Sara Bareilles

“I had a happy upbringing and I had a happy childhood,” Bareilles told Pollstar. “And I’ve always felt very close to my emotions but it wasn’t because I felt like I was ostracized or that I was an outcast in any way. … I feel that I was lucky in a sense of not having any craziness growing up.”

Bareilles, whose mix of jazz, soul and pop on vocals and piano has been compared to Norah Jones and Fiona Apple, explained that “to a certain extent, I was very innocent and pretty naïve about most things in the world. … I kind of had a childlike view on things for a very long time. And I think it just made it very easy to play… to have an active imagination and feel creative – and never really second-guess myself for that.”

Her sincerity has tumbled over into her lyrics and translated into an amazing stage presence.

“She’s really humble and that comes across on stage, how thankful she is even to have people listening politely to her music. She just makes you feel very comfortable,” Jordan Feldstein of Career Artist Management told Pollstar. “It doesn’t feel like there’s a star on stage; she makes you feel like you’re sitting in her living room.”

Paradigm’s Marty Diamond echoed Feldstein’s thoughts. He said that when he first started talking to her A&R person, she played a private concert for him at his New York apartment.

“I was sold from that moment on. She’s breathtaking,” Diamond told Pollstar. “She has an incredible voice and you can tell she’s singing from the heart. You get that she takes ownership of everything she sings. I feel like she sings to me and not at me.

“She can create intimacy no matter what size room it is and she can connect fan by fan. That’s an art form that you don’t see in a lot of artists. She connects to everyone.”

While connecting with fans has come easy for Bareilles, breaking into the biz wasn’t so simple and despite misconceptions, success didn’t come overnight.

Her hit single, “Love Song,” the story of her struggle to keep her artistic integrity intact while working with a major label, quickly climbed to the top five on the charts after being a limited-time, iTunes giveaway and being featured in a commercial for Rhapsody. But Bareilles spent years playing gigs before putting together her team and signing with Epic Records.

While waitressing and attending UCLA as a communications major, Bareilles started playing open mic nights, which led to small clubs. After playing shows for three or four years, she met Feldstein in 2004 through Maroon 5, members of which she went to school with.

“I had met with multiple managers at that time and Jordan was actually the only one that was really showing me how hard he works, bringing opportunities and bringing ideas and input,” Bareilles said. “He’s a really smart manager and he’s a proof is in the pudding kind of guy. He’s not all talk. He won’t say things unless he can back it up.

“My manager helped facilitate moving into more of the industry world but it was very slowly but surely. Lots of little steps and a lot of road warrioring.” In 2005 Bareilles signed with Epic and her debut major label album, Little Voice, was released last year. Before that she issued two demos and the indie album Careful Confessions in 2004.

Bareilles said she was “elated” when she got to the point where she could quit waitressing and exclusively pursue songwriting and performing.

“I was so proud of the fact that I had sort of achieved the option to not work if I didn’t want to. … It felt like such a privilege, an honor to get to a place where I could actually call myself a musician as my full-time career. It was a really cool moment.”

Bareilles said the audience plays a part in her songwriting.

“Live performance for me is at the heart of everything. I think that it’s the completion of the songwriting process where you create a song and then the other half of it is sharing that song with someone as an audience member. It closes the circle.

“I absolutely love live performance. I love the energy of the crowd. I love that there’s total inconsistency with the way you feel about performing and there’s nothing static about it. It’s very fluid. It has a life of its own.”

Feldstein said that as far as touring goes, “The key now is to really balance between headlining and … continuing to get her in front of more and more people [as support] because it works. When she plays in front of people she converts them into Sara Bareilles fans.”

Bareilles will head out for a run of headlining club dates and plans to support the Counting Crows and Maroon 5 tour July 25th through August 26th. Feldstein said in the fall she’ll be back for more headlining dates. In addition she’s about to make her first U.K. trip with a follow-up to Europe in June and then it’s on to Australia and Asia.

“She’s a career artist. This is the beginning of a very long and fruitful career,” Diamond said. –