Stay Wealthy Retirement Podcast

1d ago

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 math that should make anyone considering complex insurance products hit the pause button. By the end of today's episode, you'll walk away feeling more confident in the proven (sometimes boring!) academic approach to investing that we talk about so often here on the show. And if nothing else, you'll have a few holiday-dinner stats to drop between bites of pie. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Learn More *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™ → Download the 2026 Tax Cheat Sheet

Dec 11

💥 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 IRS and reduce your lifetime tax bill. You'll learn how to evaluate whether each move makes sense for your situation, so you're making informed decisions rather than chasing aimless deductions. If you're nearing retirement or already there, this episode will help you close out the year with a clearer tax picture and a smarter plan for the years ahead. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule a Call *** EPISODE RESOURCES: → Download the 2026 Tax Cheat Sheet → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™ → Careers at Define Financial

Nov 27

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 scoreboard stops moving. In this Thanksgiving special, I break down: ▶ Why he chose to say this now (at age 95!) ▶ What retirement savers and investors can learn from his message ▶ How his parting wisdom can change the way you use your time and wealth If you've ever wondered what your future self might wish you'd paid more attention to today, this conversation is for you. Tune in for the deeper meaning behind Buffett's Thanksgiving sign-off ("yes, even the jerks") and what it reveals about redefining success in the second half of life. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

Nov 20

"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 episode, we cover: ▶ The Simplicity Trap: Why "decision fatigue" lures smart retirees into risky, overly concentrated portfolios. ▶ S&P 500 Reality Check: Why the "safe" default option is actually dangerous for your retirement income. ▶ The "Flatline" Defense: How to build a retirement portfolio that protects your purchasing power during downturns. ▶ Beyond Investing: How to align your investments, taxes, and legacy for true peace of mind. If you are approaching retirement and wondering if your "set it and forget it" strategy is enough to last a lifetime this episode is for you. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, my team and I have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

Nov 6

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 to find the right balance between confidence and caution By the end, you'll see why most retirees worry far more than they need to, and how to feel confident spending your own money. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, my team and I have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

Oct 30

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 cons beyond the sales pitch) ▶ The actual costs of proper coverage I'm also sharing three critical implementation details that can make or break your coverage when you need it most. If you're approaching retirement and wondering how to protect yourself from potentially catastrophic long-term care costs, this episode will give you the clarity you need to make an informed decision. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule Your FREE Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

Oct 23

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 overpaying for protection you may never use? In this episode, I walk you through a simple 5-step process to decide if you can safely "self-fund" your long-term care needs, while still protecting your retirement plan and peace of mind. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™

Oct 16

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're being conned. Because here's the truth: falling for a scam doesn't mean you're careless or foolish—it means you're human. And understanding the psychology behind deception is the best way to protect yourself. If you think you're immune, that confidence might be exactly what scammers are counting on. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: → Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter → Learn About the Total Retirement System™