HeyJared21.FIVE - Professional Pilots Podcast
A podcast for Professional Pilots, by Professional Pilots. Join hosts Dylan and Max, both professional pilots with backgrounds in Flight Instructing, Airlines, and Business Aviation, on their quest to improve as travelers, pilots, and professionals.
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- Indexed episodes, last 90 days
- 1
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- Sep 29, 2026
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- Sep 29, 2026
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221. Are You Leaving Money on the Table Before Year-End? (opens the original)
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Tim Pope of 360 Aviation Advisors joins Dylan and Max to talk open enrollment, year-end financial planning, and one of the biggest career decisions pilots eventually face: when to upgrade. For professional pilots, the numbers matter—but so do schedule, seniority, reserve, weekends off, and the quality-of-life calculus that never fits neatly into a spreadsheet. They dig into disability coverage, estate planning, 401(k) and Roth strategies, AI-generated financial questions, and whether captain pay
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