Wiebe was born in Seattle, Washington to Ryan and Sandy Wiebe, and has a brother, Ryan, and sister, Cathy. He attended Newport High School in Bellevue, Washington. He graduated with a BS in mechanical engineering from the University of Washington in 1991. From 1996 to 1999 he worked at Boeing as a testing and analysis engineer, and from 1999 to 2001 he worked at the Bsquare corporation in Bellevue as a software testing engineer. In 2004 Wiebe earned a Master of Education at City University of Seattle.