The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots

Scott Osborn
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Welcome to The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots, where we navigate the skies of financial success with your host, Scott Osborn, The Pilot's Planner. Each episode, we soar through the challenges and opportunities unique to pilots, from debunking myths to mastering best practices in financial planning and investing. As demand for pilots reaches new heights, so too does the complexity of their financial landscapes. With Scott's expertise we tackle common pitfalls and strategic wins that can significantly boost a pilot's financial trajectory. Whether you're an aviation professional or just fascinated by the financial skies pilots navigate, this podcast promises insights that can help anyone plot a course toward financial independence. https://thepilotsplanner.com/

  1. 6D AGO

    Year-End Financial Reflection & Planning For 2026

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Financial Flight Control Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html As the year comes to a close, it’s the perfect time to pause, reflect, and reset. Scott looks back on the wins, challenges, and lessons from 2025, both financially and personally, while setting the stage for smarter planning in 2026. Are you ready for the new year? Tune in to make sure you’re ending 2025 with clarity and heading into the next one with purpose. Here’s some of what we discuss in this episode: 🎄 Holiday Life: Family, balance, and perspective 🔍 Year in Review: The top lessons from 2025 ⚖️ Financial Discipline: Managing lifestyle creep 🎯 Goal Setting: Tips for preparing for 2026  🧾 Consolidation: Reorganizing finances with intention Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Contact our team: https://retireairlines.com/contact-us/ Schedule an introductory call: http://callosborn.com/ Order your no-cost retirement toolkit: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Check out our other no-cost financial resources & guides here: https://retireairlines.com/guides-whitepapers/ The “When I Die” binder: https://retireairlines.com/wp-content/uploads/2024/10/Scott-O-FILLABLE-BINDER-10.22.24-1.pdf Watch the podcast on YouTube: https://www.youtube.com/@retireairlines

    15 min

  2. DEC 18

    United Airlines Cash Balance Plan: Allocating Your Contributions

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Financial Flight Control Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Scott breaks down United Airlines’ cash balance plan for pilots and explains how it addresses overfunded 401(k) accounts. He covers how the plan works, the benefits of tax-deferred growth, and how to decide between the Cash Balance Plan and United’s HRA/RHA options. By the end of this episode, you'll better understand the pros and cons to help make the best choice for your retirement. Here’s some of what we discuss in this episode: ✈️ CBP Overview: how United’s plan is structured 📈 Tax Deferral: the benefits of reducing taxable income today 🧾 Plan Details: spillover from overfunded 401(k)s 🧑‍✈️ Pilot Factors: income, career stage, and benefits ⚖️ Pros & Cons: flexibility, limits, and tradeoffs  Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Contact our team: https://retireairlines.com/contact-us/ Schedule an introductory call: http://callosborn.com/ Order your no-cost retirement toolkit: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Check out our other no-cost financial resources & guides here: https://retireairlines.com/guides-whitepapers/ The “When I Die” binder: https://retireairlines.com/wp-content/uploads/2024/10/Scott-O-FILLABLE-BINDER-10.22.24-1.pdf Watch the podcast on YouTube: https://www.youtube.com/@retireairlines

    12 min

  3. DEC 11

    2026 Key Planning Numbers Every Pilot Should Know

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Financial Flight Control Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html As the new year approaches, Scott breaks down the key planning numbers and contribution limits pilots need to understand before 2026 kicks off. This episode is all about checking your settings, updating your strategy, and making sure you’re taking advantage of every opportunity. As 2025 wraps up, now’s the perfect time to get ahead by making decisions for a tax-efficient future. Here’s some of what we discuss in this episode: 📊 2026 Planning Priorities: what pilots should reevaluate heading into the new year 💵 IRA & Roth Limits: using updated contribution rules to your advantage 💰 Roth Tax-Free Bucket: why shifting money strategically can reduce lifetime taxes ⚠️ Tax Rate Risk: how rising brackets could impact future retirement income 🧭 Action Steps Ahead: simple adjustments that strengthen next year’s plan Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Contact our team: https://retireairlines.com/contact-us/ Schedule an introductory call: http://callosborn.com/ Order your no-cost retirement toolkit: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Check out our other no-cost financial resources & guides here: https://retireairlines.com/guides-whitepapers/ The “When I Die” binder: https://retireairlines.com/wp-content/uploads/2024/10/Scott-O-FILLABLE-BINDER-10.22.24-1.pdf Watch the podcast on YouTube: https://www.youtube.com/@retireairlines

    13 min

  4. DEC 4

    MBCB Plan for American Airlines: Should You Opt In or Not?

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Financial Flight Control Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Scott breaks down the brand-new Market-Based Cash Balance Plan (MBCB) and what this decision means for American Airlines pilots hitting their 401(k) limits. The goal isn’t to push pilots one way or the other, but to help you understand what’s really at stake before that opt-in deadline hits on December 15th. If you’ve been staring at that email wondering what to do, this episode will give you clarity fast. Here’s some of what we discuss in this episode: 🛫 What the MBCB Plan Is: a pilot-specific overview in plain English 📄 How the Plan Works: where excess 401(k) dollars actually go ⏳ Opt-In / Opt-Out Deadline: why the window matters for 2026 benefits 🧾 Tax Bucket Impact: how this decision affects future retirement taxes 📊 Scenario Planning: evaluating who the plan helps and who it may not Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Contact our team: https://retireairlines.com/contact-us/ Schedule an introductory call: http://callosborn.com/ Order your no-cost retirement toolkit: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Check out our other no-cost financial resources & guides here: https://retireairlines.com/guides-whitepapers/ The “When I Die” binder: https://retireairlines.com/wp-content/uploads/2024/10/Scott-O-FILLABLE-BINDER-10.22.24-1.pdf Watch the podcast on YouTube: https://www.youtube.com/@retireairlines

    16 min

  5. NOV 20

    Thanksgiving, Gratitude & Growing Wealth: Essential Pilot Financial Strategies

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Financial Flight Control Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Gratitude has a way of grounding us, shaping our attitude, and influencing how we approach our financial lives. Discover how gratitude transforms not just our outlook, but our wealth. In this episode, Scott unpacks why a grateful mindset is key to building financial health, making confident decisions, and finding fulfillment in both work and life. Here’s some of what we discuss in this episode: 🛫 Gratitude & wealth: mindset that supports long-term financial growth 👨‍✈️ Career gratitude: how thankfulness impacts career decisions 💳 Lifestyle & debt: resisting lifestyle creep through gratitude 🎁 Charitable giving: giving smarter with tax-efficient strategies 📈 Investor mindset: gratitude vs. greed in portfolio decisions Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Contact our team: https://retireairlines.com/contact-us/ Schedule an introductory call: http://callosborn.com/ Order your no-cost retirement toolkit: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Check out our other no-cost financial resources & guides here: https://retireairlines.com/guides-whitepapers/ The “When I Die” binder: https://retireairlines.com/wp-content/uploads/2024/10/Scott-O-FILLABLE-BINDER-10.22.24-1.pdf Watch the podcast on YouTube: https://www.youtube.com/@retireairlines

    13 min

  6. NOV 13

    Automating Savings Outside of 401k For a Smarter Retirement

    Most pilots automate their 401(k) savings without thinking about it, but what about everything outside that one account? Scott breaks down how to automate savings into the other tax buckets that will actually give you flexibility, control, and lower taxes in retirement. Discover why diversifying how and where you save could be the smartest way to unlock more financial options down the road. Here’s some of what we discuss in this episode: 🤖 Automated Savings: why automation matters beyond the 401(k) ⚖️ Tax vs. Income: balancing today’s pain with tomorrow’s payoff 🪣 Tax Buckets: Roth, pre-tax, and taxable accounts explained 💼 After-Tax Accounts: why every pilot needs one 📈 Lifestyle Creep: capturing raises through automated increases Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Contact our team: https://retireairlines.com/contact-us/ Schedule an introductory call: http://callosborn.com/ Order your no-cost retirement toolkit: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Check out our other no-cost financial resources & guides here: https://retireairlines.com/guides-whitepapers/ The “When I Die” binder: https://retireairlines.com/wp-content/uploads/2024/10/Scott-O-FILLABLE-BINDER-10.22.24-1.pdf Watch the podcast on YouTube: https://www.youtube.com/@retireairlines

    16 min

  7. NOV 6

    Delta Pilots: Unlocking the Power of Your NQDC Plan

    In this episode, Scott breaks down the Delta Non-Qualified Deferred Compensation (NQDC) plan, showing how it differs from a traditional 401(k) and how you can strategically use it to manage your taxes and retirement income. He explains the eligibility rules, contribution limits, and how to decide if this plan fits into your overall retirement strategy. By the end of the episode, you’ll have a clear understanding of both the benefits and risks, so you can make informed decisions for your financial future. Here’s some of what we discuss in this episode: ✅ Eligibility: Who qualifies for the Delta NQDC plan  💸 Contribution Limits: Key differences from 401(k) 💰 Tax Benefits: How this can be used as a strategic tax planning tool for some ⚠️Risk Considerations: The potential impact if Delta faces financial issues 📅 Enrollment Period: How annual enrollment gives you control over your deferrals Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Contact our team: https://retireairlines.com/contact-us/ Schedule an introductory call: http://callosborn.com/ Order your no-cost retirement toolkit: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Check out our other no-cost financial resources & guides here: https://retireairlines.com/guides-whitepapers/ The “When I Die” binder: https://retireairlines.com/wp-content/uploads/2024/10/Scott-O-FILLABLE-BINDER-10.22.24-1.pdf Watch the podcast on YouTube: https://www.youtube.com/@retireairlines

    13 min

  8. OCT 30

    The Market Is Scary Good. What Does That Mean For You?

    When the market feels unstoppable, it’s easy to wonder if now’s the time to invest or sit tight and wait for the next drop. In this episode, Scott explains what it really means when the market is “scary good” and how to stay grounded when emotions run high. Are you approaching retirement or just getting started? This episode will help you see through the hype and stick to your long-term plan. Here’s some of what we discuss in this episode: 📊 Market Emotions: how excitement and fear drive poor decisions 💡 Smart Strategy: what to do (and not do) when markets hit record highs 📰 Noise vs. Reality: why headlines don’t tell the full investment story 📈 Long-Term Focus: keeping perspective through cycles and corrections ⏳ Opportunity Cost: the danger of waiting on the sidelines too long Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Contact our team: https://retireairlines.com/contact-us/ Schedule an introductory call: http://callosborn.com/ Order your no-cost retirement toolkit: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Check out our other no-cost financial resources & guides here: https://retireairlines.com/guides-whitepapers/ The “When I Die” binder: https://retireairlines.com/wp-content/uploads/2024/10/Scott-O-FILLABLE-BINDER-10.22.24-1.pdf Watch the podcast on YouTube: https://www.youtube.com/@retireairlines

    15 min
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About

Welcome to The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots, where we navigate the skies of financial success with your host, Scott Osborn, The Pilot's Planner. Each episode, we soar through the challenges and opportunities unique to pilots, from debunking myths to mastering best practices in financial planning and investing. As demand for pilots reaches new heights, so too does the complexity of their financial landscapes. With Scott's expertise we tackle common pitfalls and strategic wins that can significantly boost a pilot's financial trajectory. Whether you're an aviation professional or just fascinated by the financial skies pilots navigate, this podcast promises insights that can help anyone plot a course toward financial independence. https://thepilotsplanner.com/

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