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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

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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42:24

Is Downsizing Right for Your Retirement?

Big Picture Retirement® ·

2024/10/21

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 attachment to your family home and the hidden costs of moving. Tune in to help decide if downsizing is the right move for you. 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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21:39

How Long Will I Live? Planning for Longevity in...

Big Picture Retirement® ·

2024/10/14

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 important to plan for a longer life. We also share tools that can help you estimate how long your savings need to last, whether you’re planning on your own or with a partner. Making a solid plan for how long you’ll need your money is key to a secure

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35:13

3 Ways to Pay for Long-Term Care

Big Picture Retirement® ·

2024/10/07

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 and explain why planning ahead is critical. Plus, we’ll introduce a tool that can help you estimate the actual costs of care in your area. Whether you’re planning for yourself or a loved one, this episode will give you the insights you need to make an

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38:27

Monte Carlo Simulations: Is Your “Probability of...

Big Picture Retirement® ·

2024/09/30

In this episode, we take a closer look at Monte Carlo simulations—a tool used in retirement planning to estimate your chances of success. But are those percentages really reliable? Can an 85% or 90% success rate give you confidence in your retirement plan? We’ll explain how these simulations work, how different assumptions can lead to very different results, and why you shouldn’t just rely on past returns. If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and

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38:05

The Stock Market Gamble Most Investors Lose

Big Picture Retirement® ·

2024/09/23

In this episode, we explore the realities of stock-picking, revealing that it’s a gamble where the odds are heavily stacked against the average investor. Studies show that most individual stocks underperform or lose value over time, so we make a strong case for the smarter and more reliable approach. 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

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29:37

How Kamala Harris’s Housing Plan Could Drastically...

Big Picture Retirement® ·

2024/09/16

In this episode, we unpack Vice President Kamala Harris’s ambitious plan to lower housing costs, which would be funded by adopting Senator Elizabeth Warren’s sweeping estate tax overhaul. We explore the major changes proposed, including reducing the estate tax exclusion to $3.5 million, significantly increasing estate tax rates, and imposing new restrictions on popular estate planning tools like GRATs and grantor trusts. We also discuss the broader implications of these changes, such as the

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35:59

Ed Slott Explains How to Outmaneuver the Tax Trap in...

Big Picture Retirement® ·

2024/09/09

Today we're joined by Ed Slott, the expert’s expert on retirement planning, to talk about how to make the most of your retirement savings and avoid costly tax surprises. Ed explains why converting to Roth IRAs could be a smart move, the risks of sticking with traditional IRAs, and how to get ready for the taxes that come with required minimum distributions (RMDs). With Ed’s advice, you’ll learn how to approach retirement planning with a clear, long-term strategy. Check out Ed Slott’s book, The

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46:04

Listener Voicemails: Super-funding 529s,...

Big Picture Retirement® ·

2024/09/03

In this episode, we’re answering more listener voicemails about Social Security, gifting money, and estate planning. First, we help a listener who’s trying to figure out the best way to maximize his wife’s Social Security benefits. He’s getting close to his full retirement age in 2025 and wants to make sure they get the most out of their benefits. Next, we talk about a question regarding "superfunding" a 529 plan. A listener’s mom wants to contribute a large amount upfront for her niece’s education,

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33:40

Listener Q&A: Demystifying Brokerage Statements,...

Big Picture Retirement® ·

2024/08/26

Today, Devin and Alexander are back answering listener questions. Tune in as we explore: Jamie's request for a detailed walkthrough of a monthly brokerage account statement, explaining where to find and understand fees, and demystifying various financial terms in plain English. Carl's situation as a 58-year-old with a diversified $1.1 million nest egg, seeking advice on overcoming the fear of retiring despite having solid financial resources, zero debt, and multiple income streams from pensions

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35:17

Listener Voicemails: Social Security, Trusts, and IRA...

Big Picture Retirement® ·

2024/08/19

In this episode we’re answering listener voicemails and tackling some tough questions about Social Security, RMDs, estate planning, and more. First up, we help Diane, whose husband is a minister, figure out why his Social Security benefits don’t include his housing allowance, even though he pays taxes on it. Then, we talk through a listener’s concerns about how changing the title on a brokerage account could affect the revocable living trust her parents set up. We also explain how Required Minimum

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38:53

Listener Q&A: Navigating RMDs, Investment Strategies,...

Big Picture Retirement® ·

2024/08/12

In this episode of Big Picture Retirement, Devin is joined by Alexander Davis, a financial advisor at Carroll Advisory Group, to address some of the most pressing questions from our listeners. Together, they answer a range of questions, including: Charles' query on the order and process of completing Required Minimum Distributions (RMDs) before making Roth Conversions. Ted's strategy on transitioning maturing tIRA CDs into investment grade and Treasury short and intermediate-term bond funds, and

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28:58

Listener Q&A: Tax Strategies, Inheritances,...

Big Picture Retirement® ·

2024/08/05

In this episode, Devin and John dive into a variety of listener questions, discussing annuities, maxing out retirement plans, why HSAs aren't widely talked about, IRMAA, and more. Tune in as we explore: Claudia's Situation: Understanding the distribution requirements for inherited qualified and unqualified MYGA accounts in light of recent tax law changes. We discuss the tax implications of cashing out one account at the rollover date versus waiting, and which account is better to save for

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42:55

Listener Q&A: Navigating Taxes, Trusts, and More

Big Picture Retirement® ·

2024/07/29

In this episode of Big Picture Retirement, we’re back answering more of our listener-submitted questions. Join us as we cover: Anna's Query: When will NESARA begin? Ron's Question: Clarification on calculating taxes on Social Security benefits using our Cheat Sheet, specifically addressing whether AGI already includes SS benefits or if an additional 50% is added. Anne's Concerns: Discussing the threshold for needing trusts for individuals with borderline amounts ($750,000 - $1.5 million) and

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94 results

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