Just over a year ago, 38 Mentors from Educate!, an organization that provides youth with skills training in leadership, entrepreneurship and workforce readiness, along with mentorship, to start real businesses at school in Africa, taught their first lessons in over 90 secondary schools across Northern Uganda, a region where they had never before implemented a program. Now, with a year of operation and nearly 4,000 scholars graduating from the region this spring, the organization has identified a few valuable lessons that have strengthened the operations and impact. In this article, the authors share the lessons they have learned from innovating the Educate! model to succeed in this setting, and they feel it can help other organizations looking to expand their reach into challenging environments. To solve the most pressing problems facing youth today, the authors considered it crucially important for education organizations to learn how to innovate and adapt their models to serve the most difficult--and rewarding--situations. The authors share basic information about Educate! and about Northern Uganda, focusing on how they adapted the model to maximize impact within the constraints of this region. They close with the most valuable lessons they learned, which they believe can be applied to a variety of education models looking to scale and innovate in order to serve populations within challenging environments.