Social enterprises have developed a strong presence in business, especially due to the prevalence of a “conscious consumer” mindset. Among many models, the One-for-One model—donating a product for every product sold—has emerged as a key component of several companies. With this model gaining popularity, there is no current research surrounding how the One-for-One structure has evolved in specific settings. This paper aims to fill the knowledge gap by exploring whether external pressures (mainly the general public, impacted communities, and financial stakeholders) have caused an evolution in the model. The research methodology utilizes a qualitative case study analysis of the enterprises Warby Parker and SoapBox Soaps by integrating interviews and archival sources. This paper finds that there has been no significant change in the current One-for-One model, setting up interesting questions about the future of the model and its iterations.