Jagriti Yatra is a unique annual train journey spanning 15 days and over 8000 kilometres across India, designed to bring together participants (Yatris) to engage with social innovators and changemakers across diverse sectors. The initiative is grounded in the concept of ‘Middle of the Diamond India’ - a demographic conceptualization of India - through which it seeks to inspire youth from Tier 2 and Tier 3 districts to become job creators and build India through enterprise. Set in 2023, this case reflects on Jagriti Yatra’s 15-year journey and explores the strategic dilemma of whether the initiative should pursue internationalization. Students will learn about how entrepreneurial ecosystems are created on the move and the role of storytelling and role-modeling in it. The case is well-suited for teaching sessions on entrepreneurial ecosystems, rural entrepreneurship, and narrative-driven entrepreneurship.