Tom Santiago (aka Owlstallion) moved around a lot as a missionary kid to a single parent mother (Iowa, Florida, Missouri, Arkansas, Mexico, Nicaragua, Haiti, Romania, Austria). After finishing high school, he studied Philosophy and Religious Studies and then went to graduate school for Communication while working in libraries and computer labs before moving to Chicago.

In Chicago he cofounded a band with Tom McGettrick (Mar Caribe) playing rhythm guitar on the first album Songs from Under the Flight Path. He then left Mar Caribe circa 2011 and dabbled with music on a soundcloud account as The Future People of Tomorrow while focusing on his career as a technical writer. He returned to music-making after having stopped smoking cigarettes and developed an interest in synthesizers, samplers, and drum machines and started making and performing music at open mics under the name Owlstallion.

Last year, he collaborated with Anna Soltys co-writing songs which she published via the Rise Up music project. This collaboration was joined by Joey Spilberg leading to the formation of the band Kaima Versus Owlstallion.