Episodes

  • The Roth Conversion
    May 28 2026

    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.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
  • The Roth IRA Rules Everyone Needs to Understand
    May 7 2026

    Most people know Roth accounts are “tax-free.”

    But very few people actually understand the rules that make them so powerful.

    In this episode of The Divorce the IRS Podcast, we continue building on the concept of the “ideal number” and explore one of the most important wealth-building tools available: the Roth IRA.

    We break down the key Roth IRA rules everyone should understand, including contribution limits, income restrictions, withdrawal ordering rules, and the all-important five-year rule that can determine whether your growth comes out tax-free or not.

    You’ll learn why Roth accounts are fundamentally different from traditional pre-tax retirement accounts, and why tax-free growth can dramatically change your long-term financial outcome. Unlike tax-deferred accounts, Roth accounts allow your money to grow without creating a future tax liability hanging over your retirement.

    This episode also explains some of the biggest Roth misconceptions people have, including confusion around contribution eligibility, investment options, and the mistaken belief that high earners cannot benefit from Roth strategies.

    We also discuss the flexibility Roth IRAs provide, including the ability to withdraw contributions at any time without taxes or penalties, and why simply opening a Roth account, even with a very small contribution, can start an important five-year clock that may benefit you later.

    If your goal is to build tax-free wealth and create more control over your future retirement taxes, understanding these foundational Roth rules is essential.

    And this is just the beginning.

    In the next episode, we’ll dive into one of the most popular advanced Roth strategies available today: the backdoor Roth.

    In This Episode

    • The difference between Roth IRAs, Roth 401(k)s, and Roth 403(b)s
    • Why Roth accounts are truly tax-free, not tax-deferred
    • The Roth IRA five-year rule and why it matters
    • Roth contribution limits and income phaseouts
    • How Roth withdrawal ordering rules work
    • Why contributions can be withdrawn tax and penalty-free
    • Common Roth misconceptions people get wrong
    • Why opening a Roth IRA early can be a smart move

    What’s Coming Next

    • How the backdoor Roth strategy works
    • Legal ways high earners can still utilize Roth accounts
    • Advanced Roth conversion and shifting strategies
    • How to move more money into the tax-free bucket over time

    • 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
  • The Ideal Number That Helps You Pay Less Tax in Retirement
    Apr 29 2026

    Most people think the key to lowering taxes in retirement is simple: use Roth accounts.

    But what if the real strategy is more nuanced than that?

    In this episode of The Divorce the IRS Podcast, we break down one of the most important concepts in retirement tax planning: finding your “ideal number” in tax-deferred accounts and using a combination strategy to minimize taxes over your lifetime.

    While Roth IRAs and Roth 401(k)s are powerful tools, their value goes far beyond tax-free growth. When used correctly, they can help reduce your retirement tax rate, avoid Social Security taxation, limit Medicare premium increases, and even help sidestep issues like the widow’s penalty.

    But here’s the key insight: maximizing Roth alone is not the full strategy.

    We explain why having some money in pre-tax accounts can actually work in your favor, especially when you understand how to use your standard deduction each year. By coordinating withdrawals between tax-deferred and tax-free accounts, you can potentially generate income in retirement while paying little to no tax.

    Using a simple example, we show how the standard deduction allows you to withdraw from pre-tax accounts tax-free, and how going beyond that threshold triggers taxes at the lowest brackets.

    This episode introduces the “ideal number”, the amount you should have in tax-deferred accounts by retirement to fully use these rules without exposing yourself to unnecessary taxes from required minimum distributions later on.

    If your goal is to build wealth while paying the least amount of tax possible over your lifetime, this is a conversation you cannot afford to miss.


    Calculate your ideal number:
    https://baobabwealth.com/ideal-number/

    Watch the Ideal Number Video:
    https://baobabwealth.com/the-ideal-number-for-tax-efficient-retirement-what-most-people-miss/

    In This Episode

    • Why Roth accounts are powerful but not a complete strategy
    • How combining tax-free and tax-deferred accounts lowers lifetime taxes
    • How the standard deduction creates tax-free retirement income
    • The concept of the “ideal number”
    • Why too much in pre-tax accounts creates future tax risk

    What’s Coming Next

    • Roth conversion strategies to reduce future taxes
    • How to shift assets toward tax-free income
    • Advanced strategies to minimize taxes in retirement

    • 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
    8 mins
  • Tax Time Bomb 8: Paying Taxes from the Grave
    Apr 21 2026

    What happens to your money after you pass away?

    For many families, the answer is more complicated and more costly than expected.

    In this episode of The Divorce the IRS Podcast, we break down the final tax time bomb, often described as paying taxes from the grave. It is a hidden risk that can leave your heirs with a significant tax burden, even if your intentions were to pass along as much wealth as possible.

    We walk through how tax-deferred accounts like IRAs and 401(k)s are treated when inherited, and why recent rule changes have made this issue even more important. For non-spouse beneficiaries, the requirement to withdraw funds within a limited timeframe can create a tax spike, especially if those heirs are in their peak earning years.

    We also explore how this tax burden can be larger than expected, depending on who inherits your assets and what their financial situation looks like. Without proper planning, what you leave behind could be taxed at a higher rate than what you experienced during your lifetime.

    The good news is there are ways to prepare. We discuss strategies that may help reduce or eliminate this burden, including the use of Roth accounts and how certain types of life insurance can be structured to offset future taxes for your heirs.

    This is not just about what you leave behind, it is about how efficiently it is passed on.

    If leaving a legacy matters to you, this is a conversation worth having as part of your overall financial plan.

    In this episode, you will learn:

    • How inherited retirement accounts are taxed
    • Why the 10-year withdrawal rule can create a tax spike
    • How your heirs’ tax bracket impacts what they actually keep
    • The difference between passing assets to a spouse versus other beneficiaries
    • Strategies that may help reduce or eliminate taxes for your heirs

    Make sure to subscribe so you do not miss the next episode, where we begin to tie these strategies together and show how to apply them within your financial plan.

    • 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
  • Tax Time Bomb 7: The Widow’s Tax Penalty That Can Cost You More Even With Less Income
    Apr 13 2026

    What happens to your taxes when one spouse passes away?

    For many couples, the answer is surprising and costly.

    In this episode of The Divorce the IRS Podcast, we break down one of the most overlooked risks in retirement planning, often called the widow’s or widower’s penalty. It is a tax shift that can increase your tax burden even as your income declines, creating a difficult financial situation during an already emotional time.

    We walk through a real-world example to show how a surviving spouse can end up paying more in taxes despite having less income. From changes in filing status to reduced deductions and tighter tax brackets, the impact can be significant if it is not planned for in advance.

    The good news is there are ways to prepare. We explore two strategies that may help reduce or offset this risk, including the role of tax-free income sources and how certain planning tools can help maintain flexibility in retirement.

    This is not a topic many people want to think about, but it is one that deserves attention as part of a well-rounded financial plan.

    If you are married and thinking about retirement, this is a conversation worth having sooner rather than later.

    In this episode, you will learn:

    • What the widow’s or widower’s tax penalty is
    • Why taxes can increase even when income decreases
    • How filing status and deductions change after a spouse passes
    • A real example showing the financial impact
    • Strategies that may help reduce the long-term tax burden

    Make sure to subscribe so you do not miss the next episode, where we cover the final tax time bomb and how taxes can continue even after you are gone.

    • 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
    10 mins
  • Tax Time Bomb 6: Required Minimum Distributions (RMDs)
    Apr 1 2026

    In this episode of The Divorce the IRS Podcast, we continue our series on retirement tax time bombs by breaking down one of the most overlooked triggers of higher taxes later in life—Required Minimum Distributions (RMDs).

    While many retirees assume they can leave their tax-deferred accounts untouched for as long as they’d like, the reality is very different. Once you reach age 73, the IRS requires you to begin withdrawing a portion of your IRA and traditional 401(k) balances each year—whether you need the income or not. And every dollar withdrawn is subject to taxation.

    We explain how RMDs are calculated using IRS life expectancy tables, how the required withdrawal percentage increases over time, and what this looks like in a real-world scenario. More importantly, we highlight how these forced withdrawals can create unintended consequences, including higher overall tax exposure, increased taxation of Social Security benefits, and rising Medicare premiums.

    We also explore the challenge many retirees face when they don’t need the income—yet are still required to take it. Once those funds leave the tax-deferred environment, they are often placed into accounts where earnings are taxed annually, potentially compounding the long-term tax burden.

    Finally, we introduce strategies that may help reduce or avoid the impact of RMDs altogether, including the role of tax-free accounts like Roth IRAs and Roth 401(k)s. By understanding how and when to shift assets, you can begin to take more control over how your retirement income is taxed.

    If you want to avoid being forced into higher taxes later in retirement and better understand how to plan around RMDs, this is an episode you won’t want to miss.

    • 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