Experimentation in the face of uncertainty is a complex system’s answer to the established notions of risk and loss avoidance in the financial arena. Bay and Bäckius are adding to the traditional conceptions of experimentation the notions of mental models and ontology. They argue that experimentation is the creation of something new in the face of uncertainty and risk. The emergent, derived from a set of adjacent possibilities, is allowed to redefine both “that which is” and “the yet to be”. Bay and Bäckius illustrate this with examples drawn from the field of financial derivatives and the Swedish region of Gotland.