The Pilot’s Advisor Podcast

What if the biggest step forward is letting go of what you can’t control? In this episode, Ryan reflects on personal growth, staying grounded amid uncertainty, and adapting to a changing world. The common thread is learning where to focus your energy and where to stop letting fear, noise, or other people’s opinions hold you back.

Here’s what we cover in this episode:

🧠 Personal Growth: Push past insecurity and s...

Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. Ryan goes over a few today that he thinks are worth asking. None of these questions are really about money. That's kind of the point. Sometimes the best way into a financial conversation is to start somewhere else entirely.

Here’s what we cover in this episode:

🎯 Purpose: Building meaningful routines after ...

Inflation doesn't arrive as a bill in the mail, but over time it can quietly take a serious bite out of your purchasing power.

Ryan uses a humorous quote about the rising cost of a haircut to explain a much bigger retirement-planning problem: your money has to keep pace with what life will cost in the future.

For pilots planning decades into the future, the challenge is finding the right balance between protecting what you've accum...

Retirement planning today doesn't look like it did even a decade ago, let alone the way it looked for our parents. On this episode, Ryan provides several realities you need to be aware of in 2026 to build toward a successful retirement. Retirement isn't the same finish line it used to be, and pretending otherwise makes it harder to plan for. The realities change. A good plan should be able to change with them.

Here’s what we...

✈️ Retire Pilots the Right Way!

🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/

Ever had a job that humbled you, but quietly set the stage for everything that came next? Ryan puts Walter on the spot with a hilarious story about his stepmom’s crush on him, which leads into real talk about rejection, first jobs, and knowing what you don’t want to do. They unpack how detours, mentors, an...

✈️ Retire Pilots the Right Way!

🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/

More people in their 60s and 70s are staying on the job than ever before, and it's not always about the money. Ryan digs into the real reasons retirees keep showing up to work. Working longer isn't automatically the wrong call. Sometimes it's exactly right. The real question is whether it's a choice or a fallback. Tha...

✈️ Retire Pilots the Right Way!

🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/

What started as a nostalgic conversation about first cell phones quickly turned into something much bigger. Ryan looks back at early mobile phones, instant messaging, and how technology gradually made all of us more available all the time. Technology may have changed how we communicate, but the value of honest guidanc...

There's an entire television network dedicated to doing things yourself — home renovation, landscaping, interior design, all of it. And the DIY mentality is genuinely admirable. But when it comes to retirement planning, the stakes of a bad install are a little higher than a crooked backsplash.

Today, Ryan talks about what DIY planning actually looks like in practice. DIY has its place. But some projects are worth calling a pr...

FedEx pilots are about to receive a significant lump sum, and what happens next could have a lasting impact on their financial future. In this episode, Ryan is joined by David Befort to discuss a strategy pilots may want to understand before that money gets spent, transferred, or committed elsewhere. A lump sum can disappear quickly, but the right strategy may allow it to keep working for years to come.

Here’s what we cover ...

Ever felt like your advisor is speaking a different language? Ryan unpacks what to do when financial jargon gets in the way of understanding your money. He talks about why clear communication matters more than technical terminology and when it might be time to ask for clarification. or a second opinion. Tune in to find out if your advisor’s lingo is a red flag or just a translation issue.

Here’s what we cover in this ep...

Ever wonder if your “safe” cash is actually holding you back? In this episode, Ryan answers a listener’s question from a pilot who has built up $150,000 in cash but is hesitant to move it because of the security it provides. He explains the difference between liquidity and leaving too much money idle. Stick around to find out if your cash strategy is helping, or quietly hurting, your future.

Here’s what we c...

✈️ Retire Pilots the Right Way!

🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/

Dave Ramsey has built one of the most recognized brands in personal finance. Millions of people have followed his advice out of debt and into savings. But when it comes to how much you should pull from your retirement accounts each year, Ramsey takes a position that some financial professionals find hard to get behind...

✈️ Retire Pilots the Right Way!

🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/

Trump Accounts are here, but are they really the best way to jump-start your child’s financial future? Ryan explains what these new 530A Trump Accounts are and how they stack up against other options. While the concept of teaching kids to invest early is powerful, Ryan questions whether these accounts are truly ...

This year's Fourth of July carries a little extra weight as we celebrate 250 years of American independence, and that's worth a moment. But between the hot dogs, the parades, and the fireworks, we started thinking about how many of our favorite holiday traditions have a pretty natural financial parallel. So that's what Ryan’s doing today… and the comparisons might surprise you.

Here’s what we cover in this episod...

If you're a pilot, there's a good chance your retirement savings are sitting in a target date fund you selected years ago and haven't thought about since. The problem is that the fund doesn't know anything about your pension, your spouse's income, your retirement timeline, or the unique challenges pilots face. In this episode, Ryan explores a little-known feature inside many 401(k) plans and shares research that may change the way ...

Many pilots assume that as retirement gets closer, they should automatically become more conservative with their investments. But according to Ryan, that's not always the right move. He explains why risk management has less to do with your age and more to do with your time horizon, income sources, and retirement goals. If you're trying to strike the right balance between growth, protection, and income planning, Ryan shares a valuab...

Risk is unavoidable. The real question is whether the risk you're taking makes sense for where you are in life.

In this episode, Ryan explores three common financial personalities among people in their 30s and 40s, and the steady contributor quietly building wealth over time. If you're trying to figure out whether you're taking too much risk—or not enough—Ryan offers a practical framework for evaluating where you stand ...

It's summer and nothing says summer quite like Tom Cruise as Maverick soaring across the sky in Top Gun. This year marks the 40th anniversary of the original film, and with Tom Cruise's birthday on July 3rd, Ryan figured it was the perfect excuse to revisit some of the most iconic quotes from the franchise and see what they have to say about your financial life. Because Maverick didn't become the best by flying blind and hoping for...

In this episode, Ryan is joined once again by CPA Zach Smith to unpack the FedEx TA 26 retirement choices, this time from a tax and long‑term planning angle. Instead of just chasing the biggest paycheck, they explore how pensions, 401(k)s, and new cash-balance options can create either freedom or a “ticking tax time bomb” in retirement. If you’re a FedEx pilot facing this decision, this conversation will challenge...