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Winning Retirement Radio

Winning Retirement Radio

By: Greg and Kristin Taylor and Kristen Charles
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🎙️ 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.

2026 Legacy Retirement Group Economics Leadership Management & Leadership Personal Finance
Episodes
  • Inflation, Social Security & the Real Cost of Retirement

    Inflation, Social Security & the Real Cost of Retirement
    Jun 9 2026

    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.
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    12 mins
  • The Retirement Affordability Question

    The Retirement Affordability Question
    Jun 2 2026

    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.
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    12 mins
  • When Retirement Changes Overnight

    When Retirement Changes Overnight
    May 19 2026

    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.
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    9 mins
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