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The Pilot’s Advisor Podcast

The Pilot’s Advisor Podcast

By: Ryan Fleming
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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.Copyright Ryan Fleming 2022 Economics Personal Finance Politics & Government
Episodes
  • What Pilots Are Googling About AI & Retirement
    Apr 16 2026

    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

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    21 mins
  • Will AI Replace Pilots in the Next 5 Years?
    Apr 9 2026

    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

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    13 mins
  • Life Insurance For Pilots: Term, Whole, or Universal Life?
    Apr 2 2026

    ✈️ 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

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    18 mins
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