I ran the online classics publication Eidolon from 2015 to 2020. Eidolon sought to make Classics “personal and political, feminist and fun,” publishing more than 500 articles and receiving 3 million total views in its five years of active existence. Because our editors (and many of our writers) were scholars who grew up consuming and producing digital content, we were able to bring a measure of academic rigor and methodology to inform urgent personal and timely essays. Eidolon’s position as both insiders and outsiders to the discipline of Classics made it uniquely suited to address some of the most challenging and necessary conversations facing the field, from white supremacist classical appropriation online to sexual harassment and racial discrimination within the discipline. But the lack of institutional support that allowed total freedom also made the publication vulnerable and contributed to its closure in late 2020. It’s wonderful to have fans, but a publication also needs champions. I argue that, for an online publication to be exciting and fresh but also resilient, it must maintain a delicate balance between fearlessly commenting on the most pressing issues of the day (without, perhaps, waiting for the temporal distance and perspective that academics usually prefer!) while still cultivating the institutional support necessary to weather inevitable challenges. And, most importantly, you need to have fun while doing it.