Financial and retirement planning guidance from pilot and financial advisor Ryan Fleming. The show will help you figure out how to take your financial plan from takeoff to landing with smooth sailing along the journey.
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 valuable framework for thinking about risk. Here's what we cover in this episode: ✈️ Risk Management: Matching risk to your situation
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 and where you want to go. Here's what we cover in this episode:
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 the best. He had a plan, a co-pilot, and enough self-awareness to know when the risk was worth it. Here's what we cover in this episode:
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 how you think about taxes, flexibility, and your family's legacy. Here's what we cover in this episode:
USE THIS: FedEx TA26 Retirement Option Tool. Check out our educational modeler - https://retirepilots.com/fedex-ta26-tool/ FedEx pilots are facing a major decision with three very different retirement options, each with long-term implications for income, flexibility, and legacy in the 2026 tentative agreement. While the details are still evolving, the choice between a pension-style income, a hybrid approach, or a more flexible contribution-based plan could shape your financial future for decades. In this episode, Ryan breaks down each option in simple terms, highlighting the pros, cons, and key factors to consider. Here's what we cover in this episode: ✈️ Three options offer very different retirement outcomes
AI isn't just a buzzword, it's quickly becoming one of the biggest unknowns in retirement planning. Pilots in their 50s and 60s are actively searching for answers about how this technology could impact their future. Ryan tackles the most common AI-related questions pilots are Googling right now, and where human judgment still plays a critical role. Here's what we cover in this episode:
AI is changing everything right now, and aviation isn't going to be immune to that. The question is… what does it actually mean for you as a pilot? Ryan breaks down what AI is really going to do to the cockpit, what parts of the job might change, and why he doesn't see pilots going anywhere anytime soon. But there are some shifts coming, and they're worth paying attention to. We also zoom out and talk about how AI is impacting the broader economy, what that could mean for your portfolio. Here's what we cover in this episode:
✈️ Retire Pilots the Right Way!
When global conflict makes headlines, it's natural to wonder what it means for your money. In this episode, Ryan breaks down how markets are reacting to the ongoing conflict in Iran and what investors should be paying attention to right now. While volatility and rising energy costs can create concern, the bigger picture often tells a very different story. Ryan reminds us that short-term headlines don't always change long-term outcomes. Here's what we cover in this episode:
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
✈️ Retire Pilots the Right Way!
The 4% rule gets talked about like gospel in retirement planning. But let's be honest, it's always been more of a rough guess than a golden rule. Now, its original creator is revising it to 4.7%. So, does that mean your retirement paycheck just got a raise, or is this just another headline that oversimplifies a complex decision? In this episode, Ryan explores the implications of the updated withdrawal rate, highlighting the crucial caveats that may make or break your retirement strategy. Here's what we cover in this episode:
In this episode, Ryan delivers a “pilot report,” offering a timely look at today's economic turbulence. From global conflict and rising interest rates to inflation pressure and a shifting housing market, Ryan explains how these forces are shaping your financial flight path, and what adjustments you might need to stay on course. Ryan also shares practical, down-to-earth financial advice, especially geared toward young adults, recent grads, or anyone feeling a bit behind. Here's what we cover in this episode:
Today we're talking about Type A personalities. If you're driven, competitive, and goal-oriented then you're part of the club that often struggles during difficult markets. When things get tough, your instinct is to work harder, push more, and fix the problem. But in investing, that instinct can sometimes backfire. In this episode, Ryan explains why Type A pilots, used to control, precision, and quick decisions, can be their own worst enemies when markets get volatile. Here's what we cover in this episode:
Today, Ryan's taking us through some of the key concepts of The Psychology of Money by Morgan Housel. This book isn't just about money strategies. It's about why we make the choices we make, even when they don't seem to make sense. You might find that your mindset is a bigger advantage than any investment tip. Here's what we cover in this episode:
If you've recently changed jobs, chances are your old 401(k) is still sitting right where you left it – out of sight and out of mind – and it could potentially cost you. In this episode, Ryan answers a question from a pilot who recently made the jump to a major airline and wants to know if he should roll over his old 401(k) or leave it where it is. Ryan breaks down the pros and cons of keeping the 401(k) with a former employer versus moving it into an IRA, and what smart investors should consider before making the call. Here's what we cover in this episode:
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