Episodios

  • Social Security, HSA Rules, SPIA Funding, and FIA Details: Q&A #2524
    Jun 14 2025

    Jim and Chris address questions on Social Security survivor benefits, unreimbursed HSA expenses, SPIA funding from multiple accounts, and Fixed Indexed Annuity details. (7:45) Georgette asks whether drawing her own reduced Social Security benefit at 62 will affect her ability to switch to her deceased husband’s full survivor benefit at age 67. (23:15) A listener […]

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    1 h y 22 m
  • Understanding Annuity Types and Features: EDU #2524
    Jun 11 2025

    Chris’s Summary:Jim and I discuss annuity types and features during Annuity Awareness Month, focusing on immediate vs. deferred annuities and fixed vs. variable structures. We cover how each type works, what they offer, and where caution is warranted. Jim’s “Pithy” Summary:Chris and I continue our Annuity Awareness Month series by diving into the foundational aspects […]

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    1 h y 22 m
  • Bond ETFs, Social Security, 401k Annuities, and Annuitization: Q&A #2523
    Jun 7 2025

    Jim and Chris answer questions on defined maturity bond ETFs, Social Security account linking and spousal offsets, 401k annuities vs IRA Annuities, and annuitization definitions.(14:30) Jacob joins the guys to explain how estimated net acquisition yield works for defined maturity bond ETFs, including how to interpret it and evaluate risk when holding through maturity.(38:30) A […]

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    1 h y 25 m
  • Annuities in Retirement Planning: EDU #2523
    Jun 4 2025

    Chris’s Summary:Jim and I kick off our annual Annuity Awareness Month series by explaining how using annuities in retirement planning can help manage longevity risk and provide guaranteed income. We cover when they’re worth considering, what they actually solve for, and how they might fit into a plan—if at all. We also explain why many […]

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    1 h y 9 m
  • Social Security Filing, Roth 5-Year Rule, HSA Strategy, and Bond Principal: Q&A #2522
    May 31 2025

    Jim and Chris answer listener questions on Social Security filing, a PSA on SSA’s online application process, the Roth 5-Year Rule, HSA strategy, and bond principal risk. (8:00) A listener asks whether Social Security’s claim that delayed retirement credits aren’t applied until the end of the following year is accurate, and whether anyone receives them […]

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    1 h y 16 m
  • Flexible Retirement Spending: EDU #2522
    May 28 2025

    Chris’s Summary:Jim, Jake, and I use this Dialogue EDU episode to explore how we approach flexible retirement spending. We respond to listener emails about DIY simplicity, budgeting for irregular expenses, and how we assign assets to spending needs. The conversation highlights why we prioritize adaptability over rigid withdrawal rules. Jim’s “Pithy” Summary:Chris, Jake, and I […]

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    1 h y 13 m
  • Social Security, IRA Basis, and Roth 5-Year Rule: Q&A #2521
    May 24 2025

    Jim and Chris answer listener questions on Social Security timing, the Earnings Test, nondeductible IRA basis, and the Roth 5-Year Rule. (16:15) Georgette asks whether filing retroactively in December, with Social Security payments issued in January, ensures that all income—including the retroactive amount—will be reported on the following year’s tax return. (28:00) A listener working […]

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    1 h y 36 m
  • Spending Confidently in Retirement with Kevin Sebesta: EDU #2521
    May 21 2025

    Chris’s Summary:Jim and I are joined again this week by Kevin Sebesta from the Rock Retirement Club in this EDU episode. We explore what helps retirees start spending confidently—especially when markets are volatile or the saver mindset is hard to shake. Kevin shares how structure, support, and community all play a role, and why building confidence […]

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    1 h y 20 m
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