Winning Retirement Radio

261 Episodes

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The Problem With “One-Stop Shop” Financial Firms

2026-03-1010:17

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. 💬 Ready for your own “financial check-up”? Schedule a call with us to get started. See omnystudio.com/listener for privacy information.

Should You Wait Until 70 to Claim Social Security?

2026-03-0310:08

“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! 🧐 Curious if you’re on track for retirement? Fill out this short form for a FREE consultation. See omnystudio.com/listener for privacy information.

Is Financial Secrecy a Form of Cheating?

2026-02-2411:07

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. 📆 Make sure your retirement is on track—grab your FREE consultation today. See omnystudio.com/listener for privacy information.

Can AI Plan Your Retirement? What Technology Can—and Can’t—Do.

2026-02-1710:43

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.

Plugging the Leaks: How Efficient Is Your Retirement Plan?

2026-02-1010:20

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. 🔍 Gain clarity and confidence—book your no-cost retirement review today! See omnystudio.com/listener for privacy information.

Does Your Financial Advisor Need to Be Local?

2026-02-0311:23

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. 🕒 Don’t leave retirement to chance—claim your FREE consultation now. See omnystudio.com/listener for privacy information.

Should You Talk to Your Kids About Your Retirement Plans?

2026-01-2710:26

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. 🤔 Feeling stuck with your retirement planning? Download a FREE copy of Legacy’s My Retirement Kit to help become better organized: See omnystudio.com/listener for privacy information.

Questions to Ask an Estate or Elder Law Attorney

2026-01-2009:42

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! 👉 Ready to take the guesswork out of retirement? Get your FREE copy of Legacy’s My Retirement Kit today—your step-by-step guide to getting organized and staying on track! See omnystudio.com/listener for privacy information.

WRR - Are You Ready to Retire? It’s Not Just the Numbers

2026-01-1310:24

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.

From AI to Identity: Are You Really Ready to Retire?

2026-01-0612:02

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. 🗂️ Get Organized. Get Confident. Get Your FREE Retirement Kit from Legacy! See omnystudio.com/listener for privacy information.

From Double-Doubles to Dream Retirement: Are You Really Ready?

2025-12-2312:03

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 purpose, this episode challenges listeners to think beyond money and start planning for a retirement that’s actually fulfilling. 📄 Snag your FREE copy of Legacy's My Retirement Kit to help you get organized today! https://www.legacyretirementgroup.com/podcast-requestSee omnystudio.com/listener for privacy information.

From Home Alone to Retirement Reality: Knowing What You Can Afford to Risk

2025-12-1612:36

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 income, protected growth, and long-term growth). The result? Confidence—and tears of relief. 🔎 Feeling confident—or just want to be sure—you’re on the right path to your version of a Winning Retirement? Complete a short form and schedule your FREE complimentary consultation. See omnystudio.com/listener for privacy information.

Retirement Planning in a High-Tech World: Why Humans Still Matter

2025-12-0912:36

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. 💭 Unsure if you’re on track for retirement? Fill out this short form for a free consultation. https://www.legacyretirementgroup.com/schedule-an-appointmentSee omnystudio.com/listener for privacy information.

Spend It Now or Save It for the Kids? The New Reality of the Great Wealth Transfer

2025-12-0211:40

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. 📂 Need a little help getting organized? Download a FREE copy of Legacy’s My Retirement Kit: https://www.legacyretirementgroup.com/podcast-request 🔎 Keywords: retirement income planning, great wealth transfer, baby boomer spending, inheritance planning, generational wealth, giving while living, retirement lifestyle budget, Columbus Ohio financial advisor, protected income in retirement, retirement expenses, spending in retirement, retirement planning podcast, legacy planning strategies, Adventures by Disney trip retirement, how much do retirees really spend, outliving your money See omnystudio.com/listener for privacy information.

Family, Finances & Trust- Should You Hire a Relative as Your Advisor

2025-11-2507:45

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. 💬 Ready for your own “financial check-up”? Schedule a call with us to get started. https://www.legacyretirementgroup.com/schedule-an-appointment 🔎 Keywords: financial advisor family member, should family manage money, trusting a financial advisor, retirement planning Columbus Ohio, Legacy Retirement Group, choosing a financial advisor, financial trust issues, retirement income planning, advisor experience vs. family, money and family boundaries, why hire an outside advisor, retirement decisions, financial transparency, Winning Retirement podcastSee omnystudio.com/listener for privacy information.

Are You Too Emotional for the Market? Finding Your Real Risk Comfort Zone

2025-11-1806:25

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. 📆 Make sure your retirement is on track—grab your FREE consultation today. 🔎 Keywords: market volatility, emotional investing, diversification, risk tolerance, investment risk, asset allocation, long-term investing, retirement planning, portfolio stress, concentration risk, investor psychology, portfolio X-ray, risk score, conservative investing, aggressive investing, market highs, market dips, retirement income planning, financial comfort zone, behavioral finance, stock market risk, investment strategy See omnystudio.com/listener for privacy information.

Forced Retirement After 60: How to Plan When the Unexpected Happens

2025-11-1110:10

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. 🔑 Keywords: forced retirement planning, early retirement at 60, retirement after job loss, preparing for early retirement, retirement income planning, flexible income plan, retirement readiness, financial planning after layoff, 401(k) IRA pension, retirement planning for women over 60, Greg and Kristen Taylor, Legacy Retirement Group, Winning Retirement podcast, retirement advisor, financial freedom in retirement, job outsourcing and retirementSee omnystudio.com/listener for privacy information.

“Don’t Roth Convert?” The Truth Behind Tax-Free Retirement Promises

2025-11-0411:05

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. 🔍 Gain clarity and confidence—book your no-cost retirement review today! 🔑 Keywords: retirement planning, Roth conversion, retirement taxes, IRA, 401(k), 403(b), tax strategies, required minimum distributions, financial planning, retirement income, Legacy Retirement Group, Winning Retirement Radio See omnystudio.com/listener for privacy information.

Because Mom Said So: Outdated Rules and Smarter Retirement Strategies

2025-10-2812:49

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 follow. They break down why classics like the 4% rule, the Rule of 100, and “never touch your principal” may no longer make sense—and explain the new mindset smart retirees are using today. Plus, they highlight the real retirement ages that matter: the Rule of 55, 59½, 65, and 73. If you want to retire confidently, it’s time to know which rules to keep, which to toss, and the one rule Greg lives by: protect your income, grow the rest! 🕒 Don’t leave retirement to chance—claim your FREE consultation now. See omnystudio.com/listener for privacy information.

The Truth Hurts (But It Helps): Why Honesty Matters With Your Doctor—and Your Advisor

2025-10-2112:24

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 famous iron-skillet cake) to the emotional side of discussing spending habits and savings goals, they reveal why honesty—especially when it’s uncomfortable—is the key to a healthier life and a stronger financial future. Greg also shares how a “functional medicine” approach to health inspired the way he helps families uncover the root causes of financial stress. 💬 Ready for your own “financial check-up”? Schedule a call with us to get started!See omnystudio.com/listener for privacy information.

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