Social Security Claiming Strategies, Part 2: EDU #2544
October 29, 2025
If you would like to skip Jim and Chris discussing Jim’s travel plans and the guys’ frustration with low-cost airline pricing, you can skip ahead to (10:30). Chris’s SummaryJim and I continue our discussion on Social Security claiming strategies, revisiting the debate between Professors Derek Tharp and Laurence Kotlikoff. We explore how academic disagreements overlook the practical...
Listen NowHSA Contributions, Social Security, Fee Disclosures, TSPs: Q&A #2543
October 25, 2025
Jim and Chris discuss listener questions on how Medicare enrollment affects HSA contributions, Social Security survivor benefits and IRMAA adjustments, financial advisor fee disclosures, and the Thrift Savings Plan (TSP) as a tool in retirement planning.(10:00) A listener asks whether enrolling in Medicare in December with coverage starting in January limits HSA contributions due to the...
Listen NowSocial 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...
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