For twelve years he worked in various situations, some of the time being "secretary to a gentleman," showing that he had improved his time while in school to be able to hold such a position. In 1836 he had established himself as "a merchant and foreign commercial agent" at 13 Broad Street Buildings. One of the men for whom Mr. Holloway, then thirty-six years old, did business, was Felix Albinolo, an Italian from Turin, who sold leeches and the "St. Come et St. Damien Ointment." Mr. Holloway introduced the Italian to the doctors at St. Thomas's Hospital, who liked the ointment, and gave testimonials in its favor. Mr. Holloway, hoping that he could make some money out of it, prepared an ointment somewhat similar, and announced it for sale, Oct. 15, 1837. He stated in his advertisement in the paper that "Holloway's Family Ointment" had received the commendation of Herbert Mayo, senior surgeon at Middlesex Hospital, Aug. 19, 1837. Albinolo warned the people in the same paper that the surgeon's letter was given in connection with his ointment, the composition of which was a secret. Whether this was true or not, the surgeon made no denial of Mr. Holloway's statement. A year later, as Albinolo could not sell his wares, and was in debt, he was committed to the debtors' prison, and nothing more is known of him or his ointment. There were various reports about the Holloway ointment, and the pills which he soon after added to his stock. It was said that for the making of one or both of these preparations an old German woman had confided her knowledge to Mr. Holloway's mother, and she in turn had told her son. Mr. Holloway as long as he lived had great faith in his medicines, and believed they would sell if they could be brought to the notice of the people. Every day he took his pills and his ointment to the docks to try to interest the captains and passengers sailing to all parts of the world. People, as usual, were indifferent to an unknown man and unknown medicines, and Mr. Holloway went back to his rooms day after day with little money or success. He advertised in the press as much as he was able, indeed, more than he was able; for he got into debt, and, like Albinolo, was thrust into a debtors' prison on White Cross Street. He effected a release by arranging with his creditors, whom he afterwards paid in full, with ten per cent interest, it is said, to such as willingly granted his release.