in 2000, lopresti hired producer and interscope a&r executive, michael james, to be executive producer of her first release under her new indie label, "say it records". the debut album and title track, "dear mr. penis head", was inspired by a phone call lopresti had with an entertainment attorney who used 30 minutes of the phone call to list the numerous reasons he believed she should quit making music. "dear mr. penis head" caught the attention of indie music pioneer, ani difranco, who called the album one of her favorites of the year.