Demystifying Backdoor Roth IRAs with Zach Smith
Ryan is joined by Zach Smith of Pilot Tax to discuss why many high-income pilots run into Roth limitations and what that means for long-term planning.
I’m 62: Should I File For Social Security Or Wait?
Filing now could put money in your pocket sooner, or it could quietly cost you tens of thousands over a lifetime.
Am I Behind in My Retirement Savings? Here’s What You Can Do
Ryan unpacks why comparison is not a retirement plan, and how it can distort what “behind” really means.
Should You Have More Than One Financial Advisor?
Having two financial advisors might seem like you’re getting twice the wisdom, but it often creates confusion instead of clarity.
Southwest’s New NEC Roth Option: What Pilots Must Know
With little advance notice, Southwest rolled out a new NEC Roth option that allows company contributions to flow into a Roth 401(k), creating a powerful opportunity for long-term tax-free growth. Here's what you need to know.
2025 Year In Review: What Actually Mattered for Your Money
2025 was loud… tariffs, market swings, tax headlines, and nonstop uncertainty. But not everything that made the news actually mattered for your long-term plan.
Cash Balance Plan or HRA? A Tough Call for United Pilots
The election window for 2027 Pilot Contributions is open until December 31 for the proposed United Airlines Pilot Cash Balance Plan (the ‘CBP’).
The 5 Retirement Questions Smart People Ask
In this episode, Ryan continues last week’s discussion on elevating the retirement planning conversation for pilots
Why Better Questions Build Better Retirements
Most people think the key to better retirement planning is getting better answers, but Ryan argues it really starts with ask-ing better questions.
Planning for Retirement When You Marry Later in Life
Getting married in your 50s often means you’re combining lives, but not necessarily combining finances. How do you build a retirement plan together when you’ve both already built your own?
