In 1849 he went to work as a bookkeeper for Amos J. Williamson, the publisher of the New York Dispatch, a weekly newspaper.
Street teamed up with Francis Shubael Smith, then an editor at the Dispatch in 1855 when they bought a failing magazine together.
Jacob left Canada to travel back to England in 1858–1860, and then he went to New York City where he stayed with his cousin Francis Scott Street.
He was suffering from liver disease for several years but died from a cerebral hemorrhage at his home at 137 Bedford Avenue in Brooklyn.
He was buried in Green-Wood Cemetery in Brooklyn, New York in a coffin of red cedar with gold trimmings.