For Kingston Creative, Revitalizing a City Relies on Entrepreneurship

art in kingston jamaica

Standing squarely at the intersection of art and entrepreneurship, Kingston Creative is an initiative whose stated goal is no less than the revitalization of an entire city. But it’s all in a day’s work for Jennifer Bailey, assistant professor of technology and operations management at Babson College, who is a member of the team that launched the undertaking just over a year ago.

“We are at the point,” says Bailey, “where we are ready to take Jamaica to the next level.”

Going Home, Giving Back

Bailey grew up in Jamaica and attended high school there; she left the island for college and grad school in the United States. But the country she still calls home has never been far from her mind.

“I had always wondered how I could engage and contribute in Jamaica, but I didn’t necessarily know where to start,” she says. When she got an email from Andrea Dempster Chung, an old friend, asking if she’d be interested in helping to create a new community arts organization based in Kingston, Bailey didn’t hesitate: “In a word, I said yes! Entrepreneurship and creativity—there’s nothing I don’t absolutely love about it.”

For her part, Dempster Chung was particular appreciative of Bailey’s willingness to give back to her home country. “It’s so easy to migrate and be consumed in day-to-day life in the country you’re in. When people reach back and ask ‘How can I help the country I came from?’ it’s not easy, and it’s to be applauded,” she says.

Dempster Chung, who now serves as Kingston Creative’s executive director, launched a bookstore in Kingston in 2007 that soon became a literary gathering place in a city with a paucity of such spaces. She had been pondering her next project when Kingston was named a UNESCO Creative City in 2015. The designation is similar to UNESCO’s World Heritage Sites, but, notes Bailey, “The heritage sites are more backward looking; creative cities are more forward looking, growing a base for the future.” The aim is to promote cities that have identified creativity as a strategic factor in sustainable urban development.

Kingston made the list because of its musical heritage and culture. Music, acknowledges Bailey, may be what comes to mind when pondering Kingston’s creative potential. But, she says, “When you visit, you see that all kinds of creativity are alive and well.”

Kingston Creative's Executive Team
Members of the Kingston Creative executive team on an art walk, left to right: Doris Gross, Andrea Dempster Chung, Ueli Bangerter, and Jen Bailey

Rising to the Challenges

But the problem, say Bailey, Dempster Chung, and a third partner, Allan Daisley, was that Kingston’s creativity wasn’t being leveraged. Daisley, who is managing director of Startupbootcamp Digital Health, in Miami, says, “There are a lot of people who have great talent, but many are barely able to make a living; because of the space they’re in, they don’t have the exposure or education.”

The three put their heads together and came up with a roadmap for Kingston Creative, rolling it out in early 2017. In November of that year, they presented the idea at Imagine Kingston, a conference on the regeneration and revitalization of the city, and they haven’t looked back since.

The group’s goals range from modest to grand, and many have already been realized. Five key projects were launched in 2018 or are in the works:

  • Friday evening networking events for the arts community
  • Art walks built around various themes, held the last Sunday of each month
  • Market Street, a makers’ market tied to the art walks
  • A series of outdoor murals in an area slated to be the new arts district
  • A creative hub and co-working space for artists of all kinds

The Sunday art walks in particular have proven popular, drawing upward of 60 participants and giving local artists a showcase for their work. “It’s taken on a life of its own,” says Daisley.

He notes the group was mindful of being sensitive in its approach to the arts community. “Caribbean people in general have had a history of others coming in and telling them what’s good for them,” he says. “We brought in the community and presented it as ‘What do you think?’ as opposed to ‘Here, take this, we know best.’ We asked them what they thought would work.” As a result, there is a high level of engagement among members of the community: some 70-plus volunteers work in groups or “pods” focusing on community, brand, digital, arts district, art events, creative hub, and real estate.

City officials and local developers have also voiced support. But, says Dempster Chung, “Getting people on board is still a hurdle, if I’m being realistic. We have momentum, but not necessarily buy-in.”

Bailey is a bit more sanguine. “This is the beauty of a smaller country: resources are limited, but the upside is that we’re able to mobilize easily.” Jamaicans, she says, tend to be connected by only about 2.5 degrees of separation (Dempster Chung actually places the figure at one degree), and she’s been able to capitalize on that for Kingston Creative. An arts organizer in Boston might have trouble lining up a meeting with, say, the director of the Museum of Fine Arts (MFA), Bailey notes; in Jamaica, you’re more likely just to run across such a person.

As with most nonprofits, fundraising is key. Toward that end, the organization has launched a “First 50” campaign, to identify 50 companies willing to donate J$1 million (about $7,800). Bailey notes with satisfaction that the first such company to commit was Jamaica’s famous Red Stripe beer, a brand she terms “iconic.”

Kingston’s recent history has been challenging, and many neighborhoods still struggle. Dempster Chung says the downtown area that the group hopes to revitalize as an arts district has a perception problem: even locals think of it as crime-ridden and dangerous (unfairly, she says), and those who live there are often stigmatized. At the same time, she says, “It is primo real estate. It’s a historical district that would normally be overrun with tourists, but it’s been abandoned.” Efforts like Kingston Creative may just help turn the tide.

Two Critical Pillars

Bailey calls the arts district and the planned hub the “two critical pillars” of the initiative. Building the hub is, she says, “our primary focus in 2019. We are in the final rounds to roll out the hub. It’s an accelerator format, to give artists skills to scale their ventures.” As a veteran of both the arts and entrepreneurship—she has co-taught a course with Mass College of Art and has been involved with the MassChallenge global accelerator as a mentor and trainer—Bailey is leading the charge on the hub.

“[Bailey] is about innovation and entrepreneurship,” says Dempster Chung. “Her expertise is perfect for the hub side of this—taking young creatives from ‘This is a hobby’ to ‘This is a business.’ Her expertise is right in that pipeline.”

Bailey sees significant overlap between creativity and entrepreneurship. “Though I’m not an artist myself,” she says, “one of the things I have in common with creatives is the day-to-day passion I find in entrepreneurship.” And Jamaica, she says, is perfectly poised to create new opportunities in that arena. “Jamaican people are creative. We take the resources around us and make something new and creative and entrepreneurial out of it. That’s the essence of who we are; that’s the wave we’re riding.”

Jennifer Bailey is eager to engage interested members of the Babson community in Kingston Creative. To find out more, contact her on Twitter at @ProfJenBailey or email her at

Posted in Entrepreneurial Leadership

More from Entrepreneurial Leadership »