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Divorce the IRS

Divorce the IRS

By: James Miller
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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.

© 2026 Divorce the IRS
Economics Personal Finance
Episodes
  • The Roth Conversion
    May 28 2026

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    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.com
    • Visit Baobab Wealth
    • Visit Baobab Wealth Abroad
    • Buy a copy of Jimmy's book, Divorce the IRS
    • Follow us on Facebook
    • Subscribe to us on YouTube
    • Connect with us on LinkedIn


    Show More Show Less
    9 mins
  • Mega Backdoor Roth Explained
    May 25 2026

    One of the biggest misconceptions in retirement planning is the idea that high earners are locked out of Roth IRAs forever.

    They’re not.

    In this episode of The Divorce the IRS Podcast, we break down one of the most powerful advanced Roth strategies available today: the Mega Backdoor Roth.

    This strategy allows certain investors to move significantly larger amounts of money into Roth accounts through their employer-sponsored retirement plans, even if they earn too much to contribute directly to a Roth IRA.

    We explain how the Mega Backdoor Roth works inside many 401(k) and 403(b) plans, including the role of after-tax contributions, Roth 401(k) salary deferrals, employer matching contributions, and IRS total contribution limits.

    You’ll learn how some retirement plans allow participants to contribute far beyond the standard employee contribution limits and why understanding your specific plan provisions is critical before implementing this strategy.

    We also walk through a detailed example showing how investors may be able to move tens of thousands of additional dollars into Roth accounts each year through after-tax contributions and Roth conversions.

    If your goal is to build more tax-free retirement income and maximize long-term tax flexibility, understanding the Mega Backdoor Roth strategy could be an important piece of your retirement plan.

    In This Episode

    • What the Mega Backdoor Roth strategy is
    • How Roth 401(k) contributions differ from Roth IRAs
    • Why high earners may still have powerful Roth opportunities
    • Understanding total 401(k) contribution limits
    • How employer matching and profit sharing factor into the calculation
    • What after-tax 401(k) contributions are
    • How after-tax contributions may later convert into Roth assets
    • Why some plans allow in-service Roth conversions
    • A real-world Mega Backdoor Roth example explained step-by-step
    • Important planning considerations before implementing the strategy

    What’s Coming Next

    • Roth conversion strategies explained
    • How retirees may create more tax-free retirement income
    • Tax planning opportunities involving pre-tax retirement accounts
    • Advanced Roth planning concepts for long-term retirement flexibility

    • Visit Divorce-the-IRS.com
    • Visit Baobab Wealth
    • Visit Baobab Wealth Abroad
    • Buy a copy of Jimmy's book, Divorce the IRS
    • Follow us on Facebook
    • Subscribe to us on YouTube
    • Connect with us on LinkedIn


    Show More Show Less
    7 mins
  • The Backdoor Roth IRA Strategy Explained
    May 14 2026

    One of the biggest misconceptions in retirement planning is the idea that high earners are locked out of Roth IRAs forever.

    They’re not.

    In this episode of The Divorce the IRS Podcast, we break down one of the most widely used advanced Roth strategies available today: the backdoor Roth IRA.

    The backdoor Roth strategy gives higher income earners a legal pathway to move money into Roth accounts, even when their income exceeds the standard Roth IRA contribution limits. While the process itself is relatively simple, there are several important tax rules and planning nuances that investors need to understand before implementing it.

    We walk step-by-step through how the strategy works, beginning with a nondeductible IRA contribution and ending with a Roth conversion. You’ll learn why this strategy exists within the tax code, how it functions mechanically, and why Roth accounts continue to play such a powerful role in long-term tax planning.

    This episode also explores several important areas that often create confusion, including IRS Form 8606, the step transaction doctrine, how small amounts of growth are treated before conversion, and why the pro rata rule can create unexpected tax consequences for investors who already own other IRA accounts.

    We also discuss why existing rollover IRAs can complicate the process and some of the strategies investors use to simplify future Roth conversions.

    If your goal is to create more tax-free retirement income and gain greater control over future taxes, understanding how the backdoor Roth works is an important piece of the puzzle.

    And this conversation doesn’t stop here.

    In the next episode, we’ll dive into another advanced Roth strategy that may allow some investors to move substantially larger amounts into Roth accounts: the Mega Backdoor Roth.

    In This Episode

    • How the backdoor Roth IRA strategy works
    • Why high earners can still legally utilize Roth accounts
    • The role of nondeductible IRA contributions
    • Why Roth conversions have no income limits
    • How IRS Form 8606 factors into the strategy
    • The IRS step transaction doctrine explained
    • How taxes apply to growth before conversion
    • What the pro rata rule is and why it matters
    • Why rollover IRAs can complicate Roth planning
    • Strategies that may help simplify future conversions

    What’s Coming Next

    • How the Mega Backdoor Roth strategy works
    • Advanced Roth funding opportunities for higher earners
    • Ways some investors move significantly larger amounts into Roth accounts
    • Additional tax-free retirement income strategies

    • Visit Divorce-the-IRS.com
    • Visit Baobab Wealth
    • Visit Baobab Wealth Abroad
    • Buy a copy of Jimmy's book, Divorce the IRS
    • Follow us on Facebook
    • Subscribe to us on YouTube
    • Connect with us on LinkedIn


    Show More Show Less
    11 mins
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