From Combat to Entrepreneur and Thoughts on Pyschedelics with Justin Jackson

Meet Justin Jackson. There’s no friend I admire more. In fact, he’s my new favorite podcast guest and will be back for Round 2 in October.

Justin’s a former Marine gunship pilot with over 25 years of service, who transitioned from combat deployments to entrepreneurship. He’s built companies ranging from a cybersecurity firm with elite hackers to a mission-driven brewery honoring Gold Star families.

Nowadays, he’s a husband, dad, and dog-father to a Rhodesian Ridgeback puppy named Lincoln. Professionally, he leads “On Glideslope,” a leadership development venture.

In this episode, we rewind to our high school days at Cy Falls, where Justin took over centerfield duties after I graduated (he was Class of 2000). He had the good fortune of playing for Coach Brent McDonald before playing at the Naval Academy. We discuss the mental & emotional side of baseball.

Then we get into the role Top Gun played in Justin deciding to be a Cobra attack helicopter pilot. He talks about the contrast between a quiet Iraq deployment and a much more intense tour in Afghanistan’s Helmand Province—flying low over desert landscapes, supporting Marines under fire, and the kind of brotherhood only combat can forge.

Justin’s a natural storyteller with a rare mix of tenacity and humility.

Hope you enjoy this conversation as much as we did.