Episodes

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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Dec. 12, 2024

Inbox Questions | Capital Gains on the Sale of Home

Today, we tackle a question from Patrick about the nuances of capital gains taxes on the sale of a primary residence. We break down how community property laws can impact your tax liability, the role of improvements in calculating your cost basis, and...

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Dec. 9, 2024

What Trump’s Tax Policies Mean for Your Retirement

How could Trump’s tax policies impact your retirement plans? In this episode, we break down the potential changes, from tax cuts to shifting brackets, and discuss what they could mean for your savings, Social Security, and investment...

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Dec. 5, 2024

BOI Reporting Delayed: The Future of the Corporate Transparency Act

In this episode, we’re diving into the latest legal drama surrounding the Corporate Transparency Act (CTA). A federal judge in Texas has temporarily blocked this law, which would have required U.S. businesses to report detailed information about...

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Nov. 4, 2024

What Your Will WON’T Do

In this episode, we’re breaking down common myths about what a Will can actually take care of. A lot of people think a will covers everything, but it’s not that simple! We’ll explain how probate works, why some assets don’t go through your...

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Oct. 29, 2024

5 Ways to Make Your Retirement Recession-Ready

In this episode, we break down simple strategies to protect your retirement savings when the market gets rough. We’ll start with why staying calm is key and how planning ahead can help you avoid emotional decisions. You'll learn how to match your...

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Oct. 21, 2024

Is Downsizing Right for Your Retirement?

Today we discuss the pros and cons of downsizing in retirement. We discuss how selling your home can reduce expenses, simplify your lifestyle, and free up money for travel or investments. But we also cover the potential downsides, like emotional...

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Oct. 14, 2024

How Long Will I Live? Planning for Longevity in Retirement

In this episode, we talk about an important part of retirement planning that many people overlook—figuring out how long you might live. We explain why using average life expectancy or guessing based on family history can be risky, and why it’s...

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Oct. 7, 2024

3 Ways to Pay for Long-Term Care

Long-term care is a reality that many retirees will face, but the question is—how will you pay for it? In this episode, we break down the three primary ways to cover long-term care expenses. We’ll walk you through the pros and cons of each option...

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