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Winning Retirement Radio

Winning Retirement Radio

By: Greg and Kristin Taylor and Kristen Charles
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About this listen

🎙️ 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.

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Episodes
  • From Deferred to Dangerous: The Tax Trap in Retirement

    From Deferred to Dangerous: The Tax Trap in Retirement
    Jul 22 2025

    In this episode, we share a heartfelt story about a travel-loving mom who never lost her sense of adventure, even at the age of 90. Then we dig into the surprising history of taxes—from the ancient Egyptian Pharaoh’s grain grabs to the modern-day IRS—and how those same tax burdens can sneak up on your retirement. Learn how to spot the warning signs, avoid common tax pitfalls, and why using tools like TestMyRetirement.com can help you keep more of what you’ve worked so hard to save.


    Need a little help getting organized? Download a FREE copy of Legacy’s My Retirement Kit.

    See omnystudio.com/listener for privacy information.
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    12 mins
  • Laundry Rules And Roth Strategies

    Laundry Rules And Roth Strategies
    Jul 8 2025

    In this episode, we go from laundry piles to financial files! We discuss whether we really have to wash new clothes before wearing them (spoiler: yes), and the importance of kids having household responsibilities.

    Then, the conversation shifts to another kind of clutter: unused subscriptions and hidden financial costs. Greg compares this to tax-deferred retirement accounts like 401(k)s—convenient now but potentially costly later. They break down the difference between delaying and saving on taxes, as well as the pros and cons of Roth conversions.

    Wondering if you’re on track for retirement? Fill out this short form for a FREE consultation.

    See omnystudio.com/listener for privacy information.
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    14 mins
  • Love Languages, and Annuities: What Holds It All Together?

    Love Languages, and Annuities: What Holds It All Together?
    Jul 1 2025

    Greg and Kristin kick things off with a fun fact about sea otters that might just resemble Greg’s love language in real life. From playful jabs to deeper relationship dynamics, the conversation takes a meaningful turn, exploring the importance of planning and staying connected in retirement as well. They break down a real-life scenario: if you're 65 and have $300,000 set aside to put into a fixed indexed annuity, how much could it pay and for how long? The duo explains the three main income strategies for annuities—withdrawals, annuitization (aka "annui-cide"), and income riders—plus the pros, cons, and hidden details to watch out for. It’s everything you need to know about annuities with a dose of laughs, love, and financial wisdom.


    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.
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    14 mins
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