This episode explores the evolution and future of Duolingo, from its origins as a PhD project focused on making language learning accessible, to its current status as a diversified education app teaching math, music, and soon, chess. Luis von Ahn, co-founder and CEO, discusses the initial problem of learner motivation and how gamification, including short lessons and streaks, became central to Duolingo's success, noting the surprising power of passive-aggressive notifications in re-engaging users. Against the backdrop of debates around ease versus rigor in education, von Ahn argues that motivation is paramount, emphasizing Duolingo's focus on clocking necessary hours through engaging methods, even if it means sacrificing some "flow." More significantly, the conversation pivots to the transformative role of AI, particularly large language models, in content creation and personalized conversation practice, enabling Duolingo to offer a wider range of courses and tutoring-like experiences. As the discussion progresses, von Ahn shares insights into Duolingo's unique brand, driven by internet memes and a willingness to take risks, and how the company leverages its vast user data to optimize learning experiences. Emerging industry patterns reflected in Duolingo's strategy suggest a future where AI-driven personalized education becomes more scalable and accessible, potentially reshaping traditional schooling models.