It has long been the focus of many countries around the world to see their entrepreneurs grow and to introduce interventions to assist them, as they realise the impact these entrepreneurs have on their economies. Technology is believed to be one of the biggest tools that entrepreneurs can use to assist them in growing sustainable businesses. There is an increased need for small businesses to employ information and communication technology (ICT) to enhance their businesses as part of their countries’ socio-economic development. This, in turn, leads to an increased need for digital literacy interventions for these entrepreneurs. Many interventions have tried to assist a country’s residents to adopt ICT and enhance their digital literacy levels. However, many of these did not have the desired outcomes. Many barriers prevent these initiatives from being successful, for example difficulty in retaining the current workforce, a lack of skills and human capital development, a lack of resources, security concerns, mistrust regarding ICT and ICT service providers and a lack of trust. Data were gathered over three years (2012, 2013 and 2017) to determine whether there has been any change in the uptake of technology over time, whether technology is indeed the answer to many entrepreneurs’ problems and whether some of the barriers could be overcome. An interpretivist paradigm using a qualitative approach was employed and 193 entrepreneurs were interviewed over three years to see if there was any change in their adoption of technology, which should be the case if one recognises the pace at which technology is changing. The identified barriers no longer seem to exist for South African entrepreneurs. It emerged that technology adoption and digital literacy studies should be industry-specific and should not be based on a generic approach. Thus, digital literacy cannot be used as a broad term and needs to be focused for each sector. This article proposes that most entrepreneurs have addressed one of the main barriers. These main barriers include a lack of expertise, in-house knowledge or a one-stop shop to assist with ICT queries and problems. Most of the entrepreneurs now have access to an information technology consultant or expert who can help them to become more digitally literate. Although many new technologies are being developed, certain standard software systems, such as the Microsoft Office package, will always be used. Thus, these standard software systems should be the focus of digital literacy training interventions. These interventions should be simple and easily accessible to everyone.