James Forten (1766–1842) was in business in Philadelphia for almost half a century. A sailmaker by trade, he invested the profits from his sail-loft in real estate, bank stock, and shares in various ventures, including railroads. He was also a money-lender. Throughout his long career in business, Forten struggled to be accepted as an astute and successful member of the business community who happened to be a man of color. As this essay demonstrates, that was how some of his white peers saw him. To others, however, he was a man of color first and a man of business second.