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. 3D AGO

    The Backdoor Roth: A Powerful Strategy For High-Income Pilots

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Wealthy Pilot Toolkit” today: https://retireairlines.com/pilot-retirement-toolkit/ The “Backdoor Roth” might sound complicated - or even questionable - but it’s completely legal and incredibly powerful. In this episode, Scott demystifies how high-income earners can legally build tax-free retirement income using a simple, repeatable strategy. He explains income limits, the pro rata rule, and why small annual contributions can quietly grow into seven figures over time. If you’ve outgrown Roth contribution limits but still want tax-free growth, this is low-hanging fruit you don’t want to ignore. Here’s some of what we discuss in this episode: ✈️ Why high earners get blocked from direct Roth contributions  💰 How the non-deductible IRA + conversion strategy works  ⚠️ The pro rata rule and why mixing IRA dollars can create tax headaches  📈 The power of compounding small annual contributions  🚀 Mega Backdoor Roth vs. standard Backdoor Roth explained Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

    15 min

  2. FEB 12

    Pilot Taxes: Tax Filing vs Planning (And Why It Matters)

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Wealthy Pilot Toolkit” today: https://retireairlines.com/pilot-retirement-toolkit/ Filing your taxes checks a box, but it doesn’t tell you if you’re leaving opportunities on the table. Scott breaks down the difference between simply getting a return done and having a long-term tax plan. You’ll also hear why timing, coordination, and follow-through matter just as much as accuracy. It’s a practical reminder that smart tax decisions rarely happen at the last minute and without proper planning. Here’s some of what we discuss in this episode: 🧾 Filing vs. Planning: Compliance versus long-term strategy ⚠️ Procrastination Risks: How delays create mistakes 📋 Filing Checklist: Key items people overlook 🔍 Return Review: Using last year to plan ahead 🔁 Advanced Strategies: Roth conversions and more Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

    17 min

  3. FEB 5

    What to Expect When You Become A Financial Planning Client

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Wealthy Pilot Toolkit” today: https://retireairlines.com/pilot-retirement-toolkit/ Most people know financial planning is important, but few really understand what happens after you say “yes” and become a client. Scott pulls back the curtain on his step‑by‑step planning process, specifically through the lens of pilots. You’ll get a feel for how he analyzes your situation and helps you follow through without getting bogged down in complexity. If you’ve ever wondered what happens behind the scenes when you hire a financial advisor, this episode gives you a clear, no‑nonsense look. Here’s some of what we discuss in this episode: 🧭 Initial Review: Understanding the full financial picture 🎯 Plan Design: Aligning goals with strategy 🛠️ Implementation: Putting the plan into motion 🔄 Ongoing Management: Adjusting as life and markets change 🗣️ Communication: Staying aligned over time Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

    18 min

  4. JAN 29

    Should Geopolitics Drive Your Investing?

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Wealthy Pilot Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html Geopolitical headlines are louder than ever- but should they influence your investment decisions? In this episode, Scott explains why reacting to global events, elections, or policy noise often does more harm than good. Using real-world examples, aviation parallels, and disciplined portfolio principles, Scott breaks down how investors can stay grounded, avoid emotional mistakes, and focus on long-term outcomes. Here’s some of what we discuss in this episode: ✈️ Why geopolitical headlines are a poor investing compass  🧠 The danger of emotional and reactionary decisions  📈 Why long-term perspective beats short-term noise  🔄 Understanding second- and third-order economic effects 📋 Investing with a checklist, not a headline  Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

    16 min

  5. JAN 22

    Should Pilots Listen To Economists In 2026?

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Wealthy Pilot Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html After a year marked by volatility, uncertainty, and more than a few economic curveballs, it’s understandable if optimism doesn’t come easily. But at least one economist is arguing that the outlook for 2026 may be brighter than many people expect. Today, Scott breaks down the case for a stronger economy ahead- while also explaining why pilots should be cautious about letting economic predictions drive their financial decisions. Here’s some of what we discuss in this episode: 📊 The economy and the market are not the same thing  💰 Why consumer cash flow could improve in 2026  ⛽ How energy prices and interest rates impact growth  ⚠️ The dangers of relying on economic predictions  🎯 What investors can actually control long term Bloomberg News Opinion Column: https://www.fa-mag.com/news/five-reasons-to-be-optimistic-about-the-2026-economy-85324.html?section=68 Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

    21 min

  6. JAN 15

    Trump Accounts: Free Money or Future Headache?

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Wealthy Pilot Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html A new government-backed savings account for kids is on the way, and on the surface, it sounds like a win. Free money, long-term investing, and a head start for the next generation. But once you look closer, Trump Accounts raise some questions. Scott walks through the pros, the trade-offs, and how to decide whether these accounts fit into your family’s broader plan. Here’s some of what we discuss in this episode: 👶 New Kids’ Accounts: What Trump Accounts are and who qualifies 💰 Free Money Factor: Why the government contribution matters 🧾 Rules & Restrictions: Contribution limits and account mechanics ⚖️ Pros vs. Cons: Where these accounts help and where they fall short Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

    16 min

  7. JAN 8

    401(k) Contribution Limits for 2026: What Pilots Need to Know

    📱 Get your customized planning started by booking a call: http://callosborn.com/  ✈️ Order your no-cost “Wealthy Pilot Toolkit” today: https://keap.page/lde199/the-pilot-s-planner-toolkit.html A new year is the perfect time to revisit the numbers driving your retirement plan- and in this episode, Scott walks through the most important 401(k) updates pilots need to understand for 2026. From standard contribution limits to catch-up and “super catch-up” opportunities, Scott explains what’s changed, who it affects, and why contribution strategy matters just as much as contribution size. The conversation goes deeper into new rules requiring catch-up contributions to go into Roth accounts, the long-term value of tax diversification, and the hidden risks of relying too heavily on pre-tax savings. Here’s some of what we discuss in this episode: 💡 401(k) contribution and catch-up limits for 2026  🦸 “Super catch-up” opportunities for ages 60–63  🧾 New rules requiring catch-up contributions to be Roth  ⚖️ Pre-tax vs. Roth strategy and tax diversification  🚨 The hidden risk of the widow’s tax trap  🎯 Why contribution strategy matters as much as contribution amount Resources: Our website: https://retireairlines.com/ Phone: (419) 314-4139 Schedule an introductory call: http://callosborn.com/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

    17 min

  8. 12/23/2025

    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 Schedule an introductory call: http://callosborn.com/ Check us out on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

    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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