How does media impact institutional entrepreneurs and their ability to create change? We draw from research on social movements and media frames to examine the paradox that media-informed discursive opportunities pose for institutional entrepreneurs engaged in efforts to transform or create social institutions. Through content analysis of 8473 newspaper articles covering the 2011 Occupy Wall Street movement, we highlight the paradox of discursive opportunities: the same types of media frames that initially encourage more disruptive tactics also subsequently increase the perceived threat of such disruption, thereby encouraging swifter counteraction. Our findings hold implications for the importance of media as a potential catalyst for entrepreneurial activity in the realm of social movements hoping to engage in reform.