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 …

Because Mom Said So: Outdated Rules and Smarter Retirement Strategies

Revisiting the “rules” we grew up with—and the financial ones that could be hurting your retirement. We all remember the rules our parents swore by—don’t sit too close to the TV, wear your coat, turn off that car light! Greg and Kristen share a few laughs about those old sayings, then connect them…

The Truth Hurts (But It Helps): Why Honesty Matters With Your Doctor—and Your Advisor

Honesty isn’t just good for your health—it’s vital for your wealth. A new study finds that up to 80% of adults admit to lying to their doctors about their lifestyle habits—usually to avoid judgment or bad news. Greg and Kristen open up about how this same fear can show up in retirement planning, t…

Taxes in Retirement: How to Maximize Income and Minimize What You Owe

Learn how to keep more of your money in retirement with smart income and tax strategies! Most people picture Social Security or a 401(k) when they think about retirement income — but that’s just the beginning. In this episode of Winning Retirement, Greg and Kristen explain how to coordinate multip…

Calculators, Golf Clubs, and the Retirement Equation

From the $550 calculator watches of the 1970s to today’s free online tools, we’ve always relied on numbers to help us make decisions. But when it comes to retirement, not every “calculator” gives you the full picture. In this episode, Greg and Kristen share why online tools—and even AI—can be misle…

Empty Nests, Bad Haircuts, and Big Money Decisions

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) t…