Much has been written on the skills and capabilities of a new generation raised with social media, smartphones, and immediate access to data and information via the Internet. Today's college students grew up using the Internet, where they both generate and consume data. But do incoming college students have the skills necessary to thrive in a digital world that requires the ability to generate, analyze, and share insights from data? This paper presents a study, performed at two small New England institutions each with a business focus, which examines the digital skill sets of first-year college students in relation to the skills they have developed before entering college. The authors also consider whether there is a "digital divide" among first-year college students in relation to their previous technology skills. When applying the Databilities framework for evaluating data literacy competencies, results show that teaching data literacy skills to first-year college students will be critical to their academic success as future information technology workers.