Scholars have proposed that taking risks in organizations is important for explaining innovation performance. Scholars traditionally have analyzed this link from two unconnected perspectives. From a managerial perspective, entrepreneurial orientation and leadership theories have been used to explain the positive relation between risk taking and innovation. From an employee perspective, creativity theory suggests that a risk-taking climate helps to explain innovative behaviors. However, there is little empirical research analyzing this link. This study examines the possibility of a connection between managers’ risk-taking propensities, employees’ risk-taking climate, and innovation performance. To do so, we test a quantitative model where the impact of the manager’ risk-taking propensity on innovation is mediated by its effect on employees’ risk-taking climate. Structural equation modeling is used to test the research hypotheses on a data set of 182 firms from the Spanish and Italian ceramic tile industry.