The Penniman story starts with H.W.H. - dubbed "Hardly Waist High" and "Hard Working Harry" (the latter being more descriptive). Penniman, who came to California in 1895 from Florida, enrolled in the Vander Nailen School of Engineering in San Francisco, where he qualified as a civil engineer.

Penniman came to Santa Cruz in 1900 and opened offices on Pacific Avenue. In 1904 he associated himself with the firm of H.E. Makinney, Abstractors, which later became Makinney and Dake.

When one of the employees left Makinney and Dake to form his own abstract company, the remaining employees were required to agree not to enter the abstract business in Santa Cruz as long as either partner was alive. The last partner died in 1914. That same year Penniman entered the title business as "H.W.H. Penniman, searcher of Records."

In 1925 the name of the company was changed to Penniman Santa Cruz County Title Company, with H.W.H. as sole proprietor. That year George, his oldest son, joined the staff.

New quarters were needed in 1930, and that year a partnership was formed by his widow and two sons. In 1940, with sons George and Warren as stockholders, Penniman Title Company was formed to serve as a trustee under a deed of trust. The partnership was continued as the Penniman Santa Cruz Title Company.

The first branch office was established at Watsonville in 1952. To keep pace with the continued growth of Santa Cruz County, a second branch office was opened in 1964 at Felton in the San Lorenzo Valley.

In 1989, the Loma Prieta earthquake caused so much damage, Penniman Title Company eventually closed its doors in November 1991. A majority of the employees immediately went to work for Santa Cruz Title Company. Soon thereafter, Santa Cruz Title acquired use and control of the "Penniman Title Plant".