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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
  • 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
  • War with Iran, Energy Prices, and Your Money: What You Need to Know
    Mar 26 2026

    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

    Show More Show Less
    11 mins
  • Tax Mistakes New Retirees Make
    Mar 19 2026

    ✈️ 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

    Show More Show Less
    20 mins
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