Wiebe was born in Seattle, Washington to Ryan and Sandy Wiebe, and has a brother, Ryan Wiebe, and sister, Cathy Lowell. He attended Newport High School in Bellevue, Washington. He played for the school's basketball and baseball teams and also played the drums for the school's symphonic and jazz bands. Wiebe graduated with a Bachelor of Science degree 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 degree at City University of Seattle.