He founded the Nigerian newspaper Thisday in 1995. In 2000 Obaigbena founded the annual Thisday Awards which honour those who made contributions to Nigerian society in the political arena, global business, Women of distinction, and leading figures in the Nigerian education sector.
In 2013 he launched an international TV news channel with an African focus, Arise News. He is a regular attendee and sessions moderator for the World Economic Forum and has served as a member of the Nominating Committee of the Young Global Leaders of the World Economic Forum. He is Chairman of the Newspaper Proprietors’ Association of Nigeria (NPAN) as well as Chairman of the Nigerian Press Organisation – comprising the NPAN, the National Union of Journalists and the Nigerian Guild of Editors where he is a fellow.