The Retirement Caddie

The retirement you’ve been saving for can get more expensive before you know it. Matt Eilers discusses how rising travel and lifestyle costs can influence retirement spending and why inflation deserves a place in the planning conversation. He also explores balancing today’s bucket-list goals with tomorrow’s expenses, creating retirement income, and determining where annuities may...

The most misunderstood retirement tool may be getting judged by outdated opinions. Matt Eilers breaks down the emotional debate surrounding annuities and explains why they should be viewed as financial tools, not labels. He explores how annuities fit into retirement income planning, why today's interest-rate environment has changed the conversation, and the importance of evaluating options based o...

How do you know when you're truly ready to retire, and not just hoping the numbers work out? In this episode, Matt Eilers explains why having a collection of accounts and investments is not the same as having a retirement plan. He discusses creating retirement income, evaluating Social Security timing, accounting for inflation, and stress-testing different retirement scenarios. Matt also explores...

What if the key to retirement isn't chasing happiness, but creating financial contentment? Inspired by a conversation from Jay Leno, Matt Eilers explores why covering essential expenses should be the foundation of every retirement income plan. He discusses the importance of coordinating income sources, the limitations of relying solely on the traditional 4% withdrawal rule, and how retirees can pr...

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...

The biggest threat to a retirement plan may be the costs you never expected to face. In this episode, Matt Eilers discusses how retirees can prepare for healthcare expenses, long-term care needs, and other financial surprises that can emerge later in life. He also explores the role of technology in modern financial planning and shares why legacy planning is about more than passing on assets. Inspi...

Is your retirement plan designed for YOUR life—or just following outdated rules?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...

What if the biggest threat to your retirement isn’t a market crash, but the risks you never planned for? In this episode, Matt Eilers discusses why retirement planning should go far beyond investments and account balances. Using NFL quarterback Josh Allen's approach to preparing for the unexpected, Matt explains the importance of stress-testing your retirement plan against market downturns,...

A surprise buyout, a health change, or even living longer than expected can reshape retirement faster than you think. In this episode, Matt Eilers discusses how major life events can impact your retirement strategy and why every financial decision should fit into a broader retirement plan. From evaluating buyout offers and unexpected lump sums to preparing for the different stages of retirement, M...

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 visi...

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...

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 rema...

The biggest wealth transfer in history is already underway—but is the next generation ready for it? In this episode, Matt Eilers explores how families can prepare for passing down assets and the important conversations that often get delayed. He discusses the difference between “live-on” money and “leave-on” money, why inheritance can sometimes create unexpected chall...

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...

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. Th...

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...