One For The Money

Episode 119: Five Strategies for Retiring Early

Early retirement requires a different playbook. In this episode, I explain five strategies for bridging the gaps before Social Security and Medicare, managing taxes, and funding your lifestyle with greater flexibility.

In the tips and tricks segment, I share how Roth IRA contributions can provide an additional source of penalty-free funds before age 59½.

Key points

• Build a taxabl...

Episode 118: Building a More Satisfying Retirement

What does a successful retirement really look like?

In this episode, Jonny explores why retirement satisfaction depends on more than just the size of your portfolio. Research shows that four factors play an important role: income, savings, health, and social connection.

You’ll learn why a comprehensive retirement plan should go beyond investments and include thoughtful planning ...

Episode 117: Social Security Claiming Strategies and Tips for Married Couples

In this episode of One for the Money, we take a close look at one of the most important retirement decisions you can make: when to claim Social Security. While the timing can have a meaningful impact on your lifetime retirement income, too many people still make this choice without a clear strategy. We break down the key claiming ages, the tradeoffs betwee...

Episode 116 – The Alphabet Soup of Employee Stock Benefits

• Why employee ownership can be a powerful wealth-building tool
• Overview of ESOPs, ESPPs, RSUs, and the NUA tax strategy
• How ESOPs and ESPPs give you company stock through contributions or discounted purchases
• How RSUs work, when they’re taxed, and why they often lead to concentrated employer stock
• What NUA is and when it can reduce taxes on appreciated company sto...

In this episode of One for the Money, I revisit author Morgan Housel—best known for The Psychology of Money—and explore his newer, even more impactful book, The Art of Spending Money. I share why building wealth is only half the equation and why learning to spend that wealth intentionally, in line with your values and life experiences, is its own crucial skill. You’ll hear practical ideas for using money as a tool...

Debt, Deficits, and Your Financial Future

In this episode of One for the Money, Jonny zooms out: yes, we’re living in the most prosperous era in human history—but America’s debt and spending habits are a growing reason for concern.

In this episode:

• How Washington turned the U.S. into a “transfer society” and why interest on the debt now rivals defense spending
• What trillion‑dollar deficits really mean ...

One for the Money — Episode 113

The Case for Optimism (5th Annual)

Each July, the One for the Money podcast makes the case for optimism — and this year's edition may be the most compelling yet. Despite an unsettling headlines landscape that includes the ongoing wars in Ukraine and Iran and persistent political dysfunction, the data tells a different and far more hopeful story. This episode is your annual reminder of just ...

Episode 112: Family Matters & Money - For Better or For Worse

Money can’t buy love or happiness—but it can absolutely impact both.

In this episode of One for the Money Podcast, I share how money can either strengthen or damage the relationships that matter most in our lives. Research consistently shows that strong relationships are one of the greatest predictors of happiness, health, and longevity. The question becom...

In this episode, I break down one of the newest and most talked-about financial policies introduced in 2025: Trump Accounts. Created as part of the “One Big Beautiful Bill,” these tax-advantaged investment accounts are designed to give American children a financial head start from birth.

I cover how these accounts work, who qualifies, the role of government and private funding, and whether they make sense for your family...

Episode 110: The Hidden Power of 529 Plans (and How to Use Them Like a Pro)

Welcome back to the One for the Money podcast!

In this episode, we dive into one of the most powerful—and often misunderstood—tools for college planning: 529 plans. With graduation season in full swing, this topic hits especially close to home as families prepare for the next big (and expensive) chapter.

🎓 What’s Inside This Episode

A Persona...

Episode Summary

With Mother’s Day right around the corner, this episode highlights an important—and often overlooked—reality in financial planning: too many women are still taking a back seat when it comes to managing their financial future.

Drawing from real client experiences, this episode explores why financial planning works best when both partners are actively involved, and why it’s especially critical fo...

It’s Tax Day — the one day of the year when millions of Americans collectively ask the same question: Did I pay too much… or too little?

But another question quickly follows: Is everyone else paying their fair share?

In this episode, we explore one of the most debated topics in economics and politics — the fairness of the U.S. tax system. We examine how income and wealth are taxed differently, look at what th...

Episode 107 Show Notes

Pay Taxes Now or Later? 7 Strategic Reasons to Consider Roth Conversions

This episode airs on April 1st — just two weeks before the April 15th tax filing deadline — which makes it the perfect time to talk about proactive tax planning.

While everyone has to pay taxes, no one should ever leave a tip.

In this episode, we discuss why paying taxes strategically now — through Roth contributions and Ro...

Retirement isn’t just the closing of one chapter — it’s the opening of another.

In this episode, I explore how shifting your mindset from retirement to ReFirement can dramatically improve both your financial outcomes and your overall fulfillment. Rather than viewing retirement as a period of rest and withdrawal, I discuss how intentional planning can turn it into a season of renewed purpose, contribution, and perso...

Episode 105: The Real State of Retirement in America

Retirement is supposed to be the reward after decades of hard work—but for many Americans, it’s filled with uncertainty, stress, and fear.

In this episode of the One for the Money Podcast, we take an honest look at what retirement really looks like in America today, based on recent survey data from current retirees. The findings are eye-opening—and in som...

Episode 104: Should You Pay Off Your Mortgage Early?

Is owning a home really the American Dream… or is owning it free and clear the real goal?

In Episode 104 of One for the Money, we tackle one of the most common—and emotionally charged—financial questions homeowners ask: Should you pay off your mortgage early?

The answer isn’t just about math. It’s about psychology, peace of mind, and how your ...

There aren’t enough homes. Homes are too expensive. And mortgage rates are too high.

In Episode 103 of One for the Money, I break down how the U.S. housing crisis was created, why it persists, and what realistic solutions could actually improve affordability.

This episode goes beyond headlines and politics to diagnose the root causes of the crisis—using plain economics, real-world examples, and historical context. We also...

The stock market can feel like a rollercoaster—especially when the drops are steep. Declines of 20% or more are known as bear markets, and while they can be frightening, they’re also a normal part of investing.

In this episode, I explain why bear markets shouldn’t be feared, how often they really occur, and—most importantly—what actions investors should (and shouldn’t) take when they happen. Drawi...

Happy New Year, and welcome to episode 101 of the One for the Money podcast!

This episode airs on January 1st—a perfect moment for financial resolutions and fresh starts. If getting back on track with your money is one of your goals for the new year, this episode will help you make one of the most important decisions in your financial life: whether to hire a financial advisor, and how to choose the right one.

In This Episode

I&r...