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Gray during a presentation at the Nantucket Project Finance Forum in 2013.
But Gray, who comes from a small town in northern California, took an untraditional path to the military. He said he always planned on becoming a soldier: "My whole life I always knew I wanted to do my service," he says. "It was just the mater of the timing of it."
He ended up joining the armed forces at an unlikely point in life, two years into a competitive and intense finance PhD program at the University of Chicago. "I was kind of thinking, it's not like my opportunity costs are going to get any lower," he recalls. "If I'm ever going to actually do this I just have to go for it."
He convinced his program advisor to grant him a four-year sabbatical, which is three years longer than what students are typically allowed. This was in 2004, when the campaign in Iraq was intensifying.
Gray soon graduated towards the top of his Marine training class. He chose to become a "ground intelligence officer," basically an infantry soldier with intelligence duties and expertise - a "grunt with a map" in Marine parlance, according to Gray. He was entrusted with training and organizing Iraqi army personnel and was in the country at a time when the US began paying Sunni tribal leaders to join the fight against Al Qaeda: the "Anbar Awakening" that led to Al Qaeda in Iraq's defeat in the late 2000s.
Gray left the Marines in 2008 and returned to his PhD program, somewhat to his professors' and classmates' surprise - "they didn't' think I would show up again" after his military career, Gray recalls. His experience in Iraq would end up having an unmistakable resonance in his post-military life and when attempting to launch Alpha Architect, a financial services startup that he says now manages $200 million in assets. Working with Iraqi soldiers and officials and applying his military and intelligence training in an active war zone gave Gray invaluable insights into human nature that he later brought to his business.
"It was all about understanding the psychology of people and really trying to get through that," he says of his work in Iraq. "It meant realizing that everyone has cultural baggage and behavioral influences. You think everyone would be rational. But that's simply not the case."
That realization applied to more than his Iraqi counterparts - it was crucial to being able to function in a war zone. "People are highly emotion-driven," he explains. "That's something you learn a lot about in the military and you learn to control that. When you're getting shot at you don't duck. You get up and shoot back when your emotion says to turn the other way."
The military's honor and service-driven ethos also helped him hone his own unique sense of what he wanted his business to stand for. "We're trying to be more user-friendly and honorable than the traditional kind of dog-eat-dog Wall Street company," he says, explaining that his company is geared around investor
Gray explains that in the Marines, the officers eat last - the leaders aren't in it for themselves, just by virtue of what the organization values. So Gray wanted to create a company distinguished through its transparency, a place that would buck the traditional "middle man"-like function of a typical financial firm. Right now, he has 10 full-time employees, including a recently hired ex-Marine captain.
Since leaving the Marines, Gray has finished his PhD at Chicago, written a book about his experiences in Iraq, and taught at Drexel University before deciding to go into business.
He says that veterans can successfully transition to civilian life so long as they're able to leverage their connections in the civilian world, especially among fellow ex-military personnel who are in a position to help them.
"Just reach out to someone who's also a vet - who's already been successful and made that transition and learn from them," says Gray.