Winning Retirement Radio

Hosted by Greg and Kristin Taylor, and Kristen Charles

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Episodes

Latest episode

Sep 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

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.

July 28, 202610 min

Do You Really Need $1 Million to Retire? The Truth About Retirement Income?

Do you really need $1 million—or more—to retire comfortably? In this episode of Winning Retirement , Greg and Kristen break down a recent Investopedia study estimating that the average American couple needs $1.16 million for retirement and explain why there's no universal retirement number. They discuss the limitations of the 4% withdrawal rule , why market timing can make or break a retirement plan, and how unexpected expenses like healthcare, home repairs, and vehicle replacements can quickly change your financial picture. You'll also learn why focusing on your retirement income gap —instead of an arbitrary savings goal—can provide greater confidence and long-term financial security. Whether you're approaching retirement or already retired, this episode explains how personalized income planning, liquidity for life's surprises, and strategies for long-term growth can help create a more resilient retirement plan. Topics covered: Do you really need $1 million to retire? Why the 4% withdrawal rule isn't one-size-fits-all How market volatility affects retirement income Planning for unexpected retirement expenses The importance of guaranteed income and liquidity Why retirement planning should be based on your lifestyle—not national averages See omnystudio.com/listener for privacy information.

July 21, 202610 min

The Legacy You Leave: Estate Planning, Roth Conversions & Passing Down More Than Money

What will your family remember—and inherit—when you're gone? In this heartfelt episode of Winning Retirement, Greg and Kristen Taylor explore the difference between leaving behind possessions, wealth, and a lasting legacy. Inspired by estate sales and treasured family heirlooms, they discuss why the most valuable inheritance is often character, faith, and family values. They also explain practical estate planning strategies, including wills vs. trusts, beneficiary designations, financial and healthcare powers of attorney, and how Roth conversions can potentially create a larger tax-free inheritance for your children. If your goal is to leave your loved ones—not the IRS—the biggest benefit, this episode offers valuable retirement and estate planning insights. 💬 Ready for your own “financial check-up”? Schedule a call with us to get started. See omnystudio.com/listener for privacy information.

July 14, 202610 min

How Much Do You Need to Retire on $100,000 a Year?

How much money do you need to retire comfortably in the United States? Is $1 million enough? And how much savings does it take to generate $100,000 a year in retirement income? In this episode of Winning Retirement , Greg and Kristen answer common retirement-planning questions and explain why there is no one-size-fits-all retirement number. They discuss the 4% withdrawal rule, Social Security, guaranteed income, income annuities, market volatility, taxes, and strategies for creating reliable, tax-efficient retirement income. Whether you're planning for retirement or already retired, you'll learn how to determine the retirement savings you need based on your income goals—not just your nest egg. ✅ Your retirement deserves a plan—grab your FREE complimentary consultation . See omnystudio.com/listener for privacy information.

July 7, 202612 min

Love, Retirement & Second Chances: The Money Talk Every Couple Needs

Greg and Kristin share stories from their own relationship before diving into the unique financial challenges of dating and remarriage later in life. From blending finances and protecting assets to estate planning, prenups, family dynamics, and retirement strategies, they explain why honest money conversations are essential before saying "I do" again. ✅ Your retirement deserves a plan—grab your complimentary consultation . See omnystudio.com/listener for privacy information.