Cowherd grew up in Grayland, Washington and attended Eastern Washington University. He began his career as the play-by-play voice for the Pacific Coast League’s Las Vegas Stars.
He eventually became a sports director at KVBC-TV in Las Vegas, Nevada, where he was named Nevada’s Sportscaster of the Year five times. He also served as sports anchor at WTVT-TV in Tampa, Florida. He moved to Portland, Oregon, in 1996, where he spent nearly two years doing sports talk radio. In 2001, The Herd moved from an afternoon time slot on all-sports radio KFXX to the morning drive time.