Oct 31, 2025

Changing jobs is more common than ever, but what happens to your old 401(k) when you move on? In this episode, Jake and Nick break down your four main options and the pros and cons of each. They’ll explain when to leave it, when to roll it, and when to rethink your entire retirement strategy. Don’t just “set it...

Oct 24, 2025

What could Fleetwood Mac possibly teach you about retirement planning? Turns out, plenty. Today, Jake and Nick take five classic Stevie Nicks songs and translate them into powerful financial lessons about independence, communication, and learning how to plan unexpected “landslides.” You’ll learn why flexibility...

Oct 17, 2025

Health Savings Accounts (HSAs) might be one of the most underrated tools in all of financial planning and today we’re going to tell you why. Nick and Jake will explain the three major benefits of an HSA and how to use it strategically before and during retirement. You’ll learn how to make the most of this “triple...

Oct 10, 2025

Retirement brings freedom, but navigating health insurance can quickly become one of the most confusing parts of the transition. In this episode, Nick and Jake walk through the key types of insurance every retiree should evaluate, from health and long-term care to life, homeowners, and umbrella coverage. Find out how...

Oct 3, 2025

Want to pay less tax now, or never pay tax again? That’s the real question behind the Traditional vs. Roth debate. When it comes to saving for retirement, few questions get asked more often than: Should I use a traditional account or a Roth? The truth is, there isn’t a one-size-fits-all answer.

In this episode, Jake...