Stephen Akintayo, entrepreneur and thought leader known for bold ideas and unapologetic ambition, is the latest guest on #WithChude, where he sits down with Chude Jideonwo for a searching and unfiltered conversation about power, purpose, faith, and the cost of visibility. The episode marked by candour and reflection, Akintayo revisits defining moments that have shaped his public journey, including the intense scrutiny that followed his decision to charge $18,000 for mentorship and the pressure of making high-stakes decisions in full view of critics and supporters alike.
As he approaches 40, Akintayo frames impact, not wealth, as his most meaningful achievement. He speaks openly about discipline as a daily practice, the necessity of starting projects that are “far bigger than the resources I have,” and the inner grounding required to keep moving forward amid controversy. In one of the episode’s most provocative moments, he argues that politicians who have not added real value do not deserve streets named after them, insisting that legacy must be earned through service, not symbolism. Throughout the conversation, he returns repeatedly to gratitude, crediting his sense of direction and resilience to a faith that places God firmly at the centre of his life and work.
The episode also reveals a more personal side of Akintayo, including his surprising admission that he was eager to turn 40, seeing the milestone as a marker of clarity rather than decline. He reflects on a belief he holds deeply, that business leaders like him have a role to play in supporting ministries in critical times, and on the responsibility that comes with influence. This conversation captures Stephen Akintayo not as a headline or a controversy, but as a man thinking aloud about calling, courage, and consequence, reflective, unguarded, and deeply intentional.
WATCH EPISODE: https://vimeo.com/1159154880
