Weiland is a San Francisco native.  Before becoming a lawyer, Weiland aspired to be an illustrator and went to a high school that specialized in the arts.  However, during his undergraduate studies at University of California, Irvine, his aspirations changed to law.  Upon graduation, Weiland returned to his home in San Francisco, where he earned his law degree from the University of California, College of the Law, San Francisco (formerly Hastings).

After law school, Weiland served as a prosecutor in Tehama County, and subsequently worked as panel counsel at Farmers Insurance where he was responsible for defending civil lawsuits that involved personal injury, premise liability, landlord tenant law, and property law.  Weiland also worked at a law firm that represented public entities, where he gained experience in litigating complex civil actions in federal and state court.  

In his spare time, Weiland likes to keep active by running, hiking and biking.  In the winter, he will often spend his weekends on the mountains snowboarding.