The “Lean Start-up” Methodology challenges preconceived notions of business model rigidity which have been associated with establishing “brick and mortar” firms, enabling entrepreneurs to adopt a prototyping approach to business model development. This research in progress paper explores the challenges inherent in developing the business model for a social media app; “Huddle” [pseudonym for blind review] through the process of an Action-Case Study Research Method. The study concludes that the challenges associated with developing new IT-enabled business models have not declined, but instead manifest themselves in different forms. Specifically, the key challenges IT-enabled start-up ventures encounter include; (1) understanding the IT fashion and developing an app which is concordant with IT fashion, (2) demonstrating the ability of the app to be “monetised” and (3) mitigating the uncertainty of potential investors through effective communication. Further insights will be determined as the app is developed and released to market.