More than 60 teenage boys from 14 secondary schools across Barbados are stepping confidently into the world of entrepreneurship, leadership and innovation through the Mr Executive 2026 Senior Boys Business Challenge.
During the preliminary round on Sunday afternoon, the young entrepreneurs showcased their ideas and customer service skills at a Market Day held at Sky Mall. The event marked a major milestone in a programme that continues to reshape how young men are prepared for leadership, business and responsible citizenship.
Established in 2017 at St Leonard’s Boys’ School by veteran educator Winston Cumberbatch, the Mr Executive Challenge was created to address a critical gap in the development of young men. What began as an internal school initiative has since evolved into a national inter-school competition, drawing participation from 14 secondary schools and engaging more than 60 students in this year’s cohort.
“This challenge was designed specifically for our young men,” Cumberbatch explained. “It is about more than selling products. It is about teaching initiative, discipline, creative thinking and responsibility; the kinds of skills that are not always taught in a classroom but are essential for life.”
Market Day serves as the programme’s first major competitive phase, giving students a real-world environment in which to test their business ideas. This year, 14 youth-led ventures set up booths throughout the mall, offering a wide range of products including pastries, cookies, lemonade blends, popsicles, hair oils, candles, ornaments, fashion shirts, bracelets, fruit-based treats and children’s items.
Students were responsible for every aspect of their ventures, including branding, pricing, marketing, customer engagement and sales, under the watchful eye of judges and mentors drawn from the business community.
“We do not limit them in what they can come up with,” Cumberbatch said. “Once they believe an idea can be viable, we encourage them to think outside the box, work together and develop something original. This is how innovation is born.”
The challenge is structured to move beyond team-based activities. After the group phase, students are assessed individually, with one participant from each school eventually advancing to the finals to represent their institution. At that stage, competitors face additional tasks designed to test leadership, communication, ethical reasoning and executive presence.
According to Cumberbatch, the programme plays a vital role in changing how young men see themselves, and how society sees them.
“Too often, young men are defined by negative narratives,” he said. “This challenge allows them to show that they are more than what they are sometimes labelled as. They can build businesses, think creatively and contribute positively to their communities.”
He added that the long-term impact of the initiative is already evident, pointing to past participants whose lives have been redirected through mentorship and structure.
“There are young men who were heading down the wrong path, and this programme helped rescue them,” he said. “When young people begin to believe in themselves and are supported by responsible adults, it doesn’t just change them, it changes their families, their schools and the wider society.”
In 2022, the Barbados Entrepreneurship Foundation joined the initiative, strengthening the programme with a dedicated entrepreneurship and business module. The partnership has expanded the challenge’s reach while deepening its focus on business ethics, strategic thinking and professional conduct.
Cumberbatch believes exposure to initiatives such as the Mr Executive Challenge is essential to national development.
“This may not be the cure for every issue in society,” he acknowledged, “but wherever we find something that works and helps our young men, we should support it fully and allow it to grow.”
As students confidently pitched their products and engaged customers throughout the day, the impact of the programme was evident in the passion and professionalism displayed by the young entrepreneurs. (DT)
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