Runs of gains and losses are particularly salient to decision makers because of their perceived departure from randomness, as well as their immediate impact on the financial status of the decision makers. Past research has focused on decision making biases that relate to faulty conceptions of chance and luck, such as the gambler’s fallacy and the hot hand effect. Participants in the current study bet on the outcomes of a long sequence of simulated coin tosses. Risk preferences were found to change as a function of run valence (i.e., losses vs. gains), run length, and financial status. Individuals were found to differ in the effect of all of these factors, in their responses to runs of gains and losses in sequential risky choice.