WRR - Are You Ready to Retire? It’s Not Just the Numbers

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. G…

From AI to Identity: Are You Really Ready to Retire?

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), …

From Double-Doubles to Dream Retirement: Are You Really Ready?

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 …

From Home Alone to Retirement Reality: Knowing What You Can Afford to Risk

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 “experien…

Retirement Planning in a High-Tech World: Why Humans Still Matter

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…

Spend It Now or Save It for the Kids? The New Reality of the Great Wealth Transfer

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 t…

Family, Finances & Trust- Should You Hire a Relative as Your Advisor

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 …

Are You Too Emotional for the Market? Finding Your Real Risk Comfort Zone

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 w…

Forced Retirement After 60: How to Plan When the Unexpected Happens

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 be…

“Don’t Roth Convert?” The Truth Behind Tax-Free Retirement Promises

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 …