Afterschool math hours are most often spent on homework help, tutoring, drill, and test-preparation with instructors who may not be certified teachers or mathematics educators. While such "extra math help" may be of value, it is unreasonable to expect students to enjoy learning experiences based on workbook-style exercises. The In Addition project, a program of New York University's Steinhardt School of Education, re-envisions afterschool math, which seeks to engage children in learning mathematics that is about curiosity, questions, and intrigue, incorporating inquiry-based mathematical learning into the urban community. This paper reflects on the program's founding principles and on what the authors have learned in their first year of implementation: how they worked to shape their daily practice around inquiry-based math learning in the context of the urban community and the pitfalls encountered along the way.