The inaugural Technology Entrepreneurship Roundtable brought thirty leading tech professionals and entrepreneurs to the Cornell University School of Hotel Administration during the spring 2015 semester. Participants examined the growth of the cloud and the resulting opportunities for entrepreneurs to break into established markets, notably by using mobile devices in remote and shared office spaces, streamlining documents and systems to prevent redundancy, and decreasing operating and switching costs while minimizing the need for established infrastructure. Given the economic flexibility afforded by renting assets, rather than owning them, consumers and entrepreneurs have driven the expansion of the so-called sharing economy. The support of venture capital has been critical for such entrepreneurial technology in the hospitality and travel industry. Technology is also key to the growing customer desire to have a personalized travel experience, which can become a challenge to established brands. Many of these tech-supported enterprises are disruptors that respond to consumers’ desire for options as they travel. To counter the disruptions and re-emphasize their standing, brands need to use market analytics when engaging with customers and to plan for using predictive analytics.