Talk held at the Cologne AI and Machine Learning Meetup #CAIML DocCheck is a medical community for health care professionals. Doctors, pharmacists, students and other healthcare professionals use this platform for online learning, to exchange with peers and to actively contribute their expertise. They seek detailed information in the extensive medicine wiki DocCheck Flexikon, read the bi-weekly edition of DocCheck News, share and discuss medical images in the image archive DocCheck Pictures, or buy medical products and supplies in the online shop. Each of our user groups has different intentions and interests: A student might want to learn anatomical topics in some order and a cardiologist is usually interested in different news than a pharmacist. The ultimate goal is to find the most relevant and interesting assets for each target group to enable targeted mailing and feed personalization. At this point, to improve user experience, we provide related content across different media types in a fully automated fashion. For instance starting from a medical text about a specific disease, we want to offer the most relevant related articles but also news, pictures, videos or even products from the online shop. In this talk, we will focus on the websites with the highest click frequency: the medicine wiki Flexikon. We will show how we automatically find related assets using both content based models as well as models derived from user behaviour. Both approaches are backed by machine learning techniques, namely Latent Dirichlet Allocation and Association Rule Learning. We will give some technical details and share insights on the practical aspects and pitfalls.