The Retirement Caddie

An 88-year-old forced to work after losing his pension is a wake-up call for anyone without a plan for reliable retirement income. In this episode, Matt Eilers explains how to create your own “personal pension” using today’s tools, so you don’t have to rely on luck or viral miracles. Learn how to engineer predictable paychecks from your assets, safeguard against market risk...

Are you stuck in the “one more year” trap—working longer than you need to? This episode of The Retirement Caddie with Matt Eilers explores why purpose, not just money, should drive your retirement decision. Hear real stories about waiting too long, the risks of postponing your dreams, and how a clear financial plan can reveal when you’re truly ready to walk away from the ni...

What does lasagna for breakfast have to do with retirement planning? In this episode, Matt Eilers shares how retirees live “out of time”—and why knowing when you can retire is one of life’s biggest decisions. From optimizing Social Security and investment drawdowns to building a tax-efficient income plan, Matt breaks down some of the math and logic behind retirement timing....

What if the most important gift you give your family this season isn’t under the tree, but a clear financial plan for the future? In this episode, Matt Eilers explains why open conversations about money, legacy, and taxes matter—especially during the holidays. Discover how a well-crafted plan can ease tough decisions for loved ones, prevent tax headaches, and empower both spouses to fe...

Are you ready for the big changes retirement brings—or is your plan stuck in the past? This episode of The Retirement Caddie with Matt Eilers explores how shifting careers, evolving tax laws, and changing risk tolerance demand a flexible financial strategy. Learn why mapping out your income plan matters, how new rules like Secure Act 2.0 could impact your savings, and why real financial plan...

What if the biggest threat to your legacy isn’t a lack of wealth, but a lack of planning? In this episode, Matt Eilers reveals why estate planning is essential for everyone—not just the ultra-wealthy—and how simple tools like wills, powers of attorney, and trusts can preserve your assets, your wishes, and your loved ones. Learn how to avoid probate nightmares, make tough decision...

Is your retirement plan designed for YOUR life—or just following outdated rules?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 needs. Learn why “one-size-fits-all” advice falls short, how to avoid ticking tax...

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 to confidence and clarity. Learn how to avoid the junk drawer approach, designate assets for inc...

What does caddying on the golf course have to do with planning your retirement? In this episode, financial advisor Matt Eilers shares how his journey from aspiring golf pro to “retirement caddie” shapes the way he guides clients toward financial freedom. From understanding your investment “clubs” to navigating the retirement “course,” Matt breaks down why planni...

What happens when one spouse is left to manage the finances alone—and is your retirement plan truly ready for that moment? This episode of The Retirement Caddie with Matt Eilers explores why both partners must be involved, how to build a plan that covers emergencies, predictable income, risk, and care needs, and why tax strategy is a hidden blind spot for many families. Learn how to empower...

Is your legacy plan a blessing—or a ticking tax time bomb for your heirs? This episode of The Retirement Caddie with Matt Eilers explores why leaving assets behind isn’t just about good intentions. Learn how to avoid common mistakes that can trigger unexpected taxes, probate headaches, and family stress. Discover why a written financial plan, updated beneficiaries, and tailored strateg...

Are you stuck in the “one more year” trap—working longer than you need to? This episode of The Retirement Caddie with Matt Eilers explores why purpose, not just money, should drive your retirement decision. Hear real stories about waiting too long, the risks of postponing your dreams, and how a clear financial plan can reveal when you’re truly ready to walk away from the ni...

Are you ready for the big changes retirement brings—or is your plan stuck in the past? This episode of The Retirement Caddie with Matt Eilers explores how shifting careers, evolving tax laws, and changing risk tolerance demand a flexible financial strategy. Learn why mapping out your income plan matters, how new rules like Secure Act 2.0 could impact your savings, and why real financial plan...

What if your retirement “guarantee” isn’t as secure as you think? Matt Eilers unpacks the lessons from the Publishers Clearinghouse bankruptcy, explains why annuity safety depends on the strength of the insurance company, and reveals how independent advisors can help you scrutinize every option. Learn why A-ratings, renewal rate integrity, and company history matter—and how...

What if retirement isn’t about quitting work, but designing a life built around your passions and purpose? Matt Eilers explores how uncovering your “why” leads to a tailor-made wealth plan—one that supports family, travel, hobbies, or even working because you love it. Learn why cookie-cutter solutions fall short, and how real relationships and flexible planning help you ada...

What if the biggest challenge in retirement isn’t saving, but creating predictable income when pensions disappear? Matt Eilers explores how Americans can build their own “personal pension” for lasting security, separating growth from income to weather market swings. Learn why predictability matters, how annuities fit into the puzzle, and why a flexible plan can help you change yo...

What if retirement isn’t about quitting—it’s about redefining purpose? In this episode, Matt Eilers shares how planning for retirement starts with understanding what truly fulfills you. Whether you love your work or dream of stepping away, Matt explains why every financial plan should begin with your goals—not products. From first visits that feel more like conversations to...

What does lasagna for breakfast have to do with retirement planning? In this episode, Matt Eilers shares how retirees live “out of time”—and why knowing when you can retire is one of life’s biggest decisions. From optimizing Social Security and investment drawdowns to building a tax-efficient income plan, Matt breaks down some of the math and logic behind retirement timing....

What does caddying on the golf course have to do with planning your retirement? In this episode, financial advisor Matt Eilers shares how his journey from aspiring golf pro to “retirement caddie” shapes the way he guides clients toward financial freedom. From understanding your investment “clubs” to navigating the retirement “course,” Matt breaks down why planni...

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...