The Retirement Caddie

A Conversation with Bill Murray and his family

Matt had the special chance to sit down with Bill Murray and his family at the 25th Annual Caddyshack Golf charity event. An incredible opportunity for The Retirement Caddie to talk to the legends of Caddyshack! Ready to get out of the rough and get your retirement plan in place? Contact [https://medalistwealth.com/#contact] Matt today! Facebook [https://www.facebook.com/medalistwealth/] | Instagram [https://www.instagram.com/medalistwealth/] | LinkedIn [https://www.linkedin.com/company/medalist-wealth-management/] | YouTube [https://www.youtube.com/@medalistwealth] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Best Of: Avoiding Lamborghini Fever: Smart Moves After an Unexpected Windfall

An inheritance may feel like a blessing—but it can also create challenges you never expected. In this episode, Matt Eilers breaks down the financial realities of the great wealth transfer, from hidden tax traps to handling retirement accounts that must be emptied within 10 years. He explains why planning ahead matters, how to avoid “Lamborghini fever,” and what to consider before receiving cash, property, or investment accounts. Matt also discusses how a clear financial plan helps you make thoughtful decisions with any inheritance and keeps your overall retirement strategy on track. Ready to get out of the rough and get your retirement plan in place? Contact [https://medalistwealth.com/#contact] Matt today! Facebook [https://www.facebook.com/medalistwealth/] | Instagram [https://www.instagram.com/medalistwealth/] | LinkedIn [https://www.linkedin.com/company/medalist-wealth-management/] | YouTube [https://www.youtube.com/@medalistwealth] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

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 are left to the courts. He explains common misconceptions around estate planning, why it’s not just for the wealthy, and how clear documentation can reduce confusion and stress for loved ones when it matters most. Ready to get out of the rough and get your retirement plan in place? Contact [https://medalistwealth.com/#contact] Matt today! Facebook [https://www.facebook.com/medalistwealth/] | Instagram [https://www.instagram.com/medalistwealth/] | LinkedIn [https://www.linkedin.com/company/medalist-wealth-management/] | YouTube [https://www.youtube.com/@medalistwealth] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

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 market volatility, and why a personalized income plan matters more than ever. Discover how independent advice, a written strategy, and a “blind spot review” can help you retire—no matter what your goals look like. Ready to get out of the rough and get your retirement plan in place? Contact [https://medalistwealth.com/#contact] Matt today! Facebook [https://www.facebook.com/medalistwealth/] | Instagram [https://www.instagram.com/medalistwealth/] | LinkedIn [https://www.linkedin.com/company/medalist-wealth-management/] | YouTube [https://www.youtube.com/@medalistwealth] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

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 conversation reframes annuities as tools—not good or bad by default—and explores where they fit (and where they don’t) alongside stocks and other investments. Matt also explains why education, second opinions, and matching tools to goals matter more than advice from headlines or the water cooler. Ready to get out of the rough and get your retirement plan in place? Contact [https://medalistwealth.com/#contact] Matt today! Facebook [https://www.facebook.com/medalistwealth/] | Instagram [https://www.instagram.com/medalistwealth/] | LinkedIn [https://www.linkedin.com/company/medalist-wealth-management/] | YouTube [https://www.youtube.com/@medalistwealth] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.