The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots
by Scott Osborn
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From 15 epsHost
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Recent episodes
IPOs, SpaceX, and Why "I Should Have Bought That" Is Almost Never True
Jun 18, 2026
16m 39s
The Golden Handcuffs Trap: When High Income Starts Destroying Your Freedom
Jun 11, 2026
18m 29s
Why Pilots Should Think Twice About Market-Based Cash Balance Plans
Jun 4, 2026
17m 16s
Pensions Are Dying: Here’s How to Build Your Own
May 28, 2026
16m 28s
The ‘When I Die’ Flight Plan: Estate Planning Every Pilot Family Needs
May 21, 2026
17m 41s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/18/26 | IPOs, SpaceX, and Why "I Should Have Bought That" Is Almost Never True | 📱 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/ SpaceX's highly anticipated public debut has investors everywhere wondering if they're missing the next big opportunity. Scott breaks down the hype surrounding IPOs and explores how disciplined investors can avoid costly emotional decisions. He shares practical guidance on treating IPOs like speculative... | 16m 39s | ||||||
| 6/11/26 | The Golden Handcuffs Trap: When High Income Starts Destroying Your Freedom✨ | financial freedomgolden handcuffs+3 | — | Wealthy Pilot ToolkitRetire Airlines+1 | — | high incomefinancial pressure+3 | — | 18m 29s | |
| 6/4/26 | Why Pilots Should Think Twice About Market-Based Cash Balance Plans✨ | tax deductionscash balance plans+3 | — | Wealthy Pilot ToolkitRetire Airlines+1 | — | tax deductionscash balance plans+3 | — | 17m 16s | |
| 5/28/26 | Pensions Are Dying: Here’s How to Build Your Own✨ | retirement planningpensions+3 | — | Wealthy Pilot Toolkitretireairlines.com+1 | — | pensionsretirement income+3 | — | 16m 28s | |
| 5/21/26 | The ‘When I Die’ Flight Plan: Estate Planning Every Pilot Family Needs✨ | estate planningfinancial organization+3 | — | Wealthy Pilot ToolkitRetire Airlines | pilot family | estate planningpilot family+3 | — | 17m 41s | |
| 5/14/26 | Spirits Down: How to Survive Tough Times Without Self-Sabotage✨ | career turbulencefinancial decisions+3 | — | Wealthy Pilot ToolkitSpirit Airlines+2 | — | pilotsfinancial planning+3 | — | 16m 05s | |
| 5/7/26 | 3 Mistakes Pilots Make with Their 401k✨ | 401k mistakesfinancial planning+3 | — | Wealthy Pilot ToolkitRetire Airlines+1 | — | 401kfinancial asset+3 | — | 14m 28s | |
| 4/30/26 | The $400K Rule: When Pilots Need To Rethink Their 401(k) Strategy✨ | 401(k) strategyfinancial planning+3 | — | Wealthy Pilot ToolkitRetire Airlines | 401(k) | 401(k)financial strategy+3 | — | 16m 42s | |
| 4/23/26 | The “ACE Method” for Pilot Investing✨ | pilot investingretirement benefits+3 | — | Wealthy Pilot Toolkitretireairlines.com+1 | — | ACE Methodpilot retirement+3 | — | 19m 28s | |
| 4/16/26 | Your Tax Return Is a Report Card- Are You Passing?✨ | tax returnsfinancial strategy+3 | — | Wealthy Pilot ToolkitRetire Airlines+1 | — | tax returnfinancial feedback+3 | — | 14m 58s | |
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| 4/9/26 | Financial Lessons From Artemis Mission✨ | financial planningretirement+3 | — | Artemis missionWealthy Pilot Toolkit+1 | — | financial lessonsretirement plan+3 | — | 15m 53s | |
| 3/26/26 | What March Madness Teaches About Your Money✨ | financial decisionsinvesting behavior+4 | — | Wealthy Pilot Toolkitretireairlines.com | — | March Madnessfinancial decisions+3 | — | 16m 58s | |
| 3/19/26 | Is It Better To Be Good or Lucky In Investing?✨ | investingluck+3 | — | Wealthy Pilot ToolkitRetire Airlines | — | investingluck+3 | — | 17m 39s | |
| 3/12/26 | Where to Put Money Other Than A 401K✨ | retirement savingsinvestment strategies+3 | — | Wealthy Pilot Toolkitretireairlines.com+1 | — | retirement401(k)+4 | — | 16m 08s | |
| 3/5/26 | Geopolitical Tension: Invest or Pull Back?✨ | geopolitical tensioninvesting strategies+3 | — | Wealthy Pilot Toolkitretireairlines.com+1 | — | geopolitical tensioninvesting+3 | — | 17m 36s | |
| 2/19/26 | The Backdoor Roth: A Powerful Strategy For High-Income Pilots✨ | Backdoor Rothtax-free retirement+3 | — | Wealthy Pilot ToolkitRetire Airlines+1 | — | Backdoor Rothtax-free income+3 | — | 14m 33s | |
| 2/12/26 | 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... | 17m 00s | ||||||
| 2/5/26 | 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... | 18m 20s | ||||||
| 1/29/26 | 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 princi... | 16m 08s | ||||||
| 1/22/26 | 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 eco... | 20m 50s | ||||||
| 1/15/26 | 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 t... | 16m 11s | ||||||
| 1/8/26 | 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 ... | 16m 50s | ||||||
| 12/23/25 | 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 y... | 14m 48s | ||||||
| 12/18/25 | 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 ep... | 11m 47s | ||||||
| 12/11/25 | 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 ... | 13m 21s | ||||||
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