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PODCAST

Big Picture Retirement®

Devin Carroll, CFP® & John Ross, JD

Planning for, or already enjoying, your retirement? This is the show for you. The success of your retirement hinges on how well you connect the dots between legal, tax, and financial planning. Join your hosts John Ross, JD and Devin Carroll, CFP® as they dig beneath the surface to help you gain the confidence and clarity needed to navigate your retirement journey successfully.

business investing

All Episodes

23:13

Inbox Questions | Cryonics and Trusts: Planning for a...

Big Picture Retirement® ·

2025/02/13

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 science fiction than practical planning? John can barely contain his excitement as we explore the legal, financial, and philosophical implications of planning for a revival hundreds of years down the line. If you’re thinking, "I love the Big Picture

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43:14

The 4 Mindsets That Shape Your Retirement Success

Big Picture Retirement® ·

2025/02/10

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 decisions. From blind optimism to overconfidence, we explore the strengths and pitfalls of each mindset—and how you can evolve to make better choices. Whether you're just starting to plan or reevaluating your approach, this episode will help you identify your

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21:37

Inbox Questions | Why Use Your IRA First for...

Big Picture Retirement® ·

2025/02/06

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 benefits for your overall financial plan, and how it fits into managing your retirement assets. If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you --

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31:43

Tariffs: Balancing the Pros and Cons

Big Picture Retirement® ·

2025/02/03

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, pros, and cons of tariffs, exploring their impact on consumers, businesses, and global trade. Learn how these taxes can stimulate domestic production, drive up consumer costs, and even transform entire industries, like the U.S. auto market. Whether you're

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08:13

Inbox Questions | Should Early Social Security Factor...

Big Picture Retirement® ·

2025/01/30

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 Social Security benefit difference with the investment growth of withdrawals saved by filing early. Is he onto something, or is there a missing piece? Tune in to explore how Social Security timing fits into a Big Picture retirement strategy and hear our take

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27:54

Supreme Court Ruling: The Hidden Risks in...

Big Picture Retirement® ·

2025/01/27

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 why the IRS may not respect your agreed-upon valuation. Discover why it’s critical to review and, if necessary, restructure your buy-sell agreements to avoid unexpected estate tax burdens. We'll explore alternatives like cross-purchase agreements and

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18:32

Inbox Questions | Will GPO Repeal Affect My Benefits?

Big Picture Retirement® ·

2025/01/24

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 about whether his Social Security check will be reduced when he retires from TRS (Teacher Retirement System). If you’ve ever wondered how these rules might affect your benefits, this episode is packed with answers and insights. If you’re thinking, "I love

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24:55

The Unexpected Early Retirement

Big Picture Retirement® ·

2025/01/20

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 backup plan is essential and what steps you can take to protect your financial future, even if your retirement timeline changes. If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us

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13:36

Inbox Questions | Reducing Taxes and Managing RMDs

Big Picture Retirement® ·

2025/01/16

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 minimum distributions (RMDs) and long-term care expenses. We explore the pros and cons of massive Roth conversions, the impact of IRMAA on Medicare premiums, and other strategies for keeping income taxes as low as possible. If you’re thinking, "I love

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32:08

A Smarter Way to Manage Retirement Income

Big Picture Retirement® ·

2025/01/13

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 avoid selling investments during market downturns, create a clear plan for where your money will come from, and adjust your approach based on your comfort with risk. This straightforward method helps you stay on track, worry less, and enjoy the retirement

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16:03

Inbox Questions | Prescription Prices: A Rant and a...

Big Picture Retirement® ·

2025/01/09

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 manage healthcare expenses in retirement. If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll

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25:44

Smart Financial Planning: Balancing Data with Peace...

Big Picture Retirement® ·

2025/01/06

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 of why Devin and his wife chose to pay off nearly $500,000 in debt, despite the numbers telling them not to. We explore the emotional cost of debt, the value of financial freedom, and how to balance logic with what truly feels right. If you’re thinking, "I

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12:40

Inbox Questions | When Should You Stop Using TurboTax?

Big Picture Retirement® ·

2025/01/02

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, RMDs, and other scenarios that could make filing trickier than expected. If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward

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09:38

Inbox Questions | When Should You Use An LLC?

Big Picture Retirement® ·

2024/12/20

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 he should transfer them to an LLC. If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll

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32:22

5 Reasons 2025 Could Be a Turbulent Year for Stocks

Big Picture Retirement® ·

2024/12/16

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 the risks investors should watch for. We also examine how protectionist trade policies, signs of an economic slowdown, and a possible Federal Reserve policy pivot could create turbulence. If you're looking to stay ahead of the curve and prepare for what’s

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07:02

Inbox Questions | Capital Gains on the Sale of Home

Big Picture Retirement® ·

2024/12/12

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 other key considerations to keep in mind when selling your home. If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a

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32:04

What Trump’s Tax Policies Mean for Your Retirement

Big Picture Retirement® ·

2024/12/09

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 strategies. If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this show! This helps us support more people -- just like you -- move toward a confident retirement. Just scroll down to the “ratings and reviews” section,

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21:59

BOI Reporting Delayed: The Future of the Corporate...

Big Picture Retirement® ·

2024/12/05

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 their stakeholders to the government. What does this mean for business owners? Is this a win for small businesses or just a delay in the inevitable? We'll break down the law, the court’s decision, and what might happen next—all in plain English. If you’re

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45:54

What Your Will WON’T Do

Big Picture Retirement® ·

2024/11/04

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 will, and what your will can’t control — like retirement accounts or jointly owned property. We’ll also talk about other tools you might need to make sure your plans really happen the way you want. Join us to learn what your will really does and avoid surprises

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30:32

5 Ways to Make Your Retirement Recession-Ready

Big Picture Retirement® ·

2024/10/29

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 investments with both your comfort level and your financial goals, plus why a balanced mix and a short-term “spending bucket” can keep you from selling at the wrong time. We’ll also cover how fees impact your savings and why it’s worth checking if they’re

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87 results

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