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The Pilot’s Advisor Podcast

The Pilot’s Advisor Podcast

Written 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
  • Am I Behind in My Retirement Savings? Here's What You Can Do
    Jan 22 2026

    ✈️ 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

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    12 mins
  • Should You Have More Than One Financial Advisor?
    Jan 15 2026

    ✈️ 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

    Show More Show Less
    15 mins
  • Southwest’s New NEC Roth Option: What Pilots Must Know
    Jan 5 2026

    ✈️ 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

    Show More Show Less
    12 mins
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