When about sixteen Paul secured employment as a common seaman on a vessel bound for the Gulf of Mexico on a whaling voyage. His next trip took him to the West Indies. On a third voyage, the Revolutionary War having broken out, he was captured by the British and held in New York for three months. On his release he repaired to Westport to engage in agricultural pursuits until the times were more propitious for life on the sea. In the meantime he carried on the study of arithmetic and navigation. Having equipped himself for a life at sea both by study and service as a common seaman, Paul, aided by his brother David, built, at the age of twenty, an open boat to trade with the Connecticut people. But the hazard of the sea and the refugee pirates were too much for David. He left his younger brother and went to the farm, whereupon Paul had for the time being to give up the venture. Soon, however, he was at sea again but lost everything. The undaunted youth, nevertheless, would not give up. He made a boat himself from keel to gunwale, and in it he started to consult his brother concerning future undertaking. On the way he was discovered by the pirates who seized him and his vessel. He was lucky to reach home. He was now no better off than when he first began. David, however, agreed to build a boat for him if he would furnish the material. When the boat was completed Paul, with borrowed money, bought a cargo and started for Nantucket. On the way he was chased by the pirates and compelled to return to Westport to refit his boat which was damaged by striking a rock. He still persevered, reached Nantucket, and sold his cargo. Financially it was not a profitable voyage. On a second voyage the pirates robbed him of his cargo and inflicted personal injuries, but a third voyage netted good returns. Soon he procured a covered boat and employed a helper. From now on the business adventures of Cuffe brought him large profits. The war was over and the new Constitution was in operation--two reasons why the sea was safer and business more promising. With his new eighteen ton boat he sailed from his rented home on the Westport River for Saint George for a cargo of codfish. The voyage was the foundation for a profitable fishing industry near his home for many years. At this time Michael Wainer, his brother-in-law, an Indian, entered his service. His brother-in-law was a good seaman and with a new twenty ton vessel, the _Sunfish_, the men made two trips to the Strait of Belle Isle and Newfoundland. With the profits from the ventures he built in connection with another person, the _Mary_, a forty-two ton schooner.