Winning Retirement Radio

This week, it’s all about this powerful statistic: nearly 70% of family wealth is lost by the second generation, and 90% by the third. So why does that happen? Greg and Kristin break down the biggest reasons families lose wealth over time, including a lack of communication, a lack of financial education, and failing to pass down values along with money. You’ll also hear real-life stories about clients—both the successes and the struggles of wealth transfer—and learn how open conversations, proper planning, and intentional legacy-building can make all the difference. Because in the end, your legacy isn’t just about the money you leave behind—it’s about the impact you make while you’re here.  

Does chewing gum really boost your memory? Maybe—but remembering the healthcare costs that Medicare doesn’t cover might be even more important! While Medicare does a solid job covering doctor visits and hospital stays, there are still significant gaps—especially when it comes to dental work, vision care, prescription drugs, and long-term care. Greg and Kristen explain why these costs can catch retirees off guard and share strategies that can help people prepare ahead of time, including HSAs, planning for Medicare savings in your budget, and exploring options for long-term care protection. If you’re approaching retirement or already there, understanding Medicare’s coverage gaps could help you protect both your health and your financial future.

Some financial firms promote themselves as a “one-stop shop,” offering attorneys, accountants, and advisors all under one roof. So why doesn’t the team at Legacy Retirement Group do the same? In this episode, Greg and Kristen explain the philosophy behind their approach. Rather than trying to do everything internally, Legacy focuses on what it does best—retirement investment planning, income planning, and tax strategy—while collaborating with independent specialists when clients need legal, tax, or estate expertise. In retirement planning, coordination and collaboration often beat trying to do everything in one place.

“Wait until 70. You’ll get 8% more per year.”
Sounds simple, right? Not so fast. In this episode, Greg and Kristin tackle one of the most common retirement questions: Should you delay Social Security to maximize your benefit? Learn why there’s no one-size-fits-all answer. While waiting can increase your monthly benefit and potentially protect a surviving spouse, it can also mean draining retirement assets too quickly if you don’t have enough saved. Social Security isn’t the retirement plan. It’s one piece of the income puzzle. The real key? Building a written retirement income plan that’s stress-tested against market volatility, inflation, and tax changes. Because in retirement, cash flow is king!  

Greg and Kristin dive into the emotional and practical side of money in marriage by sharing personal stories, real client experiences, and the hard truth about what happens when financial transparency breaks down. From hidden credit card debt to mismatched risk tolerance, they explain why communication is critical—especially as retirement approaches. Because once you stop earning paychecks and start creating your own income, financial secrets don’t just hurt feelings… they can derail the plan.  

From dial-up internet and AOL chat rooms to Alexa, smart faucets, and artificial intelligence, technology has come a long way since the 90s. But when it comes to retirement planning, how far should we really take it? Yes, AI can track your spending, calculate projections, and even answer retirement questions. But can it walk with you through a market drop—or a medical emergency? Find out where technology helps… and where human guidance still matters most.   ✅ Your retirement deserves a plan—grab your FREE complimentary consultation.  See omnystudio.com/listener for privacy information.

In this episode, the team at Legacy Retirement Group uses everyday household efficiency challenges as a powerful analogy for retirement readiness. Greg and Kristen explain how many people think they’re being efficient—whether it’s with energy usage or their investment portfolio—but hidden leaks often go unnoticed until conditions change. Hear how market volatility can expose inefficiencies in a portfolio, and why diversification isn’t just owning multiple funds. If you want to stop wasting heat, money, and peace of mind, this episode helps you find—and fix—the leaks.  

In this episode, Greg and Kristin explore whether proximity really matters when choosing a financial advisor—or if something else matters more. Greg and Kristen share a powerful story about a local woman who loved her longtime advisor but sought a second opinion after moving closer to Columbus. The conversation highlights why focus, experience, coordination, and comfort matter far more than zip code. You’ll hear what to look for in a retirement-focused advisor, why “perfect” doesn’t always mean complete, and how the right questions—and the right fit—can change everything.  

Retirement planning isn’t just about money—it’s about family dynamics, communication, and expectations. In this episode, Greg and Kristin tackle a question many parents wrestle with: Should we share details of our retirement plans with our children? They explore how family roles around money have shifted over the years and why financial conversations no longer need to be taboo. They discuss the benefits of transparency—reducing anxiety, preventing surprises, and helping heirs develop financial literacy—while also addressing the very real reasons some families choose caution.

Before you hire an estate or elder law attorney, make sure you’re asking the right questions. Greg shares the red flags, the must-asks, and how to know if an attorney is protecting you—or just selling paperwork. Walk through the key questions every family should ask before hiring an attorney, including what’s really protected, how incapacity and long-term care are handled, how often plans should be updated, how advisors work together, and—yes—what it actually costs! 

How do you really know when it’s time to retire? While finances are a critical piece of the puzzle, Greg explains why they’re only part of the story. After more than 30 years helping families prepare for retirement, he’s seen firsthand that a successful retirement depends on much more than math. Greg breaks down the four pillars of retirement readiness—financial, emotional, social, and spiritual—and why ignoring any one of them can derail even the best-laid plans. With real client stories, humor, and straight talk, this conversation is a reminder that retirement isn’t about surviving—it’s about thriving. And the goal isn’t just to stop working…it’s to step confidently into the next chapter of who you are.   ✍️ Ready to design your ideal retirement? Schedule a FREE consultation by completing this brief form.  See omnystudio.com/listener for privacy information.

Time Magazine named the “Architects of AI” its 2025 Person of the Year—and that sparks a wide-ranging conversation about how fast technology has changed everything from writing papers to planning our futures. Greg and Kristen reflect on tech evolution (from typewriters and flip phones to ChatGPT), the pros and cons of AI, and why change—while uncomfortable—is unavoidable. From there, the discussion shifts to a much bigger life transition: retirement. Should couples retire at the same time, or separately? Greg breaks down the three pillars of true retirement readiness—financial, emotional, and social—and explains why being “ready” goes far beyond the numbers. They explore identity after work, the loss (and replacement) of daily purpose, and how finding something bigger than yourself can lead to a truly fulfilling retirement. This episode is a reminder that just like technology, retirement works best when you evolve with intention.  

What In-N-Out Burger, retirement goals, and purpose after work all have in common. The conversation starts with a hot topic—In‑N‑Out Burger finally making its way east of the Mississippi—and quickly turns into something much deeper: What does it actually mean to be ready for retirement? A simple conversation with a nurse sparks a powerful realization—many people don’t know whether their retirement goal should be an age, a dollar amount, or something else entirely. Greg breaks retirement readiness into four critical areas: being financially ready, emotionally ready, socially connected, and having a real sense of purpose once the paychecks stop. The episode explores why retirement planning isn’t just about assets and accounts—it’s about dependable income, confidence through life’s “what-ifs,” and knowing who you are when your job title disappears. From early retirees living the lake-house dream to stories that highlight the importance of belonging and

A $3M widow, a $50K income gap, and a plan that finally made sense—this is what real retirement clarity sounds like. Kevin McCallister’s Plaza Hotel spree is a fun throwback—until you compare what it would cost today and realize how fast prices (and big life goals) have changed. From NYC “experience” trips to an Investopedia breakdown suggesting millions are needed to fund the modern American dream, the conversation turns to the real issue: most people nearing retirement don’t actually know what they can afford to risk. Greg and Kristen unpack why “water cooler” investing advice—especially among high earners—can be misleading when nobody knows each other’s full financial picture, timeline, or true retirement needs. Then they share a powerful client story: a widowed woman with roughly $3 million saved who needed $50,000 a year on top of Social Security and a pension—and finally got a plan aligned with her comfort level (including protected

Tech tools are everywhere — but when it comes to retirement, can an algorithm really replace a trusted advisor? Managing money looks nothing like it did for our parents, especially with pennies slowly going away. With digital wallets, chip cards, and AI-powered investing tools, it’s easy to wonder: Is technology phasing out the traditional retirement advisor? Greg and Kristen explain why the answer is a firm no—especially for retirees. They break down the difference between investment guidance from a robo-advisor and true holistic retirement planning, which includes income planning, inflation strategy, tax efficiency, healthcare, and legacy planning.  This episode highlights the emotional, human side of retirement planning—the back-and-forth conversations, the guidance through life changes, and the peace that comes from working with someone who genuinely cares. Technology is a great tool… but it can’t replace a relationship.  

The “Great Wealth Transfer” may not look the way we expected — and the stories might surprise you. After embracing the holiday season, we discuss how the “Great Wealth Transfer” is happening — but not exactly how the headlines predicted. Greg and Kristen unpack a new Charles Schwab study showing that many high-net-worth Baby Boomers are choosing to enjoy their money now rather than pass it all down. They explain why the real key isn’t whether you leave money behind — it’s knowing what you actually spend, planning for the lifestyle you want, and creating enough protected income to support the life you choose. Whether you want to give, save, or spend it all, a solid income plan brings the confidence to enjoy retirement on your terms.  

When it comes to managing your money, should you trust family — or is a fresh set of eyes the smarter move? From parents who jokingly say they’ll “move in” if their advisor-son loses the money, to widows who struggle to trust anyone new, the Taylors explore the emotional, practical, and financial challenges of working with someone who shares your last name. They discuss why trust can’t be assumed — it must be earned — and why experience, objectivity, and the ability to have tough conversations matter more than familiarity. Whether you’re considering hiring a family member or wondering if it's time to step outside your comfort zone, this episode will help you think more clearly about trust, transparency, and choosing the right guide for your retirement journey.  

If market dips shake you up, your portfolio may be built for someone else—not you. The markets may be hovering near all-time highs, but that doesn’t mean investors feel calm. In this episode, Greg and Kristen tackle one of the biggest issues in retirement investing: emotional risk. They discuss why market swings feel so personal, how over-concentration can create unnecessary stress, and why the real question isn’t “Am I aggressive or conservative?”—it’s “How much am I truly comfortable losing?” If market volatility keeps you up at night, this episode can help you understand the root cause and build an investment strategy that lets you finally sleep well.  

What would you do if your job were suddenly outsourced in your 60s? Greg and Kristen talk about how to prepare—financially and emotionally—for a retirement that may come sooner than expected.   A woman in her early 60s called the team worried that her position might be outsourced—a fear that’s becoming more common as companies evolve and technology reshapes the workplace. Greg and Kristen explore what to do if you’re facing a possible forced retirement: from taking an honest look at your spending and savings (401(k), IRA, pension, etc), to building a flexible income plan that can adapt when life changes. They also share stories from families who’ve discovered the freedom that comes from simply knowing they’re ready—plus, the importance of working with an advisor who builds a plan around you, not a product.   ✅ Your retirement deserves a plan—grab your complimentary consultation.  

An ad claims you can skip Roth conversions and avoid taxes. We reveal what’s real—and what’s just marketing. When a Facebook ad promises you can “eliminate taxes on your retirement accounts—no Roth conversion required,” it’s hard not to click. But is it too good to be true? Greg and Kristen dive into the buzz around “tax-free retirement” webinars and explain why eliminating taxes completely isn’t realistic—but reducing them absolutely is. Greg shows how different strategies—like timing Roth conversions, managing required minimum distributions, and planning around Medicare and income brackets—can save hundreds of thousands in taxes over a lifetime. They also unpack why some advisors discourage Roth conversions (and when that advice might actually be right), plus one simple truth every retiree should remember: there’s no one-size-fits-all plan.