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...
In this episode, we break down the newly signed One Big Beautiful Bill Act (OBBBA) and what it means for retirees. From the extension of the 2017 tax cuts to new rules around Roth conversions, Social Security taxation, and a ...
Today we answer a question from Ken, a recent retiree at 63, about how his Social Security claiming decision impacts his wife’s future spousal benefit. We break down how spousal benefits are calculated, whether the FRA (Full ...
Most retirees think tax planning ends with knowing their tax bracket, but that’s just the beginning. In this episode, we unpack how different income sources interact in retirement, and how seemingly smart decisions can trigge...
Today we answer a question from Chris about The Good Life Abroad and whether we plan to take a trip with the company. We share our thoughts on the concept, what interests us about their offerings, and whether a future review ...
Today we answer a question from Sandi about how much umbrella insurance coverage you really need — especially as you approach retirement. We discuss why someone might choose a $2 million policy, how assets like home value, re...