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:

1. The unconventional path into Air Force Special Ops
2. What it feels like to deploy with barely 250 flight hours
3. Flying through Saharan fuel-risk zones and Pacific icing
4. The culture differences inside military aviation
5. Why humility matters more than ego in elite units
6. Building a company after walking away from a “dream job”

This one is raw, honest, and packed with perspective.

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