It was a pleasure to attend Healthy City Design 2024 and join the panel discussing “Learning from the Past: Entrepreneurial Approaches to Delivering Transformative Social Outcomes for Our Poorest Communities.” This session provided a fantastic platform to address systemic challenges, share lessons, and explore innovative solutions to improve outcomes for underserved communities. Reflecting on the discussion, several key themes resonate strongly, particularly the importance of data, trust, and the built environment in shaping transformative change.