Winning Retirement Radio

Hosted by Greg and Kristin Taylor, and Kristen Charles

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Episodes

Latest episode

Oct 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

October 6, 202611 min

How Can Couples Plan for Retirement When They Disagree About Money?

What if you’re afraid of losing money in retirement, but your spouse is comfortable taking investment risks? How much should you keep in cash—and how do you build a retirement plan that works for both of you? Greg and Kristen Taylor of Legacy Retirement Group in Columbus, Ohio, explore retirement planning for couples with different spending habits, financial fears, and risk tolerance. Through a real client story and their own married-life banter, they explain how reliable retirement income, cash reserves, and investments can work together to support shared goals. Learn how to talk through money disagreements, understand what helps each spouse feel secure, and plan for a retirement you can both enjoy. Have questions about your own retirement plan? Visit LegacyRetirementGroup.com. See omnystudio.com/listener for privacy information.

September 29, 20268 min

WRR - What Retirement Risks Are You Overlooking?

We tend to notice dramatic risks, but what happens when the paycheck stops? Greg and Kristin discuss why market downturns can feel different in retirement, how withdrawals can compound losses, and why inflation, taxes, healthcare costs, and longevity all deserve a place in a written retirement plan. See omnystudio.com/listener for privacy information.

September 22, 202612 min

Stop Watching the Market: How Often Should Retirees Check Their Investments?

How often should you really check your retirement accounts? In this episode of Winning Retirement , Greg and Kristen explain why watching your portfolio every day can fuel anxiety and lead to emotional decisions. They discuss what retirees should actually look for during portfolio reviews, why your risk tolerance matters, and how a purposeful retirement strategy can help you stay focused on long term goals instead of short term headlines. Plus, learn how a three bucket approach to growth, dependable income, and liquid savings can help create greater confidence through changing markets and economic conditions. See omnystudio.com/listener for privacy information.

September 15, 20267 min

Can You Really Afford to Retire? Turning Retirement Math Into a Real Plan

Being told you’re “97% likely” to have enough money for retirement may sound reassuring, but retirement is more than a probability on a spreadsheet. In this episode of Winning Retirement , Greg and Kristen explain how to determine whether you’re truly ready to retire by looking at reliable income, Social Security and pensions, lifestyle expenses, income gaps, inflation, and market risk. They also discuss why the transition from saving money to withdrawing it requires a different strategy and how segmenting assets for income, growth, and liquidity can help create a more purposeful retirement plan. Because the real question isn’t simply, “Do I have enough to retire?” It’s “Do I have a plan that lets me live the retirement I want with confidence?” See omnystudio.com/listener for privacy information.

September 8, 202610 min

Finding Purpose After Retirement: How to Get Your Spark Back

Retirement may solve the work question, but it can create an unexpected one: What gives my life purpose now? In this episode of Winning Retirement , Greg and Kristen explore why some retirees struggle with boredom, a sense of lost identity, and a lack of direction after leaving their careers. They share real-life examples of retirees who found renewed purpose through travel, volunteering, stronger relationships, physical activity, faith, and simply having something meaningful to look forward to. You’ll also hear why preparing emotionally for retirement can be just as important as preparing financially, and how having a clear retirement income and financial plan can provide the confidence to enjoy what comes next. Because retirement isn’t the finish line. It’s a new journey, and having purpose, connection, and a plan can make that journey a whole lot more fulfilling! See omnystudio.com/listener for privacy information.

September 1, 202611 min

Retirement Rules You Don’t Have to Follow

Should you retire at 65, pay off your mortgage, move your investments to safety, or claim Social Security because that’s what everyone else seems to do? Not necessarily. In this episode of Winning Retirement , Greg and Kristen explain why some of the most common retirement decisions shouldn’t be made simply because they’re considered “normal.” They discuss retiring before Medicare eligibility, balancing investment risk and income, deciding whether to pay off a mortgage, and choosing the right time to claim Social Security. The takeaway: There’s no universal roadmap for retirement. The right strategy is the one built around your income needs, goals, taxes, lifestyle, and the future you actually want. See omnystudio.com/listener for privacy information.

August 25, 202611 min

Do You Really Need a Written Retirement Plan?

What happens when retirement throws you something you didn’t plan for? In this episode of Winning Retirement, Greg and Kristen explain why preparing for retirement is a lot like preparing for a big game—you may have great players and plenty of savings, but you still need a strategy. They discuss why the transition from saving for retirement to living on your savings changes the game, how a written retirement plan can help prepare for market volatility and unexpected challenges, and when working with a financial advisor may become more important. If you’re wondering whether you really need a written retirement plan—or if your savings alone are enough—this episode offers practical insights for preparing for the “what ifs” ahead. See omnystudio.com/listener for privacy information.

August 18, 20267 min

Will Your Money Last as Long as You Do?

One of the biggest fears in retirement is running out of money. In fact, one survey found that 67% of Americans worry more about outliving their savings than dying. In this episode of Winning Retirement , Greg and Kristin discuss how to turn retirement uncertainty into confidence with a plan designed to provide reliable income through changing markets and economic conditions. They explore retirement income planning, taxes, healthcare costs, market risk, and how to enjoy the money you've worked hard to save without constantly worrying about whether it will last. The goal isn't simply to survive retirement—it's to build a strategy that helps you thrive throughout it! See omnystudio.com/listener for privacy information.

August 11, 202611 min

What Will You Leave Behind? Building a Legacy Beyond Money

What does it really mean to leave a legacy? In this episode of Winning Retirement, Greg and Kristin share the treasured keepsakes and family memories that mean more than money—and discuss why planning what happens to your belongings can be an important part of retirement and estate planning. From organizing important documents and identifying valuable assets to giving meaningful possessions to loved ones while you're still here, they explore practical ways to make things easier for your family. Most importantly, they explain why your true legacy isn't simply the wealth or possessions you leave behind—it's the memories, values, lessons, and love you leave inside the people who matter most. See omnystudio.com/listener for privacy information.

August 4, 202612 min

How Retirement Planning Has Changed: What Still Works—and What Doesn't Anymore

Retirement planning has evolved just as dramatically as the shift from manual transmissions to today's high-tech vehicles. In this episode of Winning Retirement, Greg and Kristen Taylor explore which retirement principles have stood the test of time—and which strategies no longer work in today's financial world. They discuss why guaranteed pensions have become rare, how longer life expectancies have changed retirement planning, and why creating reliable retirement income is more important than ever. You'll also learn why taxes, healthcare planning, investments, and legacy planning must work together to create lasting financial confidence. If you're wondering how to replace a pension, avoid running out of money, or build a retirement plan that fits today's realities, this episode offers practical guidance to help you retire with greater peace of mind. See omnystudio.com/listener for privacy information.