The Retirement Caddie

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

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

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

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, mortgages, taxes, healthcare, Social Security timing, and why income planning—not just asset totals—drives retirement readiness. Matt also explains why retirement decisions aren’t one‑size‑fits‑all and how overlooked details can quietly change the outcome if they’re not addressed as part of a coordinated plan. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 | YouTubeSee omnystudio.com/listener for privacy information.

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 time bombs, and why a tailored plan matters more than ever in today’s changing landscape. Discover the power of making your money serve you, not the other way around. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 real‑world risks shape retirement decisions, from market volatility and inflation to healthcare and legacy planning. It’s a candid discussion about shifting focus from accumulation to living with intention, and why a retirement plan should serve your life—not the other way around. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 income, growth, and emergencies, and build a retirement strategy that fits your unique goals. Discover why advice from the water cooler won’t cut it when it comes to your financial future. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 reductions, market swings, higher taxes, and inflation, and explains why durability and adaptability matter more than chasing a “magic number.” The conversation centers on building income strategies that can handle uncertainty, so retirement decisions aren’t driven by headlines, hope, or last‑minute reactions. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 explores the shift from asset allocation to asset designation, why retirement requires a different planning mindset, and how income, risk, and healthcare planning all change once paychecks stop. The conversation focuses on preparing for each phase of retirement so surprises don’t dictate decisions later on. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 building flexible, evolving strategies, this episode explores how to create a retirement plan that fits your life, not just your timeline. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

What if the real risk in retirement isn’t falling down—but not being prepared to get back up? In this episode, Matt Eilers uses lessons from sports and real life to explain why preparation matters more than prediction in retirement planning. He breaks down the danger of “buy and hope” investing, why relying on outdated withdrawal rules can backfire, and how planning for income, risk, taxes, and market downturns creates clarity when life happens. The conversation focuses on building plans that account for uncertainty—so a bad market or unexpected expense doesn’t derail your retirement paycheck. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 | YouTubeSee omnystudio.com/listener for privacy information.

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 strategies matter more than fitting into someone else’s box. Find out how to turn your wishes into a clear, actionable legacy. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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

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

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, and better prepare your income to last as long as you do. Discover the questions every retiree should answer—and how a real plan brings more optimism when it comes to retirement. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 nine-to-five. Discover how to break free, find meaning beyond work, and start living every day like it’s Saturday. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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 feel more optimistic about their financial future. Learn how to turn family meetings into moments of clarity, not confusion. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 planning goes far beyond last year’s rate of return. Discover the value of ongoing education, proactive adjustments, and planting seeds for your future. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 decisions easier for your family, and ensure your legacy is carried out exactly as you intend. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 time bombs, and why a tailored plan matters more than ever in today’s changing landscape. Discover the power of making your money serve you, not the other way around. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 income, growth, and emergencies, and build a retirement strategy that fits your unique goals. Discover why advice from the water cooler won’t cut it when it comes to your financial future. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 planning early—whether you're 10 years out or just one—is critical.See omnystudio.com/listener for privacy information.

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 your household, avoid outdated approaches, and ensure your financial future is a true team effort. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 strategies matter more than fitting into someone else’s box. Find out how to turn your wishes into a clear, actionable legacy. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 nine-to-five. Discover how to break free, find meaning beyond work, and start living every day like it’s Saturday. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 planning goes far beyond last year’s rate of return. Discover the value of ongoing education, proactive adjustments, and planting seeds for your future. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 a truly independent approach can help you avoid financial blind spots and find lasting peace of mind. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 adapt when life throws curveballs Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 your financial ending—no matter when you start. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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 building flexible, evolving strategies, this episode explores how to create a retirement plan that fits your life, not just your timeline. Ready to get out of the rough and get your retirement plan in place? Contact Matt today! Facebook | Instagram | LinkedIn | YouTubeSee omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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 planning early—whether you're 10 years out or just one—is critical.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.