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.
Other topics discussed:
- Justin’s relocation to Okinawa
- Family travel while in Okinawa
- How Justin and I know each other
- Remembering our days at Cy Falls High School
- Playing for Brent McDonald
- College baseball experience at the Naval Academy
- Encountering Justin Verlander in college
- Learning how to run
- NCAA tournament appearance at Naval Academy
- Naval Academy dating restrictions
- Early influences & motivations for joining the military
- Shift from wanting to be a Navy fighter pilot to joining the Marine Corps
- Impact of 9/11 on his career decisions
- First deployment to Iraq in 2008
- Afghanistan deployment in 2009
- Cameraderie within helicopter squadrons
- First losses during deployment
- Pat Tillman’s death & impact
- Life without women in the desert
- Visiting Dachau concentration camp in Germany
- US involvement in Iraq & Afghanistan
- White supremacy investigations in the military
- How drones are changing modern warfare
- Retiring from the military & transitioning to civilian life
- Military pension structure for reservists
- Pay structure & tax advantages of a military officer
- Investment wins & losses
- Shorting real estate in 2008
- Embarrassing miltary call signs
- Struggles veterans face transitioning to civilian life
- ‘Psychedelic’ potential treating PTSD
- Rick Perry’s advocacy for Ibogaine
- Loss of “elite” identity after leaving the military
- Positive impressions of Brisbane, Australia
Connect with Justin:
- Instagram: @j_lanejackson
- Facebook: Justin Jackson
- Substack: Through Feather and Fire
Listen here:
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