Pierson was born in Phoenix, Arizona. Pierson attended Mountain Pointe High School, where he started acting and performing in a short-form improv group. He went on to attend NYU, joining the sketch comedy group Hammerkatz NYU in the fall of 2003. He worked as both assistant director and director during his 3-year tenure with the group. Pierson graduated from NYU's Dramatic Writing Department in 2007 with a degree in writing for television. He also made three brief appearances on NBC's Community, on which his Derrick Comedy co-star Donald Glover plays a main character, as a Greendale Gazette member.
Career
Derrick Comedy
Pierson, along with other Hammerkatz alumni Donald Glover, Dominic Dierkes and Dan Eckman, formed the group Derrick Comedy after meeting at NYU. Pierson is both one of the principal actors and writers for Derrick Comedy. Derrick Comedy has performed as an improvisational comedy group at the UCB Theatre in New York, but are best known for their sketches that appear on YouTube and CollegeHumor. Pierson has played roles including an emo teenager and a man making a plea to the Godfather. Pierson co-wrote Derrick Comedy's first feature-length film, Mystery Team, in which he also plays a self-described boy genius named Duncan.
Other works
On January 21, 2010, Pierson's first novel, The Boy Who Couldn't Sleep and Never Had To, was released on Random House. The story follows two high school students who are social outcasts. When one of the students, Eric, reveals that he never sleeps, the two boys end up on the run. His book came to a broad audience when he personally answered a high school student's questions regarding the work on Yahoo! Answers on August 13, 2012. On the page, the student asked for help in reviewing the book, a task which had been assigned to her by her teacher. She stated that lack of time, among other things, caused her to be unable to read the book. The author's reply to the student was first recognized by Techcrunch, and this coverage helped encourage more users to buy and read his book. One of Pierson's primary influences for his novel was the late J.D. Salinger. He is currently working on turning the book into a film, which will be directed by Dan Eckman. Pierson's second novel, Crap Kingdom, was released in 2013. Childish Gambino is the rap moniker of his fellow Derrick Comedy member, Donald Glover. Pierson was featured on both of Childish Gambino's "I Am Just a Rapper" mixtapes, contributing verses to three different songs, "49ers ", "The Truth ", and "Different ". Pierson along with Nick Packard was also featured on Childish Gambino's "Assassins" from the 2008 Album "Sick Boi". He was also featured along with Amber Petty on Childish Gambino's "Starlight" from the 2009 album Poindexter. He is also credited with the story told during "That Power" on Childish Gambino's Camp. In 2014, Pierson had a brief cameo in as Appletech support.