The Jamaicans who built real wealth,
and how they actually did it.

How it happened

In 1983 he borrowed money to buy about half a million dollars of shares in Mackenzie Financial, a Canadian fund company. The stock rose roughly seven times, and in 1987 he used the gains to buy AIC Limited, a small mutual fund firm in Ontario that he grew into one of Canada's largest. In 2002 AIC bought about three quarters of National Commercial Bank from the Jamaican government for around US$127 million, paid over nine years. He has chaired NCB ever since, and Forbes has listed him as a billionaire since 2010.

The strategy

• Own very few businesses. He has said you should hold fewer than the number of fingers on your hands.
• Understand them properly. He only buys companies whose business he can explain and defend.
• Hold them for the long run. His slogan is literally "Buy. Hold. And Prosper."
• Borrow carefully to buy a great asset, but only when you are sure of the asset, not the timing.

How it happened

Home-schooled by her grandfather in Clarendon, she co-founded Jamaica Money Market Brokers in 1992 with Dr Noel Lyon at a time when money market returns were something only companies and wealthy people got. JMMB set its minimum to open an account at one thousand Jamaican dollars. In 1994 the Bank of Jamaica named it one of the first seven primary dealers. By the time she died in 1998 the firm had four branches and more than twenty thousand accounts. She was posthumously awarded the Order of Jamaica in 2022.

The strategy

• Find a product the wealthy already use and remove the barrier that keeps everyone else out.
• Make the minimum small enough that a first-time saver can say yes today.
• Build the company on values and treat clients as family. She said her greatest desire was not to make a lot of money for herself but to have a clean heart and a pure spirit.
• Grow by earning trust in one market, then take the same model to the next.

How it happened

She was a designated floor trader when the Jamaica Stock Exchange opened in 1969. In 1977 she founded Barita Investments with ten thousand Jamaican dollars. She became the first woman to chair the exchange, first in 1984 and again from 1995 to 2000, and in that second term pushed through the central securities depository and electronic trading, the plumbing that lets you buy shares from your phone today. Barita listed on the exchange in 2010, and in 2018 she sold three quarters of it to Cornerstone for about three billion Jamaican dollars.

The strategy

• Be in the room early. She was on the floor the day the exchange opened and built her firm around it.
• Start with what you have. Ten thousand dollars and a licence was enough to begin.
• Build the infrastructure everyone else will need, then benefit from it for decades.
• Know when to sell. After forty years she took a buyer's offer rather than holding on for its own sake.

How it happened

He started Appliance Traders in 1968 with a distributorship for Fedders air conditioners. In 1981 he bought a run-down hotel in Montego Bay called Bay Roc, put about four million US dollars into it and opened it as Sandals. In 1992, during a currency crisis, he sold a million US dollars a week into the market to steady the Jamaican dollar, a move still known as the Butch Stewart Initiative. He launched the Jamaica Observer in 1993 and led the group that bought Air Jamaica in 1994. He died in January 2021 at 79, and his son Adam now runs the company.

The strategy

• Find out what people want, give it to them, and exceed their expectations. Those were his own words for the whole approach.
• Take the big bet when you see it. He said he rolled the dice and risked his savings on Bay Roc.
• Reinvest relentlessly. Profits went back into the next property rather than out of the business.
• Own a category. Sandals didn't just sell rooms, it sold a kind of holiday nobody else was doing as well.

How it happened

He started Island Records in Jamaica in 1959, recording local artists when the big labels weren't interested. The label went on to sign Bob Marley, Grace Jones and U2. In 1989 he sold it to PolyGram for a sum widely reported at around three hundred million US dollars. Rather than leave, he put the money back into Jamaica: the GoldenEye estate, Strawberry Hill in the Blue Mountains, the Island Outpost hotel group, and in 2009 a rum brand carrying his own name. He was inducted into the Rock and Roll Hall of Fame in 2001 and received the Order of Jamaica in 2004.

The strategy

• Back talent early, before it's obvious. The best deals are the ones nobody else is competing for yet.
• Stay small and distinctive. He called the big labels supermarkets and Island a very classy delicatessen.
• Let the creators create. He gave artists more freedom than rivals did, and kept the ones who mattered.
• Turn one success into the next. The record money became property, the property became hospitality, the hospitality became rum.

How it happened

An engineer with a Harvard MBA, he joined GraceKennedy in 1981 as a corporate planner and became co-managing director in 1986, the year the company listed on the stock exchange. As chief executive from 1995 he launched what the company called its 2020 Vision, a plan to move from being an importer and trader into higher-margin food and financial services and become a global consumer group serving Jamaicans wherever they live. He was chairman and CEO from 1998 to 2011 and stepped off the board in 2018. He now sits on other boards and invests in and mentors start-ups.

The strategy

• Set a long horizon and name it. A twenty-five year vision gave every yearly decision a direction.
• Move up the value chain. Trading other people's goods is a thin margin; owning the brand is not.
• Follow the diaspora. Jamaicans abroad are a market, and Grace products went where they went.
• Lead on integrity, excellence and optimism. Those were the three values he named when asked what mattered.

How it happened

Born in Bog Walk in 1936, he worked as a lab technician before going into trading at 23, first pepper and peas, later a distributorship for Henkel adhesives. He founded LASCO Distributors in 1988 and began manufacturing in 1994, creating products like LASCO Food Drink aimed squarely at working Jamaicans. In October 2010 he consolidated eight companies into three and listed all of them on the newly created Junior Market. He later said the Junior Market propelled the group's growth. Two of the three moved up to the Main Market in 2024. He received the Order of Jamaica in 2001 and died in 2023 at 86.

The strategy

• Serve the mass market. Products priced for the many, sold in volume, beat premium products sold to a few.
• Start in distribution, then make the thing yourself once you know what sells.
• Use the stock exchange as a tool. Listing gave the group capital and gave ordinary Jamaicans a way to own it.
• Consolidate before you list. Three clean companies are easier to value than eight tangled ones.

How it happened

Fourth of twelve children, she was excluded from the male-only family business after university, so she started her own. It began with Dairy Castle, a soft-serve stand in Manor Park, then a chicken restaurant. Island Grill, dated to 1991 at Twin Gates in Kingston, was the breakthrough. By her own account, putting jerk seasoning on the grilled chicken was what made it take off. The chain grew to seventeen stores, including a King Street location downtown opened in 2020. During the pandemic she kept staff on payroll and subsidised their meals without taking on debt. She has since handed the chief executive role to Tania Waldron-Gooden and stays on as founder and deputy chair.

The strategy

• Take a Jamaican thing everyone already loves and make it consistent, fast and clean.
• Use local produce. It's cheaper, it's fresher, and it's the point.
• Look after staff first. Her people came before margins in the worst year the industry has seen.
• Take the chance. Her advice to would-be founders is that otherwise your life will be dominated by the big "what if".

How it happened

She spent ten years at Air Jamaica, rising from clerk to vice president of marketing and sales, and started six businesses before the one that stuck. In 1997 she founded Paymaster, which let people pay several bills in one place instead of standing in a different line for each utility. It became the Caribbean's first multi-transaction bill payment agency. In 2015 Digicel bought eighty percent of the parent company and she stayed on as executive chairman. She served twice as Jamaica's ambassador to the United States, and in 2026 she bought Digicel's stake back to become sole owner again. She was elected to Parliament in September 2025.

The strategy

• Solve a pain everyone has and nobody has fixed. Bill queues were a national problem hiding in plain sight.
• Expect to fail a few times first. Six businesses came before Paymaster.
• Sell a stake when a bigger partner can grow it faster, and keep enough control to buy it back.
• Build on rails. Once the payment network existed, online and mobile payments could ride on top of it.