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PODCAST

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

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

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All Episodes

19:28

The “ACE Method” for Pilot Investing

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/04/23

📱 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/ Pilots have access to some of the best retirement benefits out there, but that doesn’t mean everything is set up the right way. Scott introduces a simple framework to help clarify how your money is structured and working for you. It’s about being intentional with what you have and making sure each piece...

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14:58

Your Tax Return Is a Report Card- Are You Passing?

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/04/16

📱 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/ Your tax return isn’t just paperwork, it’s feedback. Every year, it shows you exactly how efficient (or inefficient) your strategy really is. The problem is, most people glance at the number they owe or get back, and move on, missing the bigger picture entirely. Today, Scott shares how to read your “tax...

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15:53

Financial Lessons From Artemis Mission

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/04/09

📱 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/ What does a mission to the moon have to do with your retirement plan? More than you might think. The Artemis mission is one of the most complex, carefully planned endeavors in the world, and it offers a powerful lens for thinking about your financial future. Scott explains how the most successful outcom...

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16:58

What March Madness Teaches About Your Money

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/03/26

📱 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/ March Madness brackets are fun… until they fall apart. But what happens when that same mindset shows up in your financial decisions? In this episode, Scott draws smart parallels between bracket predictions and investing behavior. From bias and recency thinking to chasing winners and betting on “Cinderel...

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17:39

Is It Better To Be Good or Lucky In Investing?

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/03/19

📱 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/ Is successful investing about skill or simply being lucky? In this St. Patrick’s Day–themed episode, the conversation explores the popular idea of “luck” in investing and why relying on it can be risky. Scott explains how many investors mistake lucky outcomes- like a winning stock pick or perfectly time...

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16:08

Where to Put Money Other Than A 401K

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/03/12

📱 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/ For many people, retirement saving feels simple: contribute to the 401(k) and call it a day. But what happens when you want to save more than that? Scott explains how to think about saving and investing outside a workplace plan and why a good strategy includes more than just your retirement account. He ...

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17:36

Geopolitical Tension: Invest or Pull Back?

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/03/05

📱 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/ Every time global tensions flare up, the same question resurfaces: should investors make a move? Oil spikes. Headlines turn dramatic and talking heads predict disaster. Scott zooms out and examines what history shows, what usually happens next, and how to avoid letting short-term fear override long-term...

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14:33

The Backdoor Roth: A Powerful Strategy For...

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/02/19

📱 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 rul...

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17:00

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

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/02/12

📱 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...

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18:20

What to Expect When You Become A Financial Planning...

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/02/05

📱 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...

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16:08

Should Geopolitics Drive Your Investing?

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/01/29

📱 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 princi...

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20:50

Should Pilots Listen To Economists In 2026?

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/01/22

📱 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 eco...

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16:11

Trump Accounts: Free Money or Future Headache?

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/01/15

📱 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 t...

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16:50

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

The Wealthy Pilot"s Podcast: Financial Flight... ·

2026/01/08

📱 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 ...

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14:48

Year-End Financial Reflection & Planning For 2026

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/12/23

📱 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 y...

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11:47

United Airlines Cash Balance Plan: Allocating Your...

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/12/18

📱 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 ep...

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13:21

2026 Key Planning Numbers Every Pilot Should Know

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/12/11

📱 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 ...

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16:12

MBCB Plan for American Airlines: Should You Opt In or...

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/12/04

📱 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 h...

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12:58

Thanksgiving, Gratitude & Growing Wealth: Essential...

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/11/20

📱 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 confid...

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16:10

Automating Savings Outside of 401k For a Smarter...

The Wealthy Pilot"s Podcast: Financial Flight... ·

2025/11/13

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

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