Last month, we had the chance to immerse ourselves among Charlottesville, VA's leading civic organizers, entrepreneurs, tech innovators, and futurist visionaries at the 2018 Tom Tom Founders Festival. As a co-sponsor of the Festival's Applied Machine Learning Summit, our team at Capital One wanted to do more than just talk about machine learning -- we sought to create an interactive experience showcasing a real-live example of the technology in an engaging, participatory way, while also highlighting some of the area's amazing local artists. A central theme of Tom Tom is "learn[ing] to see your world in a new way." We took inspiration from that ethos to create a pop-up art gallery that would further explore the idea of viewing the world from a new perspective, powered by a machine learning technique called style transfer. Enter our Style Transfer Gallery, where festival participants were invited to have their picture taken, which was then superimposed into the style and technique of each featured artist -- Laura Wooten, Theodore Taylor, Shannon Wright, and Brandon Robertson -- and projected among an array of digital screens.