On Jocko Podcast, Chris Cappy shares his journey from Long Island filmmaker to military service member and defense analyst. Growing up with an early passion for filmmaking, Cappy's life took a turn after witnessing 9/11, leading him to join the National Guard and serve in Iraq with the Pennsylvania 56th Stryker Brigade. Following his military service, he worked at "The Daily Show with Jon Stewart" and in corporate roles before finding his niche in video storytelling.
The conversation explores Cappy's transition from soldier to founder of Cappy Army, where he combines his military background with media expertise. His work includes on-the-ground reporting in Ukraine, providing perspectives on modern warfare and soldiers' experiences. Through his coverage of defense and geopolitical topics, Cappy brings his documentary-style approach to help audiences understand complex military matters.
Sign up for Shortform to access the whole episode summary along with additional materials like counterarguments and context.
Chris Cappy grew up on Long Island with his conductor father and IRS agent mother. Despite significant age gaps with his siblings and struggles in school, Cappy found discipline through baseball and karate. His father played a crucial role in nurturing his early passion for filmmaking, helping him create stop-motion movies and learn video editing. Though initially pursuing film school, Cappy eventually realized traditional film careers weren't his calling.
Deeply affected by witnessing 9/11's impact firsthand, Cappy joined the National Guard in 2008 and volunteered for deployment to Iraq with the Pennsylvania 56th Stryker Brigade. Despite initial hesitation and anxiety, he persevered through training at Fort Polk and served north of Baghdad, where he faced the constant threat of IEDs. His experiences led to profound personal reflection on the nature of war and its psychological impact on soldiers.
After returning from Iraq, Cappy struggled with substance abuse but found renewed purpose while working at "The Daily Show with Jon Stewart," where he learned valuable lessons about leadership. Following positions at IBM and Cisco, he found his niche at Task & Purpose, eventually founding Cappy Army to combine his military experience with his passion for video storytelling.
Cappy's on-the-ground reporting in Ukraine provided unique insights into soldiers' experiences and modern warfare adaptation. His interactions with Ukrainian soldiers challenged his preconceptions and offered authentic perspectives on the conflict. Now covering broader geopolitical and defense topics, Cappy has earned respect within military and defense communities for his nuanced, evidence-based analysis and ability to condense complex information for his audience.
1-Page Summary
Chris Cappy shares his personal experiences growing up on Long Island, his family life, struggles in school, and his early passion for filmmaking nurtured by his father's encouragement.
Cappy recalls fond memories of growing up on Long Island, where he would grab coffee and bagels and ride the train for free, thanks to his father, who was a train conductor for the Long Island Railroad for 35 years. Cappy’s father not only worked hard to support his family but also fostered Cappy’s early interest in trains and the city. His mother, an IRS agent, jokingly advised him to keep her occupation secret due to the usual stigma attached to tax collectors.
Cappy has quite an age difference with his siblings; his older brother is eight years his senior, while his younger sister is six years his junior. Initially, this age gap led to a distant relationship with his sister, especially given his travels around the world. However, they now live closer to each other and share a strong bond. Both of his siblings are described as math and science geniuses. Cappy, on the other hand, struggled in school, finding himself seeking attention, often by being a class clown, which led to behavioral issues that were further complicated by his parents' divorce.
Despite his struggles in school and frequent troublemaking, Cappy found a sense of discipline in sports and the martial arts. He played baseball and practiced karate, activities that helped shape his focus. By late adolescence, he began to concentrate more on school and stayed out of trouble.
Cappy’s passion for cinema was apparent from a young age—he was knowledgeable about actors and devoutly interested in the making of movies. His father played a pivotal role in cultivating this interest, assisting him in creating stop-motion movies and accessing video editing software. Cappy began teaching himself video editing and special effects while he was still young.
From the age of 10, Cappy was engr ...
Cappy's Personal Background and Early Life
Chris Cappy's path to military service and his time in Iraq have forged a journey of deep introspection and confrontation with the realities of war.
Chris Cappy’s choice to join the military was heavily influenced by the repercussions of 9/11, which he observed firsthand. He saw cars left unclaimed in Long Island train stations, a grim reminder of those who did not return from Manhattan on that tragic day. By the age of 18, Cappy felt fortunate that he could opt for art school instead of battle, but a conversation while getting drunk at art school challenged him to align his actions with his beliefs about the war. This led him to join the National Guard in 2008, partly inspired by the historic role of the 69th Infantry Division's response to the same attacks that spurred him into action.
Volunteering for deployment with the Pennsylvania 56th Stryker Brigade, 1st of the 111th, he positioned himself as "the guy from New York, the backfill," integrating into a unit where interpersonal bonds had already been established. This inherently came with challenges due to different backgrounds, as his squad was composed of individuals who were stop-lossed, reclassified from other military duties, or simply needed to fill the ranks.
Despite hesitation, Cappy volunteered for deployment to Iraq, facing resistance from his New York unit. His resolve was initially shaken during boot camp, and he struggled with intense anxiety before deployment. Briefing videos depicting soldiers in harrowing situations exacerbated his fear, prompting a desire to seek release from his commitment.
The train-up at Fort Polk, Louisiana, lasted three months, where Cappy eagerly learned about the Stryker units. Despite his excitement, the forthcoming deployment generated considerable trepidation, leading Cappy to approach a chaplain in a moment of vulnerability, contemplating quitting. However, after a night of consideration and counsel from the chaplain, he chose to persevere and fulfill his commitment.
In Iraq, he was stationed just north of Baghdad, dealing with the pervasive threat of IEDs and a strategic environment w ...
Cappy's Military Service and Experiences in Iraq
Chris Cappy's personal and professional life illustrates the complex journey that some veterans face as they transition back into civilian society and seek meaningful careers after military service.
Cappy's reintegration into civilian life was marred by a personal struggle with substance abuse and a quest for self-improvement.
After returning from Iraq, Chris Cappy struggled with substance abuse, turning to MDMA, cocaine, [restricted term], and acid to fill an internal void. He had a striking moment of realization while under the influence of acid, confronting the narcissism and selfishness that he described as being detrimental to his well-being. This epiphany made him see that his lack of success and the issues in his life were self-inflicted, contradicting reassurances from his mother. Despite recognizing the need to change and strive to be a better person, Cappy acknowledged that transformation was a slow and challenging process, prone to setbacks and relapses.
Cappy interned and later worked full-time at "The Daily Show with Jon Stewart" while attending NYU. He describes the experience as transformative, especially in terms of recognizing exceptional leadership. Jon Stewart's attention to knowing everyone's name and fostering talent by promoting from within was something Cappy admired. He valued Stewart's commitment to the veteran community and maintained that his time at "The Daily Show" was instrumental in shaping his understanding of effective leadership.
Initially, Cappy worked remotely for IBM, where his video editing satisfied the company needs, but his role eventually evolved away from video production.
While working for IBM, Cappy only needed to edit a few videos per month to meet his obligations, an arrangement that IBM found worth his salary.
However, Cappy found a different position at Cisco that allowed him to return to New York, a move he felt he needed "so badly." At Cisco, he began makin ...
Cappy's Post-Military Transition and Career Journey
Chris Cappy, also known as Chris Capilouto, has been reporting from the front lines in Ukraine to provide an on-the-ground perspective that challenges preconceptions and voices the real experiences of soldiers involved in the conflict.
Cappy wanted to live the life and tell the stories of being on the ground in Ukraine rather than writing about fictional characters. He drove through Ukraine, encountering checkpoints and even experiencing Kiev's normalcy amidst missile threats. Chris Cappy's fact-finding mission was part journalistic endeavor and part intelligence gathering, akin to what the U.S. might conduct. He mused about how Ukraine is under martial law, fighting for its existence, based on his insights from interactions with soldiers and experiences such as going on a drone mission with a Ukrainian vampire drone team.
Chris Cappy covered the stories of soldiers like Jonathan, who voluntarily sought assault positions to be in the crux of the fight. Chris's reporting from Ukraine, where he had deep discussions with soldiers, contrasted with traditional fights and pointed out the many ways Ukrainian forces were adapting to modern warfare.
Cappy’s exposure to the ground realities in Ukraine, including the story of an exhausted soldier forced to serve beyond his will, who was still motivated by the fight for his homeland, provided him with a new viewpoint. His reporting also touched on the risks in evacuation due to drones and mines and the difficult decisions soldiers needed to make regarding electronic warfare systems.
Upon returning, Cappy has longed for more on-the-ground reporting across various front lines. His reporting now dives into broader defense topics, leveraging the tactical and technological insights he gathered in Ukraine. His platform aims to be a resource for soldiers to gain different perspectives on war, hinted at by his reflective video during Afghanistan's withdrawal, which aime ...
Cappy's Reporting on the War in Ukraine
Download the Shortform Chrome extension for your browser