This episode explores the impact of artificial intelligence (AI) on the sports betting industry, specifically focusing on its application in enhancing user experience and personalization. The conversation begins with Stephen Taylor-Matthews's account of building and selling his sports betting platform, GoGaming, to Underdog, highlighting the role of cloud technology and strategic partnerships in its success. Against this backdrop, the discussion pivots to the evolving landscape of digital marketing, where AI is reshaping search behavior and SEO strategies, moving away from traditional Google search dominance. More significantly, the conversation delves into the development of AI-powered chatbots for sports betting, exemplified by FanDuel's new chatbot and Taylor-Matthews's own company, Polydate, which aims to simplify the creation of same-game parlays (SGPs). For instance, the chatbot allows users to describe their desired bet in natural language, receiving tailored SGP options in return. In contrast to FanDuel's approach, Polydate focuses on improving the AI technology itself rather than directly integrating it into a sports betting platform. This discussion reveals emerging industry patterns reflected in the significant investments made by major players like DraftKings and Flutter in AI technology, suggesting a future where personalized, AI-driven user experiences will become the norm, potentially widening the gap between large and small operators.