Stay Wealthy Retirement Podcast

On Christmas Day, a woman picked up her 74-year-old mother's phone and found messages from someone she didn't recognize.

What she uncovered had been unfolding for nearly a year, cost her mom hundreds of thousands of dollars, and started with something millions of people do every day.

And to her mom, none of it felt suspicious.

That's what can make scams like this so difficult to recognize, even for careful, intelligent people.

But other financial threats don't require criminals to earn your trust at all.

In this episode, I'm...

Warren Buffett has shared exactly how the money his family inherits should be invested: 90% in a low-cost S&P 500 index fund and 10% in short-term government bonds.

It's simple, inexpensive, and recommended by the greatest investor of all time.

And if you've owned the S&P 500, your company's stock, or a single big winner for decades, it may be a big reason you're able to retire.

But once your portfolio has to provide a paycheck, that concentration can carry risks it didn't before.

In this episode, I'm sharing how to decide whether...

Last week, I explained why waiting until 70 to claim Social Security deserves a closer look, even when it makes sense on paper.

Weighing that decision depends on understanding how the program works.

And a few common assumptions can make that harder than it needs to be.

They can influence when you retire, how you plan for taxes, and what your spouse may receive down the road.

In this episode, I'm walking through 7 common Social Security myths and where the confusion comes from.

Here's what you'll learn:

→ What th...

If you've researched when to claim Social Security, you've probably heard to wait until age 70. 

And there's good reason for that advice.

Waiting means a larger monthly benefit for life, which can be especially valuable if your retirement lasts several decades.

But while you wait, you'll need to cover your expenses from other sources.

That means considering how comfortable you are drawing from savings, how a market downturn could affect your plan, and how many healthy, active years you have ahead.

So, how do you weigh those trade-offs?

📥 Grab Your Free Charitable Giving Planning Resources: 

Charitable giving can be simple, but the tax and planning decisions behind it often are not.

Get four practical resources to help you make more informed giving decisions:

A QCD guide, a donor-advised fund guide, a breakdown of which assets may be best to give, and an overview of the charitable-giving vehicles available when your planning gets more complex.

→ Download All 4 Resources Here

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🎙️ Episode Description:

Earlier this year, the U.S. Tax Court threw out a $665,000 charitable deduction.

The d...

Once required minimum distributions begin, the IRS decides how much comes out of your IRA each year.

But it doesn't decide when...

You can take it all in January, wait until December, or spread it out across the year.

At first glance, the choice seems almost meaningless.

The required amount is the same, and the distribution still lands in the same tax year.

But the timing can matter in ways that aren't always obvious.

And even if you're years away from taking RMDs, this is a decision...

One multi-decade study suggests nearly half of working households may be at risk of falling short in retirement.

But another respected study found that fewer than 20% were actually behind.

So which one should you believe?

The answer reveals a weakness in the way we typically measure retirement progress.

Here's what you'll learn:

→ Why 2 respected studies reach such different conclusions about who's really at risk

→ The 3 ways the "save a percentage" rule can break down for families 

→ Why the years when saving feels impossible may be more no...

Most retirement planning treats the transition like a single event.

But in reality, you're navigating THREE different shifts at the same time.

And while traditional planning is well-equipped to handle the first, it spends far less time on the second and almost none on the third.

Here's what you'll learn:

→ Why 50% of retirees plan to spend little or none of their savings

→ Why even a well-funded retiree can treat every withdrawal like a threat

→ 5 questions that work better than "Can I afford it?"

By the end, y...

You've spent decades building a nest egg large enough to fund the retirement you want.

The next challenge is making sure it can support that same lifestyle for the next 30 years.

At 3% historical inflation, the $100,000 lifestyle you retire on could cost $240,000 a year by age 90.

And the assets that feel safest — cash, CDs, and money market funds — have historically done the least to keep up.

In this episode, I'm simplifying a century of market history into 8 numbers that shape how long your money lasts.

Here's what you'll learn:

→...

Two retirees can have the same age, the same nest egg, and the same monthly expenses.

Give them the exact same retirement income plan, and one may feel completely comfortable while the other loses sleep the moment markets fall.

That's because retirement income planning involves more than math.

It also depends on how much certainty you want, how much flexibility you're willing to give up, and which risks you're comfortable carrying yourself.

In this episode, I'm breaking down a practical framework that organizes nearly every retirement income strategy into four distinct...

Americans now say they need $1.5 million to retire comfortably, according to a recent survey.

That's nearly 60% higher than the "magic number" reported roughly five years ago, which helps explain why so many retirement savers feel behind.

But that number is a survey average, and measuring yourself against it could cost you years you can't get back. 

In this episode, I'm sharing why retiring at 62 may be more realistic than you think.

Here's what you'll learn:

→ The new Vanguard research that challenges the conventional Social Security advice

→ How one c...

Last week, I made the case that many retirees can safely spend more than their plans suggest.

Today, the largest bank in the country puts that idea to the test.

But instead of relying on surveys, JP Morgan studied real bank transactions from over 5 million American households.

The data reveals three spending patterns most retirement plans ignore.

And together, they can decide whether a nest egg lasts a full 30-year retirement... or runs out years early.

In this episode, you'll learn: 

→ What millions of real bank transactions reveal about retirement spending...

Most retirement plans assume your spending will rise with inflation every year for the rest of your life.

But a new study tracking thousands of American retirees found almost the exact opposite:

As many as 85% of households spent less, after adjusting for inflation, than they had 10 years earlier. 

Even more surprising? That includes retirees who could comfortably afford to maintain their lifestyle!

In this episode, I'm breaking down what this new research means for your retirement plan.

You'll learn:

→ Why retirement spending declines even as healthcare costs kee...

📥 Grab Your Free Estate Planning Resources: 

Helping an aging parent with their money is a responsibility few families are prepared for.

Get three practical resources to help your family take action:

A one-page cheat sheet of today's episode, a detailed estate-planning review checklist, and a simple guide to the key documents every family should review.

→ Download All 3 Resources Here

***

🎙️ Episode Description:

Helping an aging parent with their money sounds simple: You step in, pay the bills, and make sure everything is handled.

Unfortunately, love and tr...

Kevin O'Leary says you only need one thing to retire safely: 

$5 million in Treasury bills. 

Not stocks. Not real estate. Just T-bills — and you've "safeguarded your family for life."

It sounds like the ultimate safe retirement plan.

But when a recent research article tested this advice against 40 years of market history, the results told a very different story.

In this episode, I break down the research behind the "T-Bill and Chill" strategy and what it really means for your retirement plan.

Here's what you'll learn:

→ The two...

Research shows that retirees following traditional withdrawal rules rarely come close to depleting their portfolios.

In fact, many end up leaving behind balances that are surprisingly large.

Which raises an important question: why is it so hard to spend the money you spent decades saving?

Today, I'm revisiting my conversation with Brian Portnoy, Ph.D., CFA to explore the psychology behind the fear of spending and what retirees can do to move through it.

Longtime listeners will also recognize Brian as the source of a quote I've shared many times on...

Today, we're stepping away from the spreadsheets, tax strategies, and retirement tactics to have a little fun.

I'm sharing six facts that challenge conventional wisdom — including one involving a famous gangster and a reminder that taxes touch almost everything.

A few highlights:

→ The surprising fate of investors who bought the exact top of the dot-com bubble

→ How much a crystal ball that picks winning funds is actually worth

→ What a 50-year backtest reveals about the real role of bonds in your portfolio

→ The one thing the longest-living retirees h...

A strong financial plan can tell you whether you can retire, but it may not tell you whether you'll feel ready. 

In this Retirement Replay, behavioral finance expert and psychologist Dr. Daniel Crosby explains why retirement is not just a portfolio decision. 

He shares the five areas happy retirees tend to prepare for, why purpose and connection matter more than many people realize, and why even people with plenty of money can still struggle to make the leap.

About Retirement Replay: After select guest interviews, we pull together the most replayed moments from th...

At 63, David has $4 million saved.

Two advisors have told him he's ready to retire, and every Monte Carlo simulation agrees... but he still can't bring himself to do it.

"I'm no longer being smart," he admits. "I'm just scared to pull the trigger."

The uncomfortable part is that no number may fix this, because what's holding David back was never on the spreadsheet.

In this episode, I'm joined by Daniel Crosby, Ph.D. — a psychologist and behavioral finance expert — to answer listener questions about the part of retirement the math can't solv...

Imagine I hand you two mutual funds and ask how you'd split your money.

Same holdings. Same cost. Line by line, they're the exact same fund.

The only difference?

One has a name you recognize and the the other is generic. 

Financially, there's no reason to prefer one over the other. 

But when researchers ran this experiment, investors didn't split their money evenly.

In this episode, I break down new research on the hidden cost of making investment decisions based on familiarity.

Here's what you'll le...

You spend 30 or 40 years protecting your future self.

Then you finally retire... and the person you were saving for never quite arrives.

There's always an older version down the road who still feels like they need protecting.

So you keep saving for tomorrow while postponing the life you could enjoy today.

But more money for "future you" isn't what makes retirement better.

In this episode, Hal Hershfield, Ph.D. — a UCLA professor of Behavioral Decision Making and author of Your Future Self — joins me to explain why.

Here...

When inflation makes headlines, it can feel like one of those retirement risks you just have to endure.

Saving, investing, tax planning, income strategy... those are levers you can pull.

Rising prices feel different. They feel like something that happens to you.

But the inflation number you see in the news is rarely the number that matters most for your retirement plan.

Two retirees can live through the same inflation environment and face very different risk — and the gap between them often comes down to a few things they can actually co...

Umbrella insurance isn't usually the first thing people think about when they picture retirement planning.

Most conversations focus on saving enough, investing well, reducing taxes, and creating income.

But in retirement, one unintentional accident can create a very different kind of risk.

Not just a temporary setback, but a threat to savings you may no longer have decades to rebuild.

In this episode, I'm simplifying how umbrella insurance works for retirement savers.

Specifically, I'm sharing:

→ Why liability risk doesn't necessarily disappear after your working years

→ What...

Two retirees. Same $1 million portfolio. Same 60/40 allocation. Same 4% withdrawal rate. Same 30-year retirement.

The only difference?

One retired in 1973. The other retired in 1975. 

Fast forward 30 years: one finished with about $280,000 and the other finished with over $3 million.

Same plan. Just two years apart.

In this episode, I'm breaking down new research that analyzes nearly a century of market history to answer a question most retirement plans don't spend enough time on:

"How much does your exact retirement date shape the outcome of your plan?"

Here's w...

Many retirement savers assume the anxiety will lift once they hit a certain number.

Maybe it's $1 million. Maybe $2 million. Maybe $5 million or more.

And then the account crosses the line, the headlines turn ugly, and the worry is still there.

A recent Wall Street Journal headline put it bluntly: "Even Rich Retirees Fear Outliving Their Money."

In this episode, I'm sharing new research from Fidelity that helps explain why having "enough" so often still doesn't feel like enough.

I'm also sharing the four things I consistently see in retirees...

The math behind "wait until 70" for Social Security is real.

Hold off claiming from 62 to 70 and your monthly benefit climbs by roughly 77%.

So why would anyone walk away from a number that big?

The short answer is that the standard break-even analysis only measures one variable. 

And for retirees with healthy pre-tax savings, there are other factors at play that can make "waiting" a more expensive decision than it looks.

In this episode, I'm turning the mic over to Josh Rendler — a partner at our firm — who walks through a cas...

Tax season is finally over.

The returns are filed, the stress is behind you, and the last thing you probably want to do is think about taxes again.

But the weeks right after tax season are one of the most valuable windows you have all year.

Every number from last year is fresh, every missed opportunity is still visible, and every mistake you just uncovered is a clue about what to fix going forward.

In this episode, I sit down with Josh Rendler, CFP®, a partner at our firm and someone w...

One of the biggest decisions you'll make in your 70s and 80s has nothing to do with your portfolio.

It's not about Social Security timing. And it's not about Roth conversions.

It's about where you'll live and, more importantly, how care will be delivered, coordinated, and paid for if your health changes later on.

Most people think of this as a lifestyle decision.

But in reality, it's a housing-and-care decision, and it's one most retirement plans barely address.

In this episode, I'm breaking down the later-life housing choices most...

According to the FBI, Americans lost nearly $21 billion to cyber-enabled fraud last year—a 26% increase from the year before.

And the single largest category? Investment-related fraud, with more than $8.6 billion in losses.

But what's most unsettling isn't the scale... it's how simple some of these scams really are.

A retired couple recently lost thousands of dollars from their IRA after a scammer tricked them into sharing a single six-digit verification code over the phone.

No hacking. No stolen password. Just one text message and one phone call.

In this epi...

A viral claim keeps making the rounds: that a 1% advisory fee will drain hundreds of thousands of dollars from your retirement savings.

The math looks alarming... and that's exactly the point.

But as with most things in finance (and life!), the truth is more nuanced than a headline or social media post makes it seem.

In this episode, I break down research from Derek Tharp, Ph.D., CFP®, that puts this widely shared math to the test and reveals where it falls apart. 

Here's what you'll learn:

→ The misleading assu...

Saving for retirement is one challenge.

Feeling comfortable (and confident) enough to actually enjoy it is another.

Even when the numbers say you're okay, uncertainty about the future can make it hard to use money for the things that matter most.

Today, I'm revisiting a conversation with Dr. Daniel Crosby where we talk about money, happiness, and why spending is often harder than saving. 

It's especially relevant for me as my family currently navigates some big financial decisions... and a birthday trip for my oldest son that almost didn't happen. 🫣

In...

If you're in or near retirement, one bad investment decision can have lasting consequences.

And new research shows just how risky stock picking can be: 

Over the last 100 years, nearly 60% of all U.S. stocks underperformed Treasury bills—one of the safest investments you can own.

Even more surprising, fewer than 4% of companies created all of the stock market's net wealth.

In other words, the odds of consistently picking the right stocks are far lower than most people realize.

In this episode, I'm breaking down this eye-opening research and wha...

Now that the One Big Beautiful Bill Act has made the 2017 tax rates permanent, more retirees are taking a fresh look at Roth conversions.

But there's one rule that even reputable sources struggle to explain clearly—and the confusion can lead to costly mistakes.

In this episode, I'm simplifying the Roth conversion 5-year rule and sharing:

→ Why the rule is so confusing (and what most people get wrong)

→ The fastest way to determine how the rule applies to your specific situation

→ 4 real-world scenarios so you can see exactly how it works...

📝 Note: The 6.5% withdrawal rate is based on an 80% stock portfolio, a 30-year time horizon, and a 90% "confidence score." Thanks for your patience while we update the episode to include that information. ~Taylor

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Most people spend far less in retirement than they likely could.

In fact, one study found married households age 65+ with more than $100k in savings withdrew just 2.1% per year on average.

And ironically, the traditional 4% rule may be one reason why.

In this episode, I'm breaking down new research on retirement withdrawal strategies—and what it reveals about...

Health insurance is keeping millions of Americans stuck in jobs they'd otherwise leave.

In fact, 1 in 5 workers ages 50–64 say they're staying put because of their employer health coverage.

And with recent changes to the ACA, that pressure is only growing. 

In this episode, I cover:

→ Why healthcare before Medicare has become a psychological roadblock to early retirement

→ Why the real cost of waiting until 65 may not be what you think 

→ The options many people overlook and the tradeoffs worth understanding

Because for most people, the healthcare...

For 30 or 40 years, a paycheck simply showed up. Then one day, it stops.

Now you're staring at a portfolio and asking:

"How do I turn this into reliable income for the rest of my life…without overpaying the IRS or outliving my money?" 

It's no surprise so many retirees gravitate toward dividends. They feel like a replacement paycheck.

In fact, the majority of investors say they prefer dividends and interest over capital gains to fund retirement.

But retirement income planning isn't just about generating cash flow.

It's abo...

Markets move every day. Headlines change every hour.

But the greatest threat to your retirement plan isn't volatility... it's something far less visible.

In this episode, I'm breaking down:

→ The three components of risk most investors focus on (and the one they ignore)

→ Why rare, extreme events have an outsized impact on long-term wealth

→ How to build a retirement plan designed to survive (and even benefit from) uncertainty

I'm also sharing why many "downside-protection" strategies sound compelling in theory, but are risky and difficult to execute in the re...

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments. 

See how they fit together in one coordinated strategy built around your numbers.

👉 Learn More and Book a Call

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Strong rallies make people uneasy.

So does the fear that one bad crash could undo decades of careful saving.

Recently, Morningstar published a great article centered around a chart mapping nearly 100 years of U.S. market history.

When you zoom out, several widely accepted beliefs about market crashes and bull markets start to look f...

Annuities are often sold as a simple solution to a complicated retirement problem.

Guaranteed income. Protection from market volatility. Peace of mind that your money won't run out.

But behind those promises is a much more complex set of trade-offs that many investors don't consider. 

Because while annuities can play a role in retirement planning, evaluating them in isolation often leads to unintended consequences (higher fees, reduced flexibility, extra taxes). 

So in today's episode, I break down how annuities actually work.

We'll walk through the major types of annuities, how...

What makes an investment "good?"

It seems like a straightforward question, but the answer is more subjective than most people realize. 

Recently, my wife asked why I thought real estate was such a BAD investment when others she knows call it the BEST they've ever made. 

Hearing it framed that way struck a different chord.

And rather than quickly defending my position with data and facts, I found myself reconsidering the question entirely.

In today's episode, I share how to evaluate investments in the real world, what separates good inv...