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. 6D AGO

    FedEx Pension, Windfalls, and the Pilot’s Legacy Playbook

    ✈️ 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 balance, protection, and long-term direction. Here’s what we cover in this episode: 📦 FedEx employees have unique pension options that require personalized planning. 💰 Choosing between lump sum or annuity isn’t one-size-fits-all — and mistakes can be costly. 🧩 Many FedEx professionals are underutilizing their 401(k) and employer match benefits. ✈️ Pilots have different timelines and flight-hour restrictions that impact retirement strategy. 🚨 Beware of advisors who don’t specialize in aviation or FedEx-specific retirement plans.   Learn more about Dave: http://ibc4pilots.com The Wealth Warehouse Podcast: https://www.thewealthwarehousepodcast.com Watch The Infinite Banking Concept Explained: https://www.youtube.com/watch?v=4fSMlg4i7pk   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

    45 min

  2. FEB 5

    Demystifying Backdoor Roth IRAs with Zach Smith

    ✈️ 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 pitfalls, and seek professional advice to ensure the strategy aligns with your specific financial situation. Here’s what we cover in this episode: 🛫 Backdoor Roth Basics: The workaround when income caps apply 🚧 Roth Eligibility Limits: Why pilots often exceed IRS thresholds 🧮 Joint Income Rules: How household earnings affect access 🔄 Conversion Process: Moving money without turbulence ⚠️ Pro Rata Rule: The hidden tax trap many pilots miss   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

    16 min

  3. JAN 29

    I’m 62: Should I File For Social Security Or Wait?

    ✈️ 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 just the birthday on the calendar. Here’s what we cover in this episode: 🧭 Claiming Decisions: How to think through when to start Social Security ⚖️ Personal Factors: Income needs, work plans, and lifestyle considerations ⏳ Waiting Strategies: Pros and cons of filing at full retirement age 📊 Real Examples: Hypotheticals that show how strategies play out 🚀 Planning Ahead: Why earlier conversations lead to better outcomes   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

  4. JAN 22

    Am I Behind in My Retirement Savings? Here's What You Can Do

    ✈️ 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 cover in this episode: 🚨 Comparison Trap – Why measuring yourself against others backfires 🧭 What “Enough” Means – Retirement readiness is lifestyle-driven 📊 The Real Math – Income needs matter more than account size 🧠 Emotional Confidence – Why even good savers feel behind 🎯 Action Steps – What to do if you truly are behind   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

    12 min

  5. JAN 15

    Should You Have More Than One Financial Advisor?

    ✈️ 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 want confidence instead of crossed signals, this episode helps clarify who should really be in control. Here’s what we cover in this episode: ⚖️ Pros & Cons: Why multiple advisors often backfire 🗄️ Financial Junk Drawer: Accounts scattered everywhere 🧩 Consolidation: Getting assets aligned and working together 🧭 Advisor Roles: One pilot vs. too many hands on the controls   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

    15 min

  6. JAN 5

    Southwest’s New NEC Roth Option: What Pilots Must Know

    ✈️ 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 the help of pilot tax specialist Zach Smith and breaking down exactly what this change means. This video explains why this option is so unique: for the first time, pilots can potentially have most of their 401(k) contributions—both employee and employer—go into Roth accounts. That’s a massive shift for pilots facing growing tax problems in retirement due to large tax-deferred balances. Ryan and Zach walk through how Secure Act 2.0 made this possible, where to find the election on the Schwab site, and why pilots should double-check their investment elections if they’ve never used Roth before. We answer all the FAQs on this here: https://retirepilots.com/2026/01/southwests-new-nec-roth-option-what-pilots-must-know/   Here’s what we cover in this episode: ✈️ What the New NEC Roth Option Is 💸 Why This Is a Big Deal for Pilots ⚠️ The Biggest Gotcha: No Tax Withholding 🖥️ How to Actually Elect the Option 🧠 Roth vs. Deferred: Distribution-Phase Reality   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

    12 min

  7. 12/31/2025

    2025 Year In Review: What Actually Mattered for Your Money

    ✈️ 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 reacting to headlines. Listen in to separate the noise from the lessons and head into 2026 with clarity and confidence. Here’s what we cover in this episode: 🌍 Tariffs & Markets: Uncertainty and volatility in the market 🧾 Big Beautiful Bill: Real financial implications 📉 Market Lessons: Having discipline during turbulence 🔮 Looking Ahead: Positioning for 2026 🎄 Year-End Note: Perspective and gratitude   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

    19 min

  8. 12/19/2025

    Cash Balance Plan or HRA? A Tough Call for United Pilots

    ✈️ 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 options and what it could mean for your retirement, we’ve invited pilot tax specialist Zach Smith to unpack what’s happening, why it’s happening, and what pilots should understand before making a decision that could impact their long-term financial flexibility. As airline compensation has increased and employer contributions have grown, more pilots are running into IRS limits on 401(k) contributions. To address the “spillover,” airlines like Delta and American introduced cash balance plans and alternative retirement vehicles. United is now following suit, but without full clarity, final plan details, or an opt-out option. Ryan and Zach walk through the two primary options United pilots are facing: the CBP or HRA, along with the trade-offs of each. Here’s what we cover in this episode: ✈️ Why Pilots Are Hitting 401(k) Contribution Limits 📉 Cash Balance Plans Explained 🏥 HRAs and Medical-Only Dollars ⚠️ The Risk of Forced Decisions Without Full Details 🧠 A Practical Approach in an Uncertain Situation   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

    14 min
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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
    202
  • Rating
    Clean
  • Copyright
    © Copyright Ryan Fleming 2022
  • Show Website
    The Pilot’s Advisor Podcast

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