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Obakeng is a television presenter who began his career in the media industry at the age of 12 on the popular children's programme, YO.TV in 2002. In 2003, Obakeng was anchor on Vaseline Clean 5s, a health and wellness program for kids. In 2004, he began working on another Kids' program, TUBE on SABC 2, where he eas anchor presenter of Just Chill, under Berry Productions. During his stay there, OB presented several shows, including Make It, Your Life, Technoplay and others until 2006. At 18 (in 2008), Obakeng became news presenter at Rainbow FM, his very first job on radio. The following year, he became a voice artist, having recorded advertisements for some of the biggest brands in South Africa in both English and Setswana. In 2011, he went on to graduate from the Y-Academy in 2011, a program conducted by Yired (Pty) Ltd, the company in charge of YFM. OB, became a news and sports presenter at YFM, and voice artist for the Nashua Titans Show and the KFC Mini Cricket Show, both of which appear on Supersport TV.

Obakeng founded Lead Young Media and Communications in 2009 with the aim of bringing development to young South Africans through media and communications. The idea is to expose the youth to the resources that surround them, that allow them to maximize their potential and make an impact in their environment. He then formed BY FORCE, which allows him to make this happen, and allows other young people passionate about the development of others to change lives too. Lead Young SA has been responsible for the putting together of tall BY FORCE events that have taken place since 2009 and the production of the Annual Gracious Girl Convention.

As a motivational speaker, his talks have been televised, helping his message to reach those hard-to-reach places, and touching lives all over.