🎙️ 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…
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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…
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 to…
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 expectancies…
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 retirement…
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 explain practical…
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,…
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-grab your…
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…
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 taxes,…
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 real goal of retirement…
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…
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 keep a…
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 comes…
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 stories about…
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…
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…
"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…
Greg and Kristin dive into the emotional and practical side of money in marriage by sharing personal stories, real client experiences, and the hard truth about what happens when financial transparency breaks down. From hidden credit card debt to mismatched risk tolerance, they explain why communication is critical-especially as retirement approaches. Because once you stop earning paychecks and…
From dial-up internet and AOL chat rooms to Alexa, smart faucets, and artificial intelligence, technology has come a long way since the 90s. But when it comes to retirement planning, how far should we really take it? Yes, AI can track your spending, calculate projections, and even answer retirement questions. But can it walk with you through a market drop-or a medical emergency? Find out where…
In this episode, the team at Legacy Retirement Group uses everyday household efficiency challenges as a powerful analogy for retirement readiness. Greg and Kristen explain how many people think they're being efficient-whether it's with energy usage or their investment portfolio-but hidden leaks often go unnoticed until conditions change. Hear how market volatility can expose inefficiencies in a…
In this episode, Greg and Kristin explore whether proximity really matters when choosing a financial advisor-or if something else matters more. Greg and Kristen share a powerful story about a local woman who loved her longtime advisor but sought a second opinion after moving closer to Columbus. The conversation highlights why focus, experience, coordination, and comfort matter far more than zip…
Retirement planning isn't just about money-it's about family dynamics, communication, and expectations. In this episode, Greg and Kristin tackle a question many parents wrestle with: Should we share details of our retirement plans with our children? They explore how family roles around money have shifted over the years and why financial conversations no longer need to be taboo. They discuss the…
Before you hire an estate or elder law attorney, make sure you're asking the right questions. Greg shares the red flags, the must-asks, and how to know if an attorney is protecting you-or just selling paperwork. Walk through the key questions every family should ask before hiring an attorney, including what's really protected, how incapacity and long-term care are handled, how often plans should…
How do you really know when it's time to retire? While finances are a critical piece of the puzzle, Greg explains why they're only part of the story. After more than 30 years helping families prepare for retirement, he's seen firsthand that a successful retirement depends on much more than math. Greg breaks down the four pillars of retirement readiness-financial, emotional, social, and…
Time Magazine named the "Architects of AI" its 2025 Person of the Year-and that sparks a wide-ranging conversation about how fast technology has changed everything from writing papers to planning our futures. Greg and Kristen reflect on tech evolution (from typewriters and flip phones to ChatGPT), the pros and cons of AI, and why change-while uncomfortable-is unavoidable. From there, the…
What In-N-Out Burger, retirement goals, and purpose after work all have in common. The conversation starts with a hot topic-In‑N‑Out Burger finally making its way east of the Mississippi-and quickly turns into something much deeper: What does it actually mean to be ready for retirement? A simple conversation with a nurse sparks a powerful realization-many people don't know whether their retirement…
A $3M widow, a $50K income gap, and a plan that finally made sense-this is what real retirement clarity sounds like. Kevin McCallister's Plaza Hotel spree is a fun throwback-until you compare what it would cost today and realize how fast prices (and big life goals) have changed. From NYC "experience" trips to an Investopedia breakdown suggesting millions are needed to fund the modern American…
Tech tools are everywhere - but when it comes to retirement, can an algorithm really replace a trusted advisor? Managing money looks nothing like it did for our parents, especially with pennies slowly going away. With digital wallets, chip cards, and AI-powered investing tools, it's easy to wonder: Is technology phasing out the traditional retirement advisor? Greg and Kristen explain why the…
The "Great Wealth Transfer" may not look the way we expected - and the stories might surprise you. After embracing the holiday season, we discuss how the "Great Wealth Transfer" is happening - but not exactly how the headlines predicted. Greg and Kristen unpack a new Charles Schwab study showing that many high-net-worth Baby Boomers are choosing to enjoy their money now rather than pass it all…
When it comes to managing your money, should you trust family - or is a fresh set of eyes the smarter move? From parents who jokingly say they'll "move in" if their advisor-son loses the money, to widows who struggle to trust anyone new, the Taylors explore the emotional, practical, and financial challenges of working with someone who shares your last name. They discuss why trust can't be assumed…
If market dips shake you up, your portfolio may be built for someone else-not you. The markets may be hovering near all-time highs, but that doesn't mean investors feel calm. In this episode, Greg and Kristen tackle one of the biggest issues in retirement investing: emotional risk. They discuss why market swings feel so personal, how over-concentration can create unnecessary stress, and why the…
What would you do if your job were suddenly outsourced in your 60s? Greg and Kristen talk about how to prepare-financially and emotionally-for a retirement that may come sooner than expected. A woman in her early 60s called the team worried that her position might be outsourced-a fear that's becoming more common as companies evolve and technology reshapes the workplace. Greg and Kristen explore…
An ad claims you can skip Roth conversions and avoid taxes. We reveal what's real-and what's just marketing. When a Facebook ad promises you can "eliminate taxes on your retirement accounts-no Roth conversion required," it's hard not to click. But is it too good to be true? Greg and Kristen dive into the buzz around "tax-free retirement" webinars and explain why eliminating taxes completely isn't…
Revisiting the "rules" we grew up with-and the financial ones that could be hurting your retirement. We all remember the rules our parents swore by-don't sit too close to the TV, wear your coat, turn off that car light! Greg and Kristen share a few laughs about those old sayings, then connect them to the outdated financial "rules" many retirees still follow. They break down why classics like the…
Honesty isn't just good for your health-it's vital for your wealth. A new study finds that up to 80% of adults admit to lying to their doctors about their lifestyle habits-usually to avoid judgment or bad news. Greg and Kristen open up about how this same fear can show up in retirement planning, too. From family stories about Kristen's late father-in-law (and his famous iron-skillet cake) to the…
Learn how to keep more of your money in retirement with smart income and tax strategies! Most people picture Social Security or a 401(k) when they think about retirement income - but that's just the beginning. In this episode of Winning Retirement, Greg and Kristen explain how to coordinate multiple income streams, from pensions and IRAs to RMDs, dividends, and rental income, while keeping taxes…
From the $550 calculator watches of the 1970s to today's free online tools, we've always relied on numbers to help us make decisions. But when it comes to retirement, not every "calculator" gives you the full picture. In this episode, Greg and Kristen share why online tools-and even AI-can be misleading, how one client discovered that firsthand, and why professional guidance matters when the…
When kids leave home, they don't just move away-they tug on their parents' hearts, too. Greg and Kristen share the laughs (and frustrations) of watching their son head to college-828 miles away-with a questionable dorm-room haircut to prove his independence. From daily check-ins (or lack thereof) to mom's Life360 "stalking," this episode blends family stories with financial wisdom. The Taylors…
Getting married later in life? Things can get… awkward. From "lady friends" to prenups, Greg and Kristen unpack the not-so-romantic side of love after 50-like protecting your retirement, keeping kids' inheritances fair, and why Medicaid doesn't care about your prenup. It's funny, a little uncomfortable, but super important. 🤔 Feeling stuck with your retirement planning? Download a FREE copy of…
It turns out that fewer young adults are reaching traditional milestones, such as moving out, getting married, and starting families. After Greg and Kristen share how that contrasts with their own family's journey, the conversation turns to retirees and how they are prime targets for marketing - and how to filter through the noise . They share practical advice for spotting red flags, verifying…
Greg and Kristen share their own family screen-time confessions along with America's, and how neighbors are turning movie nights into community fun! Then, they shift gears to retirement: When does a Roth conversion really make sense, and how can it protect your lifestyle and legacy? From screen habits to financial habits, this episode is all about finding balance in the digital age-and in your…
When do most Americans really fall asleep-and is sharing a bed helping or hurting? Kristen admits she struggles to drift off while Greg can be snoring in seconds (though he'll never admit it). Later, Greg and Kristen delve into the "free steak dinner" seminars, exploring why they attract retirees and how to distinguish between genuine education and high-pressure sales pitches. 😴 Don't lose sleep…
Greg and Kristin dive into the surprising news that you can now use Venmo and PayPal to "donate" toward the U.S. national debt. The conversation quickly shifts to a larger point: the government is always seeking new ways to generate revenue, and retirees with well-built nest eggs could become targets. From required minimum distributions to potential tax changes down the road, they explain why…
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…
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…
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…
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):…
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…
