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 plann...

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 as...

Ignoring long-term care planning can leave families facing difficult emotional and financial decisions when it matters most. In this episode, Matt Eilers discusses the real impact of unexpected health events, from caregiving burdens to the high cost of professional care. He explains why having a clear plan in place—before a crisis—can help guide decisions around assets, family roles, a...

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 re...

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&...

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...

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 house...

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

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...

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 plann...

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 matt...

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 ex...

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 as...

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 health...

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...

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 hea...

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...

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 m...

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 re...

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 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 inc...

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 house...

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...

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...

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 matt...