Jesse Ashiegbu

In this episode, Jesse Ashiegbu shares his journey from Eastern Nigeria to the UK and how his belief that “business is life” shaped everything he does. Originally coming to the UK to study filmmaking, financial pressure pushed him to find new ways to survive, leading him to teach himself barbering through YouTube. What started as a means to pay tuition evolved into Headliners Barberhop, a community-focused business built on the understanding that barbers have rare access to men’s trust and inner lives. For Chessi, barbering is not just about appearance but about caring for mental, emotional, and physical well-being, particularly for men of darker skin tones who often lack safe spaces to talk openly.

The conversation explores how Headliners Barberhop became a platform for social impact, hosting regular sessions where men gather to discuss mental and emotional health. This work recently gained recognition through a grant from Healthier Greenwich to pilot community wellbeing events across multiple barbershops. Chessi also explains his long-term vision of building interconnected business structures, including a community interest company to handle social responsibility work and a property company to support sustainable operations. Throughout the episode, he reflects on failure as experience rather than defeat, persistence over mentorship, and measuring success by impact rather than profit. Identifying as a social entrepreneur, he frames his work as creating jobs, opportunities, care, and lasting value for the community while fearlessly learning through every setback.