In 1767, Thistlewood purchased a 160-acre plantation, Breadnut Island Pen, where about 30 slaves raised provisions and livestock. That tally declined to 26 three years later, but by 1779, he increased his slave population to 32. By 1782, Thistlewood had 34 slaves, of whom nine were men, 12 women, and 13 underage. Thistlewood lacked the capital to purchase a sugar plantation, 18th-century Jamaica's most lucrative crop. Instead, he settled for a venture that was less prestigious but had the potential to be almost as profitable. Thistlewood hired out slaves during the crop season to larger sugar plantations, while on his land he planted a number of provisions, such as turnips, cabbages, parsley, nutmeg, coconuts, and coffee, which he then sold to the owners of sugar estates.