Summertime is for flip-flops and financial tune-ups. In this episode, Greg and Tom walk you through a four-part mid-year checklist: taxes, insurance, estate planning, and retirement savings. You'll hear practical tips on everything from saving money on your car insurance to gifting appreciated assets to your kids, plus what to ask your tax advisor now (not next April).

Retirement isn't just about saving money—it's about preparing for all of life's turns. This week, we wrap up our "entitlements" series with a deep dive into long-term care. It’s not an entitlement, and it’s not cheap—but it’s often necessary. In this episode, you’ll learn when to consider coverage, what it costs, who really needs it, and how to plan ahead with both traditional policies and alternative investment options.

In this episode of Retirement Roadtrip, we tackle the ripple effects of tariffs, the rising cost of goods, and the often-overlooked realities of Medicare. Greg and Tom break down why retirement planning isn’t just about your portfolio, it’s also about healthcare, hidden costs, and knowing what decisions will follow you for decades.

From navigating the Medicare alphabet soup to understanding IRMAA and the difference between skilled care and long-term care, this episode clears up the confusion and helps you plan smarter, whether you're nearing retirement or helping someone who is.

In this episode of Retirement Roadtrip, we tackle market drops, emotional decisions, and how to make smart moves with Social Security and Medicare. After a rough market week fueled by tariff talk and economic fear, Greg and Tom get real about what investors should (and shouldn’t) do next. They also break down the often misunderstood rules around filing for Social Security, spousal benefits, Medicare enrollment, and how to protect your income in retirement.

Whether you're 23 and panicking, or 65 and confused about healthcare, this episode clears the fog and helps you move forward with confidence.

In this episode of Retirement Roadtrip, we tackle the topic of tariffs, economic fear, and how investors can remain confident through uncertain times. With recent headlines stirring anxiety about trade policy and consumer confidence, Greg and Tom break down what tariffs really mean, how history can help us put things into perspective, and what steps you can take to protect your financial future. Whether you're worried about market volatility or trying to make smart moves near retirement, this episode offers clarity and encouragement when the headlines feel overwhelming.

In this episode of Retirement Roadtrip, we explore the ins and outs of real estate investing, including five key ways investors can generate wealth. While many consider real estate an alternative investment, it offers unique advantages that can provide long-term financial security. Whether you're a seasoned investor or just getting started, this episode will help you understand the fundamental principles of real estate investing and how to maximize returns.

In this episode, we explore the biggest pitfalls retirees face and how to navigate them with confidence. Retirement isn’t just about having enough money—it’s about having a plan for how you’ll spend your time, maintain your purpose, and adapt as your needs change. We break down the three phases of retirement, common mistakes to avoid, and practical strategies to ensure a fulfilling and financially secure retirement. From testing your retirement lifestyle before making big commitments to finding meaningful ways to stay engaged, this episode will help you map out a smoother road ahead.

In this episode, we explore how to prepare for retirement beyond just finances. We discuss the emotional and practical aspects of retirement, sharing personal stories, key strategies, and tips on finding purpose in this new phase of life. From the importance of 'practicing' retirement to staying engaged through volunteering or part-time work, this episode provides valuable insights for retirees looking to navigate their journey with confidence.