“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 retirement assets too quickly if you don’t have enough saved. Social Security isn’t the retirement plan. It’s one piece of the income puzzle. The real key? Building a written retirement income plan that’s stress-tested against market volatility, inflation, and tax changes. Because in retirement, cash flow is king!

 

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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 start creating your own income, financial secrets don’t just hurt feelings… they can derail the plan.

 

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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 technology helps… and where human guidance still matters most.

 

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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 portfolio, and why diversification isn’t just owning multiple funds. If you want to stop wasting heat, money, and peace of mind, this episode helps you find—and fix—the leaks.

 

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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 code. You’ll hear what to look for in a retirement-focused advisor, why “perfect” doesn’t always mean complete, and how the right questions—and the right fit—can change everything.

 

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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 benefits of transparency—reducing anxiety, preventing surprises, and helping heirs develop financial literacy—while also addressing the very real reasons some families choose caution.

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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 be updated, how advisors work together, and—yes—what it actually costs! 

👉 Ready to take the guesswork out of retirement? Get your FREE copy of Legacy’s My Retirement Kit today—your step-by-step guide to getting organized and staying on track! 

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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 spiritual—and why ignoring any one of them can derail even the best-laid plans. With real client stories, humor, and straight talk, this conversation is a reminder that retirement isn’t about surviving—it’s about thriving. And the goal isn’t just to stop working…it’s to step confidently into the next chapter of who you are.

 

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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 discussion shifts to a much bigger life transition: retirement. Should couples retire at the same time, or separately? Greg breaks down the three pillars of true retirement readiness—financial, emotional, and social—and explains why being “ready” goes far beyond the numbers. They explore identity after work, the loss (and replacement) of daily purpose, and how finding something bigger than yourself can lead to a truly fulfilling retirement. This episode is a reminder that just like technology, retirement works best when you evolve with intention.

 

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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 goal should be an age, a dollar amount, or something else entirely. Greg breaks retirement readiness into four critical areas: being financially ready, emotionally ready, socially connected, and having a real sense of purpose once the paychecks stop.

The episode explores why retirement planning isn’t just about assets and accounts—it’s about dependable income, confidence through life’s “what-ifs,” and knowing who you are when your job title disappears. From early retirees living the lake-house dream to stories that highlight the importance of belonging and purpose, this episode challenges listeners to think beyond money and start planning for a retirement that’s actually fulfilling.

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