Akintola was born in Ogbomosho to the family of Akintola Akinbola and Akanke, his father was a trader and descended from a family of traders. At a young age, the family moved to Minna and he was briefly educated at a Church Missionary Society school in the city. In 1922, he returned to Ogbomosho to live with his grandfather and subsequently attended a Baptist day school before proceeding to Baptist College in 1925. He taught at the Baptist Academy from 1930 to 1942 and thereafter worked briefly with the Nigerian Railway Corporation. During this period, he became acquainted with H.O. Davies, a lawyer and politician and joined the Nigerian Youth Movement where he assisted Ikoli and supported the latter to represent Lagos in the legislative council over the candidacy of Samuel Akisanya, who was supported by Azikiwe. He joined the staff of the Daily Service Newspaper and soon became the editor in 1943 with the support of Akinola Maja, a shareholder, replacing Ernest Ikoli as editor. Akintola was also founder of Iroyin Yoruba, a newspaper written in the Yoruba language. In 1945, he opposed the general strike led by Azikiwe’s NCNC and Michael Imoudu, earning the distrust of politicians like Anthony Enahoro. In 1946, he earned a British scholarship to study in the U.K. and completed legal studies by 1950. He started his legal career working as a lawyer on land and civic matters. In 1952, he formed a partnership with Chris Ogunbanjo,Chief Bode Thomas and Michael Odesanya.