[SOUL POP] Keegan Smith doesn't lack confidence, that's for sure.

It's etched all over his face as he winds through the crowd on the floor of the Bossanova Ballroom, a wireless mic in his hand. Gathered inside this large East Burnside performance space on a Monday night is an audience of about 100 nicely dressed, mostly college-age people. These are not the people keeping Portland weird; if we're being honest, a lot of them probably don't even live in Portland proper. But these are Keegan Smith's people, and they're digging his music.

Dressed in a gray newsboy cap, blue T-shirt and loose-fitting jeans, Smith is singing a slinky cover of Wyclef Jean's "Gone 'Til November," backed by his nine-piece band, the Fam. It is his jammy, energetic originals, however, that receive the best reactions from this crowd. The music might not appeal to everybody, but for those to whom it does appeal—fans of Dave Matthews Band and Jason Mraz, specifically—Smith is a legitimate, homegrown version of the national acts they cough up a whole paycheck to see live, except he's playing down the street, every week, for free.

"These nights are for y'all!" Smith announces from the stage.

Unfortunately for them, there are only a few of those nights left. After seven years of bouncing from one weekly gig to the next, the 35-year-old singer is ready to make the leap from local hero to mainstream star.

"I'm making hits," Smith says while on break from a recording session in Bend. "I'm not trying to make hits."

Like I said, the guy doesn't lack confidence. What he says isn't without merit, though. After graduating from college, Smith, a Portland native, wasn't sure what he wanted to do with his life. He always loved singing, so he learned to play guitar and went full bore at establishing his name around town. On the advice of music-scene veterans, Smith sought out his first weekly residency, an acoustic gig at Tonic Lounge. Over the next few years, he moved from venue to venue—he landed at Bossanova in June when his former home at the Mount Tabor Theater closed temporarily—using his dogged self-promotion skills to simultaneously build his audience, his band and his repertoire practically from scratch. 

The weekly format has its drawbacks, however. Although he's packed the Bagdad and Mission theaters for CD-release shows, Smith says playing the same place each week makes it difficult to draw a crowd to another club on any other night of the week, or to have much time to work on expanding his brand outside the city. So Smith is stepping away, but he's not slowing down. He's got two albums in the works, one more pop-oriented, the other in the eclectic style of his previous discs. He claims to have drawn the attention of Dave Matthews' management company and concert monolith Live Nation. In the next six months, he says, "we're going to explode through the roof.” 

"I've fully succeeded," Smith says of his time doing the weekly circuit. "I can keep succeeding doing this, or I can challenge myself and take a risk." At the moment, however, Smith is ascending a flight of stairs at the corner of Bossanova's stage. Once he's dancing on the platform at the top, he grabs a multicolored light box and points it at himself. The crowd of 100 erupts into cheering.

SEE IT: Keegan Smith and the Fam play the Bossanova Ballroom on Monday, Oct. 3. 9 pm. Free. 21+.