Pilot to Pilot

Author: Justin Siems

Pilot to Pilot Podcast brought to you by Allworth Airline Financial is your go-to destination for aviation inspiration, insight, and real talk from the cockpit and beyond. Pilot to Pilot aims to support all pilots who fly from students to professionals and recreational flyers. The show includes genuine discussions with pilots who work in all aviation sectors including airline captains and bush pilots to share their experiences of flying. Join our worldwide pilot community through subscription to track your flying aspirations with other aviation enthusiasts.
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Language: en

Genres: Aviation, Hobbies, Leisure

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E355: From 9/11 to Special Ops: Flying Secret Missions
Episode 355
Tuesday, 3 March, 2026

Most pilots dream of smooth 10,000-foot runways.Tyler Flagg trained to land a 30,000-pound aircraft on a 25-foot dirt strip… in total darkness.After 9/11 changed his life trajectory, Tyler went from zero aviation background to flying Special Operations missions around the globe. With minimal information and maximum responsibility, he deployed into multiple combat theaters — moving elite teams into places most people will never see on a map.In this episode:The unconventional path into Air Force Special OpsWhat it feels like to deploy with barely 250 flight hoursFlying through Saharan fuel-risk zones and Pacific icingThe culture differences inside military aviationWhy humility matters more than ego in elite unitsBuilding a company after walking away from a “dream job”This one is raw, honest, and packed with perspective.Sign up today The Flying Company