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 designe…

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 o…

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 fi…

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 di…

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 th…

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 …

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 c…

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 the…

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 t…

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 int…