There are many key factors that may enable Palestinian youth to succeed or that conversely may hinder their success as entrepreneurs. This research paper discusses the factors and conditions in terms of challenges and opportunities that can impact the youth’s successful engagement in entrepreneurship and their efforts to turn ideas into thriving profit-generating ventures with possible social and environmental benefits. A key question is tackled: What concrete barriers, opportunities and incentives in the form of activities, settings and conditions, including support structures, promote or hinder the realization of early-stage entrepreneurial projects in agriculture, handicrafts and tourism. In answering the question, we take a particular consideration of key influencing factors—that are encountered before or during the startup creation process—that may help boost or diminish the chances of the ventures’ success. We explore these factors from the perspective of entrepreneurs as they navigate their lives and startups in Palestine, a developing country grappling with political conflicts and prolonged military occupation that have resulted in the marginalization of much of the West Bank and Gaza Morrar et al. (Technol Innov Manag Rev 7(10) (2017) 1). This research paper adds to the ongoing discourse regarding entrepreneurship and startups in crisis-prone environments providing a critical discussion with regards to challenges and opportunities that exist for them.