Social Security Claiming Strategies, Part 1: EDU #2543
October 22, 2025
Chris’s Summary Jim and I examine a recent Social Security claiming strategies debate prompted by articles from Derek Tharp and Laurence Kotlikoff. The episode highlights how opposing valuation frameworks—economic modeling versus purpose-driven income planning—can lead to drastically different conclusions. We explain why assigning Social Security a clear job, such as covering your Minimum...
Listen NowSpousal Roth, Backdoor Roth, Social Security, Post-Tax Contributions, HSA Strategy: Q&A #2542
October 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 continues working and their income meets...
Listen NowIRA Rollover Mistakes and Exceptions: EDU #2542
October 15, 2025
To skip over Jim and Chris chatting about the government shutdown delaying Social Security and Medicare announcements, and Jim’s upcoming travel plans—including concerns about flight delays and his upcoming elk hunt in Utah you can skip ahead to (8:15). Chris’s SummaryJim and I walk through common IRA rollover mistakes and clarify the once-per-year rollover rule, including exceptions for Roth...
Listen NowSocial Security, HSA Held Annuities, IRA Annuities: Q&A #2541
October 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 whether their benefit is...
Listen NowMilitary Retirement Planning: EDU #2541
October 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 the importance of financial literacy...
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