The fourth son of Levi and Fannie Kowalsky, Henry was born in Buffalo, New York on August 16, 1859. His family moved to San Francisco, California in 1866 to join his father who had been living in different areas around the state. The young Henry attended Lincoln Grammar School in San Francisco until his graduation in 1874. His early attempt at business was short lived, selling his paper delivery route after only a few days of operation while still in school.