Alec Benjamin has just returned from a headlining European tour, and as the Arizona-bred singer gets comfortable on a couch at the Billboard offices a few weeks before a sold-out show at New York City’s Irving Plaza, he makes a confession. “Recently, I haven’t been that inspired,” the 24-year-old frowns. “I’m a little burnt out.”

You’d sympathize with Benjamin’s running on fumes if you were familiar with his backstory, which goes something like this: he signed to Columbia Records, attended the University of Southern California, got dropped by Columbia, played in parking lots, signed to Atlantic Records, and made it onto the Billboard Hot 100. It’s a neat summary of what he’s been through, but his trajectory is, in fact, a bit more nuanced than that. And the rising singer knows that sharing such details is the difference between an observer mistaking him for yet another cute singer-songwriter fellow with one radio hit, and for them to recognize him as a truly exceptional artist. So he’s okay with admitting he’s creatively stuck, because it’s another difficulty in a long line of those Benjamin has already overcome in his seven-year career — and one gets the feeling that he’ll work this one out, too.

Music didn’t play a major role in Benjamin’s life until toward the end of high school, when he was around seventeen. His parents “weren’t really big into music” while he was growing up, but when he became interested in a girl in high school, he began to learn guitar to impress her. It didn’t turn out the way he’d hoped, but he ended up genuinely enjoying the learning process. Soon, he was learning guitar because he wanted to sing — but he didn’t want to rely on somebody else to accompany him. “It’s the same with writing songs,” he says, noting that while YouTube covers were big at the time, that wasn’t how he wanted to become known. “I didn’t want to have to sing other people’s music, so I needed to learn how to play guitar and write.”

Living with his parents and sister in Phoenix, Arizona, across the street from his grandparents, he reached out to songwriters by email, slowly making connections. Still a teenager, he traveled to Los Angeles and the U.K. to write songs and physically immerse himself in that community, eventually landing a publishing deal (with Warner/Chappell Music) and a record deal (with Columbia Records). The latter didn’t work out. (“I was like, ‘This fucking sucks,’” he recalls of being dropped.)

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