Dropbox is a cloud storage startup founded in 2007 by Drew Houston and Arash Ferdowsi. By 2010, Dropbox had raised $257 million in capital and had 4 million users. Houston faced strategic decisions around product segmentation, targeting enterprise customers, and distribution deals. Key issues included whether to offer multiple products, integrate with other folders, determine business vs personal use, improve analytics, and partner with security firms. The case analyzes Dropbox's history and challenges.