- 1 hour 29 minutesSocial Security, Estate Planning, Annuity Safety: Q&A #2631
Jim and Chris discuss listener emails on Social Security survivor benefits after the GPO repeal, estate planning for minor children, and Annuity Safety.
(10:00) A listener asks whether the repeal of GPO permits the survivor in a mixed Social Security and non-covered pension couple to keep both Social Security benefits rather than only the higher benefit, and where this rule appears in the POMS.
(37:00) The guys review whether a revocable living trust should remain the contingent beneficiary of retirement accounts while the couple’s children are minors, despite the potential for higher taxes, and what alternatives or overlooked issues may apply.
(1:16:15) Jim and Chris address whether someone considering a $500,000 single premium immediate annuity (SPIA) should split the purchase between two insurers to reduce insolvency and state guaranty association risk.
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1 August 2026, 6:00 am - 1 hour 33 minutesCovering Retirement Income Gaps: EDU #2630
Chris’s Summary
Jim and I continue our discussion on the Fun Number
, this time tackling what comes out first and how we plan for covering retirement income gaps. We look at funding both the delay period and post-delay period, including how a SPIA quote helps determine how much to set aside today to close a future gap. We also address aging and long-term care, and the smaller, less common carve-out for a guaranteed inheritance tied to a special needs dependent.Jim’s “Pithy” Summary
Chris and I pick up the Fun Number
conversation right where we left off, and this time we’re finally cracking open the toy box to show you what has to come out before anything gets set aside for fun. I still say it best with the seesaw: younger you on one side, older you on the other, and every dollar you carve out first is a promise you’re making across that fulcrum.We walk through the delay period, those years before your Social Security or pension is fully turned on, and why we don’t discount those dollars down the way you might expect. Then Chris shifts to the post-delay period, pulling a real annuity quote to price out a future income gap and translating that future need into a present-day number using our See Through Portfolio
thinking, so you can actually see which assets are spoken for and which ones aren’t. We talk through how to close retirement income gaps step by step, and I even work in my usual gripe about the crystal ball nobody’s built yet.From there we get into the harder, more emotional carve-outs, the ones tied to aging, long-term care, and in some cases a guaranteed inheritance, before circling back to what’s actually left over for you to enjoy. There’s a reason people tend to want to spend now rather than reserve for later, and we talk about why that instinct is so hard to fight. Next week Jacob joins us to talk through how we actually invest each of these positions, so consider this the setup for that conversation.
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29 July 2026, 6:00 am - 1 hour 26 minutesSocial Security, Roth 401k, HSA Reimbursement, Pension Options, Trust Planning: Q&A #2630
Jim and Chris discuss listener emails on Social Security survivor benefit strategies, a Roth 401(k) catch-up rule loophole, HSA reimbursement for Medicare premiums, pension options including a lump sum rollover, and trust titling versus individual beneficiaries.
(13:00) — George asks whether his brother can claim his own Social Security benefit at 62 and switch to the higher survivor benefit at full retirement age.
(22:45) — A listener asks whether starting a new job in 2026 could exempt him from the new mandatory Roth 401(k) catch-up rule.
(28:45) — The guys field a question about using HSA funds to reimburse Medicare Part A premiums paid for a spouse before age 65.
(40:00) — Jim and Chris review a listener’s decision to take a pension lump sum and roll it into an IRA over the annuity options.
(1:13:00) — Georgette asks which accounts should be retitled into her trust versus left as individual beneficiary designations.
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25 July 2026, 6:00 am - 1 hour 6 minutesRetirement Budgeting – The Fun Number: EDU #2629
Chris’s Summary
“Jim and I begin a multi-part discussion on the Fun Number
, a retirement budgeting concept for how much someone can spend on what they want rather than what they need once other obligations are covered. Jim traces how the idea originated from a client hesitant to follow through with his retirement dreams despite having more than enough saved to do so. In response, a single undifferentiated portfolio evolved over time into separately identified reserve positions.Jim’s “Pithy” Summary
Chris and I are kicking off a series on the Fun Number
, the concept, along with the Minimum Dignity Floor
, that I’ve built my whole approach to retirement budgeting on. This first episode lays the groundwork for a multi-part discussion, since arriving at that number means first identifying everything else that needs to be sorted out first.To get into where the idea actually came from, I tell the story of a client who had more than enough saved but still couldn’t bring himself to buy the camper trailer he’d been dreaming about for years. Watching that play out taught me something I just couldn’t shake: money sitting inside one big portfolio, all lumped together, is money many don’t feel safe spending, no matter what the math says.
That realization led me to start pulling pieces out of a portfolio. It started with handwritten notes and a three-bucket approach that never quite solved the problem. I kept pulling pieces out, the way a kid digs through a toy box, separating out what’s needed for security and reserves so what’s left becomes visible and spendable, for whatever someone wants to do with it. That thinking eventually grew into what’s now called the See Through Portfolio
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22 July 2026, 6:00 am - 1 hour 28 minutesSocial Security, Pension RMDs, Interest Taxation, Portfolio Strategy: Q&A #2629
Jim and Chris discuss the new PROMISE Act’s potential impact on Social Security before covering listener emails on pension RMD timing, interest taxation versus capital gains indexing, and portfolio strategy around Social Security survivor benefits and multi-account allocation.
(5:30) — Chris discusses the new PROMISE Act and how it may impact Social Security.
(17:15) — George asks how long he can delay pension distributions without violating RMD rules, given his 73rd birthday falls in February 2027.
(29:45) — A listener asks whether interest income should be inflation-indexed the same way some propose indexing capital gains for wealthier taxpayers.
(43:00) — The guys field a two-part question on how a surviving spouse’s Social Security loss factors into MDF portfolio and annuity design, and how to allocate a portfolio strategy across different account types.
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18 July 2026, 6:00 am - 1 hour 1 minuteA Potpourri of Beneficiary Disputes and Tax Laws: EDU #2628
Chris’s Summary
Jim and I dig into two beneficiary disputes as part of what we’re calling a “potpourri” EDU show: the 1930s Goodman Triangle life insurance gift tax dispute and a recent Montana Supreme Court ruling on an uncashed cashier’s check. We also discuss a bipartisan proposal to raise the home sale capital gains exclusion and a separate proposal to index capital gains for inflation more broadly.Jim’s “Pithy” Summary
Chris and I dig into a variety of topics, starting with a court fight that traces back nearly a hundred years, something folks in the industry call the Goodman Triangle. Picture three people tied to one policy: an owner, an insured, and a separate beneficiary. Mrs. Goodman took out five life insurance policies on her husband, moved them into a revocable trust, and thought she was fine, until he died and the IRS said she’d made a taxable gift. She fought it and the court’s decision on the case still gets cited whenever a policy or an annuity has three different people sitting in those three roles.From there we get into a couple of proposals sitting in Congress right now. One would finally raise the exclusion on gains from selling your primary home, something that hasn’t budged since the late nineties even as home prices have doubled and tripled around the country. The House and Senate versions land in slightly different places, but both would roughly double the current numbers and index them for inflation going forward. The other proposal is a longer shot, backed by senators who don’t have much bipartisan goodwill behind them, and it would apply an inflation multiplier to stocks, real estate, and other capital assets so you’d only owe tax on the growth that’s actually real.
We close with one of our beneficiary disputes out of the Montana Supreme Court: a husband pulls eighty thousand dollars out as a cashier’s check made out to himself, hides it in the house, and dies without a will. His wife cashes it, his son sues, and the ruling comes down to whether a gift was ever actually completed.
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15 July 2026, 6:00 am - 1 hour 7 minutesHealthspan and Retirement Planning for Longevity with Dr. Snider: Q&A #2628
Jim and Chris welcome back returning guest Dr. Phillip Snider for a Q&A episode that plays a little differently than usual. Listener emails open a broader discussion of healthspan and lifespan, (including how wealth, genetics, and lifestyle factors shape longevity), retirement planning for longevity, and Dr. Snider’s recommendation for additional tests to help assess your health risks.
(5:15) — George cautions that median longevity statistics are heavily influenced by wealth, genetics, and individual behavior, and shares CDC data showing life expectancy rises significantly once someone reaches age 65.
(29:45) — A listener asks Dr. Snider to discuss the value of the cardiac calcium score in assessing longevity. She also asks about the science behind statins, including their effect on plaque stability and a possible link to reduced dementia risk.
Show Notes:
Dr. Snider’s list of recommended tests:
- CAC test (coronary artery calcium,) or heart scan – a noninvasive, low-dose CT scan that measures calcified plaque in your arteries to predict future heart attack risk.
- hsCRP (high-sensitivity C-reactive protein) – measures inflammation in the body related to cardiovascular disease risk.
- IL-6 (Interleukin-6) – elevated levels are associated with multiple conditions including cardiovascular disease, diabetes (insulin resistance), cancer, and autoimmune disorders. The sample has to be frozen before sending to the lab for processing, so it may need to be collected at a hospital lab or free-standing lab facility rather than at a doctor’s office.
- MPO (Myeloperoxidase) – measures an enzyme found in white blood cells (neutrophils and macrophages). It is a key biomarker of inflammation and oxidative stress. In the bloodstream, high MPO levels indicate that immune cells are actively attacking vessel walls, making it a powerful predictor of cardiovascular disease and plaque instability.
- Lp-PLA2 (lipoprotein-associated phospholipase A2) – measures a specialized inflammatory enzyme highly concentrated in unstable, rupture-prone fatty plaques within your arteries. Unlike general inflammatory markers (like hs-CRP), Lp-PLA2 is specifically localized to inflammation of blood vessels.
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11 July 2026, 6:00 am - 1 hour 12 minutesFunding Essential Expenses in Retirement: EDU #2627
Chris’s Summary
Jim and I review a reader-submitted article on funding essential expenses in retirement, examining how one engineer split his portfolio into what we would call the Minimum Dignity Floor
and Fun Number
, using Social Security and a TIPS ladder. We compare that approach to our own income-based framework, discuss mortality credits from income annuities, and address reader emails about how long an essentials-only spending floor should realistically last.Jim’s “Pithy” Summary
Chris and I get into a short piece a listener sent us, written by an engineer who approached retirement spending in a very engineer style way: building a model, gathering the data, and running the numbers. But he initially still came up short on peace of mind and ended up splitting his retirement into two portfolios, leaning on Social Security and a TIPS ladder for funding essential expenses, and landing on a lot of ground Chris and I have been covering for twenty-five years, even though he’s never heard of the show.I’ve got some thoughts on that TIPS ladder approach, particularly around mortality credits and what happens when you’re the one holding all the longevity risk yourself instead of pooling it. It ties into what I call the See Through Portfolio
, our approach to positioning assets so you can actually see what each dollar is doing for you rather than treating everything as one big undifferentiated pile. I also bring back my seesaw, the younger you on one side, the older you on the other, to work through what happens with whatever’s left once the essentials are covered.We close out on a couple of relevant reader emails, including one from someone who put together twenty-five years of essential spending coverage on his own. Chris and I do some math on what that actually means for him, and I end up talking about fish schooling and birds flocking, because nature figured some of this out a long time before we did.
Show Notes: Humble Dollar Article
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8 July 2026, 6:00 am - 1 hour 14 minutesSocial Security, 403b Variable Annuities, Converting Inherited IRAs: Q&A #2627
Jim and Chris discuss listener emails on Social Security spousal benefit calculations, variable annuities in a 403(b), converting Inherited IRAs, and the Social Security child-in-care provision’s effect on spousal benefits.
(10:00) — A listener asks Chris to explain why his additional high-earning years increased his own benefit so little, due to Social Security’s bend point formula, and how that translated into only a small spousal benefit adjustment for his wife. He also asks whether Social Security stops recalculating a worker’s PIA once they reach age 70.
(28:00) — Georgette asks why her 403(b) funds are classified as variable annuities rather than mutual funds, and whether they function like other variable annuities sold on the open market.
(54:30) — The guys field a question about a non-spouse inherited IRA, where the account holder wants to know whether the required RMD must be taken before completing a separate Roth conversion.
(1:05:15) — Jim and Chris address whether the child-in-care provision removes the early-claiming reduction to a wife’s spousal benefit, in a case where she claims at 62 and her husband, the higher earner, waits until 65.
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4 July 2026, 6:00 am - 1 hour 12 minutesWhat to Know About Jointly Owned Annuities: EDU #2626
Chris’s Summary
Jim and I continue our discussion on annuity insurer failures and state guarantee fund protections before turning to jointly owned annuities, examining how they differ from other jointly titled assets. We cover credited versus uncredited interest, mortality table calculations for annuitized contracts, and how a jointly owned annuity’s death benefit passes to named beneficiaries rather than the surviving owner. Contract language varies by insurer on how the surviving joint owner is treated relative to named beneficiaries.Jim’s “Pithy” Summary
Chris and I pick up where we left off last week and close out our take on that NBC article about a woman whose annuity insurer ran into serious financial trouble. I get into the timing behind a related lawsuit, why I think the agent involved should have caught the warning signs, and why the insurance company itself deserves plenty of blame too. We also break down how state guarantee funds actually work once an insurer goes under, the difference between credited and uncredited interest, and what changes once you’ve annuitized and the fund has to figure out your payments using its own mortality tables.Then we shift into jointly owned annuities, and this is the part worth paying close attention to. Most people assume a joint annuity behaves like any other jointly titled asset, where the survivor automatically ends up owning the whole thing. However, that is not always how it works. I walk through language from two different insurance contracts we have dealt with over the years, and the two companies handle a joint owner’s death in completely different ways. If you have an older jointly owned annuity with someone other than your spouse listed as primary beneficiary, this is worth looking into now, because what actually happens at the first owner’s death might not be what you expect.
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1 July 2026, 6:00 am - 1 hour 36 minutesSocial Security, SPIA, SPIA Timing, QLAC: Q&A #2626
Jim and Chris discuss listener emails on Social Security benefits for a disabled adult child, SPIA timing and funding, longevity assumptions, and QLAC planning.
(15:15) A listener asks why Social Security appears to be paying a disabled adult child benefit and child-in-care spousal benefit as a combined 50% of the worker’s PIA rather than 50% each, and how they might address the issue.
(32:45) The guys discuss whether to buy a SPIA now or wait until age 70, along with the pros and cons of purchasing one with pre-tax, Roth, or brokerage assets. They also address where a DIY investor may be able to purchase a SPIA.
(1:11:00) Jim and Chris respond to a listener considering whether expected AI-driven longevity advances should factor into the timing of a future SPIA purchase.
(1:19:15) A listener asks about using a QLAC to help accelerate Roth conversions and whether a special needs trust for a disabled adult child could avoid a large lump-sum tax hit if both parents pass early.
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