This case study analyzes the various facets of the business’s road history, encompassing strategic issues and challenges within the Canadian solo acts market, and combines both primary and secondary sources.The primary data source is a semistructured interview with one of the co-founders of Dropout Entertainment, Jesse Read, conducted on May 7, 2025. The authors intended the interview to serve as a qualitative exploration of the company, its business model, the Canadian Independent Music Video Awards (CIMVA) award and the intricacies of operating and funding a creative venture. Several follow-up emails discussed sponsorship challenges, market diversity and other market issues.Secondary resources comprise public documents from the firm’s website and its social media and YouTube accounts. Other documents reviewed included industry reports, market data and grant documents from the Mississauga Arts Fund, the Canada Council for the Arts and factor. Furthermore, Canadian music media and independent press were reviewed.To incorporate a theoretical model, an examination of peer-reviewed literature and public case studies focusing on independent media, cultural entrepreneurship and the diversity of the creative industry was conducted. Where firm-level data were unavailable, reasonable estimates were developed based on founder input and publicly available information.All information reflects the situation as of the second quarter of the year 2025. The case was also developed with the founder’s knowledge and cooperation and was subsequently versioned and peer-reviewed as suitable for teaching and learning.
In 2015, Jesse Read ventured into the music industry landscape, working from Toronto, Canada, to create Dropout Entertainment, the first hybrid studio with music promotion capabilities. Their 2024 case focuses on the CIMVAs and additional content offerings that have led to niche expansion. The firm has strategically grown but now faces several challenges related to inclusivity, financial sustainability and growth. The case firm has also received substantial negative media attention due to the lack of diversity initiatives, including the closing of the Indigenous category. Read’s long-standing (and unchallenged) role as lead strategist has resulted in founder dependency. The firm is in a unique position to break the “glass cliff” culture. The case showcases very real strategic tensions: how to encourage the growth of a socially driven “grassroots” venture. As part of the Strategy and Entrepreneurship classes, the case highlights tensions in mission-led initiatives and industry challenges, including market fragmentation, systemic opposition and the lack of founder-led responsiveness (Barney, 1991; Music Canada, 2023; Noel, 2023).
This case study is designed for use in graduate and senior undergraduate courses focused on strategy, entrepreneurship and management in creative or mission-driven industries.
