Jacobsen got his start painting pictures of ships on safes, and as his reputation grew, he was asked to do portraits of ships by their owners, captains and crew members, with many of his works sold for five dollars.
Jacobsen begyndte at male billeder af skibe, og i takt med at hans omdømme voksede blev han opsøgt af skibes ejere for at male deres skibe, kaptajner og medlemmer, og mange af hans værker blev solgt for 5 dollars.