The Center for Young Women’s Development (CYWD) in San Francisco, CA, is the Nation’s leading juvenile justice reentry youth-run organization, which focuses on providing gender-specific and peer-based programming for high-risk, low-income young women. During her time as executive director from 1998 through 2005, Ms. Simon more than quadrupled the Center’s budget and expanded their violence prevention programming to include rights education for California’s juvenile offenders and firearm policy reform initiatives. In the interview, Ms. Simon discusses her past as a troubled youth who had dropped out of high school to work at Taco Bell full-time. Her boyfriend dealt drugs and she would hide his drugs and weapons in her backpack so he would not get in trouble. When she was 16 years old she was recruited to work as a youth leader by the CYWD, later becoming co-interim director and eventually in 1998, executive director. Ms. Simon discusses the problems she has witnessed in San Francisco’s disadvantaged neighborhoods and she underscores the importance of challenging and pushing young women to achieve their potential and notes that her decision to transition out of the CYWD is in keeping with the CYWD philosophy of empowering young women to lead. The next executive director will be a young Latina woman who has worked for the CYWD for 8 years.