Digital transformation (DT) is a trending topic in nearly all industries. Enterprises digitalize processes, offer digital services and products, and enhance the customer experience. However, complex barriers hinder the ability of entrepreneurial-oriented small and medium-sized enterprises (SMEs) to advance in digital transformation. Using a questionnaire, we collected and analyzed data on the barriers to digital transformation in SMEs. The data revealed a heterogonous picture of SMEs regarding digital transformation and barriers. Based on 195 completed questionnaires, we demonstrated a significant negative influence of organizational and technical barriers and missing skills on digital transformation success. The identified predictors can explain 58% of the variance in the transformation process based on 195 respondents. We could not demonstrate a significant relationship to digital transformation success for the three additional barrier dimensions individual, lack of standards, and lack of laws. Nevertheless, respondents perceive the existence of a lack of standards and laws as well as individual barriers. Our results indicate that addressing organizational barriers is an excellent way to start a DT journey.