When Retirement Changes Overnight

In this heartfelt episode of Winning Retirement, Greg and Kristen discuss how quickly retirement plans can change when unexpected health challenges arise. Inspired by the ALS diagnoses of close friends and clients, they explore the emotional and financial impact serious illness can have on retirees…

Rich vs. Never Broke in Retirement

Greg and Kristin explore an important retirement question: Is the goal to become wealthy—or simply make sure you never run out of money? Greg shares a personal story about losing everything in a childhood house fire and how it shaped his views on financial security. They also break down the differe…

How Much Should You Help Your Adult Children?

In this episode of Winning Retirement, Greg and Kristen start with some fun family stories before tackling a challenge many families face today. With rising housing costs and more young adults living at home, parents are helping more than ever—but how much is too much? They break down the differenc…

The Real Reasons Most Families Lose Their Wealth

This week, it’s all about this powerful statistic: nearly 70% of family wealth is lost by the second generation, and 90% by the third. So why does that happen? Greg and Kristin break down the biggest reasons families lose wealth over time, including a lack of communication, a lack of financial educ…

Medicare Covers a Lot… But Not Everything

Does chewing gum really boost your memory? Maybe—but remembering the healthcare costs that Medicare doesn’t cover might be even more important! While Medicare does a solid job covering doctor visits and hospital stays, there are still significant gaps—especially when it comes to dental work, vision…

The Problem With “One-Stop Shop” Financial Firms

Some financial firms promote themselves as a “one-stop shop,” offering attorneys, accountants, and advisors all under one roof. So why doesn’t the team at Legacy Retirement Group do the same? In this episode, Greg and Kristen explain the philosophy behind their approach. Rather than trying to do e…

Should You Wait Until 70 to Claim Social Security?

“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 increa…

Is Financial Secrecy a Form of Cheating?

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 communica…

Can AI Plan Your Retirement? What Technology Can—and Can’t—Do.

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…

Plugging the Leaks: How Efficient Is Your Retirement Plan?

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 oft…