Startup entrepreneurship constitutes the backbone of the socioeconomic activity of any nation and a driver of innovation, industrial diversification and wealth generation, particularly in emerging market settings. Drawing upon narrative storytelling techniques, this case study immerses the reader into the intricacies of entrepreneurial venture creation within the dynamic startup ecosystem in the Middle East. It follows the story of a young serial entrepreneur, Omar, who decided to launch a business in the creative industry of arts in the United Arab Emirates in partnership with his friend, Ahmed. Their common venture, Mont8, showcased and promoted the artwork of budding and well-known Arab talents and was on track to become a recognizable brand in the Middle Eastern business of arts until the COVID-19 crisis shook the world taking everyone by surprise. In an attempt to build a successful post-pandemic future, Omar was convinced that Mont8 needed to fast-track its digital transformation. He envisioned an e-commerce marketplace that would empower Arab artists, designers and photographers to create customized virtual galleries on their own web-stores through the Mont8’s digital platform. Yet, Omar’s vision diverged drastically from the very conservative mindset of Ahmed, who did not want to disrupt tradition and argued in favor of a back-to-business-as-usual approach. It remains unclear whose option would be selected and whether the two partners would stay in this makeover together or rather part ways.