Businessuite · Top 100 Caribbean Companies & CEOs · Digital Issue

The Two-Listing Playbook: Inside Ian Dear’s Blueprint for Caribbean Hospitality Growth

How the founder of Margaritaville Caribbean Group is running not one, but two publicly listed companies to record results — and what it says about his leadership style.

Most CEOs consider the stewardship of a single publicly listed company demanding enough. Quarterly reporting cycles, audit committees, shareholder scrutiny, covenant compliance — it is a full-time discipline in itself. To run two separately listed public companies at once, and have both post record-breaking financial years in the same twelve-month period, is the kind of feat that invites one of two reactions from peers: admiration, or the suspicion that something has to give.

For Ian Dear, founder, Chairman and CEO of Margaritaville Caribbean Group (MCG), nothing appears to have given. In fiscal year 2025, both of his Jamaica Stock Exchange-listed subsidiaries — Margaritaville (Turks) Ltd (MTL), on the JSE Main Market, and Express Catering Limited (ECL), on the JSE Junior Market — delivered the strongest financial performances in their respective histories. That dual result is the kind of outcome that has put Dear near the top of Businessuite’s Top Caribbean CEO rankings, and it offers a useful case study in what disciplined, founder-led hospitality management looks like in Caribbean tourism.

A Tale of Two Record Years

Margaritaville (Turks) Ltd operates the Margaritaville-branded restaurant, the laid-back Beached Whale table-service concept and a Grab N Go outlet at the Grand Turk Cruise Centre. Express Catering Limited is the exclusive food-and-beverage operator in the post-security zone of Montego Bay’s Sangster International Airport, and increasingly a landside operator too. For the year ended May 31, 2025:

• At MTL, a 31% surge in Carnival Cruise Line traffic drove much of the passenger growth, while pre-shift ingredient prep and fixed-price purchase contracts held the cost line.
• At ECL, the FreePour beverage-dispensation system and cashless payments at several outlets supported margin gains, and just over US$1.0 million of dividends was declared and paid in two tranches.
• ECL’s intangible assets more than doubled as it acquired franchise rights (Freshëns, Bento Sushi, Spice Kitchen and Bar) ahead of a planned diversification beyond the airport concession.

Two different airports and ports, two different customer bases — cruise passengers in Grand Turk versus departing air travellers in Montego Bay — yet the same result: record revenue, record profit, and margin improvement achieved through operational discipline rather than simply riding a volume wave. In ECL’s case, revenue actually grew against a passenger decline, which is the harder trick to pull off.

What the Numbers Say About the Management Style

Reading the two annual reports side by side, several recurring threads emerge that say as much about Ian Dear’s leadership approach as any interview could.

1. A relentless focus on spend rate, not just footfall

Both Chairman’s Reports lean heavily on spend per passenger as the key operating metric. MTL’s report noted that revenue grew 22.2% even as passenger totals grew over 38%, framing the easing in per-head spend at very high volumes as a manageable trade-off. ECL’s report goes further, crediting the team with converting more passengers into customers or increasing consumption from each one — the language of a team that measures success in unit economics, not headline traffic.

2. Named, specific cost initiatives rather than vague “efficiency” talk

Both reports cite concrete levers: pre-shift ingredient preparation, fixed-price supplier contracts with advance notice windows, and technology investment in FreePour to curb pour waste. This is a granular, operator’s approach to margin management, the kind that comes from a leadership team — including CFO Roland Clarke, a Margaritaville veteran since 2010 — that stays close to unit-level results.

3. Building resilience into the capital structure ahead of shocks

ECL’s total assets grew from US$56.35 million to US$58.94 million, funded partly by a US$12 million bond, a Sygnus Credit Investment facility and new local-currency loans, while the company still paid dividends and worked within its debt covenants (a minimum Debt Service Coverage ratio of 1.25 times). When Hurricane Melissa struck Jamaica toward the end of October 2025, the annual report’s outlook already pointed to a phased rebuild and stabilisation programme, with disciplined cost management and prudent capital deployment. Building headroom before you need it is a hallmark of operators who have weathered COVID-19, hurricane seasons and currency volatility before.

4. A tight, overlapping governance bench used deliberately

MTL and ECL share several directors — Herrick Winston Dear as independent Chairman, Charmaine Maragh, Prof. Andrew Spencer, and Roland Clarke as an executive director. This reflects a founder who has assembled a small, trusted circle of Caribbean tourism, shipping, academic and finance veterans and rotates them across the group’s public entities to keep standards consistent, while audit committees at both companies remain weighted toward independent, non-executive directors.

5. Group scale used to de-risk single-location dependence

Both companies pay a US$250,000 annual group management fee, and MTL carried a related-party receivable from Margaritaville Limited of over US$6 million at year-end, effectively an internal treasury arrangement. The structure points to a centralised parent coordinating capital, franchise relationships (Jimmy Buffett’s Margaritaville, Bob Marley’s One Love Experience, and food-court partners such as Wendy’s, Starbucks, Cinnabon and Auntie Anne’s) and buying leverage across a portfolio of roughly 53 hospitality locations in the Caribbean.

The Builder’s Instinct

Dear’s operating philosophy shows up outside the audited numbers too. In a 2023 Jamaica Observer interview, he described the sky-bridge then planned to link Margaritaville Montego Bay with the Coral Cliff entertainment complex across the road — a property long idle on the Hip Strip. Construction stalled during the pandemic, and a storm in February 2024 forced an extended closure of Margaritaville Montego Bay for a full renovation. When the property reopened in December 2024, ahead of its 30th anniversary, Dear framed the disruption as an opportunity:

“Out of every situation comes an opportunity.”

It is a recurring pattern in how the group is run: setbacks — a derelict neighbour, a pandemic, a storm, and now Hurricane Melissa’s aftermath heading into fiscal 2026 — tend to be absorbed, reframed and built into a stronger asset rather than simply repaired. ECL’s report shows the same instinct: even as the Board flagged moderated volumes into fiscal 2026, management was constructing three additional landside outlets (Spice Kitchen and Bar, Cinnabon and Auntie Anne’s) and preparing Freshëns and Bento Sushi for 2026.

Credentials Beyond the Balance Sheet

Dear has been a Justice of the Peace for the parish of St. James since 1996 and chairs the Board of the Tourism Product Development Company Limited (TPDCo), while serving on the boards of the Tourism Enhancement Fund (TEF) and Trans Jamaican Highway. In 2020, Jamaica’s Governor-General appointed him to the Order of Distinction in the rank of Commander (CD) for his contributions to Caribbean tourism and real estate development.

He has previously served with the Jamaica Hotel and Tourist Association, the Private Sector Organisation of Jamaica, the Young Presidents’ Association, the Montego Bay Chamber of Commerce, the Jamaica Cruise Council and the Attractions Association of Jamaica — a footprint that keeps him close to the policy decisions on airlift, port development and destination marketing that move the revenue lines of both MTL and ECL. Businessuite readers will recall that Dear was named a 2018 Top Caribbean CEO, a recognition that highlighted his role as an employer of over 1,000 Jamaicans and the group’s scholarship programme for employees’ children.

The Takeaway

What emerges from a close read of two very different annual reports — a cruise-port restaurant operator in a British Overseas Territory and an airport concessionaire on the Junior Market — is a leader who runs both like an operator, not just an investor. Dear’s approach rests on a handful of repeatable disciplines: track spend per guest as closely as footfall, lock in cost protection before you need it, keep a small trusted governance bench moving across entities, build capital headroom ahead of the next shock, and treat disruption as the trigger for the next phase of construction rather than a reason to retreat.

With Hurricane Melissa’s aftermath shaping the start of fiscal 2026, and first-quarter results at both companies already reported ahead of a difficult comparison, the early evidence suggests the same playbook is being run again. For a CEO managing two public companies at once, that consistency — as much as the record numbers — is the real story.

Financial data is drawn from the audited FY2025 annual reports of Margaritaville (Turks) Ltd and Express Catering Limited for the year ended May 31, 2025, with biographical and project details from the companies’ reports and published press coverage.