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This study explores African initiatives in the small scale business sector within Kisii town and the larger region of Gusiiland in the period from 1930 to 1978. Despite the transition to a market economy with the onset of colonial rule at the end of 19th Century, African participation in trading activities within Kisii town and other market centers had remained minimal up to 1930. The slow integration of Gusiiland into mainstream colonial economic production before the 1930s was mainly attributed to its relative geographical isolation from major centers of economic production in Kenya together with the violent nature that characterized initial Gusii contact with colonial rule. Thus although Gusiiland had a good climate conducive for the promotion of commodity production and profitable exchange systems, the Gusii economy continued to be preponderantly characterized by subsistence forms of production as the local people took time to acquaint themselves with the western market economy. However, the accelerated commercialization of commodity production from the early 1930s and the penetration of the money economy transformed many Gusii households into consumers of western merchandise. Thus previous exchange systems such as barter and livestock trade which had remained uncompetitive within the colonial system, (that favored Asian and European merchants), were now rapidly transformed as Africans actively participated in such areas as produce, livestock and general merchandise trade. The expansion of economic space particularly after 1930, which was well augmented with encouraging state policy in support of African trading activities, were key factors that contributed to the rapid expansion of African entrepreneurship in Kisii town and the rest of Gusiiland. These experiences were further accelerated after 1963 when the state adopted the policies of Africanization which deliberately employed a legal framework to advantage the local people in commerce over non-indigenous communities such as the Asians and Europeans. This study has therefore focused on Gusii experiences under this economic system put in place by the colonial regime and continued into the independence period. It is revealed that as from the late 1920s the Gusii society rapidly adjusted to the western market. By the mid 1930s a significant proportion of the local population had began to show increased interest in emerging opportunities in the commercial sector either as partnerships or sole proprietorships, opened businesses that ranged from the small dukas selling a wide range of commodities needed by the local people, produce trade, maize milling, livestock trade and others. However, even with these significant inroads into the commercial sector, African traders were still uncompetitive against Asian traders most of whom had larger networks that transcended both the local and regional market centers. With strict state measures, most African trading activities were restricted to smaller market centers in Gusiiland with few having an opportunity to operate in Kisii town, which was mainly the domain of Asian and European traders up to the independence period. After 1963, with Africanization programs gaining momentum, many Gusii traders rapidly relocated to Kisii town and took over the townships’ commercial sector that was hitherto mainly in the hands of Asian traders. The new generation of traders who have emerged in Kisii town still exhibit strong attachments to their rural areas from where they continue to generate capital (mainly from farming) that supplements what they earn from their businesses. Kisii town has emerged as an important commercial hub in the south western region of Kenya as it coordinates commercial activities with several smaller towns in the region. Many traders operating in the town also have business interests in other smaller townships such as Nyamira and Keroka. This study has therefore revealed that accumulation in Gusiiland has mainly been the result of the commercialization of the agricultural sector as well as the expansion of trading activities in the area. Kisii town therefore presents a unique situation where economic opportunities can be localized by creating regional centers of production. This will in the long run address the problem of the over concentration of commercial and industrial activities in such major urban centers such as Nairobi, Mombasa, Kisumu and Nakuru. Such strategies would alleviate problems of regional economic disparities by providing communities with opportunities for self advancement within their localities and Kisii town fits quite well into this scenario.