From boda boda to corporate world – how Simon Ssekayi, a local entrepreneur, navigated business risks and reinvented himself

In Uganda’s competitive business environment, many entrepreneurs build their careers through a series of experiments, setbacks and adjustments. Ssekaayi Simon’s story is one of an entrepreneur whose ambitions moved from informal work to media and other investments, shaped by both opportunities and challenges.

Simon’s early working years were spent outside the corporate world. He started as a boda boda rider before moving into shopkeeping, a transition that introduced him to the realities of running a small business and dealing directly with customers.

His entrepreneurial interests later expanded into entertainment. Through a disco sound events business, Simon became involved in organising events, an experience that exposed him to the importance of communication, promotion and reaching audiences.

Those experiences eventually influenced his decision to enter the media industry.

In 2008, Simon established Horizon Media Uganda, starting with video production and news coverage in Ssumba, Wakiso District. The company focused on recording ceremonies, producing video content and covering community stories at a time when demand for local media services was increasing.

The venture grew within Wakiso’s media space, building a presence through local news coverage and production work. However, like many independent businesses, it faced financial pressures that affected its operations.

The collapse of Horizon Media Uganda became a significant chapter in Simon’s business journey. It exposed the difficulties of sustaining media ventures where equipment costs, staffing, advertising income and competition can determine whether a company survives.

Instead of leaving entrepreneurship, Simon shifted his focus to other areas, including property development in Buddo. The move reflected a broader approach to business after experiencing the challenges of operating a media company.

Observers of Uganda’s business sector often point out that failure is common among entrepreneurs, especially those attempting to build companies from limited resources. The ability to restructure, learn and adapt often determines whether an entrepreneur can return stronger.

Simon’s journey has attracted attention from people who view his experience as an example of persistence. Supporters argue that entrepreneurs should be judged not only by setbacks but also by their ability to rebuild after difficulties.

However, the long-term measure of any business comeback remains sustainability, accountability and the ability to create structures that can operate beyond the efforts of an individual founder.

Beyond business, Simon is a father of three daughters and remains involved in entrepreneurial activities. His career reflects the unpredictable nature of business, where ambition can lead to both opportunities and challenges.

His story raises a wider question for Uganda’s growing entrepreneurial class: how can individuals who build businesses from the ground up create ventures that survive changing markets and financial pressures?