The Pilot’s Advisor Podcast
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. We’ll teach both pilots and non-pilots what it takes to have a successful financial future. The Pilot’s Advisor Podcast® will answer your questions about 401(k)s, IRAs, taxes in retirement, long term care needs and much more.
Episodes
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...
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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 con...
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:
📊 Portfolio Exposure: Many...
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...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
We got a great question from a listener: “What’s better? Term life insurance, universal life, or whole life?” Straightforward question. Not a straightforward answer, especially if you’re in your 50s. In this episode, Ryan walks through how life insurance decisions evolve over time and why what ...
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 lon...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Nobody likes tax season, but for new retirees, the rules can feel completely different. Income changes, required withdrawals begin, and decisions that once lowered taxes can create bigger bills later. Ryan unpacks some of the most common retirement tax mistakes and how they show up in real life. A little forward...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
The Oscars celebrate the best performances in film, but what if we handed out awards for financial planning instead? Ryan takes inspiration from Hollywood’s biggest night and hands out a few “Academy Awards” of our own to the strategies and habits that make a retirement plan truly successful. Y...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Global tensions have escalated following the conflict in Iran, and investors are feeling the ripple effects. In this timely conversation, Ryan shares perspective on how markets typically respond to war, why uncertainty creates volatility, and why emotional decision-making can be costly. While headlines quickly s...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
A new government-backed savings account for kids is on the way, and it’s already raising eyebrows. On the surface, Trump Accounts look like a win: free money for newborns, long-term investing, and a built-in head start toward adulthood. But as Ryan explains, the real story lives in the fine print. Taxes, f...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
There’s something magical about a snow day. They slow everything down, and that’s exactly why they make such a powerful metaphor for money. Unexpected pauses, changing conditions, and the temptation to react emotionally all show up in both weather and finances. Ryan connects familiar winter moments t...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Big paydays can feel like smooth air, until the next decision changes the flight path. In this episode, Ryan and Dave Befort talk through the money moments FedEx pilots face when contracts, pensions, and career milestones converge. Rather than focusing on tactics, the conversation zooms out to the bigger picture...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
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. While backdoor Roth IRAs can be a powerful tool for high-income earners to achieve tax-free retirement growth, it’s essential to understand the rules, poten...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Turning 62 doesn’t feel like a big deal until Social Security enters the conversation. Filing now could put money in your pocket sooner, or it could quietly cost you tens of thousands over a lifetime. Ryan breaks down how to think through the decision to make sure your choice supports your retirement strat...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Nothing wrecks financial confidence faster than comparing your savings to coworkers, siblings, or someone bragging online. Ryan unpacks why comparison is not a retirement plan, and how it can distort what “behind” really means. You’ll also hear about what actually determines your retirement rea...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Having two financial advisors might seem like you’re getting twice the wisdom, but it often creates confusion instead of clarity. In this episode, Ryan explains why splitting assets between multiple advisors leads to conflicting strategies, inefficient portfolios, and what he calls the “financial jun...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Southwest pilots were hit with a major retirement change and fast. 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. Today we’re reacting to this big retirement ...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
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. In this year-end conversation, Ryan reflects on what truly impacted investors, what tested discipline, and why staying unemotional proved more val...
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