With over a billion monthly active users worldwide, Instagram provides a rich source of thriving communities that individuals are capitalising upon in the pursuit of entrepreneurial endeavours. The focus of this chapter is on these “Instapreneurs”: micro, everyday digital entrepreneurs who engage with and use Instagram as a platform for entrepreneurial activity. We present current debates within the literature, discussing key opportunities and risks associated with Instagram for entrepreneurship. With such a vast and globally distributed user base, Instagram has become a leading platform for brands and individual entrepreneurs to connect with and create digital communities of consumers. Drawing upon a range of case study vignettes from our own research, we explore and illustrate how Instapreneurs develop and deploy a portfolio of digital business models, and subsequently draw out emergent themes. We conclude with directions for future research opportunities to extend and further enhance our understanding of this important and emergent topic.