More than two-dozen industry leaders met in Ithaca in April 2016 for the second annual Technology Entrepreneurship Roundtable hosted by the Center for Hospitality Research (CHR) at Cornell University’s School of Hotel Administration (SHA). Participants focused discussions on integrating the latest software and hardware with the personal touch that is integral to hospitality and identifying the different preferences among younger and older consumers, among other topics. The gathering included corporate professionals, entrepreneurs, SHA students, and Cornell University’s 2016 Entrepreneur of the Year, Leland Pillsbury of Thayer Lodging Group. The wide-ranging discussion kicked off with an evaluation of cloud computing, which now gives consumers a strong and influential voice, and an overview of the important role social media plays in connecting businesses with their customers. Other issues addressed included the importance of customizing technology, such as digital room keys, based on generational preferences, weighing the use of in-house staff versus outside contractors in rolling out and maintaining new operations systems, new online marketing strategies and the need to adapt to a rapidly changing business environment, and using technology to enhance, rather than reduce, connections among staff and management.