Annuities Aren’t the Problem—Bad Explanations Are

The Small Mistakes That Can Become Big Retirement Problems

The biggest retirement mistakes often come from the small financial details people overlook today. In this episode, Matt Eilers explains how “hidden risks” like required minimum distributions, tax planning gaps, and excess market exposure can create bigger challenges later in retirement. The conversation highlights why avoiding major missteps—rather than chasing perfect outcomes—can shape long-term financial stability. Matt also discusses how proactive planning, from managing taxes to adjusting risk, can help reduce surprises and keep retirement strategies aligned with changing conditions. 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.

The Two Retirement Worries That Matter Most

What if your biggest retirement fears could be narrowed down to just two concerns? In this episode, Matt Eilers explains why most retirement worries come down to health versus wealth—and how those two forces shape every financial decision in retirement. The conversation explores income versus longevity risk, how long your money needs to last, and why a written income plan can provide clarity in an uncertain future. Matt also highlights the importance of proactive planning over emotional reactions, helping retirees better understand how to prepare for decades of changing financial needs. 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.

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 prepare for the day one partner may face retirement alone, and which legal documents every household should review. From communication gaps to mismatched risk tolerances, Matt reveals how key teamwork is as you navigate retirement together. 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.

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.