Major charitable-giving changes are set to take effect next year under the One Big Beautiful Bill Act. As a result, 2025 may be the best—and possibly last—great year to make a big charitable gift and get the full tax benefit in the same year.

Listen in to hear the changes that take place in 2026 that could make 2025 the best year to use donor advised funds.

In our listener question segment, Christie inquires about buying a home in retirement: "Should we withdraw from investments, or use a mortgage?"

Resource:

Article by Ben Mattlin in Financial Advisor Magazine: "Why Some Advisors Are Daffy For Donor-Advised Funds"

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A new report says retirees who use a so-called "bridge strategy" can actually spend more and need fewer assets to retire securely.

That's right. By delaying Social Security and using other savings to "bridge the gap," you could improve your lifetime income, reduce longevity risk, and build more peace of mind into your plan.

We will break down the research and find ways to make Social Security work harder for you.

After that, I'll answer a listener question: What's the difference between a 5 year MYGA and a 5 year SPIA?

Resource:

Article by John Manganaro on ThinkAdvisor: This Social Security Strategy Gives Retirees More to Spend

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If something promises higher returns, it comes with higher risk — even if that risk isn't easy to see. And if something promises to protect your downside, it's usually charging you for it through fees, limited upside, or long-term lockups.

Today's headline from Ben Henry-Moreland fits that idea perfectly. "Why 'Downside Protection' ETFs Don't Protect Portfolios As Well As A Stock-Bond Mix (In The Long Term)".

After that, I'll answer a listener question about taxes & avoiding underpayment penalties from a surprise inheritance. Should they make an extra quarterly payment to the IRS to avoid penalties, or is there a smarter way to handle it? I'll explain how the safe-harbor rules work, and why a simple IRA-withholding trick can sometimes do the same job even better.

Resource:

Article by Ben Henry-Moreland on Kitces.com: Why "Downside Protection" ETFs Don't Protect Portfolios As Well As A Stock-Bond Mix (In The Long Term)

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A few episodes ago, we covered Derek Tharp's research suggesting that not everyone should delay until 70 — especially those with shorter life expectancies or limited assets.

This week's headline brings the opposite perspective: Michael Finke argues that for higher-income retirees who expect to live longer, claiming early is almost always a mistake — and that fear-based decisions about Social Security's solvency can cost retirees hundreds of thousands in lifetime income.

Plus, a listener asks about giving with warm hands vs cold hands - which is a euphemism for giving during life vs giving after death. How much can they give without fear of running out of money?

Resource:

• Michael Finke article on ThinkAdvisor: Why Advisors Should Never Recommend Social Security Claiming at 62

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Do lower-cost funds tend to outperform pricier ones over time?

Jeffrey Ptak analyzed fifteen years of performance data covering virtually every U.S. mutual fund and ETF. He divided them into five "cost buckets," from the cheapest 10% all the way up to the most expensive 10%. He then compared each group's average monthly return against its peers within the same category.

The result? A clean, almost perfect staircase of performance.

The cheapest funds outperformed the second-cheapest, which outperformed the middle, which beat the expensive ones — and so on — all the way up the ladder. The longer the time horizon, the wider the gap became.

That's from Jeffrey's Peak Substack piece "It's So Simple: Fees Predict Performance", which we go through in this episode.

We also answer a listener question from Ray about a 5-year SPIA, continuing the listener question from the previous episode.

Resource:
Jeffrey Ptak article from Substack: It's So Simple: Fees Predict Performance

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Vanguard Research put out a paper called "The Emotional and Time Value of Advice" (June 2025).

It claims that there are "emotional benefits and time-saving value that paid professional financial advice provides to clients."

In other words: The benefit isn't the portfolio or financial advice, but the emotional and time-saving value getting paid professional advice can provide.

Then for our listener question: Gary wants to know how his Health Savings Account (HSA) interacts with Medicare. Can you pay Medicare premiums from an HSA at a later date like you can with qualified medical expenses paid out of pocket? Great question!

Resource:
Vanguard Study: "The Emotional and Time Value of Advice" paper

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Only about 4% of retirees actually wait until age 70 to claim Social Security, despite the financial benefits of delaying them.

This comes from an article by Derek Tharp at Kitces.com titled "The Flaws In Using A 0% Discount Rate To Justify Delaying Social Security". It takes a hard look at why the common advice to "wait until 70" might not always hold up in the real world.

Tharp argues that the assumptions baked into much of the research—especially the idea that a future Social Security dollar is worth the same as a dollar today—can tilt the math toward delay, while ignoring very real risks like mortality, sequence of returns, policy changes, and even health-span.

I'll share the points and give my commentary on the topic. Thanks for hitting the Play button!

Then in our listener question segment: We'll talk about whether it ever makes sense to use a SPIA to bridge the gap until Social Security. What are the pros and cons, and would I ever recommend one?

Resource:
Article from Derek Tharp on Kitces.com: Why Delaying Social Security Benefits Isn't Always The Best Decision

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Our retirement headline is from a ThinkAdvisor article titled "Ed Slott: Roth Conversions Are Trickier Under New Tax Law" by Melanie Waddell.

"With the extended tax cuts under President Trump's recently passed tax and spending law, 'Roth conversions should be accelerated to take advantage of more years of low tax rates,' according to Ed Slott of Ed Slott & Co.

'You never want to leave a low tax bracket unfilled,' he said. 'Low tax brackets need to be maximized each year, but how much to convert each year can be trickier now since many of the new tax breaks have income caps.'"

That's the crux of it — Roth conversions still make sense, but now they're bumping up against some new income cliffs. I take the first few minutes to share a few key numbers.

Then our listener question is actually one I asked myself after seeing a post about company financials being reported less frequently than quarterly. I go through the pros and cons of making this change.

Resources:

Article by Melanie Waddell, courtesy of ThinkAdvisor.com: Ed Slott: Roth Conversions Are Trickier Under New Tax Law

Article on Reuters by Johann M Cherian, Lewis Krauskopf and Douglas Gillison: Trump renews calls for ending quarterly reports for companies

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