Bob attended Bishop Blanchet High School in District 1, and went on to study Political Science at the University of Washington, where his classmates elected him student body president.

After graduating from college, Bob spent a year with the Jesuit Volunteer Corps in Portland, Oregon, running an emergency services office and tutoring children in an inner-city environment. Bob continued his public service and political activity by serving as Executive Director of the King County Democrats from 1991-92.

As a law student at New York University, Bob received a public interest grant to represent Yaqui Indians in Guadalupe, Arizona. He also worked with an organization that assisted Arizona death row inmates with their legal appeals. After graduating from law school, Bob continued his public service by serving as law clerk to Chief Judge W. Fremming Nielsen of the Federal District Court for Eastern Washington and later to Judge Myron Bright of the 8th Circuit Court of Appeals.

Back in Seattle, Bob joined Preston Gates and Ellis as a litigation associate. He gained expertise in local government by representing King County and the Port of Seattle in challenges to Tim Eyman-initiatives.