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.
- Indexed pieces, last 90 days
- 9
- Latest publication
- Sep 29, 2026
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- Earliest in this view
- Jul 7, 2026
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Latest pieces
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
220. How Much Adventure Can You Fit Into One Flying Week? (opens the original)
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This week we ditch the usual format and go full storytime, starting with Max’s annual Idaho backcountry mission involving Cub flying, pack rafts, mechanical drama, questionable fuel logistics, hungry foxes, and one extremely unwelcome skunk. Dylan counters with a 24-hour Anchorage layover full of 747s, floatplanes, bush planes, F Street Station, and some proper Alaska aviation sightseeing. Then he brings Gavin along in the right seat of the CJ2 for a father-son run to Roswell, complete with copi
219. Why Is the Business Jet Market So Tight Right Now? (opens the original)
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Brooks Pettit of Vaerus Jet Sales joins Dylan and Max to break down what is really happening in the business aircraft market. For professional pilots and flight departments, he covers tight inventory, strong demand, financing, tax-driven transactions, and why planning ahead matters. They also get into Challenger 3500 delivery positions, bonus depreciation, tariffs, AI-driven market research, and the realities of buying and selling aircraft in a fast-moving market. Listen in for a practical look
218. Can You Trust a Pilot on the Road? (opens the original)
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Max checks in from a musty Missouri hotel while earning his Light Sport Repairman certificate, and the guys detour through GA maintenance, Starbase, RTA wizardry, and the ongoing decline of 123.45 as a social network. Mailbag covers Sugar Alpha , Qantas’ ultra-long-haul A350 plans, where Spirit’s pilots and traffic may have landed, and whether 21.Five needs a Discord server. In Flight Advice, Dylan and Max tackle the stereotype that pilots are destined to cheat—and how couples can build trust, r
217. Constant Peg: America’s Secret MiG Operation (opens the original)
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Rob Zettel joins Dylan and Max to tell the story of flying MiG-21s and MiG-23s with the USAF’s secretive Red Eagles under the Constant Peg program. For professional pilots, it’s a fascinating look at training, aircraft handling, risk management, and what happens when experienced aviators are handed an airplane with no two-seat trainer and no simulator. Rob gets into fighting frontline U.S. fighters in the MiG-21, taking the MiG-23 to Mach 2.35, handling a serious hydraulic failure, and later tra
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