Episodes

March 20, 2025

Inbox Question | A Better Approach to the S&P 500?

John asks about buying the individual sectors of the S&P 500 and rebalancing based on performance instead of simply buying an index fund. Devin shares the pros and cons that he can see with this strategy and shares what he thinks is a better...

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March 13, 2025

Inbox Question | Cutting Work Hours at 60: Will It Reduce Social Secu…

Rosemary’s husband is scaling back to 32 hours a week as part of his transition plan before switching careers. With Social Security in mind, she asks: Will this reduced income impact their future benefits? In this episode, we break down how Social...

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March 10, 2025

How to Travel Like a Local in Retirement (Not Just a Tourist)

Planning to travel in retirement? In this episode, I sit down with Andrew Motiwalla from The Good Life Abroad to discuss how retirees can make the most of their travel experiences—without the stress. We talk about: ✅ Why travel is at the top of...

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March 6, 2025

Inbox Question | Tax Treatment of Special Needs Trusts: What You Need…

This week, we’re diving into a question about the tax treatment of Special Needs Trusts. There are two types—First-Party and Third-Party trusts—but how does each one affect taxes? We’ll break down key differences in taxation, who reports the...

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March 3, 2025

REPLAY | The Surprisingly Hardest Part of Retirement

For countless retirees, the greatest challenge isn't saving money, but spending it. After years of diligent saving, the transition to drawing down those hard-earned funds can be fraught with anxiety and uncertainty. But what if there was a way to ease...

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Feb. 27, 2025

Inbox Questions | IRA Income & Medicaid Eligibility: Will Too Much Di…

Dan asks: If monthly income from an IRA exceeds $2,908 for a single person, would that result in disqualification for Medicaid? We break down the income limits, potential strategies to navigate Medicaid eligibility, and how certain tools—like...

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Feb. 24, 2025

REPLAY | 5 Things Nobody Tells You About Retirement

We’ve heard this hundreds of time... 'I wish someone had warned me about this when I retired.' More often than not, they're referring to one of five key challenges that catch many retirees by surprise. In today's episode, we're diving into each of...

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Feb. 20, 2025

Inbox Questions | Should We Consider Roth Conversions with a High Inc…

In this episode, Tammy asks about the pros and cons of doing Roth conversions in retirement to manage Required Minimum Distributions (RMDs) down the road. With $2.9 million in combined IRAs and current income of $196,000, she’s concerned about...

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Feb. 17, 2025

What Happens to Your Crypto When You Die? Estate Planning for Digital…

Cryptocurrency has changed the financial landscape, and that includes estate planning. Unlike traditional assets, crypto presents unique challenges—there’s no customer service line to recover lost passwords, and without proper planning, your...

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Feb. 13, 2025

Inbox Questions | Cryonics and Trusts: Planning for a Future You?

In this episode, we dive into Stephen’s fascinating question about estate planning for the far future—trusts designed to preserve wealth for individuals who undergo cryonic preservation. Is this cutting-edge legal strategy realistic, or is it more...

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Feb. 10, 2025

The 4 Mindsets That Shape Your Retirement Success

Your mindset can make or break your retirement. Are you a Pollyanna, Delegator, Controller, or Realist? In this episode, we dive into the four common mindsets retirees bring to the table and how each one impacts their financial, tax, and legal...

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Feb. 6, 2025

Inbox Questions | Why Use Your IRA First for Long-Term Care Expenses?

In this episode, we tackle Richard’s question about why it might make sense to use IRA (non-Roth) accounts first to pay for long-term care expenses. We’ll explain the reasoning behind this strategy, including the tax implications, potential...

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Feb. 3, 2025

Tariffs: Balancing the Pros and Cons

From President Trump’s upcoming tariffs on Canada, Mexico, and China to the historical legacy of the “Chicken Tax,” tariffs have shaped economies and industries in ways both expected and unforeseen. In this episode, we dive into the purpose,...

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Jan. 30, 2025

Inbox Questions | Should Early Social Security Factor Into Retirement…

In this episode, we address Joe’s question about how claiming Social Security benefits early can reduce withdrawals from retirement accounts and potentially lead to greater long-term growth. Joe shares his calculation comparing the cumulative...

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Jan. 27, 2025

Supreme Court Ruling: The Hidden Risks in Life-Insurance Buy-Sell Agr…

A recent Supreme Court decision in Connelly v. United States has sent shockwaves through closely held businesses employing life-insurance-funded redemption-type buy-sell agreements. In this episode, we break down the case, the tax implications, and...

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Jan. 24, 2025

Inbox Questions | Will GPO Repeal Affect My Benefits?

In this episode, we answer Lori’s question about whether the repeal of the Government Pension Offset (GPO) will increase her survivor benefits and how it could impact benefits for those with similar circumstances. We also address Jesus’s concern...

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Jan. 20, 2025

The Unexpected Early Retirement

Sometimes life throws curveballs, and you may end up retiring earlier than planned. In this episode, we dive into JP Morgan’s data on why people retire earlier than expected and discuss how to prepare for the unexpected. Learn why having a solid...

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Jan. 16, 2025

Inbox Questions | Reducing Taxes and Managing RMDs

In this episode, we tackle Kay's questions about managing her IRA and Roth accounts in retirement. With significant assets, no LTC insurance, and children in differing financial circumstances, Kay wants to minimize taxes while preparing for required...

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Jan. 13, 2025

A Smarter Way to Manage Retirement Income

Retirement can be stressful, especially when the markets are unpredictable. In this episode, we’ll talk about a simple strategy to give you peace of mind and financial stability in retirement. You’ll learn how to set aside five years of income to...

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Jan. 9, 2025

Inbox Questions | Prescription Prices: A Rant and a Response

Today’s episode is part rant, part answer to Mike’s question about the high cost of prescription drugs under Medicare Part D. We dive into why these costs are so steep, explore alternatives like Canadian pharmacies, and discuss what you can do to...

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Jan. 6, 2025

Smart Financial Planning: Balancing Data with Peace of Mind

Financial planning often feels like a numbers game—follow the math, and you’ll make the best decisions, right? But what happens when the spreadsheet says one thing, and your peace of mind says another? In this episode, we share the personal story...

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Jan. 2, 2025

Inbox Questions | When Should You Stop Using TurboTax?

Today, we tackle a question many retirees face: Can you manage your taxes with DIY software like TurboTax, or is it time to bring in a professional? We'll explore the challenges of navigating tax complexities in retirement, including 401(k) rollovers,...

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Dec. 20, 2024

Inbox Questions | When Should You Use An LLC?

We answer a question from a 44-year-old Pittsburgh bus driver earning over six figures annually who maxes out a Roth IRA, contributes 10.5% to a 457 plan, and is covered by a pension. He owns five rental properties in his name and wonders if and when...

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Dec. 16, 2024

5 Reasons 2025 Could Be a Turbulent Year for Stocks

Could 2025 be a stormy year for the stock market? In this episode, we explore five potential triggers that could send markets into turmoil. From the unpredictability of Trump-era “tape bombs” to a potential bursting of the AI bubble, we break down...

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