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By the time Avril reached high school, her vocal prowess seemed rivaled only by her ability to play the guitar, and she began sending videotapes of her stage performances to labels and management companies throughout North America. Following a host of rejections, her talent eventually caught the eyes of Nettwerk Management, an organization that fostered other such Canadian acts as Sarah McLachlan, Sum 41 and Barenaked Ladies.
After briefly returning to Canada, Avril made the move to Manhattan to embark on her professional career, accompanied by her older brother Matt as an escort. Although she had been signed to Arista strictly as a vocalist, Avril balked at the notion of singing someone else's songs and insisted on having a hand in the writing process. When she failed to click with any New York-based songwriters, Avril made her third move of the year, this time to Los Angeles.