According to previous studies, a positive attitude towards information technology (IT) among small business owners appears to be a key factor in achieving high quality IT implementations. In an effort to extend this stream of research, case studies were conducted with small business owners. A surprising finding of this study was that high quality IT implementations resulted with owners who had either a positive or a negative attitude towards IT. Another finding was that these owners also all had an entrepreneurial, or shared, management style. By contrast, owners who had an uncertain attitude about IT uniformly practiced a traditional (non-entrepreneurial) management style. This group also uniformly had low quality IT implementations. It is proposed, based on case study data, that small business owners with an uncertain attitude towards IT might experience higher quality IT results in their organizations through practicing a more entrepreneurial, or shared, management style. The study provides insights for both computer specialists and small business owners planning IT implementations.