Winning Retirement Radio

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 sur...

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 ...

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): when t...

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 TestMyRetirem...

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 la...

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 cou...

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 i...

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, they show how retirement planning is...

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. 

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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? Comple...

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 inc...

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 ...

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 portfolio is a crucial part of this shif...

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: 

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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. 

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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!

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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 “doing the math” to NOT run out ...

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 retirement has evolved as well. Whether you ...