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...
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...
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...
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...
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...
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...
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...
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...
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...
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 ...
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...
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...
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...
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...
You’ve heard it a thousand times: “Wait until 70 to file for Social Security.” But if that’s such obvious advice, why do most retirees file earlier? In this episode, we uncover the hidden cost of waiting and the trade-offs mo...
Daryl wants a simple explanation of why Health Savings Accounts matter and what makes them such a powerful retirement planning tool. Although this show does not provide specific tax, legal, or financial advice, you can engage...
John asks if taking larger IRA withdrawals beyond his RMD to fund his daughter’s Roth IRA makes sense as a strategy to reduce future RMDs, lower estate taxes, and pass on tax-free assets. Although this show does not provide s...
Many retirees think they have a plan when what they really have is an investment pitch dressed up as planning. This episode uncovers why that illusion is dangerous, the costly mistakes it hides, and how to spot the difference...
Winning the lottery may be rare, but estate tax mistakes aren’t. In this episode, we use the recent $1.8 billion Powerball jackpot to highlight how generational wealth can be eroded by estate taxes and how tools like a BDIT c...
So far in 2025, early Social Security filings have jumped dramatically compared to last year. Nearly half of those filing early say they’re doing so because they’re worried about cuts. But will filing early really help? In th...
When should you claim Social Security? For high-net-worth retirees, this is not a simple decision. In this episode, we explain why Social Security is not just a monthly check but a strategic part of a well-built retirement pl...
For many affluent retirees, the biggest financial fear isn’t market volatility or rising taxes. It’s this simple question: What happens if I’m not the one here to manage the plan? In this episode, we talk about a deeply perso...
Should everyday investors be allowed to hold private equity, venture capital, or even crypto in their 401(k)s? A new executive order suggests it might soon be possible. In this episode, we walk through the real implications o...
You’ve done the hard work. You saved consistently, built a seven-figure portfolio, and are ready to enjoy retirement. But even millionaire retirees can make mistakes that put their plans at risk. In this episode, Devin shares...