In 2001 the "San Francisco Chronicle" characterized DeWolf as "a nationally recognized slam poet". His work has been featured on "60 Minutes", UPN and NPR. He coached the Youth Speaks team twice, one of which was featured on Brave New Voices on HBO hosted by Common and Rosario Dawson. He opened for B. Dolan on the first Church of Love and Ruin tour, for Shane Koyczan, and was featured in 2014 on All Def Poetry with his poem "Rebels Without Applause." He was awarded The East Bay Express Best of the Bay "Best Poet" twice, in both 2012 and 2013.