As far back as he can remember, Sean Gilfillan has had two distinct halves to his personality: a button-down, achievement-oriented practical side, and an artistic, musical side. And while most people with similar dualities accept that the former will most likely pay the bills while the latter is, at best, a hobby, Gilfillan never did. And that refusal has resulted in an unorthodox career path, one that generates income while nurturing his drive to be creative.
Gilfillan continued his family's history of service in the U.S. Army by attending Norwich University on a ROTC scholarship and then accepting a commission as an artillery officer. After going through training at Fort Sill in 2003 he was assigned to the First Armored Division and deployed to Iraq. After two months in-country, he was assigned to A Co., 1/6 Infantry Battalion as their Fire Support Officer.
"I was fire support, but I didn't have much to do with that specialty in central Baghdad," he said. "So I kind of morphed into infantry."
He worked closely with the locals performing what he described as "hybrid civil affairs" in the crucial Korada district. Right as his unit was due to rotate back to the states, they were extended for an additional three months. And the day they were extended seven of his fellow soldiers were killed by a suicide bomber driving a car loaded with explosives.
That loss affected him deeply. "You start questioning the randomness of war," he said. "But at that point, I decided I always wanted to be connected to the military in some way."
After rotating out of the war zone he spent a year in Germany. During that time, he figured he'd done what he'd set out to do as an Army officer, and in 2006 he transitioned to the civilian world and wound up back his hometown in Rhode Island.
"I literally had no idea what I wanted to do beyond something cool in entertainment," he admitted.
Gilfillan went on unemployment for a few months as he hatched a plan, one driven by the attitudes of the civilians with whom he came in contact.
"People were asking me crazy questions about going to war," he said. "And when I answered I could see they couldn't have been less interested."
So, with the encouragement of his new wife Sidney, he did something suitably unorthodox: He launched To The Fallen Records [now To The Fallen Entertainment], "the world's first military record label," as he put it. The name came from a large tattoo he'd had inked across his back a few years before in remembrance of the seven soldiers his unit lost on that tragic day in Iraq.
To The Fallen (TTF) exclusively featured veteran artists, primarily in the hip hop and country genres. The company was featured in Rolling Stone, Billboard, and The New York Times. The word was getting out, and Gilfillan was confident he'd started a viable business.
TTF released a couple of compilation CDs and sold them online. Orders were brisk at first, but then the bottom fell out.
"Turns out 2009 was the absolute worst time to start a record label," Gilfillan said.
Social media and streaming services like Spotify and Pandora were radically changing how consumers purchased music. Nearly overnight CDs became an archaic format.
TTF's distributor went bankrupt, so even if orders came in, Gilfillan had no way to get the CDs out. He was shouldering a massive amount of debt and running out of time.
Help came in the form of a phone call out of the blue from a sergeant major he'd served with in Iraq. The Pentagon had a reserve billet open for a counter-insurgency expert. Gilfillan was qualified by virtue of the civil affairs work he'd done during the war, and he needed the job. He said yes.
Gilfillan worked in the U.S. Army's Asymmetric Warfare Office, learning the government's budgeting process. In the course of doing the job he also learned a lot about how Morale, Welfare, and Recreation works, both good and bad.
From his experience with TTF Records, Gilfillan knew what it took to book top-flight talent. He saw that because there wasn't any centralized way for commands to put their local events together, troops weren't always getting the talent they deserved and the government was paying too much for the acts they were getting.
"Only a few active duty people understand it even though it's a $10 billion industry," he said.
In 2010 Gilfillan left the Pentagon job, and, after consulting with several financial experts, he put his learnings into action as To The Fallen Entertainment.
TTFE pursued two main missions at once: Convincing installations that centralizing the way they booked entertainment would get them higher levels of talent at less cost, and becoming an approved DoD contractor.
The latter happened, and soon thereafter TTFE was contracted to provide the U.S. Marine Corps with 50 shows across the world. Gilfillan landed acts like David Allan Grier, Gabriel Inglesias, Iliza Shlesinger, and Bubba Sparks.
Along the way, TTFE incorporated best practices for the company while doing the same for clients. At the same time, Gilfillan had his eye on bigger deals like the U.S. Army's 5-year entertainment contract.
"We checked all of the boxes to land that contract," Gilfillan said. "Diversity, size, scope -- that's what TTFE's first four years were all about."
TTFE won the Army's contract, and that gave Gilfillan the confidence to hire four employees and set up his headquarters in San Antonio.
"We're still small, but we want to be big," he said. "The trick for us is to simultaneously be trusted insiders and expert outsiders."
Gilfillan's goal is to grow TTFE into a $25-50 million company by proving its worth to more installations, showing how they can gain efficiencies across DoD.
"[DoD] has a massive enterprise advantage," he said. "TTFE wants to help them leverage it."
The future is bright, but in the face of business success, Gilfillan is careful to maintain his focus.
"The sole mission of TTFE is to boost the morale of troops and families on installations," he said. "We want bigger talent and bigger shows for them."
TTFE has now done hundreds of shows across all of the services. Next year the company is launching their "BaseFEST Program" a partnership between TTFE and installations to create what Gilfillan calls "their own unique versions of Coachella."
Gilfillan's advice for veterans transitioning behind him is to think big.
"In your own vision of where you want to be in life it's important to have an end state in mind," he said. "I wanted to be someone who's doing big stuff in the entertainment industry."
As well as a general goal, Gilfillan also says that vets in the process of getting out need to cultivate skills relevant to the industries they're pursuing.
"If you want to go into tech, you have to know how to code," he said.
And more than anything, Gilfillan recommends that vets not give into the fear that comes with leaving the structure of the military.
"I was half a million dollars in debt at one point," he said. "But I succeeded because I was willing to fail."
Editor's Note: To The Fallen Entertainment is proud to present Base*FEST Powered by USAA, a new music festival that launched this Independence Day weekend at Camp Lejeune, North Carolina. It's hitting NAS Pensacola next, and it prides itself on providing a free music festival experience to active duty military, veterans, and their local community.