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Il acheta aussi un grand nombre de terrains, tint un magasin, et « mit sur pied un commerce assez important, [qui consistait à] échange[r] des produits contre du poisson et des fourrures. Il expédiait son poisson surtout aux Antilles – une certaine quantité allait dans les ports de la Méditerranée et aux Açores – [et les navires] revenaient chargés de marchandises. » De plus, il construisit et acheta des bateaux ; ses fils, dont deux périrent en mer, en étaient les capitaines.
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Although Canso had been the most important fishing post in the province until the middle of the 18th century, by the first decade of the 19th century it was hardly a shadow of its former self: it contained only five households in 1810. Thrust into the North Atlantic, it was isolated and lonely for months of the year. Despite establishing a business in Canso, Whitman did not immediately move his family there, preferring to winter in Chester until the War of 1812, “with its attendant privateers, reduced communication extremely dangerous.” When he moved his family to Canso in December 1812 or January 1813, his split with Chester was complete, since he left power of attorney to sell all his property there. His business in Canso consisted of “fitting out fishing vessels and selling the cargoes brought home from the Banks.” He also purchased large quantities of land, had a store, and “built up a business of considerable volume, exchanging merchandise for fish and fur. He shipped his fish principally to the West Indies – some to the Mediterranean ports and the Azores – bringing back return cargoes.” He also built and bought ships, which were sailed by his sons, two of whom were lost at sea.
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