Theories concerning the entrepreneur’s attitudes towards IT are important because studies show that the entrepreneur’s positive attitude towards IT is a key factor in achieving a high quality IT implementation in his/her business. Our study, based on data from multiple cases, supports this contention. Surprisingly, the data shows that those with negative attitudes towards IT also achieve high quality IT implementations. Those with uncertain attitudes towards IT had low quality IT implementations in their businesses. The results of this study yield some useful propositions: the most interesting is the importance of entrepreneurs with negative attitudes to rely on modern management policies in order to achieve a higher quality implementation.