In this talk, I'll give a tour through 14 years of my research exploring how interactive machine learning can facilitate new approaches designing new musical instruments and other realtime interactions. I'll describe how tools like Wekinator, Sound Control, and InteractML have been used to make new music and creative experiences. I'll also discuss the research discoveries arising from the design and use of these tools, suggesting new ways of thinking about data and machine learning as creative tool, new approaches to supporting personalisation and accessibility, and new perspectives on making machine learning usable and useful for more people.