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

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

From Pilot to Pilot by Justin Siems

March 3, 2026 · 1h 9m · Season 1 · Episode 355

About this episode

Tyler Flagg shares his unconventional journey from a non-pilot to flying Special Operations missions after 9/11.

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

People in this episode

Host: Justin Siems

Guest: Tyler Flagg

Topics covered

  • military aviation
  • special operations
  • personal journey
  • flight training
  • combat deployment
  • humility in leadership

Keywords

  • Special Operations
  • military
  • aviation
  • combat
  • flight hours
  • leadership
  • humility
  • deployment

Mentioned in this episode

Organizations: Air Force

Places: Sahara, Pacific

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