Winning Retirement Radio

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 that many high-net-worth Baby Boomers are choosing to enjoy their money now rather than pass it all do...

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 challenges of working with someone who shares your last name. They discuss why trust can’t be assumed &mdas...

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 why market swings feel so personal, how over-concentration can create unnecessary stress, and why the real question isn’t...

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 becoming more common as companies evolve and technology reshapes the workplace. Greg and Kristen explore what t...

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 into the buzz around “tax-free retirement” webinars and explain why eliminating taxe...

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 Greg and Kristen share a few laughs about those old sayings, then connect them to the outdated financial “rules” many retirees still follow.

They break down why classics lik...

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, too. From family stories about Kristen’s late father-in-law (and his famous iron-skillet cake) to the emotio...

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 multiple income streams, from pensions and IRAs to RMDs, dividends, and rental income, while keeping taxes as low as possible. Lear...

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 misleading, how one client discovered that firsthand, and why professional guidance matters when the stak...

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) to mom’s Life360 “stalking,” this episode blends family stories with financial wisdom. Th...

Getting married later in life? Things can get… awkward. From “lady friends” to prenups, Greg and Kristen unpack the not-so-romantic side of love after 50—like protecting your retirement, keeping kids’ inheritances fair, and why Medicaid doesn’t care about your prenup. It’s funny, a little uncomfortable, but super important.

🤔 Feeling stuck with your retirement planning? Download a FRE...

It turns out that fewer young adults are reaching traditional milestones, such as moving out, getting married, and starting families. After Greg and Kristen share how that contrasts with their own family’s journey, the conversation turns to retirees and how they are prime targets for marketing — and how to filter through the noise. They share practical advice for spotting red flags, verifying sources, and making sure fi...

Greg and Kristen share their own family screen-time confessions along with America's, and how neighbors are turning movie nights into community fun! Then, they shift gears to retirement: When does a Roth conversion really make sense, and how can it protect your lifestyle and legacy? From screen habits to financial habits, this episode is all about finding balance in the digital age—and in your retirement planning.

🗂️ ...

When do most Americans really fall asleep—and is sharing a bed helping or hurting? Kristen admits she struggles to drift off while Greg can be snoring in seconds (though he’ll never admit it). Later, Greg and Kristen delve into the “free steak dinner” seminars, exploring why they attract retirees and how to distinguish between genuine education and high-pressure sales pitches.

😴 Don’t lose slee...

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 explain why having a smart tax plan mat...

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 customized retirement plan matters more th...

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...