Is Your Retirement Plan Built Around Your Life—or Just Your Money?

Retirement planning should feel less like a trip to the dentist and more like a conversation about what matters most to you. In this episode, Matt Eilers explains why financial planning goes far beyond investment returns and account balances. He shares how understanding your passions, family priori…

The Four Money Conversations Every Couple Needs Before It’s Too Late

What happens when one spouse handles the money—and the other suddenly has to? In this episode, Matt Eilers breaks down the essential financial conversations couples must have long before retirement forces the issue. He explains why alignment on risk, roles, and record‑keeping is important, how to p…

What Climbing 29,029 Feet Teaches About Retirement Planning

What does climbing the equivalent of Mount Everest have to do with retirement planning? Matt Eilers shares the story behind his 29029 endurance challenge, the lessons it teaches about perseverance, and the inspiration driving him to push beyond his comfort zone. Along the way, he discusses supporti…

The Great Wealth Transfer Is Here—But Is Your Family Prepared?

The biggest wealth transfer in history is already underway—but is the next generation ready for it? In this episode, Matt Eilers explores how families can prepare for passing down assets and the important conversations that often get delayed. He discusses the difference between “live-on” money and …

Why That Retirement Money Isn’t All Yours

That retirement balance may look impressive—but not all of it actually belongs to you. In this episode, Matt Eilers uses a surprising Oscar Awards rule to explain the often‑overlooked reality that Uncle Sam is a silent partner in many retirement accounts. The conversation explores why retirees shif…

Why Retirement Gets More Complex Than Expected

Retirement can feel familiar—until unexpected costs and decisions make it anything but. In this episode, Matt Eilers breaks down why areas like healthcare, taxes, and income planning often catch retirees off guard. He explains how the shift from earning a paycheck to generating income requires a mo…

Best Of: Estate Planning Isn’t Just for the Rich—Here’s Why

More than half of Americans don’t have their estate planning basics in place—and many don’t realize why that matters until it’s too late. In this episode, Matt Eilers breaks down why wills, powers of attorney, and healthcare directives often get delayed and what can happen when important decisions …

Best Of: Can You Really Retire Early—or Just Hope You Can?

Retiring early sounds simple—until you start asking the right questions. In this episode, Matt Eilers breaks down why popular retirement checklists don’t tell the full story when it comes to deciding when you can actually retire. The conversation explores needs versus wants, emergency funds, mortga…

The “What If” Scenario That Can Change Everything

Ignoring long-term care planning can leave families facing difficult emotional and financial decisions when it matters most. In this episode, Matt Eilers discusses the real impact of unexpected health events, from caregiving burdens to the high cost of professional care. He explains why having a cl…

Best Of: The Retirement Spending Smile Most People Don’t Plan For

Retirement spending doesn’t move in a straight line—and that can catch a lot of people off guard. In this episode, Matt Eilers breaks down the “retirement spending smile,” explaining why expenses often rise early in retirement, dip in later years, and increase again as healthcare needs grow. He exp…