E355: From 9/11 to Special Ops: Flying Secret Missions

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 Ops What it feels like to deploy with barely 250 flight hours Flying through Saharan fuel-risk zones and Pacific icing The culture differences inside military aviation Why humility matters more than ego in elite units Building a company after walking away from a “dream job” This one is raw, honest, and packed with perspective. Sign up today The Flying Company