Winning Retirement Radio

Hosted by Greg and Kristin Taylor, and Kristen Charles

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Episodes

Latest episode

Aug 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

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.

June 30, 20269 min

The Hidden Cost of Caregiving

More Americans are finding themselves caring for aging parents while preparing for their own retirement. In this episode, Greg and Kristen discuss the emotional and financial realities of caregiving, share personal and client stories, and offer practical strategies to help families protect both their loved ones and their retirement. From budgeting and legal planning to long-term care and having difficult family conversations, they explain why planning ahead can make all the difference. 🔍 Gain clarity and confidence—book your no-cost retirement review today! See omnystudio.com/listener for privacy information.

June 23, 20267 min

Will Social Security Change? Why Your Retirement Income Needs a Backup Plan

A new report warns that Social Security's trust fund could run short of reserves by 2032, potentially leading to benefit reductions if lawmakers fail to act. In this episode of Winning Retirement, Greg and Kristen break down what that could mean for retirees and whether claiming benefits early is the right move. They explore possible solutions Congress may consider—including higher payroll taxes, raising the retirement age, and adjusting cost-of-living increases—and discuss why Social Security should be viewed as a foundation of retirement income, not the entire plan. You'll also hear why maximizing Social Security isn't always the same as maximizing your retirement, and why having a comprehensive income strategy may be more important than ever. 🕒 Don’t leave retirement to chance—claim your FREE consultation now. See omnystudio.com/listener for privacy information.

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.