Cyberinfrastructure, the integrated framework of enabling information and computational technologies, experts, and tools, has emerged as a foundation for applications in the Information Age. The vision of Cyberinfrastructure is powerful and important, yet designing, building, deploying, evaluating, and funding capable, useful, and usable Cyberinfrastructure is a an immense challenge. In this talk, San Diego Supercomputer Center Director Fran Berman discusses the challenges and opportunities of building and deploying Cyberinfrastructure as a continuous bootstrapping process that furthers both scientific progress and technology capability.