“You’ve got to create your own luck and build the life you want”
Ronan Guilfoyle talks to Accountancy Ireland about his experience relocating from Cork to the Cayman Islands and co-founding his own boutique governance firm serving a global clientele
If not for a heavy rain shower one day just after the turn of the new millennium, life could be very different for Irish-born Chartered Accountant Ronan Guilfoyle.
Today, Guilfoyle is Director of Calderwood, an investment funds governance firm he co-founded in 2016 in George Town, the capital of the Cayman Islands.
Originally from Douglas in Cork, co-running his own venture means Guilfoyle can leave Cayman’s stifling summer heat behind to move his family home for a few months every year. This near idyllic lifestyle came about almost by chance, however.
The story begins back in the ‘90s when Guilfoyle graduated with a degree in accounting from University College Cork and went on to train as a Chartered Accountant with EY Ireland, qualifying at just 22.
One of Guilfoyle’s work colleagues at EY relocated to the Cayman Islands around that time and a seed was sown. “She was a year ahead of me and sent me pictures of the speedboats out on the sea over there, the Cayman Islands GAA Club and the Irish bar in George Town,” he says.
“I was coming to the end of my contract and one day, I got soaked in a heavy rain shower on the way from my car to the office.
“I remember opening my laptop, looking at all those photos of Cayman and asking myself, ‘What am I doing here? Why don’t I go there?’”
Sun, sea and tax-free income
A self-governing British Overseas Territory in the Caribbean Sea, the Cayman Islands is a tax-neutral jurisdiction in which residents pay no direct tax.
“I thought to myself, ‘It’s tax-free money and a year in the sunshine would be lovely’, and I decided I would take a risk, go for a year and then come back to Ireland,” Guilfoyle explains.
As it happened, Guilfoyle would not return to Cork or a career in Irish practice.
“I was advised that fund administration was the ‘place to be’ workwise in Cayman—that it would be new and interesting from an accounting perspective, so that’s what I did.
“I moved over there and joined a company called Admiral Administration, which is now part of Mitsubishi UFJ Financial Group.
“I got promoted within six months and was making a decent living in tax-free dollars. That was 2002 and the euro had just come in. The dollar was worth more than the euro back then.”
In September 2005, Guilfoyle’s former boss at Admiral offered him a job at institutional governance, risk and compliance services provider DMS Group (now Waystone).
“At exactly the same time, I was asked to open an office for Admiral in Dublin. I had two options within a day, and I remember thinking I was really enjoying Cayman and that my experience working over there had gone so well in terms of the work itself, salary and promotions,” Guilfoyle says.
“I didn’t really fancy going back to Dublin, trying to find somewhere to live and getting back into the commute to and from work. I was enjoying the Cayman way of life.
“I played football here in the National League and had a lot of Irish and English friends. Life was pretty good and, ultimately, I decided to join DMS as it tenth employee.
“I subsequently convinced DMS to open an Irish office in Cork. That was the company’s first foray outside Cayman and my younger brother Ambrose, who lives in Cayman now, was our first employee in Ireland.”
Guilfoyle went on to open further DMS offices in Dublin, New York, London, Luxembourg and Hong Kong. “That expansion turned DMS into a global firm and I spent 10 years in all with the company. By that time, I had Caymanian status and I decided to leave and start my own firm.”
Calderwood: decade of success
Guilfoyle co-founded Calderwood in 2016 with co-founder Wade Kenny, offering independent directors and compliance services to investment funds globally.
“We’ve got 16 people now, and work with over 350 investment managers. Starting out, it was just me and Wade with zero clients. We’ve built a lovely firm, hiring people we know and whom we like to work with. Everyone gets along and it’s been a really interesting, enjoyable journey.”
Calderwood provides directors to the boards of investment funds based in the Cayman Islands and other jurisdictions, such as Ireland, Luxembourg and the British Virgin Islands.
“We work with large multi-billion-dollar funds right down to new start-ups and most of our team have been doing this for a long time—20 years plus. This is my twentieth year of sitting on those boards,” Guilfoyle says.
As board members, the Calderwood team look after the interests of investors. “The analogy I’ve often used is that of a referee. You are not one of the players; you’re providing oversight,” he explains.
“You’re making sure everyone’s playing by the rules and that they are doing what they are supposed to do. As long as everything is working the way it should be, you can let people do their jobs. Making sure they are doing their jobs the way they should, gives investors comfort.”
Calderwood has no involvement in investment decisions. “There is someone with far greater skill in that area who’s been hired to do that,” Guilfoyle says.
“We have oversight over who’s doing what and how they are doing it. Our job is to make sure that’s in line with the agreements they have signed and the way they’re supposed to do it.
“We do this through the board meeting process on a quarterly or semi-annual basis. We get written reports from everyone. We might also sit on audit or evaluation committees.
“The relationships we build over time are crucial to our business. A lot of referrals in our industry come from service providers, such as law firms. When you have done a good job for these people, and they have come to know and trust you, your reputation continues to build.
“We work in a competitive industry and there are lots of different players doing what we do. Our reputation, both from before we set up Calderwood and, in the years since, has helped the business to continue growing over the last decade.”
Guilfoyle also attributes Calderwood’s success to its people who, he says, bring proven experience and trusted track records to their work.
“Having seen so much over the past 20 years of serving on boards, our people are in a position to advise, help, support— and, ultimately, to add value,” he says.
“There’s not a lot of management involved in my work these days, for which I am grateful because managing people can be one of the most difficult jobs in the world.
“I had over 100 people under me when I was at DMS and managing that many people is not easy.
“When we started Calderwood, we had a clean slate to do it the way we wanted to. Not a lot of management is needed because our team is quite exceptional in just getting on with it. This has been somewhat life-changing for me.
“It means I have the freedom to relocate to Ireland during the summer months and travel to meet clients throughout Europe. This flexibility has made co-founding my own business really worthwhile from both a professional and personal perspective.
“I am very grateful. I recognise how fortunate I am, but, at the same time, you have to work your way into situations like this. You’ve got to create your own luck sometimes and build the life you want using what you know from what you’ve learned.”
Calculated risk brings reward
Ploughing your own furrow isn’t always easy and Guilfoyle has faced his fair share of naysayers over the years, particularly when he chose to leave Ireland for the Cayman Islands and, subsequently, to leave a well-established firm to start Calderwood.
“People pointed to the risks and tried to talk me out of things, but thankfully, those decisions have worked in my favour. Looking back, those times were stressful, but they were also exciting.
“Ultimately, those decisions proved to be sound and I’m glad I made them. It takes a lot of work to get to this level, but it has been enjoyable. I still work hard today, but I am also enjoying the fruits of my labour.”
Guilfoyle’s advice to other professionals is to “take a chance sometimes”. “Don’t be afraid to travel, see the world and learn about something new—new cultures, new experiences, new industries,” he says.
“I am very fortunate I made the decision to move to the Cayman Islands at the start of my career. That said, I still love Ireland and greatly appreciate being able to divide my time each year between Cork and Cayman.
“Being both Irish and Caymanian, it’s nice that in the future we will be able to spend time in both places to suit our lifestyle.”