At the end of the revolutionary war, he bought large amounts of depreciated Continental currency that was worthless at the time. At the war's end, the U.S. government made good on its notes at one percent of face value, while Massachusetts paid its own notes at par, then he started to export buisness from West Indies and Europe.
Because he was uneducated, which makes things harder for him.
His buisness tactics were peculiar. He sell bed warmers, which is to heat beds in cold places during New England Winters, where h resell it to West Indies, which is a tropical place, then he sell wool mittens at the same place, and somehow he got profit.
People make jokes about him to sell coal at Newcastle, but due to the time there was a demand on that place, it was sold at premium. On another occasion, practical jokers told him he could make money by shipping gloves to the South Sea Islands. His ships arrived there in time to sell the gloves to Portuguese boats on their way to China.
He exported Bibles to East Indies and stray cats to Caribbean islands and made a profit because Eastern missionaries were in need of the Bibles and the Caribbean welcomed a solution to rat infestation. He also hoarded whalebones by mistake, but ended up selling them profitably as corset stays.
Thanks to his fortune he recieved from being a buisness man, he become rich, despite the problems.