Retirement’s Version of Independence Day

Financial independence may be the retirement milestone worth celebrating most. Damon Roberts discusses America’s 250th anniversary while exploring how retirees can replace uncertainty with a structured financial plan. The conversation covers Social Security, taxes, investment risk, income planning,…

What Today’s Market Signals Could Mean for Your Retirement

What happens to your retirement plan when inflation starts climbing again? This episode with Matt Deaton breaks down the latest inflation trends, how rising energy costs ripple through the economy, and why the Federal Reserve faces a tough balancing act. You’ll also hear how market volatility, valu…

Are Taxes Today Your Biggest Retirement Opportunity?

Are today’s low tax rates creating an opportunity—or a future challenge? This episode with Matt Deaton explores Roth conversions and why relying solely on projections and assumptions can lead to flawed decisions. The discussion focuses on understanding current versus future tax rates, how income so…

Inside Mar-a-Lago: Lessons on Work, Wealth, and the American Dream

A behind-the-scenes look at Mar-a-Lago turns into a conversation about the American Dream. This episode with Damon Roberts & Matt Deaton features clips from Donald Trump Jr. on work ethic, education, and legacy, alongside a discussion on how planning shapes real-world retirement outcomes. The conve…

What Sets Successful Retirees Apart

What separates confident retirees from everyone else? This episode with Damon Roberts & Matt Deaton breaks down the key habits behind successful retirement strategies, from consistent saving to managing risk and building income. The discussion highlights how preparation, not guesswork, shapes finan…

The Income Problem No One Solves Before Retirement

Retirement fear isn’t about numbers—it’s about not knowing where your paycheck comes from. This episode with Damon Roberts & Matt Deaton breaks down why running out of money still tops the worry list and how income strategies beyond the 401(k) can reshape confidence. From pensions disappearing to c…

Why Some People Refuse to Retire

What if your retirement plan isn’t about stopping work at all? This episode with Damon Roberts & Matt Deaton explores why more people are choosing to keep working, how flexibility changes financial decisions, and the hidden pitfalls of Social Security timing and healthcare costs. It also tackles mi…

The Retirement Myths That Still Trip People Up

What if some of the most common retirement “truths” don’t hold up anymore? Damon Roberts and Matt Deaton continue their myths-and-misconceptions series by unpacking assumptions around Social Security, withdrawal rules, healthcare costs, and retirement planning shortcuts. They explore how income, ta…

Does the 4% Rule Still Make Sense?

Is the 4% rule still relevant in today’s retirement landscape? Damon Roberts and Matt Deaton break down diversification, income planning, and the assumptions behind popular retirement rules of thumb. They discuss market volatility, withdrawal strategies, and why relying on a single guideline can cr…

Success, Money, and Loving the Craft (Interview with Vince Gill)

What happens when a legendary musician reflects on longevity, money, and knowing when to stop—or not stop—at all? In this special archive episode, Vince Gill joins Matt Deaton. In their conversation, Vince shares stories from decades on the road, lessons learned watching others struggle with succes…