This report seeks to analyze how paid family/medical leave affected state economies in California and New Jersey, which established paid family leave programs in 2004 and 2009, respectively. The report combines empirical analysis of existing policy with primary sources through interviews with nine business owners of diverse industries and sizes (1–170 employees) within the District of Columbia. These business owners speak to the costs and benefits of the proposed program. Through their responses, we can begin to analyze how the larger business community can manage the changes associated with D.C.’s proposed paid leave policy and maximize its benefits. The interviews highlight both how to manage the cost of the tax that would fund the proposal and how to maintain productivity while employees take leave.