This chapter examines startups and entrepreneurship resulting from the innovations of students and faculty as an avenue for University-Industry (UI) engagement. From interviews with innovation leaders at major universities, research institutions, and corporations, we identified programs and collaborations that enable startups and Intellectual Property (IP)-based startups (“spin-outs”) to make the leap from the lab to market and/or stimulate the creation of new startups or entrepreneurial solutions. Overall, we observed that UI collaborations infrequently result in startup formation or direct funding from corporations or their Corporate Venture Capital (CVC) groups. Startup creation and direct support are limited by a variety of well-established structural and market-based forces. There is nevertheless ample opportunity for the collaborations to spur meaningful innovation and entrepreneurship broadly with the potential for startup creation. The value of these collaborations is usually expressed as direct monetary gain (e.g., research funding for the university or enhancements to existing products for industry) as well as experiential knowledge gathering that enhances both stakeholder organizations’ human capital (including students and alumni) and IP assets. Several emerging programmatic initiatives that have shown promising opportunities for successful collaboration are described as food for thought.