Retirement Starts Today

Latest Episodes:

"One free lunch, please." Why Buffered ETFs might not fit the bill. Nov 03, 2025

Show notes

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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Why Advisors Should Never Recommend Social Security Claiming at 62 Oct 27, 2025

Show notes

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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It's so Simple… Oct 20, 2025

Show notes

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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Cut Your Retirement Stress in Half (New Vanguard Study) Oct 13, 2025

Show notes

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

Connect with Benjamin Brandt

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Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Delay to 70? Not So Fast - The New Case for Claiming Early Oct 06, 2025

Show notes

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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Roth Conversions after One Big Beautiful Bill Sep 29, 2025

Show notes

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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Collect Social Security Early & Invest in the Market? Sep 22, 2025

Show notes

Should I collect Social Security early & invest the proceeds into the stock market? This is the age-old question I see on a nearly daily basis in retirement forums.

An article from Morningstar - written by Christine Benz and features a conversation with Social Security expert Mary Beth Franklin - gives me the basis for sharing six obstacles for claiming instead of waiting.

Also, we share a listener question about whether retirees should stick with the traditional 60/40 stock-and-bond portfolio or branch out into alternatives like gold, REITs, or managed futures to help with risk management and withdrawal rate.

Resource:

Article by Christine Benz featuring Mary Beth Franklin on Morningstar: Does It Make Sense to File Early for Social Security and Invest in the Market?

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Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Insert Clickbait Title [Here] Sep 15, 2025

Show notes

Inflammatory headlines are "Clickbait", and I am not immune to falling for them.

"Social Security recipients set to face an $18,000 benefit cut in just seven years" is the most recent culprit in my Google feed - with an image of a Social Security check with a wrecking ball smashing straight through it.

The good news is the headline is pretty far from reality for most people, and I explain why.

Listen in to understand who might actually be impacted, and why most people actually won't.

Source:

Article by Emily Peck on Axios: "Social Security recipients set to face an $18,000 benefit cut in just seven years"

Connect with Benjamin Brandt

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Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Retirement Dreams or Retirement Nightmares? Lessons from Today's Retirees Sep 08, 2025

Show notes

"Only 5% of retirees say they're living the dream and 19% are living the nightmare." says Deb Boyden in an article from Yahoo Finance. Deb provides three lessons to protect your future, which we dig into to see how it applies to your retirement:

Lesson 1: You're Probably Not Saving Enough Lesson 2: Expect the Unexpected Lesson 3: Winging It Won't Get You There

In our Listener Question segment, we talk about the pro rata rule and Roth conversions. It's one of those areas that seems simple on the surface but trips a lot of people up once you start digging in, so we unpack what the pro rata rule really means and why, in most cases, an extra step at the point of retirement, and a bit of double-checking will keep things as clean and simple as possible.

Resource:

Article on Yahoo Finance from Deb Boyden: "Only 5% of retirees say they're 'living the dream' and 19% are 'living the nightmare.' Here are 3 lessons to protect your future"

Connect with Benjamin Brandt

Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
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Work with Benjamin: https://retirementstartstoday.com/start

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Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Why Your Old Spending Habits Won't Work in Retirement Sep 01, 2025

Show notes

If you've saved more than a million dollars, that puts you ahead of 90% of your peers. Statistically, that makes you a super saver. But one of the biggest challenges super savers face is this: it's hard to spend your own money.

In this episode, I share one exercise that can help break some of those old habits and open the door to a more fulfilling retirement.

A Practical Exercise

Think back over the last year or two and pick a trip that you really enjoyed. Itemize all the spending decisions you can remember:

Where did you go?
How did you get there?
How long did you stay?
What did you eat?
What souvenirs did you buy?

Take each line item and triple it.

Then think of two or three ways you could possibly spend that new tripled amount.

Listen to the rest of the episode and learn how we can rewire our brains from saving mode to spending mode.

Connect with Benjamin Brandt

Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
Work with Benjamin: https://retirementstartstoday.com/start

Follow Retirement Starts Today in:Apple Podcasts, Spotify, Overcast, Pocket Casts, Amazon Music, or iHeart

Get the book!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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