Beyond the Scorecard: Building a Retirement Plan That Fits You

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 marke…

Personal Pension: How to Build Income That Lasts

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 e…

Best Of: The “One More Year” Trap: Are You Missing Out on Life?

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 cle…

Best Of: Lasagna for Breakfast? What Retirement Really Looks Like

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 incom…

From Blind Spots to Bright Futures

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 e…

Best Of: Why Your Financial Plan Needs a Map—Not Just a Return

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 ma…

Beyond Wealth: The Estate Planning Mistakes You Can’t Afford

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 wish…

Why Creative Planning Beats Cookie-Cutter Advice

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…

Is Your Retirement Plan Just a Pile of Stuff?

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 t…

Best Of: From Golf Pro to Retirement Caddie: Matt Eilers’ Playbook

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” t…