If you want to land your albums in the bin at Starbucks, you have to be a patient and persistent operator in the music business, please the right listeners, and have fans who fit the corporation’s target demographic. It helps—if only a little—to be a really good musician.

Jamie Kent doesn’t do things like most musicians do them. He wanted his CDs on Starbucks’ shelves, so he walked in and put them there. Kent created a character called Mischief Man, donned a mask, tights and cape, and set forth upon the streets of Manhattan to visit the borough’s 171 Starbucks locations that sold CDs.

In the video documenting that herculean endeavor, you can see Kent’s brazen buddy-system method in action. While Mischief Man talked coffee and, presumably, superhero exploits with the cashier, his co-conspirator dumped a few copies of Neoteny in the bin. Later, to make sure the prank would come to light, Kent or a fan went back to try to buy one.

“They’d keep scanning the SKU number, but it wouldn’t work,” Kent says. “So sometimes they’d call another Starbucks and ask if they carried this Jamie Kent album. And at that point, they did!”

Kent says he half-hoped Starbucks would come after him for his guerrilla tactics, creating controversy and, for him, notoriety. Instead, he says, Starbucks surprised him. They found his exploit funny. It made the company’s quarterly newsletter, and they sold the CDs he’d placed, though no official pickup followed.

Mischief Man might sound like nothing but an amusing gimmick, but Kent doesn’t pursue music-making flippantly. Most everything he does is a well-calculated ploy to get him closer to his goal. That goal isn’t small. Kent already makes a living as a musician, itself a meaningful feat. But he wants to do more than support himself—he wants to make an enduring mark. Thanks to his mix of musical and non-musical skills, he might just do it.

With his band The Options—he also plays solo regularly—Kent delivers his songs with such no-holds-barred energy that it’s almost a mismatch with his primarily acoustic instrumentation. His face contorts; the attack of his vocals propels the tunes with force. He wields his guitar more than strums it.

On stage at Chicopee’s Maximum Capacity, Kent displayed his penchant for mixing old-school jazz into his pop- and country-flavored Americana. Before long, the audience of hipsters belted out “hi de hi de hi de hi” with such conviction it was easy to wonder whether they knew “Minnie the Moocher” was older than most of their grandparents.

Kent says he’s a big believer in the Malcolm Gladwell idea that it takes 10,000 hours of doing something to really master it, and he’s getting there—“I do 200 or so shows per year. I do all kinds of shows—the ones that make me happiest are the ones where people are listening to my songs, waiting to buy a CD.” That, he says, fuels his passion for music-making.

 

Being a good musician is certainly a boost when it comes to making a career out of music, but many is the player who puts in the hours to master an instrument only to find the business of music impenetrable. Kent, on the other hand, made an unusually prescient choice early on: “I went to Babson College to study entrepreneurship. I chose it over Berklee [College of Music].”

Kent says the first couple of years were a bit of a culture shock for someone pursuing music. He found himself studying macroeconomics, not ear training. Though, he says, “I did study voice at New England Conservatory during college.”

Now, thanks in part to his choice of schools, Kent possesses an unusual kind of savvy. His thinking about music as an occupation is refreshing and, often, extremely effective. Only five years out of college, he’s supporting himself in a career that proves permanently unattainable to most who pursue it.

His methods were unorthodox from the beginning. Before the fundraising site Kickstarter became a common route to funding, Kent began a fan organization called The Collective. “It’s a community of fans that invested in my career. In return, they get free tickets, free music, and access to a special section where people can vote on things like where we should tour, album art, even track order on CDs. It’s become a really cool outsourcing to my fans—they’re my advisers as well,” says Kent. “Anybody who contributes gets access. They’re part of it forever.”

Kent says musicians often face a Catch 22. If you can’t afford to live through music alone, you have to get a different job, which means you don’t have time to pursue music with enough persistence to make it a career. “The Collective enabled me to do that,” he says. “I built up enough shows, fans and venue contacts to allow me to focus on music full-time.”

A larger organization sprang from that initial version of the Collective. The Collective Music Group is a group of Northampton-area musicians who work together in pursuit of full-time music careers. Kent runs it with the help of several others, including marketing and media directors. “My end goal is to have a record label that educates musicians on how to manage their own careers and even have the label itself funded through the Collective,” says Kent. “I need to get a lot bigger myself before that happens.”

 

In the meantime, more modest goals are proving attainable. Two annual compilation discs called Valley Rising have appeared, and a third is in the works. “One goal of Valley Rising is to have people share fans. When we do the release show at the Iron Horse, there are 10 bands, and 10 tickets for each band to sell. That way, they all get to play to each other’s fans,” Kent says.

The Collective also played a large role in bringing Northampton musicians to Austin, Texas’ annual South by Southwest music showcase, long a hotbed of music industry talent-scouting. For the 2014 installment last March, some 10,000 people RSVPed the Collective to claim one of the 150 spots available aboard a riverboat that wound its way through Austin with Northampton musicians on board for entertainment.

This summer, members of the Collective along with bands from farther away take part in a summer concert series on the courthouse lawn in Northampton. (Things get started July 18, when the bill includes Roger Salloom and Matthew Szlachetka.)

Though there’s plenty of business to attend to, Kent seems focused strongly on the non-business art of songwriting these days. He’s partnered with others, a process he enjoys. In part, that came courtesy of his winning a songwriting award last January from the music licensing organization ASCAP. The results of that focus are clear in the music. Kent’s sound has evolved from a jazzier brand of acoustic pop to something with unmistakable country overtones. On 2012’s Navigation, the instrumentation included banjo and organ, and the songs range from upbeat, uplifting pop/funk to a more contemplative, acoustic singer/songwriter vibe. The album’s unifying factor is Kent’s rough-hewn but relaxed vocal style.

His most recent release, a five-song EP called Embers and Ashes, sees him searching for the revelatory via an introspective brand of Americana. The songs are markedly different from the sounds on Navigation, and it’s easy to hear that Kent’s going through growing pains, looking at songwriting in a way that’s more careful, less given to the abandon of a moment. There’s a hint of country in the rock on Embers and Ashes, a record that also tips the hat to old-school rock influences like Tom Petty and Bruce Springsteen.

Nashville, Kent says, has crept into his songwriting. It’s a city, he says, that’s proven a good fit for his hard-work aesthetic, and a corner of the music industry that works primarily through relationships. To Kent, that fit makes a lot of sense. He says he doesn’t feel that his natural proclivities lend themselves to the hipster attitudes that often drive the indie rock world, and feels a strong affinity for the rural South thanks to growing up on a former horse farm near Leeds.

Though he’s doggedly practical as a businessman, it’s clear that Kent’s songs are explorations of authentic emotion and longing for something grand. He’s no more immune to the allure of stadiums full of adoring fans than any other young musician. In our conversation, he offers an aside. It’s a quick moment, and the words are delivered almost sheepishly. He mentions people who simply want to make some money with music, and says he, in contrast, “wants to be the next Bruce Springsteen.”

It brings up an interesting question: fast forward 20 years, and where will Kent be? Will Northampton see one of its mainstays go big via Nashville? Will he return to his pop roots? Will he have brought half of Northampton’s musicians along for the ride?

Wherever we find him, it seems clear he will have arrived there thanks to the same bright instincts that brought him to a riverboat in Austin, and to Manhattan in tights.•