Episodios

  • Spousal Roth, Backdoor Roth, Social Security, Post-Tax Contributions, HSA Strategy: Q&A #2542
    Oct 18 2025

    Jim and Chris discuss listener questions on spousal Roth IRA eligibility, backdoor Roth contributions using a solo 401k, Social Security timing, post-tax contributions to an IRA and 401k , and an HSA strategy coordinating withdrawals with Roth conversions.(9:30) George asks whether he can contribute to a spousal Roth IRA after his retirement if his wife […]

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    1 h y 16 m
  • IRA Rollover Mistakes and Exceptions: EDU #2542
    Oct 15 2025

    Chris’s SummaryJim and I walk through common IRA rollover mistakes and clarify the once-per-year rollover rule, including exceptions for Roth conversions and employer plan transfers. We explain the differences between direct and indirect rollovers, how constructive receipt is determined, and when a spousal rollover might cause unexpected tax penalties. We also outline when 60-day rollovers […]

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    1 h y 21 m
  • Social Security, HSA Held Annuities, IRA Annuities: Q&A #2541
    Oct 11 2025

    Jim and Chris discuss a listener PSA on estimating early retirement benefits, followed by questions on Social Security benefit calculations and reductions, HSA held annuities, and IRA annuity pro rata rule application.(14:45) George shares a PSA explaining how to input future earnings on the SSA site to better estimate early retirement benefits.(25:15) A listener asks […]

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    1 h y 23 m
  • Military Retirement Planning: EDU #2541
    Oct 8 2025

    Chris’s Summary:Jim and I are joined by Rear Admiral Brian Luther to discuss veterans benefits and military retirement planning. We explore how Navy Mutual supports service members, examine the survivor benefit plan, and talk about the role of annuities in managing longevity risk. Rear Admiral Luther also shares insights on TRICARE, VA health care, and […]

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    1 h y 13 m
  • Social Security, Roth Conversions, RMD Calculations: Q&A #2540
    Oct 4 2025

    Jim and Chris discuss listener questions on Social Security spousal benefits, a listener PSA on IRMAA repayment silence, IRMAA reduction eligibility and planning considerations, and a PSA on how 60-day rollover Roth conversions affect year-end RMD calculations.(7:45) A listener points out a possible error from a recent episode and looks for clarification whether delaying benefits […]

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    1 h y 20 m
  • Delay Period Strategy: EDU #2540
    Oct 1 2025

    Chris’s SummaryJim and I return for an EDU dialogue episode focused on a listener’s delay period strategy. His plan includes laddered CDs, equity ETFs, delayed Social Security, and Roth conversions. We use his plan to discuss bracket drift, spending liquidity, and how rising markets can complicate a fixed glidepath. We also cover the tax planning […]

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    1 h y 10 m
  • Social Security, 60-Day Rollover, Inherited IRA, and Deferred Income Annuity: Q&A #2539
    Sep 27 2025

    Jim and Chris discuss listener questions on Social Security disability, dependent benefits for an adult child, a 60-day rollover nuance, inherited IRA RMD rules, and a deferred income annuity strategy.(15:00) George asks whether his brother, who is on SSDI and will transition to retirement benefits at 67, can suspend and restart his benefit to grow […]

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    1 h y 48 m
  • Tax Planning Strategies: EDU #2539
    Sep 24 2025

    This week, with Jim away at a conference, Chris is joined by Jake for an EDU episode that takes the shape of a Q&A, focusing on tax planning strategies. The guys cover a series of emails that highlight how different tax rules and opportunities intersect with retirement planning, income management, and financial decisions. (10:30), the […]

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    1 h y 19 m