Winning Retirement Radio

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 expl...

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 customi...

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 saf...

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...

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...

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...

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—conve...

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...

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 plann...

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, t...

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.&...

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...

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 wi...

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 exp...

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...

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 portf...

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...

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...

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 tr...

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 “do...

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 retiremen...

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 Gr...

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 ne...

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 ne...

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?...