Winning Retirement Radio Podcast By Greg and Kristin Taylor and Kristen Charles cover art

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
  • Medicare Covers a Lot… But Not Everything

    Medicare Covers a Lot… But Not Everything
    Mar 17 2026

    Does chewing gum really boost your memory? Maybe—but remembering the healthcare costs that Medicare doesn’t cover might be even more important! While Medicare does a solid job covering doctor visits and hospital stays, there are still significant gaps—especially when it comes to dental work, vision care, prescription drugs, and long-term care.

    Greg and Kristen explain why these costs can catch retirees off guard and share strategies that can help people prepare ahead of time, including HSAs, planning for Medicare savings in your budget, and exploring options for long-term care protection. If you’re approaching retirement or already there, understanding Medicare’s coverage gaps could help you protect both your health and your financial future.


    📂 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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    11 mins
  • The Problem With “One-Stop Shop” Financial Firms

    The Problem With “One-Stop Shop” Financial Firms
    Mar 10 2026

    Some financial firms promote themselves as a “one-stop shop,” offering attorneys, accountants, and advisors all under one roof. So why doesn’t the team at Legacy Retirement Group do the same?

    In this episode, Greg and Kristen explain the philosophy behind their approach. Rather than trying to do everything internally, Legacy focuses on what it does best—retirement investment planning, income planning, and tax strategy—while collaborating with independent specialists when clients need legal, tax, or estate expertise. In retirement planning, coordination and collaboration often beat trying to do everything in one place.


    💬 Ready for your own “financial check-up”? Schedule a call with us to get started.

    See omnystudio.com/listener for privacy information.
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    10 mins
  • Should You Wait Until 70 to Claim Social Security?

    Should You Wait Until 70 to Claim Social Security?
    Mar 3 2026

    “Wait until 70. You’ll get 8% more per year.”
Sounds simple, right? Not so fast.

    In this episode, Greg and Kristin tackle one of the most common retirement questions: Should you delay Social Security to maximize your benefit?

    Learn why there’s no one-size-fits-all answer. While waiting can increase your monthly benefit and potentially protect a surviving spouse, it can also mean draining retirement assets too quickly if you don’t have enough saved. Social Security isn’t the retirement plan. It’s one piece of the income puzzle. The real key? Building a written retirement income plan that’s stress-tested against market volatility, inflation, and tax changes. Because in retirement, cash flow is king!

    🧐 Curious 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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    10 mins
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