Our Past Shows
Here you will find a year's worth of our past radio shows. Please understand, due to compliance and supervisory guidelines, there is a lag time from when a show first broadcasts to when it can be listed here for later playback. If the show you want is not available, please check back again soon.
Although Jim and Chris strive to make their show ─ and the information presented − topical and pertinent at the time of original broadcast, please recognize the financial world is constantly changing and evolving. These recorded broadcasts may contain outdated or obsolete information. Never make any financial, tax or investment decisions with information contained on these shows without first consulting with your legal, tax and/or financial advisor(s).
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Social Security, SPIAs, SEPP 72(t): Q&A #2605
January 31, 2026
Jim and Chris discuss listener emails on Social Security timing for HSA contributions, investing in a SPIA vs buffered ETFs, and using SEPP 72(t) income to manage ACA credits.(7:00) A listener describes delaying a Social Security filing to avoid Medicare Part A backdating that would have reduced prior-year HSA contributions, while still receiving full retroactive benefits.(28:00) Georgette asks...
Listen NowAsset Positioning for Retirees: EDU #2604
January 28, 2026
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...
Listen NowSocial Security, ERISA, LTC: Q&A #2604
January 24, 2026
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...
Listen NowInvesting for Retirees: EDU #2603
January 21, 2026
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...
Listen NowSocial Security, HSA, and Annuities: Q&A #2603
January 17, 2026
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...
Listen NowRoth IRA Mistakes, Part 2: EDU #2602
January 14, 2026
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...
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