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 informative and topical conversations that help build your financial savvy and intellect as you build towards a financial future suited specifically for you.

The Retirement Caddie is a business podcast hosted by Matt Eilers, with 51 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Matt Eilers hosts The Retirement Caddie, a business show with 51 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  The Retirement Caddie

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

  Aug 18, 202610 min

  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 priorities, travel goals, and lifestyle dreams helps shape a retirement plan that reflects your unique vision. Matt also discusses why retirement planning should be an ongoing process, not a one-time event, and how a personalized approach can adapt as life changes over time. Ready to get out of the rough and get your retirement plan in place?   Contact Matt today! Facebook | Instagram | LinkedIn | YouTube See omnystudio.com/listener for privacy information.

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  The Retirement Caddie

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

  Aug 11, 202611 min

  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 Matt today! Facebook | Instagram | LinkedIn | YouTube See omnystudio.com/listener for privacy information.

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  The Retirement Caddie

  What Climbing 29,029 Feet Teaches About Retirement Planning

  Aug 4, 202612 min

  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 supporting Kids Food Basket , the realities many families face with rising food costs, and why inflation remains one of the biggest risks retirees need to prepare for. Learn how building inflation into a retirement income strategy can help address the rising costs that continue to impact everyday life. Ready to get out of the rough and get your retirement plan in place?   Contact Matt today! Facebook | Instagram | LinkedIn | YouTube See omnystudio.com/listener for privacy information.

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  The Retirement Caddie

  Why That Retirement Money Isn’t All Yours

  Jul 21, 202611 min

  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 shift from focusing on growth to focusing on what they keep, how taxes, RMDs, inflation, and healthcare intersect, and why retirement planning needs to go far beyond picking investments. It’s a candid discussion about rules, strategy, and building a plan that reflects this phase of life. Ready to get out of the rough and get your retirement plan in place?   Contact Matt today! Facebook | Instagram | LinkedIn | YouTube See omnystudio.com/listener for privacy information.

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  The Retirement Caddie

  Why Retirement Gets More Complex Than Expected

  Jul 14, 202611 min

  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 more detailed strategy, especially when multiple tax rules and rising expenses come into play. The conversation highlights why planning ahead for these “unknowns” can make a big difference in how retirement unfolds and how clearly understanding your income sources can shape long‑term decisions. Ready to get out of the rough and get your retirement plan in place?   Contact Matt today! Facebook | Instagram | LinkedIn | YouTube See omnystudio.com/listener for privacy information.

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