Online teacherpreneurs are K-12 classroom teachers who engage in educational entrepreneurship, sharing their teaching ideas and resources virtually, through online marketplaces such as TeachersPayTeachers.com. A common practice among online teacherpreneurs is to collaborate virtually in private social media networks, where they build professional and personal relationships with teacherpreneur peers. This study explored one such group, Spanish Teachers on Teachers Pay Teachers, a Facebook group of 40 K-12 Spanish teacherpreneurs who interacted on a daily basis with the expressed goal of improving their businesses. An analysis of group members' open and closed-ended survey responses (n = 25) indicated that this collaboration was an active community of practice, where participants negotiated relationships and learned together. The community fostered a cycle of continual engagement where teacherpreneurs felt emotionally supported and empowered by one another to realize new achievements in entrepreneurship as well as teaching practice. Online teacherpreneurship and the virtual collaborations it inspires may represent a unique, grass-roots opportunity for teachers to positively impact K-12 education.