Best Devin Carroll Podcasts (2025)

1
Inbox Question | Company Stock in 401K 8:45

1d ago8:45

8:45

In this episode, Brian asks some great questions about using Net Unrealized Appreciation (NUA) for company stock inside a 401(k). We dive into the rules, timing, and strategies that could lead to major tax savings—if you do it right. We cover: What exactly is NUA and why it matters Can you use NUA before retirement? Do you need to be age 59½? Can y…

1
The 3 Parts to a Perfect Estate Plan: Part 2a: Non-Probate Transfers 26:42

5d ago26:42

26:42

In this episode, we explore how to pass on your assets smoothly and efficiently—without dragging your loved ones through probate court. You’ll learn why probate can be costly and time-consuming, and how non-probate strategies like beneficiary designations, joint ownership, and revocable living trusts can help you keep more money in your family’s ha…

1
Inbox Question | Running a Business & Collecting Benefits: What Counts Toward the Earnings Limit? 6:57

9d ago6:57

6:57

In this inbox episode, we break down how the Social Security earnings limit works—especially for C corp owners who split income between salary and dividends. Learn what counts toward the limit, what doesn’t, and how smart income structuring can help you avoid benefit reductions. Although this show does not provide specific tax, legal, or financial …

1
The 3 Parts to a Perfect Estate Plan – Part 1b: Planning for Incapacity 46:11

12d ago46:11

46:11

In the first part of our series on estate planning, we laid the groundwork for why incapacity planning matters and what documents you need to get started. But there’s more to it than just having your paperwork in order. In this second episode on planning for incapacity, we take the conversation further by focusing on what happens when long-term car…

1
The 3 Parts to a Perfect Estate Plan – Part 1a: Planning for Incapacity 31:04

19d ago31:04

31:04

Today kicks off a brand-new series on estate planning. Estate planning is one of those things everyone knows they should do—but far too many people put it off, sometimes until it’s too late. And the truth is, whether your financial situation is complex or pretty straightforward, having a solid estate plan isn’t just about what happens after you're …

1
Inbox Question | A Better Approach to the S&P 500? 7:42

1M ago7:42

7:42

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 approach. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin…

1
Inbox Question | Cutting Work Hours at 60: Will It Reduce Social Security? 4:53

2M ago4:53

4:53

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 Security calculates benefits, whether lower earnings in the final working years can reduce your check,…

1
How to Travel Like a Local in Retirement (Not Just a Tourist) 35:56

2M ago35:56

35:56

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 most retirees' bucket lists ✅ How to plan trips that align with your passions ✅ The best underrated desti…

1
Inbox Question | Tax Treatment of Special Needs Trusts: What You Need to Know 9:36

2M ago9:36

9:36

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 income, and what trustees need to consider when filing returns. If you or a loved one rely on a Special Need…

1
REPLAY | The Surprisingly Hardest Part of Retirement 36:06

2M ago36:06

36:06

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 this tension? In this episode, we explore the often unexpected emotional hurdles of retirement spe…

1
Inbox Questions | IRA Income & Medicaid Eligibility: Will Too Much Disqualify You? 10:08

2M ago10:08

10:08

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 Qualified Income Trusts (Miller Trusts)—can help individuals qualify despite exceeding the income cap. Tune…

1
REPLAY | 5 Things Nobody Tells You About Retirement 33:41

2M ago33:41

33:41

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 these five areas. If you're on the cusp of retirement, this is crucial viewing to help you steer clear…

1
Inbox Questions | Should We Consider Roth Conversions with a High Income? 8:14

2M ago8:14

8:14

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 future tax implications. While we can’t give personal advice, we’ll break down the potential benefits, dra…

1
What Happens to Your Crypto When You Die? Estate Planning for Digital Assets 22:34

2M ago22:34

22:34

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 digital assets could be lost forever. If you’re thinking, "I love the Big Picture Retirement podcast!” pleas…

1
Inbox Questions | Cryonics and Trusts: Planning for a Future You? 23:13

3M ago23:13

23:13

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 lega…

1
The 4 Mindsets That Shape Your Retirement Success 43:14

3M ago43:14

43:14

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—an…

1
Inbox Questions | Why Use Your IRA First for Long-Term Care Expenses? 21:37

3M ago21:37

21:37

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 thi…

1
Tariffs: Balancing the Pros and Cons 31:43

3M ago31:43

31:43

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 thes…

1
Inbox Questions | Should Early Social Security Factor Into Retirement Calculations? 8:13

3M ago8:13

8:13

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 o…

1
Supreme Court Ruling: The Hidden Risks in Life-Insurance Buy-Sell Agreements 27:54

3M ago27:54

27:54

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 …

1
Inbox Questions | Will GPO Repeal Affect My Benefits? 18:32

3M ago18:32

18:32

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 Sys…

1
The Unexpected Early Retirement 24:55

3M ago24:55

24:55

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 reti…

1
Inbox Questions | Reducing Taxes and Managing RMDs 13:36

4M ago13:36

13:36

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 Ro…

1
A Smarter Way to Manage Retirement Income 32:08

4M ago32:08

32:08

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 f…

1
Inbox Questions | Prescription Prices: A Rant and a Response 16:03

4M ago16:03

16:03

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 podcas…

1
Smart Financial Planning: Balancing Data with Peace of Mind 25:44

4M ago25:44

25:44

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 no…

1
Inbox Questions | When Should You Stop Using TurboTax? 12:40

4M ago12:40

12:40

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 lo…

1
Inbox Questions | When Should You Use An LLC? 9:38

4M ago9:38

9:38

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!”…

1
5 Reasons 2025 Could Be a Turbulent Year for Stocks 32:22

5M ago32:22

32:22

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 ec…

1
Inbox Questions | Capital Gains on the Sale of Home 7:02

5M ago7:02

7:02

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 B…

1
What Trump’s Tax Policies Mean for Your Retirement 32:04

5M ago32:04

32:04

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 th…

1
BOI Reporting Delayed: The Future of the Corporate Transparency Act 21:59

5M ago21:59

21:59

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 b…

1
What Your Will WON’T Do 45:54

6M ago45:54

45:54

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 a…

1
5 Ways to Make Your Retirement Recession-Ready 30:32

6M ago30:32

30:32

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-…

1
Is Downsizing Right for Your Retirement? 42:24

6M ago42:24

42:24

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 t…

1
How Long Will I Live? Planning for Longevity in Retirement 21:39

7M ago21:39

21:39

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 …

1
3 Ways to Pay for Long-Term Care 35:13

7M ago35:13

35:13

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…

1
Monte Carlo Simulations: Is Your “Probability of Success” Trustworthy? 38:27

7M ago38:27

38:27

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 differen…

1
The Stock Market Gamble Most Investors Lose 38:05

7M ago38:05

38:05

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 Reti…

1
How Kamala Harris’s Housing Plan Could Drastically Change Wealth Transfer 29:37

8M ago29:37

29:37

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 re…

1
Ed Slott Explains How to Outmaneuver the Tax Trap in Retirement 35:59

8M ago35:59

35:59

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 distr…

1
Listener Voicemails: Super-funding 529s, Sophisticated Trusts, and Boosting Social Security Benefits 46:04

8M ago46:04

46:04

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. …

1
Listener Q&A: Demystifying Brokerage Statements, Retirement Readiness, and Investment Strategies 33:40

8M ago33:40

33:40

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 …

1
Listener Voicemails: Social Security, Trusts, and IRA Math Mysteries 35:17

9M ago35:17

35:17

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 conce…

1
Listener Q&A: Navigating RMDs, Investment Strategies, and Retirement Income Planning 38:53

9M ago38:53

38:53

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 mak…

1
Listener Q&A: Tax Strategies, Inheritances, Annuities, and More 28:58

9M ago28:58

28:58

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 c…

1
Listener Q&A: Navigating Taxes, Trusts, and More 42:55

9M ago42:55

42:55

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 additiona…

1
Navigating Social Security: Listener Questions Answered 35:51

9M ago35:51

35:51

In this episode of the Big Picture Retirement podcast, we dive into listener questions about Social Security, tackling a wide range of scenarios to help you navigate the complexities of your benefits. Lois asks about the earnings limit for survivor benefits versus other benefits for someone born in 1955. She’s been told she must repay two months of…

1
Listener Questions Answered: Reverse Mortgages, Healthcare Before Medicare, and More! 44:28

10M ago44:28

44:28

In this episode, we tackle a diverse range of listener questions from reverse mortgages, annuities, Roth conversions, healthcare before the Medicare age, and a lot more. Tune in as we discuss: Al's Question: Recommendations for reverse mortgages and the conditions under which they can be beneficial. Paul's Inquiry: Using deferred annuities, specifi…

1
Answering Listener Questions on Social Security 40:22

10M ago40:22

40:22

In this episode, Devin dives deep into the Social Security questions sent in by our listeners. Topics include questions on the earnings limit, spousal benefits, survivor benefits, and the big one...how future benefit cuts could impact retirees If you’re thinking, "I love the Big Picture Retirement podcast!” please consider rating and reviewing this…

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