[9] Jimmy Neil Smith, the founder of the National Storytelling Festival (and the National Association for the Preservation and Perpetuation,[10] which would later become the International Storytelling Center), refers to DeSpain as “a pioneer of the American renaissance in storytelling.” After visiting 36 countries, DeSpain chose Thailand – "the land of smiles" – as his home base in 2017.

[9] In 1966 DeSpain started his educational career as a Speech Communication and Oral Literature instructor at the University of Massachusetts in Amherst.

[1] While sitting on a beach in Mexico at age 25, DeSpain decided that storytelling would be his life's work.

Pleasant worked as a house painter, short-order cook and dishwasher during the first five years as he followed his muse, but his trials were rewarded.

'"[7] In addition to oral storytelling at local venues, he wrote a weekly column featuring a wide range of stories for The Seattle Times.

During his storytelling career, DeSpain has traveled the world gathering traditional and true stories, and performed them along the way for audiences of all ages.

Audiences are an essential component in his art, and DeSpain says, “Three elements – story, listener, teller – must come together as one during the experience.”[9] In all of his stories, DeSpain delivers one central message: “My main force in the telling and the writing is to point out in an entertaining way that we human beings are far more alike than we are different, no matter the culture, the time, the language, or the religion.”[9] DeSpain is also enthusiastic about sharing the art of storytelling, and often follows up his school performances by teaching children how to tell their own stories.