Stay Wealthy Retirement Podcast

After decades of filing taxes together, most couples assume their retirement plan will continue largely unchanged if one spouse passes away. But for many surviving spouses, the first surprise is a higher tax bill, even when income hasn't changed much. In this episode, I explain how a feature of the tax code can increase taxes after the loss of a spouse. Using a real-world example, I show why tax b...

Every year, Wall Street rolls out its market predictions. Targets get published, expectations get set, and the headlines make it sound like the future is just a spreadsheet away. But markets have a long history of humbling even the most confident forecasts, and that creates a real problem for retirement savers. Because, while short-term forecasts are usually noise, ignoring market expectations alt...

Every January, we go through the same routine. Limits adjust, brackets shift, and most years it's just a quick refresh. But 2026 is different. Sweeping tax legislation passed last summer is introducing some of the biggest changes we've seen in a while. And buried inside those updates are two new rules that have already caused widespread confusion (even among experts). In this bonus episode, I walk...

After decades of saving and doing the right things, most people expect retirement to feel clear.  But for many, it doesn't. Not necessarily because they didn't save enough, but because key financial decisions were made in isolation. In this episode, I walk through the seven questions every retirement saver should be able to answer. I also share the exact planning framework my team and I use to mak...

It's that time of year again—time to step back from the complex tax strategies, Roth conversion debates, and retirement planning deep dives… and have a little fun. 😊 In this annual "surprising stats" episode, I'm sharing 7 counterintuitive facts about the markets and investing. Some are counterintuitive. A few might make you question things you've believed for years. And at least one involves mat...

💥 Download the freshly updated 2026 Tax Planning Cheat Sheet (PDF):  www.youstaywealthy.com/cheatsheet *** Most year-end tax advice is generic... max out your 401(k), bunch your deductions, donate to charity. But for diligent retirement savers with healthy nest eggs, the real opportunities are more nuanced.  In this episode, I break down three tax strategies that can help you avoid overpaying the...

The Oracle of Omaha is officially "going quiet."  In a rare and deeply personal announcement, Warren Buffett published what appears to be his final press release to shareholders. This episode isn't about taxes, investing, or the latest market headlines. It's about how one of the most successful investors of all time is thinking about money, family, aging, and what actually matters when the scorebo...

"Just buy the index." It's the simple advice that built your wealth and got you to the finish line. But here's what often gets overlooked: The strategy that got you to retirement won't necessarily keep you there. When you switch from saving to spending, the math changes. Suddenly, relying on a "simple" S&P 500 strategy exposes you to risks that didn't matter when you had a paycheck. In this episod...

Everyone fears running out of money in retirement—even millionaires.  What most people don't realize is that research shows most retirees rarely spend down their savings. In fact, many actually see their wealth grow throughout retirement, even during some of the toughest markets in history. In this episode, we unpack: ▶ Why that happens ▶ What the data really says about retirement spending ▶ How t...

Sales of "traditional" long-term care insurance have fallen 92% since 2002. Meanwhile, hybrid policies have surged to over 500,000 sales a year.  But which option actually makes sense for your situation?  In this episode, I break down everything you need to know before buying long-term care insurance, including: ▶ The optimal age to purchase ▶ Traditional vs. hybrid policies (the real pros and con...

You've heard it before—70% of Americans over 65 will need long-term care. While that number is technically true, it's also misleading. Because here's what many people don't realize: the vast majority of retirees will never face a catastrophic, six-figure care event. In fact, nearly two-thirds will spend ZERO out of pocket during their lifetime! 🤯 So how do you prepare responsibly without overpayi...

Americans lost a record $16 billion to scams in 2024—nearly 40% from investment fraud alone. The trend is moving in the wrong direction.  In this episode, I share the story of a small-town financial advisor who built trust over decades, until that trust unraveled into one of the most devastating scams they'd ever seen. More importantly, I break down 8 red flags that experts say could indicate you'...

Most experts say the smartest Social Security move is to wait until age 70 to claim. On paper, the logic seems simple—delay claiming, and you'll lock in a larger monthly check for life. But here's what's interesting: only about 10% of Americans actually wait that long. 🤯 Nearly one-third claim Social Security at 62, and the majority file before full retirement age.  So are millions of retirees ma...

We've been told our whole lives that retirement happens at 65—maybe 62 if you're lucky. But in my experience, that traditional timeline isn't always the reality. In fact, for many people, retirement may be much closer than they realize. After nearly 20 years of building retirement plans, I've noticed a recurring theme: Most people overestimate how much they think they need and underestimate how re...

Even if you're not on Medicare right now, chances are someone you love is—and sooner or later, you'll face those decisions yourself. That's why it's worth paying attention to an important letter that arrives every September: the Annual Notice of Change. Most people glance at it, toss it aside, and never think twice. But with big shifts coming in 2026, ignoring it could be a costly mistake. And tha...

Despite making insurance decisions almost daily, many retirement savers don't truly understand what they're buying or why they need it. In today's episode, I'm breaking down life insurance into simple, actionable terms. Specifically, I'm sharing: ‣ The 3 essential steps to managing insurable risks ‣ The key differences between term and permanent life insurance ‣ The exact questions to ask yourself...

Retirement is about so much more than money—it's a complete life transition. In this episode, I'm sharing my recent conversation with Adam Cmejla, where we explore the often-overlooked aspects of retirement planning. We discuss: ‣ Why retirement can feel like a grieving process—and how to navigate it ‣ The surprising role responsibility and community play in long-term happiness ‣ Smarter ways to a...

Required Minimum Distributions (RMDs) could force you to withdraw as much as 15% of your retirement account balance in a single year. But do RMDs really put you at risk of outliving your money? Why does the IRS expect you to live so much longer than the Social Security Administration does? And what proactive steps can you take before age 73 to avoid giving the IRS more than its fair share? In this...

Is retiring in your 50s actually realistic for everyday Americans? According to a recent NerdWallet survey, the average target retirement age for households earning $100,000+ isn't 65—it's 58. And these aren't tech moguls or lottery winners. They're teachers, small business owners, and dual-income couples who've steadily built their nest eggs and now want to enjoy their healthy, active years while...

What if everything you've learned about money completely changes once you cross the $1 million mark? Many people think a healthy 7-figure nest egg means the hardest part is done, but ironically, that's when the biggest financial challenges start. Today, Nick Maggiulli returns to share his latest retirement research, which inspired his new book, "The Wealth Ladder." In this conversation, we explore...

A recent study reported that 76% of retirees regret not saving more money. But after working with hundreds of successful retirees and analyzing thousands of survey responses, I've discovered something interesting:  Their deepest regrets actually have little to do with financial shortfalls. Instead, they revolve around critical aspects of financial planning that significantly impact purpose, indepe...

Wondering how the new 'One Big Beautiful Bill Act' affects you and your retirement plan? Don't want to read 870 pages of Congressional jargon? I've got you covered! In this episode, I'm breaking it all down and sharing the 5 biggest things retirement savers need to know. I'm also addressing several broader provisions in the bill and clarifying some common misconceptions. This giant (and confusing!...

Think you need millions of dollars to retire comfortably? Think again. Most people believe they're "behind" on retirement savings because they're measuring against arbitrary benchmarks that don't reflect their unique situation. But what if retiring at 62 is actually more achievable than you've been led to believe? In this episode, I'm sharing: ► Why you should ignore popular savings benchmarks ► W...

"I planned for 30 years of expenses—but zero years of purpose." This was a recent client's confession, and she's not alone. In fact, nearly 40% of retirees say they wish they had waited longer to retire (and it's not about money).  In this episode, I'm revealing why even the most financially prepared retirees fall into identity crises and regret. I'm also sharing my 5-step "Bridge Strategy" to hel...

"Cash is king" has guided investors since the 1987 market crash. But what if this so-called "king" is actually putting your retirement plan at risk? Millions of retirees are lured by today's enticing cash yields, confusing safety nets for sound investment strategies. In this episode, I'm revealing why cash (even at 4-5%) is a deceptive long-term investment. I'm also sharing details about a critica...