He gave up the voyage to Calcutta, sold the Spanish dollars and loaded with coffee and spices for Salem.

At the Cape of Good Hope, however, he discovered that he could earn a pretty penny by sending his cargo home in other ships and loading the Benjamin again for Mauritius.
When, at length, he arrived in Salem harbor, after nineteen months away, his enterprises had reaped a hundred per cent for Elias Hasket Derby and his own share was the snug little fortune of four thousand dollars.

Part of this he, of course, invested at sea, and at twenty-two he was part owner of the Betsy, East Indiaman, and on the road to independence.
As second mate in the Benjamin had sailed Richard Cleveland, another matured mariner of nineteen, who crowded into one life an Odyssey of adventure noteworthy even in that era and who had the knack of writing about it with rare skill and spirit.

In 1797, when twenty-three years old, he was master of the bark Enterprise bound from Salem to Mocha for coffee.

The voyage was abandoned at Havre and he sent the mate home with the ship, deciding to remain abroad and gamble for himself with the chances of the sea.