Winning Retirement Radio

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 also dive into the dangers of lump-sum payouts, why some pensions and sweepstakes winners run out of money, and how careful planning can help protect both your nest egg and your peace of mind.  

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.

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 sources, and making sure financial products and lifestyle purchases align with your overall plan. Whether you’re considering a senior living community, a travel package, or even gold and Bitcoin ads, this episode helps you focus on what you really need and avoid blowing your budget on shiny objects. ✍️ Ready to design your ideal retirement? Schedule a FREE consultation by completing this brief form.  See omnystudio.com/listener for privacy information.

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 retirement planning.  

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.  

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 having a smart tax plan matters more than ever.  

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 checklist!

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! Ready to design your ideal retirement? Schedule a FREE consultation. See omnystudio.com/listener for privacy information.

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 goals — whether you want to travel, give generously, or simply stay comfy at home.

Even the happiest couples argue — and sometimes it’s on air!

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 help getting organized? Download a FREE copy of Legacy’s My Retirement Kit.See omnystudio.com/listener for privacy information.

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 taxes, as well as the pros and cons of Roth conversions.   Wondering if you’re on track for retirement? Fill out this short form for a FREE consultation.  See omnystudio.com/listener for privacy information.

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 strategies for annuities—withdrawals, annuitization (aka "annui-cide"), and income riders—plus the pros, cons, and hidden details to watch out for. It’s everything you need to know about annuities with a dose of laughs, love, and financial wisdom. Feeling stuck with your retirement planning? Download a FREE copy of Legacy’s My Retirement Kit to help become better organized. See omnystudio.com/listener for privacy information.

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. Ready to design your ideal retirement? Schedule a FREE consultation by completing this brief form. See omnystudio.com/listener for privacy information.

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?

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/listener for privacy information.

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.com/listener for privacy information.

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 track for retirement? Fill out this short form for a FREE consultation.  See omnystudio.com/listener for privacy information.

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 available. Need a little help getting organized? Download a FREE copy of Legacy’s My Retirement Kit.See omnystudio.com/listener for privacy information.

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.