In 1999, Montgomery completed her book Hey Ladies! Tales and Tips for Curious Girls, in which she incorporated a multitude of personal experiences. That same year, she moved to Seattle to host The Buzz on KQBZ radio; the show was a mix of news, local issues, and comedy. Montgomery left Seattle in 2001 to cohost a morning radio show with Ahmet Zappa on the Comedy World Radio Network, The Future With Ahmet & Kennedy, a similar mix of current events and comedy. She later cohosted a morning show with Malibu Dan, The Big House.