At the tender age of 14, he took his first sea voyage to Nicaragua on the turtling vessel, the Jemson. Due to his young age he was given the nickname "Young Captain" and embarked on numerous other fishing and turtling trips on board the Antaraus and the Wilson, amongst others. As a young adult he gained invaluable experience and joined the bigger fleet tanker companies such as the Southwell and Matyson.
As one can imagine these trips were very lengthy at times and Captain Gleason was away from Cayman for extended periods of time, however, he always maintained a close relationship with his family. Although Captain Gleason enjoyed his voyages, his heart was at home and therefore he returned to assist his wife, the late Mrs. Greta Ebanks, with the rearing of their children.
Being an ambitious and knowledgeable man he established his own boat business catering to the tourism industry by providing Northsound fishing charters and beach lunches. Captain Gleason was also one of the founders of the popular Stingray City, which is enjoyed, by visitors and locals alike!
At the age of 85, Captain Gleason still enjoys the open water and operates his 53 foot boat known as the "Seafire" offering Northsound charters.