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Military helicopter in the hazy sun

Military helicopter in the hazy sun

From Deployment to the Boardroom: Veterans Thrive in Leavey’s EMBA Cohort

From Coast Guard aviation to NSA intelligence to Marine Corps counterintelligence, Sam Hickey, Josh Michael, and Cody Boleyn brought decades of service - and very different paths - to the same Executive MBA cohort at Leavey.

“I don’t know if I’m the right type of person for this program.”

Sam Hickey said it during his admissions interview. Josh Michael felt it when he started researching executive MBA programs. Cody Boleyn wondered the same thing while applying to Santa Clara, even as he was being laid off from the job he loved at the VA.

Sam Hickey, Josh Michael, and Cody Boleyn are part of the same Executive MBA cohort at Santa Clara University’s Leavey School of Business, brought together by military service, the Yellow Ribbon Program, and a shared recognition that the skills that kept them alive in uniform needed translation for Silicon Valley.

“I don’t know if I’m the right type of person for this program,” Sam told Joshua Rosenthal during his admissions interview. He’d spent eight years in the Marine Corps, four of them as intelligence deployed to Burundi, Senegal, and Norway. He owned a gym in Denver. He had a psychology degree and a master’s in business analytics. What he didn’t have was certainty.

Rosenthal apparently saw something Sam didn’t.

“No one’s going to die from this.”

Cody Boleyn was 19 when he joined the Coast Guard in 2005 as an avionics electrical technician. The Coast Guard is unique in that its maintainers are also flight crew. You don’t just fix the helicopter. You ride in it. The decisions you make are life and death, which is why Cody struggled when he got to the civilian world and watched people agonize over choices that seemed trivial.

“No one’s going to die from this,” he kept thinking.

After his service, Cody spent a few years in defense contracting, then pivoted to the VA Benefits Administration, where he applied his logistics background to processing veterans’ claims. Helping people who were hurting was fulfilling work. Cody had found his mission.

Then budget cuts happened and “the ability to serve directly at the VBA was impacted,” Cody says, choosing his words carefully. He voluntarily accepted the Deferred Resignation Program while applying to Leavey, which meant he was starting an MBA program for working professionals while suddenly not working. The irony wasn’t lost on him.

Ask Questions. Closed Mouths Don’t Get Fed.

Sam Hickey walked into his undergraduate veteran services office in 2017 with no plan. He’d just moved to Denver with no family and no friends. He knew he had GI Bill benefits but he didn’t know how to be a college student.

“I have no idea how to be a civilian, let alone be a student,” he told the program director.

Conveniently, the director just happened to be hiring, so Sam spent his undergraduate years helping other veterans chart their own courses. He became the Student Veteran Association president, later passing that role to Josh Michael, who followed him in the same business analytics program. When Sam graduated at the height of COVID, nobody was hiring, so he got another master’s and became part-owner of a gym where he’d been working.

“The general manager was a Marine with me in 2009,” Sam explains. “Small world.”

This past weekend, the gym hit its 10-year anniversary. Sam’s been there for eight of them.

He still didn’t know if business school was right for him. But he knew enough to ask.

The Dumbest Person in the Room

Josh Michael always wants to be the dumbest person in the room.

That’s how he chose his Air Force career as an intelligence analyst. He had no idea what the job entailed, but he knew that it correlated with the highest-paying civilian opportunities.

“I didn’t realize I would be going to the NSA for the next eight years,” he says. “Which is a weird thing to say.”

After eight years of military intelligence, including a year at CIA headquarters in Langley, Josh became a civilian. He immediately noticed that people seemed oddly afraid of hierarchy, too tepid to act because they weren’t sure if it was the best direction.

“In my mind, inaction is the worst action of all,” Josh says.

His three brothers all served in the Marines because, as one of them told their Air Force veteran father, they wanted to be “real men.” Josh watched them choose misery and decided he liked air conditioning. He liked the tech side of things. He wasn’t wrong.

Thankfully, the Air Force-to-corporate America transition was easier than most because the structure and decision-making frameworks are similar.

Later, when Sam kept mentioning executive MBA programs, Josh started paying attention. He needed something flexible, and Santa Clara fit the bill. They both applied. They both got in. They both got Yellow Ribbon funding.

“Things just kept working out in our favor,” Josh says.

Leading in Chaos

The first week at Leavey put them through a crisis management scenario. They had to make fast decisions with no clear solutions and work through the given framework.

For Cody, who’d spent years making life-or-death calls in the Coast Guard, it was familiar territory.

“You’re yelling at me? Cool. I’ve been yelled at by the best of them,” he jokes. “What are you gonna do, hurt my feelings? I’m gonna get a B out of this class? Cool.”

But the scenario did something else. It highlighted the ethical responsibilities of managing people, not just profit or strategic advantage.

Cody’s now consulting with startups on government contracts, leveraging his decade-plus of defense experience and his master’s in data science. It’s not the VA work he loved, but it’s service of a different kind. And Leavey’s putting frameworks around instincts he’s always had.

Sam is applying the leadership lessons from his coursework to his gym, rethinking how he manages his team and his co-owners. The strategic management work is showing him expansion possibilities he hadn’t considered.

Josh is learning to lead differently than the military taught him. “Sometimes I’m more in the front than I’m comfortable being,” he admits. “But things need to get done.”

The Yellow Ribbon Program

Kim Day opened Sam’s unfinished application and had questions.

Sam had thrown his name in, unsure whether he was qualified or the right type of person. He expected a perfunctory recruiting call. Instead, he got genuine interest.

“I thought it was just going to be me asking questions,” Sam says. “But Kim had questions for me. I was like, okay, I could see myself here.”

The Yellow Ribbon Program makes it possible. Without it, none of them would be at Santa Clara. In fact, there are currently four veterans in a cohort of 22 students. Not statistically normal.

“I mean, it’s been great so far,” Josh says about Santa Clara’s treatment of veterans. “And I don’t think it’s performative.”

The Jesuit mission of service aligns while the Silicon Valley culture of innovation challenges. The tension between ethics and profit creates useful friction.

“They’re figuring out ways to support us to ensure that we are taken care of,” Sam says. “I feel cared for.”

What Comes Next

Sam is targeting Dolby. He’s a movie nerd, and the Bay Area has Lucasfilm, Skywalker Sound, and Pixar. He doesn’t know exactly where he’ll be in five years, but he knows the world is his oyster right now.

Josh is less certain about the future in an AI-driven world. “If this doesn’t work out in 10 years, I can always become an electrician like my dad,” he smiles.

Cody’s heart is in veteran services. He’s developing AI tools for veterans and partnering with other developers on theirs. He’s consulting and building a network. He wants to get back to the VA eventually.

“I would honestly love just to move back to the VA,” he says. “I know that sounds simple.”

All three of them keep coming back to service. Not the kind with uniforms and deployments, though those shaped them. The kind that happens when you recognize you have capabilities others need and you share them freely.

“Service is a big value of mine,” Sam says. “Which is something I’ve picked up during my time at Leavey. Like, you kind of know what your values are, but it’s really hard to put into words until you sit down and think about it.”

They’re thinking about it now. Between classes every other weekend. Between managing a gym, analyzing mortgage data, and consulting with startups. Between the lives they built in the military and the ones they’re building now.

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