Eric Schwarz cofounded Citizen Schools in 1995 to offer Boston students living in low-income communities the opportunity to participate in apprenticeships in a variety of careers. Twenty years later, Citizen Schools has served more than 50,000 mostly middle-school students in seven states coast-to-coast, engaging some 40,000 volunteer "Citizen Teachers" in the process. Schwarz, who retired recently as CEO of Citizen Schools, sat down with Bridgespan Partner Katie Smith Milway to reflect on his Citizen Schools experience and talk about his new venture, College for Social Innovation, which he describes as "something kind of like Citizen Schools but at the college level." This brief report presents highlights from their conversation.