Year over year, the majority of IT projects fail to deliver the required features on time and budget, costing billions of dollars. The task of portfolio managers is to make a selection of prospective projects, given only rough cost-benefit estimates for them. In this paper, we present LearnIT, a tool to aid portfolio managers in their portfolio selection job. LearnIT identifies past or current IT projects within a large database on the basis of similarity to a given IT project or proposal. Furthermore, LearnIT is capable of being trained with expert user feedback, via example. LearnIT also provides a means for visualizing and making evident any relationships between IT projects in order to help IT managers design templates for future projects thus increasing their success rate.