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 These recorded broadcasts may contain outdated or obsolete information.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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Planning for Taxes in Retirement: EDU #2537
September 10, 2025
If you would like to skip over Chris and Jake chatting about Jake’s recent trip to Ireland you can go to 7:00. Chris’s SummaryI am joined by Jake today, while Jim is traveling, to examine taxes in retirement. We look at why not all taxes belong in the Minimum Dignity Floor™. We also consider the trade-offs between Roth conversions and IRMAA, and the role of a cash reserve during the delay...
Listen NowSocial Security, HSA Reimbursements, and MYGAs: Q&A #2536
September 6, 2025
Jim and Chris discuss listener questions on surviving spouse Social Security benefits and Roth conversions, SSDI and pensions, the Social Security Fairness Act, managing large HSA reimbursements, and choosing between MYGAs and the TSP G Fund.(7:45) George asks whether Roth conversions count toward the earnings test when planning to claim his surviving spouse Social Security benefits.(26:30) A...
Listen NowBehavioral Finance in Retirement Planning: EDU #2536
September 3, 2025
Chris’s SummaryJim and I look at behavioral finance in retirement planning, noting that spending from secure income feels safer while drawing from assets feels like a loss. People resist balances going down after decades of saving, even though the money was built to be spent. We highlight how framing savings as deferred spending and covering the Minimum Dignity Floor™ with income addresses...
Listen NowSocial Security, Risk Philosophy, Fraternal Benefit Societies, Roth Conversions: Q&A #2535
August 30, 2025
Jim and Chris discuss listener questions on Social Security timing rules, retroactive benefits for an ex-spouse, investment strategy philosophy, fraternal benefit societies, and Roth conversions.(6:30) The guys address a listener’s question about whether applying for Social Security at 70 requires enrolling in Part B or if retroactive filing is an option without losing payments.(16:00) A...
Listen NowRoth Catch Ups and the 60-Day Rollover Rule: EDU #2535
August 27, 2025
If you are not in the mood for Jim and Chris’s delightful banter, you can skip ahead to (5:45). It should be noted that of all the episodes to start sharing that information, it’s the one in which Jim said “we didn’t even banter!”. But, from now on, right here before the guys’ summaries you can find the timestamp to jump ahead to if you want to get to the meat...
Listen NowSocial Security, PSA, Annuities, RMD Rules: Q&A #2534
August 23, 2025
Jim and Chris discuss listener questions on Social Security retroactive payments and delayed retirement credit timing, share a listener PSA on horse speed, and answer questions on fixed indexed annuity default credits, a living benefit rider with a proprietary index, and RMD rules for an inherited account. (15:45) A listener asks if the lack of a prior formal application affects eligibility for...
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