirement Plan (LIRP) is • How cash value life insurance differs from term life insurance • The evolution of Whole Life, Universal Life, VUL, and IUL policies • Why Indexed Universal Life (IUL) is commonly used for LIRP strategies • How tax-deferred growth and tax-free policy loans work • The underwriting requirements needed to qualify for coverage • Why LIRPs should typically be considered only after other tax-advantaged strategies have been exhausted • The importance of fully funding a policy for long-term success • Common mistakes that cause LIRPs to underperform • How policy fees, insurance costs, and administrative charges impact returns • What a Modified Endowment Contract (MEC) is and why it matters • The tax consequences of policy lapses and excessive borrowing • How insurance companies control participation rates and caps within IUL policies • Why investors do not receive dividends from underlying index investments • The impact of surrender charges and long holding periods • Who may be a good candidate for a LIRP and who probably is not • Why proper planning and ongoing management are critical to making a LIRP work What's Coming Next • Advanced retirement income planning strategies • Tax-efficient withdrawal strategies in retirement • Why dividends matter more than many investors realize • Divorce the IRS and FIRE: Tax planning for the Financial Independence, Retire Early movement • Real estate considerations in retirement planning • Divorce the IRS and "Die Broke": Rethinking wealth, legacy, and retirement spending Life Insurance Retirement Plans can be powerful tools in the right circumstances, but they are far from a one-size-fits-all solution. Understanding the costs, risks, and limitations before committing to a policy can help you avoid expensive mistakes and determine whether a LIRP truly belongs in your retirement strategy. Visit Divorce-the-IRS.comVisit Baobab WealthVisit Baobab Wealth AbroadBuy a copy of Jimmy's book, Divorce the IRSFollow us on FacebookSubscribe to us on YouTubeConnect with us on LinkedIn

    Should You Use Life Insurance for Retirement Income?

  6. Jun 15

    The Rule of 55 Explained: A Little-Known IRS Exception

    Many people spend years building up money inside their 401(k), only to discover that accessing those funds before age 59½ can trigger a costly 10% early withdrawal penalty. Fortunately, there are exceptions. In this episode of The Divorce the IRS Podcast, we break down one of the most important retirement planning rules for early retirees: the Rule of 55. This IRS exception allows certain workers to access money from qualified workplace retirement plans, such as 401(k)s and 403(b)s, before age 59½ without paying the typical 10% early withdrawal penalty. We explain how the Rule of 55 works, who qualifies, and why understanding the timing requirements can save retirees thousands of dollars in unnecessary penalties. You'll learn why the rule applies only to workplace retirement plans, why rolling your 401(k) into an IRA too quickly can create unexpected tax consequences, and how proper planning before retirement can preserve valuable flexibility during the early years of retirement. We also discuss common mistakes retirees make, how the Rule of 55 compares to the 72(t) strategy covered in the previous episode, and the questions you should ask your employer plan before making any retirement decisions. If you're considering retiring between ages 55 and 59½, this is an episode you won't want to miss. In This Episode • What the Rule of 55 is and how it works • Who qualifies for penalty-free withdrawals before age 59½ • Why the timing of your retirement date matters • The difference between the Rule of 55 and the 72(t) strategy • Why the Rule of 55 applies to 401(k)s and workplace retirement plans, but not IRAs • How rolling a 401(k) into an IRA can accidentally eliminate Rule of 55 benefits • The importance of understanding your employer plan's distribution rules • How old 401(k) accounts are treated under the Rule of 55 • Potential planning opportunities using roll-ins before retirement • Why the Rule of 55 eliminates penalties but not income taxes • How to evaluate the tax impact of early retirement withdrawals • A real-world example showing how a simple rollover mistake could cost thousands in penalties • Special Rule of 55 provisions for certain public safety employees • An eight-step checklist for retirees considering early withdrawals • Why retirement withdrawal strategies should be coordinated with a long-term tax plan What's Coming Next • LIRPs (Life Insurance Retirement Plans): What they are, how they work, and when they may fit into a retirement income strategy • Advanced retirement income planning strategies • Tax-efficient withdrawal strategies in retirement • Why dividends matter more than many investors realize • Divorce the IRS and FIRE: Tax planning for the Financial Independence, Retire Early movement • Real estate considerations in retirement planning • Divorce the IRS and "Die Broke": Rethinking wealth, legacy, and retirement spending Retiring early can create incredible opportunities, but only if you understand the rules before you start moving money. The Rule of 55 can be a powerful tool for bridging the gap between retirement and age 59½, helping you avoid unnecessary penalties and keep more of your hard-earned savings working for you. Visit Divorce-the-IRS.comVisit Baobab WealthVisit Baobab Wealth AbroadBuy a copy of Jimmy's book, Divorce the IRSFollow us on FacebookSubscribe to us on YouTubeConnect with us on LinkedIn

    The Rule of 55 Explained: A Little-Known IRS Exception

  7. Jun 1

    The 72(t) Rule Could Change Your Retirement Tax Strategy

    Most people assume that if they access retirement accounts before age 59½, they’ll automatically face a 10% early withdrawal penalty. That’s not always true. In this episode of The Divorce the IRS Podcast, we break down one of the most overlooked retirement tax strategies available today: the 72(t) strategy, also known as SEPP (Substantially Equal Periodic Payments). This IRS-approved strategy allows certain investors to access money from traditional IRAs and other qualified retirement accounts before age 59½ without triggering the typical 10% early withdrawal penalty. We explain how the 72(t) rule works, who typically uses it, and why it can become an important planning tool for people pursuing early retirement or trying to create tax-efficient Roth conversion strategies. You’ll learn how some investors use 72(t) distributions to create an income stream that can help pay taxes generated by Roth conversions, potentially allowing them to move larger amounts of money into tax-free Roth accounts over time. We also discuss the important rules and risks surrounding the strategy, including required withdrawal schedules, IRS-approved calculation methods, the five-year commitment requirement, and why proper planning is critical before implementing this type of strategy. If your goal is to create more tax-free retirement income, reduce future tax exposure, and understand advanced retirement planning concepts, this is an episode you won’t want to miss. In This Episode • What the 72(t) / SEPP strategy is • How to access retirement accounts before age 59½ without penalties • The difference between 72(t) and 72(q) strategies • How 72(t) distributions may support Roth conversion planning • Why Roth conversion taxes stop many investors from converting • Why using retirement money to pay Roth conversion taxes can create penalties • How the 72(t) strategy may help avoid the 10% early withdrawal penalty • The three IRS-approved withdrawal calculation methods • Differences between the RMD, annuitization, and amortization methods • Why the RMD method is generally more conservative • The five-year rule for 72(t) distributions • Why you can only make certain calculation changes once • How investors can isolate only a portion of their IRA for a 72(t) strategy • Why proper financial planning is critical before implementing advanced tax strategies What’s Coming Next • The Rule of 55 and how it works • Advanced Roth conversion planning strategies • Tax-free retirement income concepts • Backdoor and Mega Backdoor Roth strategies • Retirement tax planning mistakes to avoid Visit Divorce-the-IRS.comVisit Baobab WealthVisit Baobab Wealth AbroadBuy a copy of Jimmy's book, Divorce the IRSFollow us on FacebookSubscribe to us on YouTubeConnect with us on LinkedIn

    The 72(t) Rule Could Change Your Retirement Tax Strategy

  8. May 28

    The Roth Conversion

    LISTEN TO THE IDEAL NUMBER EPISODE: https://www.buzzsprout.com/2565788/episodes/19096145 CALCULATE YOUR IDEAL NUMBER: https://baobabwealth.com/ideal-number/ One of the biggest questions in retirement tax planning is whether it makes sense to pay taxes now instead of later. For many people, the answer may be yes. In this episode of The Divorce the IRS Podcast, we break down Roth conversions and why they can be a powerful strategy for moving money from tax-deferred accounts into tax-free Roth accounts. A Roth conversion allows you to shift some or all of your pre-tax retirement money into a Roth account. While this creates a tax bill in the year of the conversion, it may also help reduce future taxes and create more tax-free retirement income. We explain why Roth conversions are sometimes described as “refinancing your IRA” and how this strategy can help investors lock in today’s tax rates instead of waiting to see what tax rates may look like later in retirement. You’ll learn why paying taxes on retirement money today may be more attractive than paying taxes later on a much larger account balance, especially if your pre-tax accounts continue to grow over time. We also discuss important rules and planning considerations, including the five-year rule for Roth conversions, the 10% early withdrawal penalty, why you should generally avoid using converted retirement funds to pay the tax bill, and why Roth conversions can no longer be undone through recharacterization. If your goal is to build more tax-free retirement income, reduce future required minimum distributions, and create greater long-term tax flexibility, Roth conversions may be an important strategy to understand. In This Episode • What a Roth conversion is  • How Roth conversions move money from tax-deferred to tax-free accounts  • Why Roth conversions are sometimes called “refinancing your IRA”  • Why current tax rates matter in retirement planning  • How future account growth can increase future tax exposure  • Why you may not be in a lower tax bracket in retirement  • How to strategically convert only the amount that makes sense  • Why you should be careful about pushing into a higher marginal tax bracket  • Why paying the tax bill from outside funds may be important  • How the 10% early withdrawal penalty can affect younger investors  • How the Roth conversion five-year rule works  • Why Roth conversions are permanent and cannot be undone  • How Roth conversions may affect Social Security taxation, Medicare premiums, RMDs, surviving spouses, and heirs What’s Coming Next • Lesser-known strategies for early retirement planning  • Ways to create tax money for Roth conversions  • More tax-free retirement income strategies  • Advanced planning concepts for reducing future retirement taxes Visit Divorce-the-IRS.comVisit Baobab WealthVisit Baobab Wealth AbroadBuy a copy of Jimmy's book, Divorce the IRSFollow us on FacebookSubscribe to us on YouTubeConnect with us on LinkedIn

    The Roth Conversion
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Ratings & Reviews

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out of 5
4 Ratings

About

Welcome to Divorce the IRS, the Retirement Income Planning Podcast—built for people who want to pay the least amount of taxes possible and create retirement income that actually lasts. Inspired by Jimmy Miller’s bestselling book Divorce the IRS, this show takes you behind the scenes of the tax rules, retirement strategies, and planning decisions that can quietly determine how much of your money you keep. The truth is, taxes aren’t just “something you deal with later.” The U.S. tax code is massive, confusing by design, and full of traps that can hit hardest right when you need your money most. From 401(k)s and IRAs to Social Security and Medicare, many common “smart moves” can turn into expensive surprises—like required minimum distributions, Medicare surcharges, the widow’s penalty, and other retirement tax time bombs most people don’t see coming until it’s too late. With 20+ years of experience as a global wealth manager, Jimmy breaks these topics down in a clear, practical way—so you can plan proactively, avoid unnecessary taxes, and build a retirement where your delayed gratification finally pays off. Subscribe so you never miss an episode, and remember: this podcast is for general education only and isn’t legal, tax, or investment advice—always consult a qualified professional for guidance specific to your situation.

Information

  • Creator
    James Miller
  • Years Active
    2025 - 2026
  • Episodes
    30
  • Rating
    Clean
  • Copyright
    © 2026 Divorce the IRS
  • Show Website
    Divorce the IRS