Episodes

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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Sept. 30, 2024

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

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...

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Sept. 23, 2024

The Stock Market Gamble Most Investors Lose

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...

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Sept. 16, 2024

How Kamala Harris’s Housing Plan Could Drastically Change Wealth Tran…

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...

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Sept. 16, 2024

How Kamala Harris’s Housing Plan Could Drastically Change Wealth Tran…

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...

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Sept. 9, 2024

Ed Slott Explains How to Outmaneuver the Tax Trap in Retirement

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...

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Sept. 3, 2024

Listener Voicemails: Super-funding 529s, Sophisticated Trusts, and Bo…

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...

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Aug. 26, 2024

Listener Q&A: Demystifying Brokerage Statements, Retirement Readiness…

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...

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Aug. 19, 2024

Listener Voicemails: Social Security, Trusts, and IRA Math Mysteries

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...

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Aug. 12, 2024

Listener Q&A: Navigating RMDs, Investment Strategies, and Retirement …

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: ...

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Aug. 5, 2024

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

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...

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July 29, 2024

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

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...

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