Social 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 listener asks why their 75-year-old father was denied six months of retroactive spousal benefits while a widowed friend who applied at the same time received them.
(33:30) Jim and Chris respond to a listener who questions the “You won the game, why take the risk” from a previous episode and asks whether a high-equity portfolio still makes sense.
(53:00) The guys respond to a listener’s email about fraternal benefit societies that operates outside guaranty associations.
(1:12:00) Georgette asks whether converting to a Roth and then spending from it makes more sense than other withdrawal options.

Podcast: Play in new window | Download (Duration: 1:27:51 — 40.2MB)

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