The Pilot’s Advisor Podcast

Ryan Fleming
  • 4.3 (11)
  • INVESTING
  • UPDATED BIWEEKLY

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.

  1. 3D AGO

    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

    21 min

  2. APR 9

    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

    13 min

  3. APR 2

    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

    18 min

  4. MAR 26

    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

    11 min

  5. MAR 19

    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

    20 min

  6. MAR 12

    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

    18 min

  7. MAR 3

    Markets & War: What Investors Should Know

    ✈️ 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 from one crisis to the next, the core principles of investing remain the same: discipline, patience, and long-term thinking. Here’s what we cover in this episode: 🌍 Markets dislike uncertainty, but historically recover 📉 Corrections are normal (even 10–20% swings) 🧠 Emotional investing leads to costly mistakes 💵 Down markets can create opportunity ✈️ Perspective from a military and global standpoint   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

    8 min

  8. FEB 26

    The Pros & Cons of the New Trump Savings Accounts

    ✈️ 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, investment control, and long-term trade-offs all matter. Here’s what we cover in this episode: 📋 How Trump Accounts Work – Custodial structure, contribution limits, automatic investing 🎯 Problem It’s Trying to Solve – Early investing, retirement readiness, financial literacy 💸 Taxes & Criticisms – Ordinary income treatment and administrative complexity ⚖️ Better Alternatives? – Comparing custodial Roth IRAs and other strategies 📚 Financial Education Impact – Why early exposure to investing changes behavior   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

    18 min
See All (211)

Ratings & Reviews

4.3
out of 5
11 Ratings

About

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.

Information

  • Creator
    Ryan Fleming
  • Years Active
    2019 - 2026
  • Episodes
    211
  • Rating
    Clean
  • Copyright
    © Copyright Ryan Fleming 2022
  • Show Website
    The Pilot’s Advisor Podcast

You Might Also Like