Starting with Thomas More’s Utopia (1516), the first major Anglophone text reacting to Euro-American colonialism, this chapter traces how Early American texts – such as Walter Ralegh’s Discoverie of Guiana (1596), John Winthrop’s “A Modell of Christian Charity” (1630), and William Byrd II’s History of the Dividing Line (post-1728) – reflect the dizzying complexity of economic exchange in the Atlantic colonies before US independence. As European encounters with Indigenous cultures unsettled long-held assumptions about economic value and English colonies adopted multiple systems of exchange to survive, these texts show their colonial actors improvising to navigate ever-shifting conditions. In doing so, I argue, these actors engage in the kind of intersubjective thought experiments that Adam Smith describes in his social and political theories. While contemporary US culture often imagines Smith ushering America into economic modernity, then, these texts show the vector of influence moving in the opposite direction, with Anglophone New World literature showing, very early, the possibilities and problems of the commercial imagination.