The Pilot’s Advisor Podcast

Hosted by Ryan Fleming

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215

Latest episode

Jun 2026

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About the show

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.

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60 recent

June 11, 2026Episode 2117 min

What Does Smart Risk Actually Look Like in Your 30s & 40s?

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: 🚀 Aggressive Investing: Why speculation isn't a strategy 💵 Playing It Too Safe: The hidden risk of cash 📈 Power of Compounding: Time is your greatest asset ⚖️ Finding Balance: Taking risk with a purpose ✈️ Pilot Perspective: Why discipline beats prediction Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/ Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

June 4, 2026Episode 21019 min

Maverick, Goose, and the Financial Danger Zone

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: 🚀 Need for Speed: Avoiding get-rich-quick investing 😎 Ego & Mistakes: Keeping emotions in check ⚠️ Danger Zone: Understanding risk and volatility 📜 Future Planning: Preparing for life's uncertainties 🤝 Find a Co-Pilot: Why guidance matters in retirement Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/ Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

May 1, 2026Episode 20932 min

FedEx Pilots’ Guide to TA 2026: The Smart Tax Moves

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: 💰 Three Choices: Each leads to very different outcomes 🧨 Tax Pressure: Income stacking creates future problems 🛡️ Guaranteed Income: Stability comes with tradeoffs 🧾 Limited Control: Some plans restrict your flexibility 🚀 More Flexibility: After-tax dollars give you options 💡 Smarter Mix: Roth + brokerage create long-term advantages FedEx TA26 Retirement Option Tool: https://retirepilots.com/fedex-ta26-tool/ FedEx TA 2026: 3 Retirement Options That Could Change Everything https://pilotsadvisor.podbean.com/e/fedex-ta-2026-3-retirement-options-that-could-change-everything/ Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/ Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

April 20, 2026Episode 20831 min

FedEx TA 2026: 3 Retirement Options That Could Change Everything

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 💰 Taxes play a major role in long-term results 📊 Control vs. guarantees is a key tradeoff ⏳ Longevity impacts which option makes sense 🧠 Personal goals matter as much as the math Get the Summary of Proposed FedEx Retirement Changes: https://retirepilots.com/wp-content/uploads/2026/04/FedEx_TA_2026_Retirement_Plan_Options-PDF-Recap-for-Show-Notes.pdf Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/ Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

April 16, 2026Episode 20720 min

What Pilots Are Googling About AI & Retirement

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 investors don’t realize how much AI exposure they already have ⚖️ Risk vs Opportunity: AI could drive growth, but also increased volatility ⏳ Early Retirement Thinking: Fear shouldn’t be the reason you retire early 🧠 AI Planning Tools: Helpful for information, but not a replacement for strategy 🚧 Human Element: Emotion, context, and experience still matter in decision-making See the Morgan Stanley prediction: https://finance.yahoo.com/news/morgan-stanley-predicts-ai-won-073000488.html?guccounter=1 Invesco’s Winter 2026 DC Participant Pulse Survey: https://401kspecialistmag.com/dc-participants-open-to-private-markets-and-ai-with-guardrails-invesco-survey/ Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/ Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

April 9, 2026Episode 20612 min

Will AI Replace Pilots in the Next 5 Years?

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: 🛫 AI in aviation: Enhancing systems, not replacing pilots anytime soon 👨‍✈️ Pilot demand: Shortage continues to drive pay and workload changes 🤖 AI in society: Creating winners and losers across industries 📈 Investing impact: Diversification matters more in uncertain environments 🧠 Human element: Judgment and experience still critical in flying and planning Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/ Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

April 2, 2026Episode 20517 min

Life Insurance For Pilots: Term, Whole, or Universal Life?

✈️ 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 worked earlier in your career may not hold up as retirement approaches. Tune in to hear the key differences between term, whole, and universal life, and how it may impact your retirement. Here’s what we cover in this episode: 🛡️ Protection focus: Protect family, retirement, and reduce sequence risk 🕒 Term vs. permanent: Term is cheap; permanent stays and builds value 💰 Why whole (not universal): Guarantees, tax advantages, safer structure ✈️ Retirement jet engine: Backup income source in down markets 📚 Pilot resources: Tools, books, and education for deeper planning Resources for this episode: IBC4Pilots.com Becoming Your Own Banker: Unlock the Infinite Banking Concept by Nelson Nash: https://amzn.to/3NLTdfj How we help eliminate Sequence of Returns Risk: https://www.youtube.com/watch?v=vSsR7Km5XRw Permission to Spend: Maximize Your Retirement with the Best-Kept Secret in Personal Finance: https://amzn.to/4uIfXgG Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/ Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

March 26, 2026Episode 20410 min

War with Iran, Energy Prices, and Your Money: What You Need to Know

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: 🌍 Market Reaction: How the Iran conflict is impacting markets and energy prices 😬 Investor Emotions: Why fear and uncertainty lead to poor decisions 📈 Long-Term View: Markets historically recover—and often create opportunity 📉 Slow Decline: Why this “death by a thousand cuts” feels worse than it is 📊 War & Markets: What history shows about investing during conflict Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/ Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

March 19, 2026Episode 20319 min

Tax Mistakes New Retirees Make

✈️ 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 planning can make a dramatic difference over the long run. Here’s what we cover in this episode: 💸 Retirement Taxes: Many retirees underestimate taxes in the distribution phase 🧾 Tax-Deferred Reality: 401(k) withdrawals count as taxable income 📉 Withdrawal Taxes: Large income needs can create major tax bills 🧠 Tax Planning Myth: Smart strategies aren’t just for the wealthy 🟣 Roth 401(k) Confusion: Many investors misunderstand contribution rules Read The 5 Biggest Tax Mistakes New Retirees Make in the First 5 Years - https://www.kiplinger.com/taxes/tax-planning/biggest-tax-mistakes-new-retirees-make-in-first-years Retire Pilots - https://retirepilots.com Get your FREE Retirement Toolkit - https://d74164fb.pages.infusionsoft.net/ Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

March 12, 2026Episode 20218 min

And the Oscar Goes To... Your Retirement Strategy

✈️ 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. You’ll hear how the best retirements, just like the best movies, don’t happen by accident. Here’s what we cover in this episode: ⭐ Leading Role: Consistent saving drives retirement success 💰 Supporting Role: Tax planning strengthens retirement outcomes 📝 Screenplay Strategy: Income planning maps retirement story 🎵 The Score (Advisor Guidance): Financial advisors guide planning journey 🏆 Best Picture: Written financial plan ties everything together Retire Pilots - https://retirepilots.com Pilot Tax - https://pilot-tax.com/ The Pilot's Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2