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

EPISODE · Mar 3, 2026 · 1H 9M

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

from Pilot to Pilot · host Justin Siems

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

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

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

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This episode was published on March 3, 2026.

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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...

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