He is best known for developing the best-selling book series Six-Word Memoirs, a literary subgenre that took on a life of its own in popular culture as publications began holding reader contests and publishing the results.

"[2] Smith credits Ernest Hemingway's reputed shortest story, "For sale: baby shoes, never worn", with inspiring the viral literary movement.

In 2004, Smith's then-fiancée, Piper Kerman, served a 13-month sentence at the Federal Correctional Institution, Danbury, Connecticut, the result of a 1998 arrest for drug-related offenses committed about five years prior.

[7][8][9] Kerman later wrote a memoir about the experience, Orange Is the New Black: My Year in a Women's Prison,[10] which was subsequently made into a television show by Netflix productions, in which Smith's homologue ("Larry Bloom") is played by Jason Biggs.

[11] Two years later, Smith's book, Not Quite What I Was Planning: Six-Word Memoirs by Writers Famous and Obscure, co-edited by Rachel Fershleiser, was selected as a Top 100 Editors' Pick by Amazon in 2008 and became a New York Times bestseller.