Abstract Why has the creation of technology start-ups in Nairobi remained so challenging—despite support from growing numbers of motivated entrepreneurs, innovation hubs, and interested seed-capital investors? We took an in-depth look at a case study in Nairobi and discovered that because of technology entrepreneurship’s relative novelty, the key actors’ perspectives on the processes and practices associated with it are not yet aligned. The results were that the actors’ social interactions are marked by contradictions, divergences, and ambiguities that have hampered the creation of successful technology businesses in region. In this chapter, we will explore the challenges faced by today’s new forms of entrepreneurial activity in Kenya—and how to overcome them.