This paper presents an action-based research study on growing Triple Bottom Line (TBL) small and medium enterprises (SMEs) in Detroit, Michigan. The study was done in collaboration with a business incubator, the Green Garage, and focused on three different businesses within the Green Garage: the Social Club, a hair salon and barbershop; the Hilberry Theatre, a student-run theatre at Wayne State University; and Fresh Corner Café, a fresh food delivery business. While working with these businesses, the team co-created a measurement performance system to improve the sustainability performance. Through working intimately with these businesses, our team came across common characteristics integral to growing a TBL business: transformational leadership, a culture of collective learning, process innovation, and organizational change management. As a result, businesses were able to start performing and tracking sustainable behaviors and processes.