In 1797, a middling Virginia farmer sent his newly married daughter several wedding gifts and a letter. At the end of the latter, he took the time to add, “it is very Auckward to me Sally My Dear, to write letters, but where the transactions of business compell me[;] therefore Accept of this Scrawl.” This paper takes as its starting point this slippage between the economic and the familial – the ease with which eighteenth and nineteenth century men and women employed economic language and metaphors when discussing marriage and family. The title, as such, is slightly misleading in that the paper focuses on the business of family in the eighteenth and nineteenth centuries, It explores families' strategies to secure childrens' financial futures both during courtsip and after marriage, and the limitations of parents' financial investments in chronically struggling children to argue that early American family should be analyzed, in some ways, as businesses.