Winning Retirement Radio - podcast cover

Winning Retirement Radio

Greg and Kristin Taylor, and Kristen Charles•winningretirementradio.com

🎙️ 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

Bottled Water Battles & Choosing the Right Financial Advisor

Kristin and Greg dive into a new survey ranking America’s top bottled water brands—complete with strong opinions, unexpected picks, and even a little “bougie” vs. budget debate. Then the conversation shifts to serious retirement talk, with Greg outlining the key questions to ask when interviewing financial advisors, how different fee structures work, and why a truly customized retirement plan matters more than a cookie-cutter approach. It’s part lighthearted taste test, part essential financial ...

Aug 19, 2025•11 min

Emojis and the Art of Retirement Balance

This week, we discuss the new iPhone emojis and the surprising truth behind the “prayer” hands—before shifting gears into a real conversation about balance. We explore why many workers leave paid time off unused, how our team balances productivity and personal life, and the parallels between work-life balance and smart retirement planning. Whether it’s juggling risk and safety in your portfolio or making sure you actually take that vacation, it’s all about finding the mix that works for you! Rea...

Aug 12, 2025•12 min

Misheard Words and Must-Have Liquidity

In this episode, we delve into the humorous miscommunications that arise with age and simply being human. We also discuss another equally important aspect: financial liquidity in retirement. From surprise plumbing disasters to flying curtain weights (yes, really), life happens — and having the right emergency fund in place can be the difference between stress and freedom. We’ll explore how much liquidity might be right for you, why it’s not one-size-fits-all, and how it ties into your retirement...

Aug 05, 2025•10 min

Arguing with Your Spouse (and the IRS)

Even the happiest couples argue — and sometimes it’s on air! 👩‍❤️‍👨 Kristen and Greg get real about relationships, tone of voice, and why mutual respect matters at home and with Uncle Sam! Speaking of strained relationships, if you’re turning 73 this year, your mandatory date with the IRS is about to begin. We break down everything you need to know about Required Minimum Distributions (RMDs): when to take them, how they’re calculated, the difference between IRAs and 401(k)s, and how smart plan...

Jul 29, 2025•12 min

From Deferred to Dangerous: The Tax Trap in Retirement

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...

Jul 22, 2025•12 min

Laundry Rules And Roth Strategies

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 taxe...

Jul 08, 2025•14 min

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

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 stra...

Jul 01, 2025•14 min

Real Talk for Retiring Without a Million Bucks

This week, we discuss small spending habits—such as eating out, using DoorDash, and daily coffee—that most Americans admit are wasteful but struggle to quit. Then we pivot to a bigger financial picture: retirement readiness! We share the story of a couple with over $500,000 saved who asked the key question: “ Have we done enough? ” Their journey reveals how thoughtful planning, balancing risk, and maximizing income sources can make retirement possible, even without a million-dollar nest egg. Rea...

Jun 24, 2025•12 min

More Than a Number: What It Truly Means to Be Retirement Ready

Denmark is making headlines with plans to raise its retirement age to 70 by 2040, reflecting a growing global trend of adjusting retirement based on life expectancy. This sparks a bigger conversation—what is the right age to retire, and are you really ready? 🧐 Greg and Kristin explore the three key areas of retirement readiness: financial, social, and emotional. Through real-life stories, they show how retirement planning isn’t just about numbers—it’s about creating the freedom to choose when a...

Jun 17, 2025•12 min

Family Memories & Retirement Realities

In this episode, we reflect on our grandparents’ simple, family-focused lives and contrast them with the retirement worries of today, including taxes, investments, and planning. Greg and Kristin share touching family stories and emphasize the importance of planning carefully for today's retirees, particularly regarding taxable withdrawals from 401(k)s, IRAs, and the growing government debt. The website mentioned for a FREE personalized tax map report is TestMyRetirement.com . See omnystudio.com/...

Jun 10, 2025•11 min

Transitions and Purpose

Greg and Kristin reflect on the emotional journey of their son Christian’s high school graduation, and how these family milestones often parallel the retirement planning they do with clients. Listen for insight about the importance of organizing, embracing change, and finding new purpose in both family and financial life transitions. Confident you're on the right path to create your version of a Winning Retirement? Complete this brief form to schedule a complimentary consultation. See omnystudio...

Jun 03, 2025•11 min

Should We Take Warren Buffett’s Investment Advice?

We touch on Tom Cruise’s latest Mission: Impossible, and his intent to never retire, then shift to Warren Buffett’s advice to invest in a low-cost S&P 500 index fund. While that might work for younger investors, Greg and Kristin warn retirees to be cautious. Market drops can seriously impact income in retirement! Their takeaway: don’t follow headlines blindly. Build a plan with your portfolio that balances income, growth, and safety, especially as you near retirement. Unsure if you’re on tra...

May 27, 2025•12 min

The Growing Crisis of Long-Term Care

Greg and Kristin dive into a pressing issue affecting more families than ever before: the increasing need for long-term care in America. You’ll hear a personal caregiving experience, a journey that has become common among friends, neighbors, and loved ones. But here’s the catch: traditional long-term care insurance is disappearing, and the few policies still available are often too expensive, and if you don’t use them, you lose the money you paid in. Listen to learn about other strategies availa...

May 20, 2025•14 min

Tipping Points and Tax Moves

Greg and Kristen discuss tipping trends and why some people tip less with digital prompts. They also break down Required Minimum Distributions (RMDs): when to take them, how they’re taxed, and strategies to avoid costly mistakes. Unsure if you’re on track for retirement? Fill out this short form for a FREE consultation . See omnystudio.com/listener for privacy information....

May 13, 2025•12 min

Learning To Spend In Retirement

After discussing the differences between being frugal and being cheap, Greg and Kristin highlight why many retirees find it challenging to begin spending their money. In addition to having an investment and income plan, creating a spending plan is essential. Retirement represents a significant life change that many people fail to recognize, and transitioning from saving to spending from your portfolio is a crucial part of this shift. We also examine what retirement may look like for those who ow...

Apr 29, 2025•13 min

Lost and Found Giving

We recap Uber's weird lost and found items and share a tale of a misfortune-stricken philanthropist. Then explore the rewards of generosity. Kristin will also provide us with an update on the latest developments at Dare For More , one of her beloved charities. Need a little help getting organized? Download a FREE copy of Legacy’s My Retirement Kit to help you get organized: See omnystudio.com/listener for privacy information....

Apr 24, 2025•12 min

Should You Help Your Adult Kids?

After discovering that Greg and Kristin work and exercise together, we shift our focus to family matters. We examine the various reasons why retirees sometimes provide financial assistance to their adult children. Listen for stories that shed light on both sides of this important issue. Wondering if you’re on track for retirement? Fill out this short form for a FREE consultation . See omnystudio.com/listener for privacy information....

Apr 22, 2025•11 min

Reduce Stress By Having A Plan

Google searches for " how to reduce stress " have reached a record high. With the markets responding to tariff news, many individuals with retirement funds on Wall Street are feeling uneasy. Greg and Kristin discuss the importance of having a plan that considers challenging times so that your income isn’t dependent on the uncertainties of the market! 🤔 Wondering if you’re on track for retirement? Fill out this short form for a FREE consultation . See omnystudio.com/listener for privacy informat...

Apr 17, 2025•10 min

Don’t Let Math Anxiety De-rail Your Retirement

This week, we're discussing everyday things that make us feel unsettled or uncomfortable. One topic that stands out is Math Anxiety. This issue can create significant challenges during retirement. If memories of Geometry and Algebra are causing you to avoid your financial and retirement planning, remember that you don’t have to tackle it all by yourself! Greg and Kristin talk about “doing the math” to NOT run out of money in retirement. Feeling stuck with your retirement planning? Download a FRE...

Apr 15, 2025•13 min

The Only Constant In Life Is Change

The world has changed dramatically in just the past 10 years! This is especially true for Greg and Kristin as the school season comes to a close. In this episode, we reflect on various aspects of life, from movies and music to customer service and everything in between. We discuss how we approach different parts of our lives much differently than we did just a few years ago. Planning for retirement has evolved as well. Whether you have a 401(k), pension, stocks, bonds, ETFs, mutual funds, or an ...

Apr 10, 2025•12 min

Is Gold The Ticket To Retirement?

Did you know pure gold (23-24 karat) is safe to consume in small quantities? You might have seen advertisements about investing in precious metals. That's why we're exploring gold as an asset class for individuals who are in or approaching retirement as part of a diversified portfolio. This is especially relevant now, with market volatility! Also, listen to learn how much of a creature of habit Greg is! Ready to design your ideal retirement? Schedule a FREE consultation! See omnystudio.com/liste...

Apr 08, 2025•13 min

Happiness, Freedom, and Legacy Planning

Are you feeling overwhelmed when it comes to making money decisions? You’re not alone. A recent survey shows that 53% of Americans feel stuck, overwhelmed, or unsure about their finances. Greg and Kristin discuss the importance of avoiding "paralysis by analysis" and how collaborating with a fiduciary financial advisor can alleviate some of those feelings. Additionally, they emphasize the need to avoid being “Google slapped,” as Greg puts it. Wondering if you’re on track for retirement? Fill out...

Apr 03, 2025•12 min

Feeling Financially Frozen

Are you feeling overwhelmed when it comes to making money decisions? You’re not alone. A recent survey shows that 53% of Americans feel stuck, overwhelmed, or unsure about their finances. Greg and Kristin discuss the importance of avoiding "paralysis by analysis" and how collaborating with a fiduciary financial advisor can alleviate some of those feelings. Additionally, they emphasize the need to avoid being “Google slapped,” as Greg puts it. Confident you're on the right path to create your ver...

Apr 01, 2025•9 min

Giving and QCDs

Americans do a lot of giving, and often, that giving mindset doesn’t change when you stop working. In retirement, there are efficient ways to give that some take advantage of. In fact, Kristin shares how one woman made her qualified charitable distribution (QCD) goals from her retirement accounts come to life despite some paperwork obstacles. Need a little help getting organized? Download a FREE copy of Legacy’s My Retirement Kit to help you get organized. See omnystudio.com/listener for privacy...

Mar 25, 2025•10 min

What’s a Normal Retirement

Retirement can be a challenging transition. This week, we discuss how to tailor your retirement plans to your unique situation, considering your budget, portfolio, income, and more. We'll also explore the "normal" expectations of retirement and share stories of people enjoying their unique retirement lifestyles. Wondering if you’re on track for retirement? Fill out this short form for a FREE consultation . See omnystudio.com/listener for privacy information....

Mar 18, 2025•13 min

Are Annuities The Answer to Volatility?

In this episode, Greg and Kristin dive into the world of annuities, breaking down the key differences, including their advantages and disadvantages, to help you navigate retirement income concerns. 📸 Plus, the interesting story behind the first-ever selfie and when it was taken! Feeling stuck with your retirement planning? Download a FREE copy of Legacy’s My Retirement Kit to help get organized: See omnystudio.com/listener for privacy information....

Mar 11, 2025•12 min

Is Volatility Here To Stay?

This week's episode covers encouraging economic news regarding Americans and debt, the significance of maintaining an emergency fund as you approach or enter retirement, and advice for those worried about market volatility and risk exposure. Unsure if you’re on track for retirement? Fill out this short form for a FREE consultation . See omnystudio.com/listener for privacy information....

Mar 04, 2025•12 min

Couples, Get Comfortable and Let’s Talk Money!

From investing to spending, budgeting, and even charitable giving, maintaining open communication about finances is crucial for couples. 👩‍❤️‍👨 Greg and Kristin share how they avoid money miscommunications, and how they encourage the families they help to do the same. Need a little help getting organized? Download a FREE copy of Legacy’s My Retirement Kit to help you get organized. ________________ See omnystudio.com/listener for privacy information....

Feb 25, 2025•11 min

How RMDs Work

We discuss tax season and what you need to know if you're approaching age 73 and preparing to take Required Minimum Distributions (RMDs). We'll cover important topics such as how much you need to withdraw, penalties and fees to avoid, and the benefits of Qualified Charitable Distributions (QCDs). By the end of this episode, you should have a clearer understanding of your future tax obligations in retirement. Wondering if you’re on track with your future taxes in retirement? Click here for a FREE...

Feb 18, 2025•14 min

Is Your Retirement The Focus?

Does your advisor address how you’ll use your money in retirement? Have they helped you create a plan to be tax-efficient with your portfolio when you stop working? Hear insight into those questions, plus Greg’s “why” on this week’s episode. Wondering if you’re on track for retirement? Fill out this short form for a free consultation . ___________________ See omnystudio.com/listener for privacy information....

Feb 11, 2025•12 min
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