Episodes

May 11, 2026

The Social Security Earnings Limit May Be Eliminated

Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin’s team at https://carrolladvisory.co/podcast1 📍Contact John’s team at h...

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May 4, 2026

What 75 Year Old Retirees Regret Most

Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact Devin’s team at https://carrolladvisory.co/podcast1 📍Contact John’s team at h...

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April 23, 2026

Inbox Question | Leveraged ETFs for Supercharging Retirement Savings

Kevin asks about using leveraged ETFs (2x and 3x return) for his retirement savings. LEverage Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual...

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April 16, 2026

Inbox Question | QCD from a Workplace Retirement Plan

Ann asks about making qualified charitable distributions from her 457 plan. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Contact D...

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April 6, 2026

You’re Probably Looking at the Wrong Estate Tax

Unless you’re listening to this while flying in your own Gulfstream, federal estate taxes probably aren’t something you need to worry about. In 2026, they only apply to estates over $15 million, or $30 million for married cou...

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April 2, 2026

Inbox Question | Should I Use A Spendthrift Trust?

A listener asks about a spendthrift trust for his adult “airhead” granddaughter. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or John through their individual firms. 📍Cont...

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March 23, 2026

How Your AI Data Could Be Used Against You

More people are using AI tools every day to ask questions, solve problems, and even talk through personal decisions. But many users make one dangerous assumption: that their conversations are completely private. In reality, A...

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March 16, 2026

Should a Blood Test Shape Your Retirement Plan?

Advances in predictive medicine are starting to raise a fascinating question: what if we could estimate our longevity with much greater accuracy? New blood tests and biomarkers are being developed that may help identify risks...

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March 9, 2026

Why Recency Bias Is Dangerous for Today’s Retirees

Most people assume the future will look like the recent past. That’s called recency bias, and it can quietly wreck a retirement plan. If the market has been strong for years, investors start believing those returns will conti...

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Feb. 16, 2026

Five Retirement Loose Ends You Can’t Ignore

Saving for retirement is only half the job. In this episode, we discuss the five financial loose ends that can quietly drain retirement income and why addressing them early creates flexibility and peace of mind. Although this...

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Feb. 9, 2026

Planning for Single Retirees — Part 4: Long-Term Care, Incapacity, an…

In this last episode of our Planning for Single Retirees series, we tackle the part of retirement planning that matters most when you don’t have a built-in safety net: what happens if you can’t manage life or money on your ow...

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Feb. 2, 2026

Planning for Single Retirees — Part 3: Tax Planning and Roth Conversi…

The tax planning process doesn’t change for single retirees—but the margin for error does. In this episode, we explain why taxes behave differently when there’s only one tax bracket, no spousal coordination, and no survivor w...

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Jan. 26, 2026

Planning for Single Retirees — Part 2: Social Security Claiming Decis…

For single retirees, Social Security isn’t just another filing decision. It’s the foundation of the entire retirement income plan. In this episode, we explain why claiming decisions matter more when there’s no spouse, no surv...

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Jan. 19, 2026

Planning for Single Retirees — Part 1: Why Retirement Is Different Wh…

Most retirement advice is designed for married couples. But planning for retirement when you’re single comes with a very different set of risks and decisions. In this first episode of a five-part series, we explain why retire...

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Jan. 5, 2026

7 Keys to a More Financially Stable Retirement

For many people, retirement feels less like a reward and more like a financial cliff. In this episode, we break down seven key factors that lead to a more financially stable retirement. You’ll learn how small, practical decis...

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Dec. 15, 2025

How to Buy or Sell a Business the Right Way

Selling a business isn’t just about finding a buyer and shaking hands on the terms — it’s about choosing the right structure. In this episode, we break down stock sales, asset sales, common tax traps, and the key details buye...

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Dec. 11, 2025

Inbox Question | Should Advisors Provide Client References

Frank is interviewing financial advisors and asks whether it is reasonable to expect them to share client names as references. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin...

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Dec. 8, 2025

The Federal Income Tax: Coming to an End?

In this episode, we break down the headlines about eliminating the federal income tax, $2,000 tariff-funded checks, and “no taxes below $150,000.” We look at the math, the Supreme Court challenges, and what these proposals wo...

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Dec. 4, 2025

Inbox Question | Managing Allocation Across Many Accounts

Scott finds it difficult to manage asset allocation and buckets across multiple accounts and asks for an efficient way to coordinate everything. Although this show does not provide specific tax, legal, or financial advice, yo...

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Dec. 1, 2025

Key Changes for 2026

In this episode, Devin and John break down the key tax and retirement planning changes coming in 2026 and what they mean for your income, benefits, and long term strategy. We cover the latest Social Security COLA update, the ...

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Nov. 24, 2025

5 Things Your Attorney Doesn’t Want to Hear

In this episode, John talks about the 5 things that he hates to hear from his clients. You will learn why certain statements (and thinking) slow everything down, what your attorney wishes you understood before walking into th...

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Nov. 13, 2025

Inbox Question | Roth Conversion Strategy for High Earners

Meera and her husband have $4.5 million in retirement accounts and a $430K income. They want guidance on when to start Roth conversions, how much to convert each year, and whether to continue 401(k) contributions. Although th...

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Nov. 10, 2025

Is This the Worst Time to Retire? 3 Ways to Prepare (Just in Case)

Everyone’s wondering if this is the worst time to retire. With high valuations, stubborn inflation, and constant uncertainty, it’s easy to feel uneasy about your timing. In this episode, we look at what history teaches from p...

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Nov. 6, 2025

Inbox Question | Typical Costs of Estate Planning

David asks for a general idea of what estate planning services typically cost, following up on the six-part podcast series. Although this show does not provide specific tax, legal, or financial advice, you can engage Devin or...

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