Winning Retirement Radio

We tend to notice dramatic risks, but what happens when the paycheck stops? Greg and Kristin discuss why market downturns can feel different in retirement, how withdrawals can compound losses, and why inflation, taxes, healthcare costs, and longevity all deserve a place in a written retirement plan. See omnystudio.com/listener for privacy information.

How often should you really check your retirement accounts? In this episode of Winning Retirement , Greg and Kristen explain why watching your portfolio every day can fuel anxiety and lead to emotional decisions. They discuss what retirees should actually look for during portfolio reviews, why your risk tolerance matters, and how a purposeful retirement strategy can help you stay focused on long t...

Being told you’re “97% likely” to have enough money for retirement may sound reassuring, but retirement is more than a probability on a spreadsheet. In this episode of Winning Retirement , Greg and Kristen explain how to determine whether you’re truly ready to retire by looking at reliable income, Social Security and pensions, lifestyle expenses, income gaps, inflation, and...

Retirement may solve the work question, but it can create an unexpected one: What gives my life purpose now? In this episode of Winning Retirement , Greg and Kristen explore why some retirees struggle with boredom, a sense of lost identity, and a lack of direction after leaving their careers. They share real-life examples of retirees who found renewed purpose through travel, volunteering, stronger...

Should you retire at 65, pay off your mortgage, move your investments to safety, or claim Social Security because that’s what everyone else seems to do? Not necessarily. In this episode of Winning Retirement , Greg and Kristen explain why some of the most common retirement decisions shouldn’t be made simply because they’re considered “normal.” They discuss retiring be...

What happens when retirement throws you something you didn’t plan for? In this episode of Winning Retirement, Greg and Kristen explain why preparing for retirement is a lot like preparing for a big game—you may have great players and plenty of savings, but you still need a strategy. They discuss why the transition from saving for retirement to living on your savings changes the game, h...

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 designed to provide reliable income through changing markets and economic conditions. They explore retireme...

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 organizing important documents and identifying valuable assets to giving meaningful possessions...

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 financial world. They discuss why guaranteed pensions have become rare, how longer life expe...

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 discuss the limitations of the 4% withdrawal rule , why market timing can make or break a r...

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 the most valuable inheritance is often character, faith, and family values. They also expla...

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 is no one-size-fits-all retirement number. They discuss the 4% withdrawal rule, Social Security, gua...

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 conversations are essential before saying "I do" again.   ✅ Your retirement deserves a plan&mdas...

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 their loved ones and their retirement. From budgeting and legal planning to long-term care and having di...

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 the right move. They explore possible solutions Congress may consider—including higher payroll t...

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 into your retirement strategy is critical, how to prepare for life's unexpected "what ifs," and ways to...

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...

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 r...

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 mon...

Greg and Kristin explore an important retirement question: Is the goal to become wealthy—or simply make sure you never run out of money? Greg shares a personal story about losing everything in a childhood house fire and how it shaped his views on financial security. They also break down the difference between harmful debt and strategic debt in retirement, including when it may make sense to...

In this episode of Winning Retirement, Greg and Kristen start with some fun family stories before tackling a challenge many families face today. With rising housing costs and more young adults living at home, parents are helping more than ever—but how much is too much? They break down the difference between support and dependency, share real client scenarios, and explain why your retirement...

This week, it’s all about this powerful statistic: nearly 70% of family wealth is lost by the second generation, and 90% by the third. So why does that happen? Greg and Kristin break down the biggest reasons families lose wealth over time, including a lack of communication, a lack of financial education, and failing to pass down values along with money. You’ll also hear real-life stori...

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 c...

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 investmen...

“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 als...