Gambling on prize-fights was one cause of his financial problems. He may have spent at least some months in debtors' prisons. He wrote frequently for the popular press in London on boxing and music. He wrote comic operas for the London stage, and four of these were produced between 1823 and 1833. His copyright for "Hebrew Melodies" ought to have brought him income – at one point he sold it to his married sister, presumably to avoid it being lost in bankruptcy – but it became involved in complex legal disputes. He attempted a publishing business in partnership with his brother Barnett Nathan, who later became proprietor of Rosherville Gardens. Nathan published a history of music (1823), dedicated by permission to King George IV, which shows in its treatment of Jewish music a great deal of understanding of the Bible and of Jewish traditions.