A native Omahan, Holland attended the University of Omaha after graduating from Central High School. He majored in chemistry until his studies were interrupted by World War II. Holland served as an officer in the Army Chemical Corps during the war and afterward returned to the university where he decided to major in art. Following graduation, Holland took over the advertising agency his father had started. In 1964 he helped establish the Holland, Dreves, Reilly advertising agency in Omaha. In 1979 he sold his interest in the agency but remained a principal member until he retired in 1985. At that time the agency was the second largest in Omaha. The Hollands have also generously supported the arts, serving in leadership roles with many local arts organizations. The Hollands made the lead gift to the $92 million state-of-the-art performing arts center in downtown Omaha which opened in 2005 and was named in their honor. In 2006, Holland helped establish Building Bright Futures, a comprehensive initiative designed to improve academic performance and encourage community responsibility amongst youth in the Omaha area. He serves as chairman of the executive board.