In September 2018, Wole Oluyemi launched a weekly YouTube show – the #AskWoleOluyemi Show. On it, he takes questions from people on Instagram, Twitter and FaceBook, responding to them in an unrehearsed, off the cuff manner. This concept was an aftermath of the initial approach of responding to each question from his followers privately, which became very inefficient as similar questions were being responded to individually by him. In the show, questions are pre-screened by his team, but Wole never hears them ahead of time, ensuring raw, honest answers on everything from finance, to entrepreneurship, to strategy, to anything relating to SME businesses. The success of the show helped him grow his YouTube following while also paving the way for follow-on content across his various platforms.