Although it is well established that top management team (TMT) experience is highly valued in new ventures, research has largely focused on the value of experience depth. However, founding teams often bring a myriad of different types of experience to their business. Less is understood about how these experiences are perceived by key stakeholders, and prior theory suggests that TMT breadth could be viewed as either an asset or a liability. Drawing from theory on cognitive categorization, we hypothesize that the perceived value of executive breadth depends on the context in which a venture is situated. We argue that the characteristics of the environment shape the degree to which experience breadth is valued, and we show that investors assess breadth positively in opportunistic environments but negatively in threatening environments. Contrary to previous research, we show that breadth can, at times, be viewed as a distinct liability for a new venture. In supplementary analyses, we also show that these effects are not contingent upon the depth of the founding team’s experience. Further, we find that founding team breadth does have significant influences on firm strategy, including the structural positioning of the firm in an industry’s value chain and the cultivation of diverse revenue streams, but that the effect of breadth on investor perceptions is not mediated through these differences in strategy.