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From creative talent to commercial thinking: How one young entrepreneur discovered the skills business really demands
The successful staging of Guinness Pull Up was made possible with the support of one of Red Stripe’s business entertainment interns, Kimberley Foote, who worked alongside the event team behind the scenes.
Career & Education, Career & Education Front Page
July 19, 2026

From creative talent to commercial thinking: How one young entrepreneur discovered the skills business really demands

THREE years after launching her creative agency, Digital Foote Print, Kimberley Foote believed she understood the business of marketing. But it wasn’t until she earned an internship through the D&G Foundation’s Red Stripe Business Entertainment Masterclass and found herself working behind the scenes of Guinness Pull Up that she discovered what it really takes to bring a major brand experience to life.

“I thought I understood marketing,” the 25-year-old entrepreneur reflected, “but I realised there was another side of the business that I had never experienced.”

For Foote, building her own business had already been a leap of faith. After studying marketing at The University of the West Indies, and gaining experience in agencies and corporate Jamaica, she left the security of full-time employment to establish Digital Foote Print, a creative agency specialising in brand development, digital marketing, website design, and event support. Along the way, the company contributed to projects including the Boyz II Men concert in Jamaica, giving her confidence that she could compete in an increasingly dynamic creative industry.

Yet she recognised that creative ideas alone were not enough.

She wanted to understand what happens after the strategy is approved, when brands move from the boardroom into the real world.

That search for deeper experience led her to enrol in the D&G Foundation’s Red Stripe Business Entertainment Masterclass, a programme that challenged aspiring entrepreneurs to develop and pitch original business concepts while gaining practical exposure to brand execution.

Even then, she almost didn’t apply.

“I kept asking myself, ‘Why am I doing this? Am I good enough to submit?’ “

She submitted her concept anyway.

Her idea, Hustle Fest, proposed a collaborative festival where marketers, photographers, designers, videographers and other creatives could connect, learn from industry leaders, and showcase their work.

The concept earned Foote one of two internships supporting the execution of Guinness Pull Up, where she experienced first-hand what it takes to deliver a major, live brand experience.

Instead of developing creative concepts on a laptop, Foote became part of the team responsible for bringing that experience to life.

Behind the scenes she saw first-hand how quickly plans could change and how every decision influenced the audience’s experience. She observed the careful coordination required to manage artistes and their entourages as they arrived, balancing competing demands while keeping the event running smoothly. She also witnessed the importance of protecting the brand in real time, as teams worked closely with performers to ensure they adhered to the Responsible Marketing Code, stepping in when necessary to remind them of agreed content standards without disrupting the show.

“That was the biggest eye-opener for me,” Foote said. “The audience sees the performances and the excitement but they don’t see the hundreds of decisions being made behind the scenes to protect the brand and keep the experience running seamlessly. It made me realise that great marketing isn’t just about the creative idea, it’s about how well you execute it when the unexpected happens.”

The experience reshaped the way Foote now approaches her own business.

Today, every project begins with different questions: How will people experience this? What could go wrong? Have we planned for it? How do different teams work together to deliver a seamless experience? How do we protect the integrity of the brand at every touchpoint? And ultimately, what will people remember long after the event is over? Those lessons are already influencing the next chapter of Digital Foote Print.

As she prepares for the second staging of Pilates & Brunch, in partnership with Mini Jamaica and AB Lab Pilates Studio, Foote says she is placing greater emphasis on operational planning, customer experience, stakeholder coordination, and contingency planning from the earliest stages of development.

She is also continuing to develop Hustle Fest, the concept that first earned her the internship. What began as a competition pitch has evolved into a long-term vision for creating a collaborative platform where Jamaica’s creative community can connect, learn and grow together.

For Foote, the biggest transformation wasn’t simply learning how to execute a major event, it was discovering that while creativity may spark an idea, thoughtful execution is what turns that idea into a meaningful experience and, ultimately, a successful business.

Kimberley Foote, founder of Digital Foote Print, a dynamic marketing agency.

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