I first met Jim Greer at the NATO Advanced Study Institute on Syntheses of Instructional Sciences and Computing Science for Effective Instructional Computing Systems in 1990 in Calgary, Canada. It was during this meeting that I came to realize that Jim was one of those rare individuals that could help "translate" computer science principles to non-computer scientists. Through this translation process new knowledge could be developed through interdisciplinary partnerships with psychology and education. In this paper, I describe the manner in which Jim influenced my own journey in the field of Artificial Intelligence and Education. In particular, he has influenced two directions in my research, one direction is the manner in which technology can influence teaching and learning for individuals working solo. The second direction is how technology can influence teaching and learning through collaboration. In both situations I will discuss Jim Greer's influence on my research with respect to learner modelling, educational data mining, and visualization. In the context of solo learning, I will discuss BioWorld, a system that fosters clinical reasoning in medical students, emphasizing the role of student modeling and educational data mining for fostering and identifying performance differences in clinical reasoning. In the context of collaborative learning, I will discuss HOWARD, an online platform for supporting small group problem-based learning in medical students. In particular, I will discuss the role of learning analytics used in a pedagogical dashboard to foster teachers' interpretation of group learning.