Goldberg's father was a San Francisco police and fire commissioner, who encouraged the young Reuben to pursue a career in engineering. Rube graduated from the University of California, Berkeley in 1904 with a degree in Engineering and was hired by the city of San Francisco as an engineer for the Water and Sewers Department. After six months he resigned his position with the city to join the "San Francisco Chronicle" where he became a sports cartoonist. The following year, he took a job with the "San Francisco Bulletin", where he remained until he moved to New York City in 1907, finding employment as a sports cartoonist with the "New York Evening Mail".