Ssekaayi Simon: The businessman rebuilding after a difficult journey from boda boda riding

By Our Reporter

Before becoming known as a businessman and entrepreneur, Ssekaayi Simon’s journey passed through several stages that reflected the struggles faced by many young Ugandans trying to build a livelihood.

Simon attended Makamba Memorial before pursuing his secondary education in Wakiso District. His early working life was not defined by privilege, as he started out as a boda boda rider before moving into retail business as a shopkeeper.

Through determination to expand beyond daily income activities, Simon ventured into entertainment by starting a disco sound events business. The experience exposed him to event management and business operations, while also helping him build networks within his community.

His interest in communication and storytelling later pushed him into media. In 2008, Simon founded Horizon Media Uganda, beginning as a video production and news company based in Ssumba, Wakiso District.

The company focused on news coverage and video production, including recording ceremonies and community events. Over time, Horizon Media Uganda grew into a recognised video production and media operation within Wakiso, covering local stories and events.

However, the business later faced financial difficulties that eventually led to its collapse. The setback became a turning point for Simon, who shifted attention to other ventures, including property development in Buddo.

Rather than abandoning entrepreneurship, Simon continued rebuilding through different business activities. His supporters describe his journey as one marked by persistence despite setbacks.

Ssali Paddy, who has followed Simon’s business journey, said the businessman’s experience showed the challenges entrepreneurs face when trying to establish long-term ventures.

Magoola Emmanuel said Simon’s efforts deserved recognition, arguing that entrepreneurs who experience failure should be allowed opportunities to rebuild and return to business.

Away from business, Simon is a father of three daughters. His story reflects the unpredictable path of entrepreneurship, where early success, failure and reinvention often form part of building a lasting career.