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.

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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 far less certain.

In this episode, I break down the three common myths the article explores.

I also share what the data actually tells us about bear markets and what's far more likely to derail your retirement than a crash.

Not to predict the future or eliminate risk.

But to help you think more clearly about the environment we're in and how it fits into a disciplined, long-term retirement plan.

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EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

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 "guarantees" are structured, what you're really paying for, and where the risks tend to show up later in retirement.

I'll also explain when annuities may make sense, when they don't, and how to evaluate them as part of a coordinated retirement plan so you can make informed decisions with confidence.

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📆 BOOK A CALL:

For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click to Learn More and Schedule

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

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 investments from bad ones, and why some popular metrics can mislead.

If you've ever wondered why an investment looks great paper but doesn't feel right—or why others swear by strategies you'd never touch—this episode will give you a clearer framework for thinking about your own portfolio.

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📆 BOOK A CALL:

For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click to Learn More and Schedule

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

After decades of filing taxes together, most couples assume their retirement plan will continue largely unchanged if one spouse passes away.

But for many surviving spouses, the first surprise is a higher tax bill, even when income hasn't changed much.

In this episode, I explain how a feature of the tax code can increase taxes after the loss of a spouse.

Using a real-world example, I show why tax brackets shrink, why retirement income often doesn't, and how that mismatch can quietly drive taxes higher over time.

More importantly, I share a planning framework couples can use while both spouses are still alive.

We'll cover common mistakes, why the "married window" matters, and how small, intentional decisions made years in advance can meaningfully protect the surviving spouse.

This isn't about fear or worst-case scenarios—it's about avoiding unnecessary surprises and making thoughtful, proactive decisions that support confidence throughout retirement.

***

📆 BOOK A CALL:

For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click to Learn More and Schedule

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

Every year, Wall Street rolls out its market predictions.

Targets get published, expectations get set, and the headlines make it sound like the future is just a spreadsheet away.

But markets have a long history of humbling even the most confident forecasts, and that creates a real problem for retirement savers.

Because, while short-term forecasts are usually noise, ignoring market expectations altogether isn't the answer either.

So in today's episode, I break down how to think about market outlooks the right way.

We'll cover why forecasts so often miss the mark, when long-term assumptions actually matter, and how market research can be used as a planning tool (not a prediction engine).

I also share key themes from Vanguard's Economic and Market Outlook for 2026, focusing on growth, inflation, and expected returns—and why all of that matters for your portfolio and retirement plan.

***

📆 BOOK A CALL:

For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click to Learn More and Schedule

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

Every January, we go through the same routine.

Limits adjust, brackets shift, and most years it's just a quick refresh.

But 2026 is different.

Sweeping tax legislation passed last summer is introducing some of the biggest changes we've seen in a while.

And buried inside those updates are two new rules that have already caused widespread confusion (even among experts).

In this bonus episode, I walk through the most important tax updates for 2026 and explain why they matter for your retirement plan.

I also also break down those two unique rules, sharing how they work, who they apply to, and why they matter.

So even if you feel up to speed on the 2026 changes, I'm confident you'll walk away with at least one new and useful insight.

***

📆 BOOK A CALL:

For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click to Learn More and Schedule

***

EPISODE RESOURCES:

→ Download the 2026 Tax Cheat Sheet

→ Grab the Episode Show Notes

→ Learn About the Total Retirement System™

After decades of saving and doing the right things, most people expect retirement to feel clear.

But for many, it doesn't.

Not necessarily because they didn't save enough, but because key financial decisions were made in isolation.

In this episode, I walk through the seven questions every retirement saver should be able to answer.

I also share the exact planning framework my team and I use to make sure those questions are addressed in a thoughtful, coordinated way.

By the end of today's episode, you'll have a clearer framework for evaluating your retirement decisions.

And more importantly, you'll understand what it actually takes to feel confident about the years ahead.

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📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING:

For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click Here to Learn More

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

It's that time of year again—time to step back from the complex tax strategies, Roth conversion debates, and retirement planning deep dives… and have a little fun. 😊

In this annual "surprising stats" episode, I'm sharing 7 counterintuitive facts about the markets and investing.

Some are counterintuitive.

A few might make you question things you've believed for years.

And at least one involves math that should make anyone considering complex insurance products hit the pause button.

By the end of today's episode, you'll walk away feeling more confident in the proven (sometimes boring!) academic approach to investing that we talk about so often here on the show.

And if nothing else, you'll have a few holiday-dinner stats to drop between bites of pie.

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📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING:

For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning.

The result?

Less stress. Lower taxes. More confidence about the future.

If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation.

👉 Click Here to Learn More

***

EPISODE RESOURCES:

→ Grab the Episode Show Notes

→ Join the Stay Wealthy Retirement Newsletter

→ Learn About the Total Retirement System™

→ Download the 2026 Tax Cheat Sheet