For Ugandan businessman Ssekaayi Simon, the journey into media was not a straight path. Before becoming associated with media ownership, he moved through different phases of work, including operating as a boda boda rider and later running a retail shop, experiences that shaped his ambitions as an entrepreneur.
Simon, who attended Makamba Memorial and later pursued secondary education in Wakiso District, would eventually venture into business and entertainment before returning to the media industry.
His first major step into media came through Horizon Media Uganda, a company he founded in 2008. The venture started as a video production and news company based in Ssumba, Wakiso District, providing news coverage and filming services for social events and ceremonies.
Over time, Horizon Media Uganda expanded its operations and developed a reputation as a growing video production and news platform in Wakiso. The company, however, later faced financial difficulties that resulted in its collapse.
After the setback, Simon shifted focus to other ventures, including a disco sound events business and property development in Buddo. The period away from media became a time of rebuilding after the challenges that had affected his first media venture.
Years later, Simon returned to the media sector through Uganda National Media Group (UNMG), a company created after the restructuring of Horizon Media Uganda. UNMG was relaunched with a different corporate structure, operating as a private limited company with shares rather than being centred around one individual.
Supporters of the restructuring argue that the new structure represents a different approach from the previous venture. Ssali Paddy, who has followed Simon’s journey, said the businessman had created a company structure that showed lessons had been learned from the past.
“The businessman should be given a chance,” said Magoola Emmanuel, arguing that Simon’s return reflects a struggle to rebuild his place in the media industry.
UNMG’s leadership says the company intends to focus on factual and balanced journalism as it seeks to establish itself in Uganda’s changing media landscape.
For Simon, the transition from an earlier failed media venture to a new company structure represents an attempt to turn past challenges into a foundation for a second chapter in media entrepreneurship.
Outside business, Simon is a father of three daughters and remains involved in property development and other business activities.
The post From boda boda rider to media entrepreneur: Ssekaayi Simon’s long road back into Uganda’s media industry appeared first on Watchdog Uganda.



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