The Retirement Caddie
The Retirement Caddie
Medalist Wealth Management’s Matt Eilers hosts “The Retirement Caddie” radio program and now makes those on-the-air discussions available to you on demand with his podcast bearing the same name. Subscribe on your favorite streaming service and each week will bring you fresh insight and perspective to financial matters that can help shape your future plans. With each episode, Matt brings informativ…Social links:
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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 …
11:04
Best Of: Beyond the Scorecard: Building a Retirement Plan That Fits You
With over 8 million baby boomers turning 65 in the next two years, the question isn’t just “Can I retire?”—it’s “Am I truly ready?” In this episode, Matt Eilers reveals why today’s retirement demands more than a simple checklist. Learn how to spot hidden blind spots like inflation, taxes, and marke…
13:54
Annuities Aren’t the Problem—Bad Explanations Are
Annuities stir strong opinions—but most of the confusion comes from how they’re explained and when they’re used. In this episode, Matt Eilers breaks down why nearly 60% of annuity owners don’t fully understand what they bought and how that misunderstanding can derail retirement plans. The conversat…
10:25
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…
11:08
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…
11:03
Best Of: Why Creative Planning Beats Cookie-Cutter Advice
Is your retirement plan designed for YOUR life—or just following outdated rules? This episode of The Retirement Caddie with Matt Eilers explores how creative strategies like deferment, intentional tax planning, and personalized income strategies can help you build a retirement that fits your unique…
11:52
When the Paycheck Stops, What Really Matters?
One moment can change how you think about work, money, and retirement forever. In this episode, Matt Eilers reflects on a powerful story about a career spent chasing the paycheck—and what happens when the work stops but life doesn’t slow down. The conversation explores how emotions, priorities, and…
09:34
Best Of: Is Your Retirement Plan Just a Pile of Stuff?
Is your retirement plan just a pile of investments—or a written strategy designed for your life? This episode of The Retirement Caddie with Matt Eilers reveals why intentional planning beats guesswork, how to organize your assets into buckets with clear purposes, and why a written plan is the key t…
10:36
Why Hope Isn’t a Retirement Strategy
If Social Security changes, does your retirement plan change with it? This episode tackles growing concerns about the future of Social Security and why relying on congressional action can create blind spots in retirement planning. Matt Eilers discusses stress‑testing a retirement plan for benefit r…
09:58
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…
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