In this special edition of Artivate built around the expanded field of arts entrepreneurship, guest editors Adrienne Callander and Johanna K. Taylor collect scholars’ research on ideas they see as both central and pivotal in driving the field forward. In a futurecasting glossary, past, present, and future Artivate editors gather their thinking around such ideas, exploring where and how arts entrepreneurship currently happens beyond expected models. The three articles contained in this issue explore arts entrepreneurship’s overlaps from policy to activism to philanthropy through new adaptable organizational modeling. Starting with an in-depth analysis of hybrid practice as a mode of institutional entrepreneurship, the conversation turns to a view on artist activism as a form of arts entrepreneurship, followed by a case study of the Maniobra program of cultural employment supporting artists. To culminate in this issue’s galleries, an artist showcase profiles participating artists in the Maniobra program.