Part A of the case opens in July of 2009 with Becky Splitt, CEO of StudyBlue, facing a series of difficult decisions. These include: determining the appropriate business model to monetize the StudyBlue site, which customer segment to target, and how much new capital to raise (and from whom). The case tells the story of how StudyBlue was begun as a side project of Chris Klündt and Steve Wallman in 2006 and how it evolved into a full-fledge start-up with seven employees. Over the course of three years, StudyBlue develops a healthy following of college users and adds significant new features and functionality. However, by the close of the case, there is still uncertainly around how quickly it can grow revenue in the future. Given new competitors on the horizon and the window for Series A funding round closing, Splitt must make her decisions quickly. Part B of the case describes Splitt’s decision of choosing a financing partner for StudyBlue’s Series A funding round. She must weigh the benefits and disadvantages of partnering with a mature angel investor group where she would face less restrictive terms than partnering with a venture capital firm but also less money and consequently a shorter operating runway. Her other option is to partner with a venture capital partner which will guarantee savvy advisors, recruiting help and more dollars but also more restrictive terms and a potential requirement to relocate the company from Wisconsin to the west coast. Finally, Part B of the case highlights the many changes in the competitive landscape between 2009 and 2010, including the introduction of two new players and the acquisition of several others by large corporate entities.