Easton, then a newly minted Nashville resident, became an early adopter in the East Nashville arts boom and returned to Alex the Great to record Not Cool. Noticing the desperation of some less-established transplants trying to get noticed, he was determined to not simply make another singer-songwriter record. He collected a troop of Nashville performing vets in Joe Fick, JD Simo and Jon Radford, as well as a couple fellow newcomers, violinist Megan Palmer and guitarist Sadler Vaden. The chemistry was immediate; they blazed through an astonishing six songs on day one of tracking. Not Cool, despite its antithetical-to-Nashville name, was in American Songwriter’s top 50 albums of that year.
