Dobson began sending demo tapes – recorded on a home karaoke machine – to many recording companies in North America when she was 11 years old. Then at the age of 13 years, she started playing the piano. Before Dobson was signed, she said that she had been stereotyped as a contemporary R&B or popular music singer instead of a rock musician due to her race, often being compared to Brandy Norwood and Britney Spears. Dobson started writing music at the age of 13 years, and the company Jive Records attempted to develop her as a popular musician, which she eventually refused. After that experience, Dobson met Jay Levine and contracted with Nelly Furtado's manager Chris Smith. Smith arranged showcases with several recording companies. Universal Music Canada president Randy Lennox showed interest in her, and persuaded Island Def Jam CEO Lyor Cohen and his manager of A&R, Jeff Fenster, to fly to Toronto for another showcase. Dobson played a showcase for Island/Def Jam; about 30 seconds into the first song – a punk thrash track about longing, titled "Stupid Little Love Song" – the executives contracted her.
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