To increase teacher diversity, a number of states have strategically invested in Grow Your Own (GYO) programs that recruit, support, and prepare underrepresented youth to teach in urban schools. Drawing from a mujerista lens, this qualitative research examines the experiences and perspectives of two homegrown Puerto Rican teachers in Western New York. The findings demonstrate how access to multiple opportunities and support networks positively shape their pathway into teaching. However, although a GYO program played an influential role, existing barriers undermine the systemic development of underrepresented youth for careers in urban education. Recommendations for research and practice are discussed.