This essay demonstrates how concepts of financial value, investment, and risk informed the pioneering watercolorist William Trost Richards’s approaches to the medium in the 1870s and 1880s. His earliest watercolor “drawings” were characterized by semi-transparent pigments layered on bright paper—materials and methods thought to embody the luminosity and truth-to-nature that distinguished watercolor from other mediums. Contemporary art dealers, critics, and other promoters eager to grow a commercial market for watercolors as “paintings,” raised in perceived stature, identified these properties as benchmarks of their investment value. In this context, Richards began mailing 3-by-5-inch watercolors he called “coupons”—analogous to the paper chits investors returned for interest payments on bond certificates—to George Whitney, a longstanding patron. These small sample artworks served as “promissory notes,” redeemable in the form of “a better picture.” Foregrounding the speculative nature of this exchange, the coupons motivated Richards to confront the relative precariousness of his paper-based medium, ultimately leading to a series of large-scale experimental watercolors that subverted the very techniques that had underpinned both the material- and truth-value of his earlier work.