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.
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