Ben Cowan-Dewar's pursuit of a destination empire

In the Cabot co-founder and CEO's quest to develop golf resorts that exude an authentic sense of place, patience, persistence and perseverance serve as his pillars

If Ben Cowan-Dewar’s career as a golf developer had a soundtrack, "Got My Mind Set on You" would serve as the title track. Most famously covered by George Harrison in 1987, the pop hit proclaims:

But it’s gonna take money
A whole lotta spending money
It’s gonna take plenty of money
To do it right, child

It’s gonna take time
Whole lot of precious time
It’s gonna take patience and time, mmm
To do it, to do it, to do it, to do it, to do it
To do it right

The origins of the 43-year-old Canadian entrepreneur’s golf development career began in 1999 when Cowan-Dewar, then 19, founded Golf Travel Impresarios, a company that organized and operated private golf trips. Accompanying clients on those journeys, Cowan-Dewar played many of the world’s Top 100 courses, and that experience proved vital once he shifted gears and began scouring the world for a place to build a new course of equal acclaim.

“Having played almost all of the world’s best courses, I felt like I had a foundation, like I knew the ingredients,” he says. “I’ve been all over the world chasing these great golf courses and I fundamentally believe there’s no great golf course and no great resort destination that doesn’t have a spectacular piece of real estate. That’s what I went looking for.”

Cabot Cliffs — Cape Breton
Ben Cowan-Dewar's golf destination development journey began with Cabot Cape Breton in Inverness, Nova Scotia. Cabot Links opened in 2011 and was followed in 2015 by the Bill Coore and Ben Crenshaw-designed Cabot Cliffs (shown).

Cowan-Dewar found that perfect site in Cape Breton, Nova Scotia in December of 2004, but it was as he attempted to realize its potential and build a world-class golf resort that he learned the two lessons that George Harrison proclaimed in that 1987 hit cover. It took three years before he partnered with Mike Keiser and broke ground on the site; and it was during those three years that Cowan-Dewar learned that if he was going to maximize Cabot Cape Breton’s potential, he was going to need to invest significantly more capital than he had anticipated.

“I was young and naive, which helps an entrepreneur’s journey to do it when you’re young and naive,” he says. “I don’t know if I thought I could do it as much as I believed that it could be done, but when I saw the land [on the eastern shore of Nova Scotia], I knew it could be an amazing golf course.”

When Cowan-Dewar approached Keiser about the project in early 2005, the elder golf resort developer was busy collaborating with Bill Coore and Ben Crenshaw to design and build the third course at Bandon Dunes Golf Resort. As Cowan-Dewar recalls, Keiser gave him “a polite brushoff,” explaining that he didn’t think he was the right partner — he just had too much going on with Bandon Dunes’ development.

“He told me that I’ve got to get more land,” Cowan-Dewar remembers. “I told him I don’t have enough money to build it, let alone buy more land. He said: ‘You need more land because you’ll be successful and you won’t be able to expand it.’ It was the perfect Mike Keiser moment because even when he was saying no, he was helping me.”

Cowan-Dewar dipped deeper into what little savings he had left — essentially going all-in on the project — and by the end of 2006 he had made enough progress acquiring additional land and securing the necessary permits to develop the site as he intended. At that point Cowan-Dewar reconnected with Keiser, who toured the site in March of 2007. Before the end of that year, he and Keiser had forged a formal partnership, with construction slated to begin in 2008.

Early on in development, Keiser confidently declared that the Canadian resort wouldn’t look or feel like a carbon copy of Bandon Dunes. “Cabot will be different from Bandon in 20 ways,” he told Cowan-Dewar. “We just don’t know yet what those 20 ways will be.”

The statement would prove to be prophetic. However, before the duo had evidence to support Keiser’s claim, a global financial crisis set in. Unbeknownst to Cowan-Dewar, the Great Recession of 2008, while a challenging obstacle to overcome at the time, ultimately became instrumental in the development of Cabot’s second resort — a property that’s prepping for a grand opening at the end of the year.

Cabot St_Lucia
Cabot Saint Lucia is scheduled to open in 2023 and will feature the Coore & Crenshaw-designed Point Hardy Golf Club.

When construction on Cabot Cape Breton began in Inverness, Nova Scotia during the summer of 2008, the future looked bright. But a dark cloud swept overhead in October once the financial crisis set in. “We had real concerns about moving forward,” Cowan-Dewar recalls.

Over the winter, the decision was made to spend minimally on the resort’s development but to keep advancing where and how they could. “We turned [course architect] Rod Whitman loose on a bulldozer with three people working golf course construction during the summer of 2009,” Cowan-Dewar says. “Rod roughly shaped all 18 holes, and we had momentum. What Mike and I ultimately believed was if we built through the crisis and everyone else stopped, we’d be one of the only people with new product on the other side of it.”

They were right.

According to Cowan-Dewar, Golf Digest reported in 2009 that Cabot Links was one of only four golf courses under construction. It was a startling revelation, especially since Cowan-Dewar says that prior to the recession, “there had been hundreds of golf courses opening.” When golfers finally teed off at Cabot Links, the 6,860-yard layout not only emerged as Canada’s first authentic links course, it also earned accolades from Golf Digest as the world’s best new course in 2012.

In 2015, Cabot Cape Breton opened its second 18-hole course, Cabot Cliffs, a Coore & Crenshaw design. Around this time, Cowan-Dewar began to look for a similarly dramatic site in a warm-weather locale — a destination where he could build a property that could serve as a winter refuge for the avid golfers who loyally visited the Canadian resort. He eventually found it on the northeastern shore of Saint Lucia.

“To see the amount of elevation and great terrain, it felt like an amazing opportunity,” he says. “This coastline — even more than Cape Breton — gives you more of what you want with golf, where it juts in and juts out so you’re able to play shots over the coast.”

Cowan-Dewar candidly acknowledges that neither of his early land acquisitions — the site in Cape Breton or the parcel of land on the coast of Saint Lucia — were discoveries in the truest sense. Prior to Cabot’s development, notable individuals such as composer Philip Glass and sculptor Richard Serra owned summer homes in or near Inverness; and Alexander Graham Bell had a home on Cape Breton, once declaring the area as the most beautiful place on earth.

“Great people were there already, they had discovered that it was this amazing summer destination with four miles of sandy beach,” Cowan-Dewar says. “They had been there for decades. So, I had this enduring belief that we could eventually sell real estate, but we had to really execute on the first piece of the puzzle, which was build great golf and offer great accommodations.”

Similarly, when Cowan-Dewar visited the future site of Cabot Saint Lucia, he saw even more evidence to support his belief that a future Cabot property could be successful there.

“Based on the number of second homes within a three-mile radius of the site, it’s clear that people had discovered that Saint Lucia is an amazing place long before I ever came there,” he says. “Proving the success of Cape Breton put the wind in our sails. So we certainly had more confidence than we did during the early days at Cape Breton.”

That confidence was tested in early 2020, however, when the global pandemic brought business to a screeching halt across many industries. In response, Cowan-Dewar relied on his experiences steering Cabot through the dark waters of the financial crisis 12 years earlier. In particular, he and his team decided to continue building with equity. “It was just the financial crisis playbook all over again,” he says. “From March to September 2020 we had no real estate tours. We just kept building. We kept building all the way through COVID.”

Along the way, Cowan-Dewar has kept a keen eye on the market and an open ear to what discerning travelers are seeking. More significantly, he’s kept an open mind to refocusing his efforts — and the experiences that his properties provide — should the market dictate it. “It’s really about listening to the market and reacting to it,” he explains. “So, it’s been an evolution, but at its core we always believed that we could build world-class golf and that that would effectively give us something to build on.”

These days, a golf course developed without a real estate component is almost universally celebrated for preserving the purity of the golfing experience. Advocates of this approach would have you believe that any course that weaves its way through or around residential neighborhoods is less impactful than one that transports players to a landscape seemingly devoid of civilization. Cowan-Dewar has never subscribed to this philosophy. In fact, with each Cabot property that he creates, a phase dedicated to real estate development lingers in the back of his mind. 

The 21 — Cabot Citrus Farms
A partial rendering of the newest 21-hole course at Cabot Citrus Farms that can be played as two separate courses.

In Cowan-Dewar’s view, golf and real estate can exist symbiotically. This isn’t his opinion. He knows this to be true, and he points to the world’s most famous golf course as proof. “Pebble Beach is one of my favorite places on earth. It’s one of the most beautiful golf courses. And there are homes lining it,” he says. “But if I asked you to draw a photo of the homes that line the fairways you wouldn’t be able to because your eye doesn’t go there.”

Take the 14th hole, for example, a long par 5 that doglegs to the right and plays uphill to a well-bunkered green. As Cowan-Dewar points out, there are homes situated along the entire right side of the hole, but they’re positioned slightly higher than the fairway, which means golfers are unlikely to feel as though those residences are impinging on the hole. Homeowners, by contrast, enjoy two dynamic views: the golf course and the ocean.

“Those homes looking across Pebble and out at the Pacific are more valuable than if you went five miles up or down the coast and you were just on the edge looking out at the ocean,” he says. “Staring straight at the ocean with no golf almost becomes monochromatic. It’s just a singular view constantly. But if you’ve got golfers and the sun hitting the land and you’ve got the ocean, then you’ve got texture. There’s more depth. It’s more dynamic. That actually makes it more beautiful real estate.

“If you think about it, it would’ve been very easy to put some homes out on the peninsula at holes seven and eight — the sixth green, the seventh green, and eight teeing area. But then, [if they had], we wouldn’t be here talking about Pebble Beach.”

That was the model that Cowan-Dewar followed as he began developing Cabot Saint Lucia, a property that will be home to as many as 300 residences (150 villas and 150 home sites). Currently, 65 units have sold, with construction slated to begin this month as the Bill Coore and Ben Crenshaw-designed golf course also rounds into form.

RELATED: Coore & Crenshaw: The cornerstones of success

“We basically gave Bill and Ben the canvas and said build the best golf course,” he says. “If we have them at their creative best on that site with nine greens placed along the ocean, the real estate is going to be okay. We’ll be able to figure that out.”

Pine Barrens Hole_03
Cabot Citrus Farms, formerly World Woods Golf Club in Brooksville, Florida, will be Cabot's first American development. The original Tom Fazio-designed Pine Barrens course is being reimagined by Kyle Franz.

Hanging on the wall of Cowan-Dewar’s office in downtown Toronto is a poster that reads: “work hard and be nice to people.” He likes to joke that his staff bought it for him, but Cowan-Dewar owned that poster long before he had any team members to be nice to. The sentiment speaks volumes about who he is and the business ideals that he values.

On the matter of teams, Cowan-Dewar says that it was serendipitous — more so than it was planned — that key members of the development team for the golf course in Saint Lucia had previously worked on the courses in Cabot Cape Breton. In particular, he points to Keith Rhebb and Trevor Dormer, two design associates who have worked closely with Coore & Crenshaw over the years and who serve as the lead shapers of the golf course in Saint Lucia.

It was planned, however, that Cowan-Dewar would again work with Coore & Crenshaw. “When you work with people that you trust and people with whom you’ve built something great,” he says, “and you know that you’re all trying to get to the right answer…that helps a lot.

“Development is hard wherever you are, whatever you’re doing. And I’ve learned that assembling the best team and getting the best people in the world to be a part of it really makes it so much better.”

Throughout his entrepreneurial career, Cowan-Dewar has adhered to a few steadfast pieces of advice. Number one: Do what you say you’re going to do when you say you’re going to do it. Number two: Be someone that people like to work with. Finally, he reminds himself that making the right decision is always preferred, but a wrong decision can be fixed. More important, not making a decision, he says, “will kill you every time.”

Given Cabot’s activity in recent years — the announcement of a third resort, Cabot Revelstoke, in British Columbia; the acquisition of World Woods in west central Florida (currently under a comprehensive redevelopment as Cabot Citrus Farms); and the acquisition of Castle Stewart outside of Inverness, Scotland, which has since been rebranded as Cabot Highlands with a second championship-caliber golf course by Tom Doak in the works — it’s clear that Cowan-Dewar will never suffer the trappings of indecision.

Furthermore, he’s taking a long-view approach to all of the aforementioned business ventures, including his premiere development in Nova Scotia and its eagerly anticipated successor in the Caribbean. In that regard, he owes a debt of gratitude to Mike Keiser, who instilled in him the understanding that developments like these require a specific ideology.

“If you’re building something that has an incredible staying power, you really have to be a steward of that land. If you know your business is going to endure, then you have to be a steward of that business,” Cowan-Dewar explains. “This is a golf course in the ground; you can’t pick up and move your business. You’re going to be in that community as long as you’re the owner and the steward of the asset. But if you take that approach — and you take that really long view — that will help guide you to all the right decisions in development.”