Roskowe was born on August 5th, 1980 in Robbinsdale, Minnesota, USA. He grew up in Minneapolis until he was 15 years old. He then moved to Winnipeg to attend high school and lived with his sister. At the age of 19, he moved back to Minneapolis and went to the University of Minnesota for a few years, then he started having issues with his mental health. He then moved back to Winnipeg in 2002. He joined the army and went to the University of Winnipeg, but that didn't work out, because he got sick with schizophrenia when he was in his late 20's.
From 2008 to 2010, he was in and out of hospitals. He went through the Artbeat Studio program and has been making art ever since. He wrote a couple of books and intends to continue writing. He paints and does other artsty things. He likes Tegan and Sara and really likes other musicians. He has a couple of songs on iTunes himself. Roskowe is really into concerts. Now, at 38, Roskowe has had quite a few art shows in Winnipeg and is looking to have more in the future. You might see him on occasion hanging out at Studio Central in downtown Winnipeg.