At last weekend’s Youth View Awards, co-host Yendi Phillips took to the crowd to interact with some of the VIPs in the front row. Among the style icons, media personalities, and who’s who of dancehall – stars in an arena filled with bold-faced names in Jamaica’s entertainment fraternity, and at a youth-targeted awards ceremony to boot – it spoke volumes that Gary Matalon, a businessman, serial entrepreneur, and certified construction project manager by training, was seen as a well-loved face.

Contrary to what many may believe, Matalon’s path toward actually achieving what many only dream of – turning his personal passions and hobbies into a thriving career – has not been paved with gold, or filled with caviar wishes and easy-breezy champagne dreams.

In late September 2016, the entertainment and lifestyle group Kingston Live Entertainment (KLE), which Matalon, his wife and a suite of friends (turned business partners) founded in 2008, turned a corner from a lengthy period spent in the red to finally declare a profit.

The group swapped debt for equity, and completed the divestment of the Fiction and Famous nightclubs. That move reduced their operational costs by more than half, allowing them to focus working capital instead on FranJam, a franchise company founded to own, develop, manage and license the Tracks and Records Jamaican-themed restaurants. The first outpost of that company is the Marketplace-based Usain Bolt’s Tracks and Records property in Kingston.

He often refers to the long process involved with developing a system to get the franchise system done right, “We were building up the system from 2011 to 2014, and Franchise Jamaica [FranJam] was set up because now we have as an asset the expertise.”

After a few months, FranJam is poised to open the third Tracks and Records location in Montego Bay. Under construction to open adjacent to hotelier Chris Issa’s forthcoming Spanish Court Hotel on Gloucester Avenue, the project is well under way. After seven long years the franchise seems poised for quick growth, and the group’s share price on the Jamaica Stock Exchange has risen by about 50 per cent.

In 2016, KLE could also breathe easy with regards to the group’s first foray into hospitality outside food and beverage: Bessa, a lifestyle-themed beachfront villa community in Oracabessa finally won approval from the St. Mary Parish Council in 2016 and broke ground.

The upward swing continues for Matalon, as his self-described unlikely foray into television, The Innovators, is Jamaica’s first business-focused reality TV show which acts as an ‘incubator meets mentorship programme’ fostering entrepreneurship. It is the brainchild of executive producer and co-host Yaneek Page. Matalon remembers that it took more than a little coaxing to get him onscreen: “She called me about seven or eight times before she got me to agree!” and could never have predicted that they would be preparing for the seventh season of what has become a staple on Jamaican television.

After welcoming Haley – the newest addition to their family – in 2015, who joins big sister Sydney, 11, and Jacob, 9, Matalon is looking forward to 2017 becoming the year that sees the newest ventures in his portfolio, KLE and The Innovators, bear fruit.

“Before 2005 I worked with the family business, [WIHCON], but then I stepped down to go out on my own…I was born here but lived in Florida, and every holiday I would spend in Jamaica. I moved to Jamaica permanently in 1992 and had just finished high school and worked with the Greater Portmore project. We built 10,000 houses over five years and I had to start at the bottom to learn the business. I was really a labourer, and went through all the different functions on a construction site, surveying, sewage, water…”

Encouraged by his cousin Peter, Matalon returned to Florida to attend university, where he pursued studies in management and entrepreneurship. But halfway through, when it became clear that studying was not how he spent most of his time, he received a stern talking-to from the family, which whipped him into shape and directed his focus on his studies.

“After university, I was a project manager and eventually operations manager on the construction site at Angel’s in Spanish Town. I was assistant to the project manager on that big project…it gave me a good appreciation for organisational skills and the planning process, to the letter..system building and large-scale manufacturing instead of bit-by-bit construction.”

Shortly after this, Matalon was completing his Master’s with the University of Liverpool online and getting ready to welcome his first daughter with his wife Tina. Despite the mounting pressure at home, at work WIHCON was about to begin another large project and Matalon realised this was the time for him to tender his resignation and step away from the relative safety of the family nest.

“Something in this process got me thinking. I wanted to do my own thing…to escape the corporate culture… I had my own ideals and goals and wanted to do things differently.”

Stepping away was not an easy choice for Matalon to make. He was starting a family, and they were going to have to rely heavily on Tina’s income to get them through that first phase. Furthermore, not everyone in the family was too happy with his choice.

“Little Joe [Joe Matalon] was supportive, but not everyone was at first… they thought that we have a good family business, so you’re ungrateful if you don’t stay in it.”

Following his intuition, and combining the lessons learned from his years spent at the family business with his school training, Matalon partnered with seasoned engineer Deighton Levee to form Neustone, a project and enterprise management firm. Formulating a detailed process-based methodology, the firm got a few knocks before landing some plum jobs that helped set the foundation for what remains one of Jamaica’s premier project management firms with their own patented system of operation.

“We got some jobs, then a job or two fell through…it wasn’t easy to start, but it’s that kind of desperation that helps you move forward. Then we got the gig for the Richmond project from Lee Issa. We got involved early, which allowed us to implement the methodology we created and grow the business. After that we were able to buy a building and from then on we got big gigs, [such as] a call centre – VistaPrint.”

Neustone went on to win the Project Management Office of the Year award from the Project Management Institute, the first of many accolades. The company still handles major projects for local and international firms alike, such as the recently completed Marriott hotel in New Kingston.

Many may be quick to dismiss this progress from someone with storied family experience in the sector as easy only ‘for some’, but Matalon notes that his surname comes with both positives and negatives.

“Truthfully, it’s been both a help in some respects and a hindrance in others, but you learn how to manage it. The biggest problem is that people just have this perception, especially in Jamaica, that you ‘must can’ cut a cheque for something, so your negotiating position can be difficult.”

KLE was launched in 2008:

“It was purely a financial investment. The full involvement happened because we also drastically under-projected what this venture could/ was going to do. On our first financial projections for KLE, we did 10 times over the aim in terms of revenue – so we were right about the fact that there was a demand for that kind of thing. About 11 months into Fiction, six of us went to Vegas for a nightclub and bar trade show, and there we decided if we would focus on Fiction alone or leverage and build out into something else. It was primarily David Shirley [the recently appointed Chairman of the KLE board since former Chair Audrey Marks stepped down to assume duties as Jamaica’s ambassador to the United States] who was pushing that brand Jamaica is strong, and we should leverage that into a cool sports bar or casual dining restaurant for international markets.”

Matalon cites Ambassador Marks as a “godsend” personally and professionally, “She was there to guide me and take me through turbulent times… it’s a mentally tough experience starting businesses, and divesting can be more difficult than starting.” After his ups and downs with KLE, Matalon admits he’s come out on the other side as a changed person.

“Famous did not materialise as we projected. Ultimately we lacked the human resources and financial resources to make it work at the international level we were going for. We were growing a bit too fast at that stage; Odyssey [the gaming lounge] and Bessa… everything spread us thin at a time when the global economic crisis was hard. Generally there are two things happening – what’s actually in the business and then the public perception. I’ve become a much more cautious person, and it was crucial to have a support element around that’s not fazed by ups and downs…because [Ambassador Marks] is a serial entrepreneur herself; to have that strength and stability around was priceless.”

In terms of business people he emulates, Matalon names Butch Stewart.

“Look at what he created from zero”, and Richard Byles “…how he operates, the company he runs, how successful it is, and yet he’s such a cool down-to-earth person…these are people I have the utmost respect for and marvel at their success. I’ve been fortunate in my career because I’ve had smart, experienced and willing people around me — my parents, both are career people — they’ve inspired me in the earliest days to develop into someone serious, and the time spent with my cousin Peter Matalon, I really watched him and learned from him… same with Little Joe.”

At this juncture, Matalon seems stronger for sticking with the path he chose, and sits more comfortably as CEO of a stabilised portfolio:

“The chatter doesn’t bother me anymore… used to, but not anymore….unless you’re in it day in and day out, [the]real deal is no-one can really know what is happening. It’s very easy for people to draw a bunch of conclusions – once you realise it’s baseless, then it doesn’t bother as much…”

An entrepreneur at his core, Matalon also admits it is satisfying to turn something he knows and loves like dancehall culture and brand Jamaica into something tangible.

“I love business as a whole. I love the entrepreneurial process – creating things from scratch and selling an experience, problem solving, innovation – [one] gets this sense of parenting when you launch an idea that you’ve worked hard to shape. You can figure out ways to do it better and do it differently to push it to another level.

“ I’m at the stage of the game now where I am just so driven and so focused on getting things right and making it happen.”