During the recent years, scholars have paid a lot of attention to game-based and gamified learning. Although recent studies have offered some mixed results, most scholars believe that gamification increases the student engagement, collaboration, and communication. In our study, we applied gamification to learn skills required to manage a large project portfolio with many simultaneous project and project opportunities. In the empirical part of the study, we investigate post-graduate students’ feedback on the project portfolio management (PPM) workshop using both content and sentiment analysis. The complexity of the human nature makes studies on learning extremely challenging and vulnerable to human errors and biases. To increase the accuracy of our study we applied a machine learning assisted approach and used machine learning both to validate the conceptual framework of our study and to verify the correctness of the manual feedback categorization. The results of the experiment indicate that students’ sentiment towards the PPM workshop was positive, and gamification seems to be a suitable method of learning project business skills. The more detailed analysis revealed that a gamified PPM workshop is a motivating method of learning the creation of the management system for an organization and different kinds of portfolio management tasks like resource allocation, scheduling, and prioritization. Similarly, this kind workshop seems to be a less suitable way to study financial management and especially the customer and supplier network management.