Intentional or friendly acquisitions as argued in existing research are being practiced increasingly for past couple of decades, and yet the focus towards the selling company’s perspectives is observed to be relatively low compared to that of acquirers. Moreover, sellers’ position in acquisitions is often perceived as an action to counteract unforeseen/unplanned activities, whereas the recent trends of such acquisitions don’t abide by this assumption. Sellers are increasingly practicing strategically planned exits and within this narrow field of seller-initiated acquisitions, sellers that involve a broker to facilitate the acquisition transactions are put under perspective in this report. Within this novel field of research, this thesis explores the impact of selling firm’s legitimacy & broker’s impact on acquisition transactions that eventually lead to realization of higher returns to the seller. In order to achieve the research aim, systematic approach that consisted of two underlying approaches, theoretical and technical, was conducted. In the first, theoretical, phase of the research, selective literature on selling company’s underlying legitimacy aspects and broker’s orientation/type, functionalities, and driving incentives was surveyed. Precisely, the factors that were perceived as controlling factors in valuation of the seller by the acquirer were collectedly put in a framework. Observed factors in the first phase of the research lacked the literature that observed the interconnections and relationships among such underlying factors, therefore relevant justification to conduct a further technical research of acquisitions was in order. Further, in the second aspect of the methodology, an attempt was made to extend the proposed framework from the theoretical approach. A systematic approach was undertaken in order to conduct a total of four case studies categorized under two brokers and further into brokers individual cases of one early and a late maturity stage seller. Following the individual case analysis, comparative case analyses (among late-late and early-early sellers), and a cross-case analysis across the four sellers was conducted. The results of such comparative analysis provided grounds for the build up of patterns among late and early stage sellers, whereas the cross-case analysis provides the overlap of such patterns throughout the cases, which in turn are the propositions and generalized findings of the overall research. Besides such patterns and propositions, additional underlying factors to firm’s internal & external legitimacy, and broker were observed and incorporated in the afore-established framework. Both aspects of research approaches, when aligned together, reveal the importance of high impacting (1) development phase of the seller, (2) sellers formed alliances, its (3) socio-political legitimacy, (4) exit strategy planning, (5) involved broker’s incentives, (6) broker's human capital, and (7) broker initiated competitive negotiations on the over all acquisition transaction. Besides, the high impacting underlying factors, five propositions are formulated that show the impact and how such underlying factors can compensate each other when a seller’s undergoing acquisition. Further, besides the general findings, results from comparative case analyses reveal the findings precisely valid in the late or early maturity stages of the selling company. These findings are discussed further as patterns that were observed in both early and late maturity stage sellers. Relevance of this research is highly valuable in terms of the attempt it makes to bridge the observed academic gap in the field of seller-initiated acquisitions. On the other hand, the practical relevance of this study is the general findings and the maturity stage specific findings that provide an entrepreneur/manager to formulate a high impacting exit strategy that maximizes seller’s returns in the acquisition transactions by involving brokers.