Street vending business is important for the economy and the livelihood of the poor less educated people in developing countries, as it provides employment, and a means for survival. However, street vendors face a number of challenges, including low levels of education. The main objective of this study was to explore street vendors’ business activities, skills, and strategies in order to propose mobile technology based solutions to improve street vendors’ business prospects. A qualitative data consisting of interviews and focus group discussions was collected from a total of 39 street vendors in Dar es Salaam, which is the economic hub of Tanzania. The data was analyzed using qualitative content analysis, by identifying relevant themes in the data. The findings show that street vendors operate in a challenging environment and have to employ a number of additional activities and strategies as compared to formal businesses. These activities require risk identification and risk alleviation skills and strategies, and ways to deal with various kinds of uncertainty. It was found that street vendors possess low levels of business skills in all domains of business. To improve street vendors’ business prospects, a number of mobile-technology based applications can be developed in the future.