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
✈️ 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 shift ...
✈️ 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, flexibility,...
✈️ 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 to smarter long-te...
✈️ 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 of b...
✈️ 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, potential pitfal...
✈️ 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 strategy, not ju...
✈️ 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 readiness.
Here’s what we ...
✈️ 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 junk drawer.” If you...
✈️ 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 news with t...
✈️ 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 valuable than r...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
United pilots are being asked to make a major retirement election by the end of the year and the plan hasn’t even received IRS approval. The election window for 2027 Pilot Contributions is open until December 31 for the proposed United Airlines Pilot Cash Balance Plan (the ‘CBP’). To help you better understand your o...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
In this episode, Ryan continues last week’s discussion on elevating the retirement planning conversation for pilots. Find out how asking smarter, planning-focused questions about taxes, Social Security, debt, risk, and investing can empower you to make more confident retirement decisions. Move past surface-level conc...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
Most people think the key to better retirement planning is getting better answers, but Ryan argues it really starts with asking better questions. In this episode, he talks about how reframing the basics leads to clearer thinking, better decisions, and a plan that fits your life. Discover the crucial shifts in mindset...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/ 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? In this episode, Ryan answers a listener’s question about navigating financial and emotional security in later-life marriages. Fin...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
This week, Thanksgiving takes center stage and your finances get a seat at the table! Ryan serves up a fun, insightful discussion where holiday favorites like parades, turkey carving, and football run parallel with the keys to successful retirement planning. Discover why consistency in investing is like the annual pa...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
If you’re an American Airlines pilot, you’re facing a major decision: whether to participate in the newly announced Market-Based Cash Balance Plan. Ryan is joined once again by Zach Smith from Pilot Tax to break down how the plan actually works, what AA pilots need to know, and the long-term tax consequences many pil...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
This Veterans Day episode of The Pilot’s Advisor features Zach Smith from Pilot Tax for a deep dive into one of the biggest challenges facing airline professionals: retirement tax planning. Ryan and Zach explain why airline contracts that fund 18–19% of pay into 401(k)s create future RMD headaches, how Roth strategie...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
As mortgage rates fluctuate and the real estate market adjusts, pilots and investors alike are wondering, what’s next? In this episode, Ryan sits down with Christopher Zarnik, a fellow FedEx pilot and mortgage broker, to unpack today’s housing and lending landscape. Christopher also shares practical advice on navigat...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
You’ve probably said it before: “I ran the numbers; I should be fine.” But what if your math is lying to you? Today, Ryan exposes the “fuzzy math” that can quietly sabotage your financial future. Drawing on lessons from aviation and decades of experience helping pilots plan for retirement, he shows how to balance big...
✈️ Retire Pilots the Right Way!
🎁 Grab your FREE Retirement Toolkit now → https://d74164fb.pages.infusionsoft.net/
If your parents passed away relatively young, it’s natural to wonder whether you’ll face the same fate, and whether that should change how you claim Social Security. In this episode, Ryan discusses how life expectancy, health, pensions, and even your trust in the system can shape the right decision. He breaks down th...
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