Winning Retirement Radio

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 a...

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 whe...

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 expos...

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...

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. T...

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, h...

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,...

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 unavoida...

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...

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...

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 w...

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 m...

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...

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, an...

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 workpla...

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” webina...

Revisiting the “rules” we grew up with—and the financial ones that could be hurting your retirement. We all remember the rules our parents swore by—don’t sit too close to the TV, wear your coat, turn off that car light! Greg and Kristen share a few laughs about those old sayings, then connect them to the outdated financial “rules” many retirees still follo...

Honesty isn’t just good for your health—it’s vital for your wealth. A new study finds that up to 80% of adults admit to lying to their doctors about their lifestyle habits—usually to avoid judgment or bad news. Greg and Kristen open up about how this same fear can show up in retirement planning, too. From family stories about Kristen’s late father-in-law (and his famo...

Learn how to keep more of your money in retirement with smart income and tax strategies! Most people picture Social Security or a 401(k) when they think about retirement income — but that’s just the beginning. In this episode of Winning Retirement, Greg and Kristen explain how to coordinate multiple income streams, from pensions and IRAs to RMDs, dividends, and rental income, while kee...

From the $550 calculator watches of the 1970s to today’s free online tools, we’ve always relied on numbers to help us make decisions. But when it comes to retirement, not every “calculator” gives you the full picture. In this episode, Greg and Kristen share why online tools—and even AI—can be misleading, how one client discovered that firsthand, and why professi...

When kids leave home, they don’t just move away—they tug on their parents’ hearts, too. Greg and Kristen share the laughs (and frustrations) of watching their son head to college—828 miles away—with a questionable dorm-room haircut to prove his independence. From daily check-ins (or lack thereof) to mom’s Life360 “stalking,” this episode blends famil...

Getting married later in life? Things can get… awkward. From “lady friends” to prenups, Greg and Kristen unpack the not-so-romantic side of love after 50—like protecting your retirement, keeping kids’ inheritances fair, and why Medicaid doesn’t care about your prenup. It’s funny, a little uncomfortable, but super important. 🤔 Feeling stuck with your reti...

It turns out that fewer young adults are reaching traditional milestones, such as moving out, getting married, and starting families. After Greg and Kristen share how that contrasts with their own family’s journey, the conversation turns to retirees and how they are prime targets for marketing — and how to filter through the noise . They share practical advice for spotting red flags, v...

Greg and Kristen share their own family screen-time confessions along with America's, and how neighbors are turning movie nights into community fun! Then, they shift gears to retirement: When does a Roth conversion really make sense, and how can it protect your lifestyle and legacy? From screen habits to financial habits, this episode is all about finding balance in the digital age—and in yo...

When do most Americans really fall asleep—and is sharing a bed helping or hurting? Kristen admits she struggles to drift off while Greg can be snoring in seconds (though he’ll never admit it). Later, Greg and Kristen delve into the “free steak dinner” seminars, exploring why they attract retirees and how to distinguish between genuine education and high-pressure sales pitch...