The Retirement and IRA Show

If you’d like to skip over the guys chatting about cold weather and football you can to (8:15).

Chris’s SummaryJim and I are joined by Jacob as we continue our discussion on asset positioning and explain how we approach managing investment assets within a distribution portfolio. We outline why dollars are assigned based on purpose and timing and how asset positioning functions as a form of asset-liability matching. The episode addresses cash versus cash-like roles, outcome periods, and how specific tools are evaluated within a broader distribution-focused framework.

Jim’s “Pithy” Summary

Chris and I are joined by Jacob as we dig further into how we think about handling portfolios once people are in retirement, specifically through the lens of asset positioning. This episode is built around clarifying how dollars get assigned jobs based on when they’ll be needed and why that sequencing drives the structure of a distribution portfolio.

We spend time breaking down the difference between cash and cash-like holdings and why that distinction matters when money is earmarked for different time horizons. A big part of the discussion centers on outcome periods, how certain tools behave between start and finish, and why mark-to-market pricing during that window can be misleading if you don’t understand what the holding is meant to do. Jacob walks through concrete examples that show how interim movement can look unsettling even when the structure is functioning exactly as designed.

We also get into why disclosure language sounds the way it does across virtually every type of holding, including ones most people are comfortable calling cash. The point isn’t semantics — it’s understanding the gap between legal language and functional role inside a portfolio. Everything ties back to structure, timing, and purpose. This is about how distribution portfolios actually operate in retirement, and why evaluating them with the wrong expectations creates confusion that doesn’t need to be there.

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Jim and Chris discuss listener emails on Social Security survivor benefits and the earnings test, share a listener PSA on Social Security timing and IRMAA, then cover ERISA protections for retirement rollovers and a PSA from Greg on lifetime unlimited long-term care policies.(9:45) Georgette asks whether she must still take her husband’s required minimum distributions if he passes during his RMD year and how Social Security survivor benefits work, including whether she should claim a widow’s benefit or wait to take her own.(50:45) A listener asks how the Social Security earnings test applies when someone retires before full retirement age and applies midyear, and how to avoid missing a month of income due to the timing of benefit payments.(55:00) The guys share a PSA about applying for Social Security and receiving benefits within days, which caused an unexpected IRMAA impact.(1:00:35) Jim and Chris discuss whether rolling Roth and pre-tax 401(k) assets into IRAs results in losing ERISA protections, or if separate rollover IRAs are needed to preserve those protections.(1:15:15) Greg, from our office, shares a PSA clarifying that some lifetime unlimited long-term care policies still exist.

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If you want to miss all the fun banter about Jim’s Singo (song bingo) night and his trip to Kentucky and Amish country you can skip ahead to (16:00).

Chris’s SummaryJim and I are joined by Jacob Vonloh as we discuss investing for retirees, using a listener email as the starting point for a broader conversation about how investment advice and asset management work in practice. We explain why investing changes once people move from accumulation into distribution, including differences in risk tolerance, liquidity needs, and volatility. Jacob outlines how investment tools are evaluated based on time horizon and downside exposure rather than labels. We also discuss planning for aging and long-term care costs, including liquidity needs, inflation considerations, and the SEAL (Savings for Emergencies, Aging, and Long-Term Care) reserve framework.

Jim’s “Pithy” SummaryChris and I are joined by Jacob Vonloh as we start a new series of conversations inspired by listener emails, and we use those questions as a jumping-off point to talk about what really changes when you’re investing in retirement. A lot of DIY investors successfully built wealth with an accumulation mindset and then try to carry that same approach into retirement, where it doesn’t work. The problem is that accumulation investing and retirement investing are not the same thing, and pretending they are is where people get themselves into trouble. Once withdrawals begin, volatility feels different, timing matters more, and the emotional impact of market swings gets amplified in ways people don’t expect.

We spend time pulling apart how the investment advice industry presents itself, how fee structures are typically layered in, and why we’re very intentional about separating retirement planning from asset management. Jacob walks through how we evaluate investments based on when the money might be needed and how much downside someone can realistically tolerate. Buffered ETFs come up in that context, not as a recommendation, but as a clean example of how downside protection and upside caps reshape risk. The point isn’t the product — it’s that comparing retirement-stage tools to a fully unbuffered equity index without adjusting for risk is fundamentally misleading.

From there, we connect investing back to real planning issues retirees face, especially aging and long-term care. We talk about why insurance isn’t always available or sufficient, how covering one spouse can still protect a household, and why the financially hardest stretch is often when both spouses are alive and care costs begin to show up. That leads into how we think about liquidity, inflation, and time horizon working together inside what we call the SEAL reserve. This isn’t about chasing returns — it’s about structuring money so it can actually support people through retirement without forcing panic decisions at the worst possible time.

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Jim and Chris discuss listener questions on Social Security survivor benefits and divorce rules, a listener PSA on spousal benefits, HSA contribution limits, and whether annuities make sense versus Treasury bonds.

(8:45) A listener asks whether someone who is newly widowed can claim survivor Social Security now, keep working part time, and later switch to their own benefit, and also asks whether you still offer a “coffee and second opinion” or an a la carte Social Security review.

(23:00) The guys field a question from someone with two ex-spouses asking if it’s possible to combine their own Social Security with part of either (or both) ex-spouses’ benefits.

(33:30) George shares a PSA on how filing for Social Security online triggered a spousal-benefit eligibility notice for their spouse, and how the follow-up phone appointment worked without needing an in-person visit or marriage certificate.

(45:15) Jim and Chris answer a question about 2026 HSA contribution limits for two spouses on an ACA family plan who each opened their own HSA and want to avoid overfunding.

(54:45) One writer asks why they should consider annuities given fees and insurer risk when they can buy 20-year Treasury bonds, and adds a quick note about simplifying word choice from a prior email discussion.

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Chris’s SummaryJim and I continue last week’s EDU discussion on Roth IRA mistakes from an Investopedia article. We cover direct versus 60-day rollovers, the one-per-365-day IRA-to-IRA limit, and the 401(k) 20% withholding rule with the RMD and NUA exceptions. We revisit backdoor Roth mechanics and the pro rata rule, then shift to beneficiary designation forms and why naming an estate creates probate and creditor issues. We close with inherited Roth withdrawal timing under SECURE Act rules and the 10-year window.

Jim’s “Pithy” SummaryChris and I pick up where last week’s EDU episode left off, using the Investopedia Roth mistakes article as a launching point to correct what they compress or misstate. The rollover section is where people get hurt, because they describe the old IRA rule like it was “once per calendar year,” and it wasn’t. It’s a 365-day framework, and the one-per-365-day limit still matters when you do the “show me the money” version of a rollover. I also keep pushing back on indirect rollovers from a 401(k), because the 20% withholding isn’t optional. There are narrow exceptions—but those aren’t general flexibility, they’re specific rules people routinely misunderstand.

The other item that’s far more important than its position on the list is beneficiary designation forms. These accounts pass by beneficiary form first, not your will, which can create probate delays, attorney fees, and creditor complications for the people left to sort it out. Chris adds the practical version of the same mistake: circumstances change, paperwork doesn’t. Old beneficiaries stay on file, and the form controls the outcome even when it creates an awkward situation.

We also get into inherited Roth timing under the SECURE framework—who qualifies as an eligible designated beneficiary, what the 10-year window actually requires, and why Roths don’t fit the required beginning date logic the way traditional accounts do. That difference matters when you’re thinking about flexibility for heirs and how long the account can sit untouched. If the real goal is the zero in the 2-1-0 Tax Ordering Number, the logic behind leaving a Roth can look very different than what you’d conclude from a short listicle about Roth IRA mistakes.

Show Notes: Article – 11 Mistakes to Avoid With Your Roth IRA

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