Lunch express with… Charlie Kirkconnell

In 2003, Charlie Kirkconnell left the family business to pursue a law career. Less than a decade later, Kirkconnell is back in business, this time exploring the great unknown – at least in Cayman – of the knowledge-based special economic zone.

The Journal sat down with Kirkconnell over lunch at the Cracked Conch to discuss his career changes, his famous father and the exciting prospects of Cayman Enterprise City.  

When it comes to business, the name Kirkconnell is big business in the Cayman Islands. Very big. And while there have been a number of influential Kirkconnells over the years, certainly the late Captain Charles Kirkconnell ranks near the top, having been both a leading businessman and a long-time elected representative. 

Captain Charles’ son, also named Charles, is involved in a project – Cayman Enterprise City – that, if it’s as successful as he thinks it will be, it will have the same kind of impact on the Cayman Islands as did some of things his father accomplished. 

Over lunch at the Cracked Conch restaurant in West Bay, Kirkconnell talked about Cayman Enterprise City and his life growing up as the son of a Caymanian icon. 


A famous father  

First things first: It’s Charlie. 

“I tried Charles, but it just confused people because my dad was Charles, so I went back to Charlie,” he said. “When I came back from school I thought it might sound more grown up or professional to be Charles, but we had a number of confusing incidents where people called up to speak to me and ended up speaking to my dad, so I decided I just better abandon that.” 

While he was growing up, Kirkconnell said he didn’t fully appreciate his father’s stature in the Cayman community at the time. 

“To me he was just my dad,” he said. “I think as I got older I developed a greater appreciation for what he knew and how he dealt with certain situations.” 

The elder Kirkconnell spent the bulk of his early career working for the family shipping business in Jamaica, where Charlie was born and lived for the first year or two of his life. 

Captain Charles returned to Cayman with his family in the early 1970s, with the intentions of retiring.  

“That’s what he said,” Kirkconnell said, laughing. “He moved back here to retire or maybe dabble in real estate. I’m not sure at what point he started working full time again – I’m not sure if he even took a break – but within a short period after coming back to Cayman… he became involved again in Kirkconnell Brothers and he remained very active and involved right up until the very end. I think he retired again in the late ‘90s, but he still came to work.” 

Captain Charles also become very involved in politics, serving as an elected representative for Cayman Brac and Little Cayman for 12 years between 1976 and 1988, and as a member of the Executive Council for the last eight of those years. 

Through his various businesses, Captain Charles amassed a great deal of wealth, but he continued to live modestly in the family’s South Sound home. 

“He was not ostentatious,” said Kirkconnell. “He used to say ‘never live a lifestyle you couldn’t live without’… or something along those lines.” 

Kirkconnell said he learned a lot from his father, especially when it came to his approach to business. 

“I recall a number of situations where I wondered whether if he was making the right decision and I found out that he really did think things through and weighed them up and if he took a risk, it was a calculated risk,” he said. “And I think the record shows he was very successful.” 

His father believed people had to start at the bottom to learn business and his son was no different. When Kirkconnell graduated from university in the United States and joined the family business, his first job was selling Coca Cola for Kirk Beverages. 

“That was my first job, driving around – I covered the whole Island – on a weekly basis,” he said. “That was one of the things I really appreciated with my dad’s approach. He didn’t just bring me back and plop me in an office and call me the VP of something. He thought, and I agree with him and I agreed with him at the time, that I should learn the business from the bottom up. That way no one can tell you what can be done or can’t be done – you know. That was invaluable experience. I can’t say I did every job along the way, but I did quite a few of them. I learned a lot from that experience.” 

Kirkconnell said one of the things he admired most about his father was the way he dealt with people. 

“I think he was very fair with people and he was a very honest businessman as well,” he said. “He was certainly not the kind of person who would do anything for a buck.” 


Cracked Conch  

The Cracked Conch restaurant has been around, as they say in Cayman, donkey years – since 1981. It hasn’t always been at its West Bay location and it hasn’t always had its current ownership, but the restaurant has always been known for serving high-quality Caribbean cuisine.  

Now nestled on a gorgeous oceanfront property in the Northwest Point area of West Bay, the Cracked Conch remains one of Cayman’s quintessential Caribbean restaurants – even with its fabulous French executive chef, Gilbert Cavallaro. 

Because of its West Bay location, most people probably think of the Cracked Conch as a dinner venue, or maybe a weekend lunch venue. Kirkconnell and I were venturing up there for lunch on a Tuesday, so we found mostly tourists there.  

Kirkconnell told me he knows the restaurant well because he comes annually for a friend’s birthday lunch. 

“We used to go to Crow’s Nest,” he said. “We’ve been doing that lunch for well over 10 years… and we switched to up here when the Crow’s Nest closed. It’s always a relaxed setting; the food is good.” 

For starters, Kirkconnell chose the crispy calamari while I opted for one of the house specialities, conch ceviche. Unlike some conch ceviches served on Grand Cayman with diced conch and tomato sauce marinade, the Cracked Conch version has large pieces of raw conch, pounded tender and marinated with diced tomatoes, red onions, avocado, cilantro and cucumber water lime juice. 

Part of the restaurant’s allure is its setting. Although there is ample inside seating to accommodate diners on hot summer days, lunch guests will usually choose the open-air veranda that affords a stunning ocean view and nice breezes. It is, as Kirkconnell said, a pleasant and relaxing setting, reminiscent of the Cayman Islands of years past. 

For his main course, Kirkconnell orders the dish simply called ‘The Curry’ – a fish curry made with snapper, mahi mahi, tomato, coconut milk and basmati rice. I go with Tuna Nicoise, a French-influenced main course salad made with seared slices of fresh tuna, French beans, fingerling potatoes, tomatoes and black olives with a vinaigrette dressing and a perfectly cooked poached egg. 

It’s lunch, and both Kirkconnell and I have to return to work, so we just drink water, with coffee at the end of lunch. But the Cracked Conch does have an extensive international wine list as well as a number of signature cocktails on their menu. 

Normally, Express Lunch with… interviews are supposed to be short, 45
 minutes maximum. But Kirkconnell and I lost track of time, probably because of the relaxing setting. Our lunch goes almost double the usual time, but there was no lack of conversation. 


Career changes  

A long stretch of Kirkconnell’s formal education came in the United States, four years of it in boarding school and four years at university. 

He considered Tulane University in New Orleans, but eventually decided on Lehigh University in Pennsylvania.  

“I went there because I kind of wanted to go someplace that was very different than Cayman,” he said. “For whatever reason, I thought I might like the cold. As it turned out, I hated it.” 

While in school, he worked summers in the Kirkconnell family businesses in Cayman, which is where he started his career after college, eventually working his way up to top positions at Kirk Supermarket and Kirk Wholesale. 

At one point during the early 2000s he decided to take some classes at the Cayman Islands Law School. 

“The idea when I started at the Law School was that I wasn’t intending to complete the degree,” he said. “The intention wasn’t that I was going be a lawyer. The idea was that I was going to take a few classes at the law school to assist me in business.” 

Kirkconnell took courses like company law, employment law and land law, all of which he thought would help him in his business career.  

“As I got going, I found that I was enjoying it and at some point… I decided that I wanted to make a career of it.” 

Kirkconnell said that up until that point he’d been in the family business his whole life and part of the attraction of a career in law was that he would be doing something on his own.  

In February 2003, when Kirk Wholesale and Foster Brothers formed a joint wholesale venture called Progressive Distributors, Kirkconnell – then in his early 30s – had the perfect opportunity to break away from the family businesses. 

Kirkconnell’s son Jack was also born in 2003, so going away to law school wasn’t an option. Instead, he changed his intentions at the Cayman Islands Law School, deciding to study toward a degree there. 

He graduated in 2006 and started his articles at Walkers, around the time his second child, daughter Leila, was born. 

Eighteen months later, Kirkconnell was called to the Cayman Islands Bar as a practicing attorney. Although many patriarchs of family business would probably be upset if a son left the family business, Kirkconnell said his father approved. 

“One of the days I think he was proudest of me was the day I got called to the Bar,” he said, adding that his father came from an era where most men went to sea. “For him [to see] that one of his children was being called to the Bar was a very proud moment for him.” 

Kirkconnell practiced law as a funds attorney at Walkers for three years, during which time his father passed away in 2010. Although he said he enjoyed his time at Walkers, he left the firm in 2011. 

“I made a determination that… [the law profession] was not what I wanted to do for the rest of my life,” he said.  

Kirkconnell said he has no regrets for the time he spent studying and practicing law. 

“I wouldn’t trade that for anything,” he said. “I think that it was a great experience and something that will stand me in good stead for the rest of my life. It’s something I anticipate will help me for the rest of my career.” 

When he left the law profession, however, Kirkconnell wasn’t sure what he’d do after that.  

“I thought that, having a business background, I wanted to get involved in something… more dynamic. I didn’t know exactly what it was I was looking for but I decided to take some time and try and figure that out.” 

Eventually that dynamic something turned out to be Cayman Enterprise City. 


Cayman Enterprise City  

When he left Walkers, Kirkconnell said he didn’t know anything about Cayman Enterprise City, the technology-based special economic zone that was first proposed in January 2011. One day he received a call from Frank Balderamos, saying that he and Cindy O’Hara wanted to take him to lunch. 

During that lunch, Balderamos and O’Hara – who were both already involved in Cayman Enterprise City – told Kirkconnell about the project and said they saw a role for him there. 

“I have to admit that at first I didn’t fully understand exactly what it was they were doing and why it was going to work,” he said.  

Given some time to consider it and after subsequent meetings, Kirkconnell decided to get involved, as a stakeholder, director and an employee. He started working at Cayman Enterprise City part time in late 2011 and then full time in January where he fills a familiar operations role. 

“We have good expertise in every other area at the moment, but we have some operations challenges,” he said. “So I volunteered to fill that role on a temporary basis. Ultimately, my role will be as the chief strategy officer of the company. That’s the long-term. I’m doing a little bit of that now, but mainly right now I’m operations.” 

One operations challenge is establishing procedures for new tenants that are reliable and consistent. Because Cayman Enterprise City is the country’s first special economic zone, everything about the process is new to both the company and the government, Kirkconnell said. 

“Every aspect of this is brand new,” he said. “There’s a big learning curve and that’s why I jumped into an operations role, because we had to try to get some of these things under control.” 

Kirkconnell said the volume of applications at Cayman Enterprise City is low right now, but the company fully expects to have to deal with a high volume of applications in the future. 

“If we’re doing it in an inefficient way, we’re not going to be able to deal with it,” he said. “What we’re trying to do now is take the opportunity to design some of the process and put them in place so when the boom hits, we’re ready and we’re not letting people down.” 



Kirkconnell has confidence Cayman Enterprise City will have that boom.  

“A lot of that has to do with me having gotten in there now on a full-time basis and being immersed in the project,” he said, “and seeing what the sales pipeline looks like and fully understanding the value proposition we’re making to our potential clients.” 

In addition, Kirkconnell travelled to Dubai last November to see firsthand how the special economic zones there operate. 

The trip really crystallized his concept of what Cayman Enterprise City is trying to do and that the business model will succeed. 

“It works very well in Dubai and there are a lot of very good reasons why it’s going to work in Cayman as well,” he said. 

Not only does he feel Cayman Enterprise City has a good business concept, he also believes it has a very good team. 

“Cindy [O’Hara] has really put together – between her and [CEO Jason Blick] – a really high -quality team that will not only do the project, but do it the right way,” he said. 

In addition, Kirkconnell said the project has received “tremendous support from government”, as evidenced by the host of legislation amended or created to facilitate Cayman Enterprise City. 

“Obviously, without [government’s] help we wouldn’t be at this stage,” he said. “I wasn’t around at the beginning, but from the very beginning I understand government has been a big supporter of the project and continues to support it as we go along.” 

The stakeholders in Cayman Enterprise City’s are now so confident in its success that they’ve doubled the amount of office space they project to build, from 500,000 square feet they said initially, to one million square feet. 

“We’re at the point now where we feel like the 500,000 square feet… might be conservative,” Kirkconnell said, adding that the interest and feedback from potential clients has been tremendous already, despite the fact that there have limited marketing activities so far. 

Cayman Enterprise City had its first two companies establish in the special economic zone in March and had 13 other companies in various stages of licensing during that month. 

“After that, we have another 70 companies in the pipeline,” Kirkconnell said. “We expect to close a good percentage of those in the next few months. We project to have 300 companies registered by the end of the year; that’s our target.”  



One of the key value propositions for companies establishing in special economic zones like Cayman Enterprise City is that they can have a physical presence in the zone while still enjoying many, if not all, of the benefits of exempted offshore companies. This model, which has the approval of international regulators like the OECD, means that people will be working for the companies in the Cayman Islands. This will create jobs for Caymanians as well as high-earning expatriates. 

Kirkconnell said that by having those companies locating in Cayman, there were potential economic benefits “from top to bottom”. Existing businesses, from law firms and accounting firms, to office and janitorial supply companies would benefit, he said. 

In addition, Kirkconnell thinks Cayman Enterprise City will bring more innovation to Cayman. As an example, he said that one of Cayman Enterprise City’s operational needs requires a solution that no local service provider is doing and therefore, a solution must be developed. 

“I think those kinds of things down the road will lead to improved expertise in the local service providers and will also lead to new jobs,” Kirkconnell said. “Our project is definitely going to challenge local service providers. We’re going to require some solutions to problems that perhaps no one has approached them on in the past. That may very well lead to improved services for companies that are already on Island.” 

New companies will also bring new people to Cayman, helping to replace the many people who have left the Islands since the start of the economic recession in 2008. 

“One of the effects I think Cayman Enterprise City will have on the economy is that it will help the real estate market recover,” he said. “I’m optimistic the project will help the Island in a number of ways; that is one of them.”  

Kirkconnell said Cayman Enterprise City projects to create somewhere near 10,000 jobs. 

“That’s what I understand is the number below peak [population] that we’re at are now,” he said.  

“So it helps to bring the economy back to where it was.”  

In speaking with many other business people, Kirkconnell said they told him their business infrastructure was geared for a population of 10,000 to 15,000 more. 

“That’s one of the reasons why there’s some struggling going on,” he said. “If we’re able to increase the size of the economy in that way, it affects everyone – the economy generally.” 

Unlike some larger jurisdictions where population swings of 10,000 people up or down wouldn’t have a large impact, Kirkconnell said in Cayman it will. 

“With the size of the population of Cayman and the size of the economy, that’s going to have a substantial positive effect on the economy,” he said.  

K story

Charlie Kirkconnell