I sat down with Scott Shepard, an award-winning urban planner, entrepreneur, and thought leader at the intersection of AI, urbanism, mobility, and decarbonisation. We explored the evolving role of urban planning in mobility, the rise of SUMP (Sustainable Urban Mobility Plan) and the impact of micrologistics on city infrastructure. Scott shared insights on venture capital trends shaping mobility innovation and the stark contrasts between European and US investment landscapes. We delved into AI's growing influence, from large language models to autonomous mobility, and debated Europe's positioning in the new geopolitical climate. With reflections on smart city development, and the lessons Europe can draw from history and current global developments, this conversation provides fresh perspectives for future of cities-first thinking.