Donald Trump’s 2016 electoral victory was a shock for feminist scholars, yet it was no surprise to his legion of supporters in alt-right digital spaces. In this essay, we analyze one of the online forums that helped propel Trump to electoral victory. Drawing on social movement concepts and an analysis of 1,762 posts, we show how leaders of the forum the “Red Pill” were able to move a community of adherents from understanding men’s rights as a personal philosophy to political action. This transition was no small endeavor. The Red Pill forum was explicitly apolitical until the summer before the 2016 election. During the election, forum leaders linked the forum’s neoliberal, misogynistic collective identity of alpha masculinity to Trump’s public persona and framed his political ascendance as an opportunity to effectively push back against feminism and get a “real” man into the White House. We argue that while previous research shows the importance of alt-right virtual spaces in creating and maintaining racist collective identities, we know very little about how men conceptualize gender in ways that inform their personal and political action—and this is to our detriment. We conclude the essay by arguing that feminists need to understand how men cultivate extreme personal and political identities in online forums so that we can better understand how new technologies are used to move individuals from the armchair to the streets.