The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots
by Scott Osborn
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From 19 epsHost
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Recent episodes
Shiny Object Syndrome: The 401(k) Mistakes That Cost Pilots
Sep 3, 2026
16m 14s
The 5 D’s of Retirement
Aug 27, 2026
17m 48s
Why Politics (and the Midterms) Are Bad Investment Policy
Aug 20, 2026
15m 23s
3 Key Money Moves for New Major Airline Pilots
Aug 6, 2026
14m 45s
3 Key Moves for Pilots Over 50
Jul 30, 2026
15m 40s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 9/3/26 |  Shiny Object Syndrome: The 401(k) Mistakes That Cost Pilots | 📱 Get your customized planning started by booking a call: http://callosborn.com/ ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ It’s easy to get distracted by the latest hot investment, market headline, or fund that just had a great run. For the 100th episode, Scott is celebrating by tackling Shiny Object Syndrome and the investing habits that can pull a long-term retirement strategy off course. He also introduces his new book, Cleared to Retire, bui... | 16m 14s | ||||||
| 8/27/26 | The 5 D’s of Retirement | 📱 Get your customized planning started by booking a call: http://callosborn.com/ ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ According to a recent Kiplinger article, there are five keys to a retirement plan that hold up over time. They all happen to start with the same letter— which either means it's a great framework or someone really wanted it to work out that way. In this episode, Scott walks through the “5 D’s” of retirement planning and how e... | 17m 48s | ||||||
| 8/20/26 | Why Politics (and the Midterms) Are Bad Investment Policy | 📱 Get your customized planning started by booking a call: http://callosborn.com/ ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Politics and portfolios don’t always mix, but midterm season makes it really tempting to try. Scott breaks down why election headlines can lure investors into market timing, even though the data just doesn’t back bailing on a long-term plan. You’ll hear what history says about markets around midterms and why discipline usual... | 15m 23s | ||||||
| 8/6/26 | 3 Key Money Moves for New Major Airline Pilots | 📱 Get your customized planning started by booking a call: http://callosborn.com/ ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Making it to a major airline can feel like reaching the destination, but financially, it is really the start of a new flight plan. In this episode, Scott explains why new hires should give themselves time to settle into training and onboarding, then quickly turn their attention to the financial decisions that can shape the r... | 14m 45s | ||||||
| 7/30/26 | 3 Key Moves for Pilots Over 50 | 📱 Get your customized planning started by booking a call: http://callosborn.com/ ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Hitting age 50 in the cockpit? That’s your cue to get serious about the next mission, turning years of flying into a well-fueled retirement plan. In this episode, Scott walks pilots through how to rethink contributions and start building more tax-efficient income for life after mandatory retirement. Don’t skip this pre-fligh... | 15m 40s | ||||||
| 7/23/26 | Trump Accounts Are Live: Should You Open One? | 📱 Get your customized planning started by booking a call: http://callosborn.com/ ✈️ Order your no-cost Pilot Money Toolkit today: https://pilotmoneyguy.com/toolkit/ Wondering if these new “Trump accounts” are really worth your attention as a pilot? Scott breaks down where these kids’ IRAs fit into your overall flight plan and why funding priorities matter more than chasing the latest headline strategy. Stick around to see whether these new accounts actually deserve a place in your cockp... | 17m 08s | ||||||
| 7/16/26 | investingmarket analysis+3 | — | Pilot Money ToolkitPilot Money Guy | the market | market highsinvesting strategy+3 | — | 17m 19s | ||
| 7/9/26 | retirement incomefinancial planning+3 | — | Pilot Money ToolkitPilot Money Guy+1 | — | retirementincome planning+3 | — | 21m 38s | ||
| 7/2/26 | financial freedomfinancial independence+3 | — | — | America | financial freedomfinancial independence+3 | Pilot Money Toolkit | 17m 00s | ||
| 6/18/26 | IPOsSpaceX+3 | — | SpaceXWealthy Pilot Toolkit+3 | — | IPOsSpaceX+3 | — | 16m 39s | ||
| 6/11/26 | financial freedomgolden handcuffs+3 | — | Wealthy Pilot ToolkitRetire Airlines+1 | — | high incomefinancial pressure+3 | — | 18m 29s | ||
| 6/4/26 | tax deductionscash balance plans+3 | — | Wealthy Pilot ToolkitRetire Airlines+1 | — | tax deductionscash balance plans+3 | — | 17m 16s | ||
| 5/28/26 | retirement planningpensions+3 | — | Wealthy Pilot Toolkitretireairlines.com+1 | — | pensionsretirement income+3 | — | 16m 28s | ||
| 5/21/26 | estate planningfinancial organization+3 | — | Wealthy Pilot ToolkitRetire Airlines | pilot family | estate planningpilot family+3 | — | 17m 41s | ||
| 5/14/26 | career turbulencefinancial decisions+3 | — | Wealthy Pilot ToolkitSpirit Airlines+2 | — | pilotsfinancial planning+3 | — | 16m 05s | ||
| 5/7/26 | 401k mistakesfinancial planning+3 | — | Wealthy Pilot ToolkitRetire Airlines+1 | — | 401kfinancial asset+3 | — | 14m 28s | ||
| 4/30/26 | 401(k) strategyfinancial planning+3 | — | Wealthy Pilot ToolkitRetire Airlines | 401(k) | 401(k)financial strategy+3 | — | 16m 42s | ||
| 4/23/26 | pilot investingretirement benefits+3 | — | Wealthy Pilot Toolkitretireairlines.com+1 | — | ACE Methodpilot retirement+3 | — | 19m 28s | ||
| 4/16/26 | tax returnsfinancial strategy+3 | — | Wealthy Pilot ToolkitRetire Airlines+1 | — | tax returnfinancial feedback+3 | — | 14m 58s | ||
| 4/9/26 | financial planningretirement+3 | — | Artemis missionWealthy Pilot Toolkit+1 | — | financial lessonsretirement plan+3 | — | 15m 53s | ||
| 3/26/26 | financial decisionsinvesting behavior+4 | — | Wealthy Pilot Toolkitretireairlines.com | — | March Madnessfinancial decisions+3 | — | 16m 58s | ||
| 3/19/26 | investingluck+3 | — | Wealthy Pilot ToolkitRetire Airlines | — | investingluck+3 | — | 17m 39s | ||
| 3/12/26 | retirement savingsinvestment strategies+3 | — | Wealthy Pilot Toolkitretireairlines.com+1 | — | retirement401(k)+4 | — | 16m 08s | ||
| 3/5/26 | geopolitical tensioninvesting strategies+3 | — | Wealthy Pilot Toolkitretireairlines.com+1 | — | geopolitical tensioninvesting+3 | — | 17m 36s | ||
| 2/19/26 | Backdoor Rothtax-free retirement+3 | — | Wealthy Pilot ToolkitRetire Airlines+1 | — | Backdoor Rothtax-free income+3 | — | 14m 33s | ||
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