The Connecticut History Online (CHO) project began as a collaboration between three institutions to digitize and provide online access to items from their collections. Over time, the goals expanded to include more partner institutions and a wider range of materials. While grants provided initial funding, sustainability has been an ongoing challenge requiring the addition of new partners, permanent staff, and a nonprofit structure. Lessons learned include the importance of long-term funding commitments, allowing time for new partners to join, and having some partners take leadership roles to serve the broader group's interests.