“Working with my brother felt like walking and living under his shadow, and you know, Big Kev was at the heart of the Nairobi entertainment scene, a sensation, and I felt his whole persona engulf Trublaq,” Jackee Ombajo, Co-founder and Principal CEO of Trublaq Entertainment reminisces, as she finishes the tall glass of water in front of her.

Two years down the line after she shook hands with her brother, the late Kevin Ombajo and started working at Trublaq, she could still not find her voice in the business, with the constant feeling of not knowing how tangible her input was. It’s around that time that Capital fm, one of their competitors, offered her a position in their Events and Marketing department. She chose to branch out from the business she co-founded with Big Kev to find her ground in these new uncharted waters.

Unbeknownst to her, working at Capital was instrumental in building and grooming her for the role that was awaiting her at Trublaq in four years’ time. She was able to centre herself, stand on her two feet, and the cherry on the top in the end was that she knew without a single doubt that she did not want to be employed ever again. One of the perks of being employed, Jackee reiterates, was that it helped Trublaq get loans from banks in those early years, since banks deem employed people a less riskier gamble, and this smoothened their operations at least by one less hurdle.

After four years, she left Capital fm with a renewed sense of self that was more grounded and got into a partnership with her brother after several negotiations that involved buying of shares at Trublaq. She could now steer Trublaq to its True North, and she hasn’t looked back since.

Jackee Ombajo was a guest at Un.thinkable roast (our monthly 10X Growth Leaders Meet-up) in March 2020. Click here to apply for membership in Un.thinkable.