Winning Retirement Radio

Hosted by Greg and Kristin Taylor, and Kristen Charles

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Episodes

Latest episode

Jun 2026

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EN-US

About the show

🎙️ Greg and Kristen Taylor, along with their co-host Kristen Charles, explore down-to-earth tips and strategies to help pre and current retirees better achieve their goals. 📊 With discussions about everything from balancing risk, to 401(k) rollovers, Roth conversions, pension decisions, withdrawal strategies, taxes in retirement, income planning, Social Security, and most importantly... your lifestyle! 👫 Greg and Kristin's goal is to help you have confidence in your transition into retirement, and for years to come by helping you create a personalized plan for your retirement. Have specific questions? Schedule a 15-minute call with a team member. Greg Taylor is an investment adviser representative of Legacy Advisory Network, LLC, a registered investment advisor with the state of Ohio. The firm only conducts business in states where it is properly registered or is excluded from registration requirements. Legacy Advisory Network, LLC, and this radio station are not affiliated. The investment ideas and financial vehicles discussed here should not be considered to be personalized investment advice, nor are these recommendations to buy or sell any particular investment or product. The information should not be considered tax or legal advice. Individuals should first consult with competent tax, legal, accounting, and other professionals regarding the applicability and suitability of any investment ideas. Past performance is not a guarantee of future results. Investments will fluctuate, and when redeemed may be worth more or less than when originally invested. Any comments regarding safe and secure investments and guaranteed income streams refer only to fixed insurance products. They do not refer in any way to securities or investment advisory products. Fixed insurance and annuity product guarantees are subject to the claims-paying ability of the issuing company.

Listen to episodes

60 recent

June 16, 20269 min

Retiring Earlier Than Planned? Why Flexibility Matters.

Greg and Kristen discuss why nearly 6 in 10 retirees leave the workforce earlier than expected. From layoffs and workplace burnout to health challenges and family caregiving responsibilities, they explore the real-life reasons retirement plans often change. You'll learn why building flexibility into your retirement strategy is critical, how to prepare for life's unexpected "what ifs," and ways to create a reliable income while preserving assets for future opportunities and challenges.    🤔 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.

June 9, 202611 min

Inflation, Social Security & the Real Cost of Retirement

Greg and Kristen discuss summer travel, family vacations, and the rising cost of living. Then, using the latest Social Security COLA projections as a starting point, they explore why inflation remains one of the biggest threats to a successful retirement. You'll learn how inflation compounds over time, why budgeting is critical regardless of your net worth, and how a written retirement income plan can help ensure your money keeps pace with rising expenses throughout retirement. 👉 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.

June 2, 202612 min

The Retirement Affordability Question

In this episode of Winning Retirement, Greg and Kristen discuss the question many retirees are asking: “Have we done enough?” They explain why retirement planning is about more than building wealth—it’s about creating reliable income, managing taxes, and maintaining your lifestyle. You’ll also hear insights on diversification, Roth conversion strategies, and why the real goal of retirement planning is having the confidence to enjoy life without worrying about running out of money.   ✍️ Ready to design your ideal retirement? Schedule a FREE consultation by completing this brief form.  See omnystudio.com/listener for privacy information.

May 19, 20269 min

When Retirement Changes Overnight

In this heartfelt episode of Winning Retirement, Greg and Kristen discuss how quickly retirement plans can change when unexpected health challenges arise. Inspired by the ALS diagnoses of close friends and clients, they explore the emotional and financial impact serious illness can have on retirees and their families. Greg shares the story of a client whose retirement changed dramatically just months after leaving work, and why having a flexible plan in place helped provide peace of mind during a difficult time. They also break down the three major retirement risks—market volatility, taxes, and healthcare costs—and explain why true retirement planning goes far beyond investments alone. You’ll also hear why flexibility matters, the importance of family conversations, and how a comprehensive plan can help protect both your finances and your loved ones when life takes an unexpected turn.   🗂️ Get Organized. Get Confident. Get Your FREE Retirement Kit from Legacy!  See omnystudio.com/listener for privacy information.

May 12, 202611 min

Rich vs. Never Broke in Retirement

Greg and Kristin explore an important retirement question: Is the goal to become wealthy—or simply make sure you never run out of money? Greg shares a personal story about losing everything in a childhood house fire and how it shaped his views on financial security. They also break down the difference between harmful debt and strategic debt in retirement, including when it may make sense to keep a mortgage rather than pay it off. They discuss cash flow, taxes, home equity lines of credit, and why retirement planning should fit your comfort level—not someone else’s definition of success.   📄 Snag your FREE copy of Legacy's My Retirement Kit to help you get organized today! See omnystudio.com/listener for privacy information.

May 5, 202611 min

How Much Should You Help Your Adult Children?

In this episode of Winning Retirement, Greg and Kristen start with some fun family stories before tackling a challenge many families face today. With rising housing costs and more young adults living at home, parents are helping more than ever—but how much is too much? They break down the difference between support and dependency, share real client scenarios, and explain why your retirement comes first. If you’re wondering how to help your kids without putting your own future at risk, this episode is for you. 🔎 Feeling confident—or just want to be sure—you’re on the right path to your version of a Winning Retirement? Take a moment to complete a short form and schedule your complimentary consultation. See omnystudio.com/listener for privacy information.

April 7, 202612 min

The Real Reasons Most Families Lose Their Wealth

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

March 17, 202611 min

Medicare Covers a Lot… But Not Everything

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. 📂 Need a little help getting organized? Download a FREE copy of Legacy’s My Retirement Kit: See omnystudio.com/listener for privacy information.

March 10, 202610 min

The Problem With “One-Stop Shop” Financial Firms

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.

March 3, 202610 min

Should You Wait Until 70 to Claim Social Security?

“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.