He prepared for Princeton at Shady Side Academy in Pittsburgh and at the Taft School in Connecticut. At Princeton he majored in geology, took his meals at Cottage Club, and was a member of the Glee Club and the band. He enlisted in the Navy after Pearl Harbor and trained as a fighter pilot during World War II. The war ended as he was about to be deployed for combat. 

After the war Henry married Elsie Hilliard and joined his family’s business in Pittsburgh. In 1959 he took the reins and transformed the business, the Hillman Co., away from old-line industrial businesses in favor of investments in technology and real estate. Such investments notably included the development of Silicon Valley beginning in 1972. Through the foundations he funded and presided over, Henry and his wife benefitted the Pittsburgh community through generous donations in the fields of science, technology, and medicine. 

He was one of the most successful American businessmen of his generation, and a generous philanthropist to Princeton and others.

Elsie predeceased him in 2015. At the time of Henry’s death, he was survived by his four children, Juliet Lea Hillman Simonds, Audrey Hillman Fisher, Henry L. Hillman Jr., and William T. Hillman ’80; numerous grandchildren, including Talbott L. Simonds ’95; and several great-grandchildren.