Chris’s Summary
Jim and I are joined by Matt Kaufman, Senior Vice President and Head of ETFs at Calamos Investments, to discuss buffered ETFs vs stocks and cash, focusing on AQR’s recent critiques. We examine the flaws in AQR’s methodology, the broader history of buffered products, and why these tools can offer certainty in retirement planning. Matt explains how buffered ETFs differ from accumulation strategies and why they may suit specific roles in a distribution-focused portfolio. We also touch on annuity comparisons and institutional adoption by endowments.

Jim’s “Pithy” Summary
Chris and I welcome back Matt Kaufman from Calamos Investments to talk through the controversy around buffered ETFs. AQR recently published two articles criticizing these tools, and I had some questions—not just about their numbers, but about their motives. If you understand how we use buffered products, especially in retirement distribution, you’ll see why I don’t think these critiques hold up.

We talk about the emotional side of retirement—how people freeze up when they’re supposed to start spending. My dad warned me about the Debbie Downers in his assisted living facility: folks who had money but waited too long and couldn’t spend it anymore. That’s why we look at buffered ETFs as a way to give retirees confidence, not as accumulation tools. When I saw AQR lumping these products together and treating them like they were all the same, it reminded me of the way Ken Fisher says “I hate annuities and so should you.” That kind of broad-stroke bashing doesn’t help anyone.

Matt walks through the technical flaws in AQR’s analysis—especially how they mischaracterized equity exposure and ignored how buffered ETFs are actually used. We compare them to annuities, explain cap rates, and look at why institutions like the University of Connecticut are dropping hedge funds for these products. There’s more nuance here than some people want to admit, and it’s worth taking the time to understand how these work—especially if you’re in retirement and trying to protect the money you spent 40 years building.

Show Notes:

For those who would like to read the AQR articles discussed in this episode you can find them here:

The post Buffered ETFs vs Stocks and Cash: EDU #2531 appeared first on The Retirement and IRA Show.

Chris is joined by Jake and Jacob to answer listener questions on Social Security, followed by a PSA about unexpected Social Security payment timing, then additional questions on transition planning, asset positioning across account types, weighing Roth conversions against the senior deduction, and planning around IRMAA.
(6:15) George asks what percentage of taxes he should have withheld from his 2025 Social Security income if that is his only source of income.
(22:45) A listener PSA describes how their spouse’s first Social Security payment arrived earlier than expected and shares a 40-day approval timeline.
(29:45) Chris and the Jacobs respond to a question about transition planning focused on protecting principal before retirement and enabling Roth conversions by age 70.
(53:45) A listener seeks guidance on how to position retirement assets across multiple account types when it’s not yet clear which accounts spending will come from.
(1:02:45) The guys consider how a single filer should weigh the value of Roth conversions against maintaining low income to maximize the senior deduction before RMDs begin.
(1:07:00) Georgette outlines her plan to limit Traditional IRA withdrawals to avoid IRMAA and asks whether it’s better to spend from the Roth or take higher withdrawals and accept IRMAA.

The post Social Security, Transition Planning, Positioning, Roth Conversions, IRMAA: Q&A #2530 appeared first on The Retirement and IRA Show.

Chris’s Summary
Jim and I explain living benefits on annuities, covering how guaranteed income riders work and why they can appeal to those hesitant to annuitize. We describe what we call noun annuities (pre-annuitization) and verb annuities (post-annuitization), then unpack how living benefit riders like guaranteed minimum withdrawal benefits provide income without giving up access to principal. We also discuss what we refer to as the “pretend account,” alongside actual account balances and the significance of guaranteed versus hypothetical projections.

Jim’s “Pithy” Summary
Chris and I finally deliver the long-promised show on annuity living benefits! After wrapping up Annuity Awareness Month, we realized this topic still needed its own deep dive—so here it is. I explain how living benefits evolved from death benefits to guaranteed accumulation and now to income riders that let you turn your noun annuity into a verb without actually doing so. Why? Because people hate the verb! They don’t want to give up their lump sum—they want to “keep a noun a noun,” as I say—and still get some income out of it.

We also talk about the trickery behind what I call “pretend accounts”—those “mystical magical” numbers insurance companies use to calculate your guaranteed income while your real account shrinks from fees. I explain how the ten percent growth you’re promised isn’t on your actual money—it’s on that “pretend account.” And yes, your fees? Those are based on the “pretend account” too, not your real balance. It’s all sizzle, no steak for most people—unless you’re like me and you’re actually using the income. I share that I own one of these riders myself, but only because the guaranteed income benefit made sense for my Roth IRA.

Bottom line: these products aren’t always terrible. If you know you want income and you understand what you’re paying for, some of these living benefit riders might actually make sense—even after you account for the outrageous fees. But the key is understanding what you’re buying and not falling for a hypothetical illustration that doesn’t tell you what you’re actually getting.

The post Living Benefits on Annuities: EDU #2530 appeared first on The Retirement and IRA Show.

Chris and Jake address listener questions on Social Security, single premium immediate annuity (SPIA) taxation, IRMAA impacts from NQDC payments, and Roth conversions.

(9:45) George asks whether the restricted application strategy for Social Security spousal benefits is still possible, and if so, whether birth year requirements apply, along with what changed after the 2015 law change.

(22:15) The guys share a PSA about a listener’s experience with the Social Security application process, explaining how failure to submit a marriage certificate caused delays when applying for spousal benefits.

(31:00) A listener asks whether untaxed tip income affects the amount of Social Security benefits a worker may receive in retirement.

(36:00) Georgette asks whether SPIA payments purchased using Traditional IRA funds are considered taxable income for life.

(45:15) A listener asks if ongoing NQDC payments will be included in MAGI calculations and impact IRMAA.

(55:30) Chris and Jake discuss whether taxes owed from a Roth conversion can be paid when filing taxes the following year, or whether quarterly payments are required to avoid penalties.

(1:09:15) A listener asks whether living in a state that exempts Social Security from state taxes should impact Roth conversion planning.

The post Social Security, SPIA Taxation, IRMAA, Roth Conversions: Q&A #2529 appeared first on The Retirement and IRA Show.

Jim and Chris answer listener questions on Social Security filing and its effect on HSA eligibility, Social Security means testing, the timing of annuity purchases in IRAs, the Roth and Roth TSP 5-year rule.
(7:30) Georgette asks whether the six-month Medicare Part A lookback is triggered by her husband’s Social Security application date or benefit eligibility date, and how that affects HSA contributions.
(22:45) A listener worries about possible future Social Security means testing for those who are past full retirement age but not yet claiming.
(36:30) George questions whether buying a Fixed Indexed Annuity inside an IRA is problematic if RMDs begin before maturity and whether turning on a living benefit might help him spend more.
(56:00) Jim and Chris weight in on an office debate on the Roth conversion 5-year rule.
(1:05:55) The guys clarify the Roth TSP 5-year rule and whether the clock resets when transferring to a new Roth IRA.

The post Social Security, Annuities, Roth and Roth TSP 5-Year Rule: Q&A # 2528 appeared first on The Retirement and IRA Show.

Chris’s Summary
I am joined by Jake and Paul to discuss OBBBA tax changes and retiree impacts from the Inflation Reduction Act. We cover changes to brackets, deductions, personal exemptions, and estate limits. Paul explains how new SALT caps, Social Security deductions, and ACA credit rollbacks affect planning opportunities for retirees, especially those near income phaseouts or considering Roth conversions and business deductions.

Jim’s “Pithy” Summary

Chris, Jake, and Paul talk through a range of retiree-focused updates, including several OBBBA tax changes and provisions from the Inflation Reduction Act. These aren’t just technical adjustments—they have real planning implications, especially for people navigating income limits, deductions, and benefits.

They cover updates to itemized deductions, new limitations for higher earners, and what’s changing with the lower tax brackets and standard deduction. Paul walks through how these changes might help—or get phased out—depending on your situation. There’s also a new personal exemption for those over 65 that sounds straightforward but includes some cutoff points retirees need to know about.

The Social Security deduction comes up too, and it’s not what most people think. Paul clears up who qualifies and how it works. They also talk about the rollback of enhanced ACA premium credits and how enrolling in Medicare affects HSA eligibility. Some of the rules people have counted on in the past won’t function the same going forward.

They touch on other updates as well—charitable giving, estate and gift exemptions, even vehicle loan interest. Not all of it applies to everyone, but plenty of retirees could be caught off guard by the fine print.

The post OBBBA Tax Changes Explained: EDU #2528 appeared first on The Retirement and IRA Show.

Jim and Chris answer listener questions on Social Security family maximum rules, spousal and disabled child benefits, defined benefit pension concerns, and 401k managed payout funds.
(7:45) A listener is trying to understand how the Family Maximum Benefit might reduce the amounts paid to his spouse and disabled adult child once he claims his own retirement benefit.
(16:45) Jim and Chris respond to a listener who has a disabled son and is planning to claim a spousal benefit based on his wife’s record. He asks how the family maximum could affect his son’s eligibility for SSDI and future Medicare access.
(30:00) George asks for input on whether to take monthly payments or a lump sum from his pension weighing the potential risks if the company eventually transfers the pension to an insurance company.
(49:00) The guys address a question about a “Managed Payout” fund offered in a 401(k) plan and whether this might be a good way to generate retirement cash flow compared to annuities.

The post Social Security, Pension Buyouts, and Managed Payout Funds: Q&A #2527 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim and I examine broker vs advisor sold RILAs using real cap rate comparisons from 2024 to highlight how identical contracts can offer different outcomes. We explain how six-year outcome periods work, what locking in gains actually does, and when fees can reduce returns more than commissions. This episode is less about product bias and more about understanding the trade-offs between access, structure, and transparency in how these annuities are priced and delivered.

Jim’s “Pithy” Summary:

We also dig into the mechanics of locking in gains early. Some RILAs let you reset into a new term right away, while others force you into a cash-style holding account until the original term ends. That difference can make or break your returns. And if you’re thinking “buffered ETFs already do this,” you’re right—we talk about that too.

But the real highlight today is the cap rate comparison between broker vs advisor sold RILAs. Same insurance company. Same date. Same indexes. And yet, in multiple examples, the commission-based version offered meaningfully better cap rates—even after accounting for advisor fees. In one case, the broker version had a 60% cap while the advisor version capped at 30%. So much for the narrative that fee-only automatically means better. It’s a great reminder that both commissions and fees are just compensation structures—and neither tells you whether a product is actually better for the client.

The post Broker vs Advisor Sold RILAs: EDU #2527 appeared first on The Retirement and IRA Show.

Jim and Chris shares listener PSAs on IRMAA and Delayed Retirement Credits, and answer questions on Social Security Spousal Benefits, annuity use cases, and fixed indexed annuity payout concerns.

The post PSAs, Spousal Benefits, Annuity Use Cases, and FIAs: Q&A #2526 appeared first on The Retirement and IRA Show.

Chris’s Summary:
Jim and I explore registered index-linked annuities and compare RILAs vs buffered ETFs across liquidity, taxation, and cap rate dynamics. We walk through how the insurance and investment structures differ, where principal protection varies, and how commission-based and advisory products compare from a fiduciary standpoint. I also explain the tax treatment of qualified versus non-qualified annuities and why IRD status matters when evaluating options for legacy planning.

Jim’s “Pithy” Summary:
Chris and I dig into RILAs—Registered Index-Linked Annuities—and boy, do these things get pushed hard. They’re the lovechild of fixed indexed annuities and variable annuities, designed to sit in the middle of the risk spectrum. I call them the insurance industry’s answer to buffered ETFs and structured notes. The appeal? Some downside protection, some upside potential, and growing popularity with both brokers and RIAs.

But here’s the kicker: the same annuity from the same insurance company can have wildly different cap rates depending on whether it’s sold by a broker (commission-based) or an investment advisor (fee-based). I’ve seen broker-sold versions offer higher cap rates than advisory versions—even after paying a commission! That’s why I harp on this: if you’re considering one, you’ve got to compare both sides of the distribution channel. Otherwise, you might end up paying an advisor 1% a year and getting less upside than if you’d bought it through a broker. It also pays to compare RILAs vs buffered ETFs with regard to taxation, liquidity, and advisor compensation. These all factor into whether these products make sense.

I’m not anti-RILA. They can be compelling—especially in IRAs where the tax downsides of non-qualified annuities don’t bite as hard. But outside retirement accounts, the tax treatment stinks: no step-up in basis, income taxation, IRD status—it’s a mess. So, if you’re going to lock up your money, know exactly what you’re giving up in liquidity and tax flexibility. And for heaven’s sake, check those cap rates side-by-side!

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