Jamaica is the home to some very successful Jamaican entrepreneurs.  It is also the home of jerk chicken, reggae music, the legendary Bob Marley and the fastest man in history, Usain Bolt.  This small island is also known internationally as a lush tropical paradise that is the perfect place to go on vacation or as the best port of call on a Caribbean cruise.

successful Jamaican entrepreneurs

This beautiful island is gifted with some of the most resilient, creative, ambitious and successful people in the world. Many of us are blessed with entrepreneurial skills and determination.   Amidst the harsh economic crisis, there are some people who seize the moment, as we look for opportunities to make extra money.

There is so much I want to share about this beautiful island but in this article, I want to highlight five successful Jamaican entrepreneurs who are serious about business. They have charted new frontiers while overcoming major challenges
along the way.

Top 5 Successful Jamaican Entrepreneurs


successful Jamaican entrepreneurs

Michael Lee-Chin

Lee-Chin is a Jamaican businessman, investor,
philanthropist and one of the successful Jamaican entrepreneurs.

He serves as the Chairman and CEO of Portland Holdings Inc., a
privately-held investment holding company headquartered in Ontario,
Canada.   His net worth stands at approximately CA$3.95 billion as of March 2018,
making him the 20th richest man in Canada.

Lee Chin is a self-made billionaire who started his career as a road engineer for the Jamaican government.  He gradually built his way up to chairman and founder of Portland Holdings, a thriving, privately held investment company in Jamaica.  Additionally, Lee-Chin is executive chairman of AIC Limited and National Commercial Bank.

Jamaican-Canadian Lee-Chin also owns stakes in National Commercial Bank Jamaica and Total Finance in Trinidad and Tobago. His personal real estate portfolio includes 250 acres of beachfront property in Ocho Rios, Jamaica, and homes in Canada and Florida, according to Forbes.


successful Jamaican entrepreneurs

Joseph M. Matalon

Joseph Matalon is also among the successful Jamaican entrepreneurs.  I consider him one of the foremost leaders in Jamaica business. He is also part of a family with a legacy of successful business practices for decades.

He is the chairman of the ICD Group, a Jamaican investment holding company. In addition, he has been involved with a number of special committees to advise the Jamaican government on financial and economic matters, and he represents the PSOJ on the Council of the Partnership for Transformation.

Mr Matalon serves as Honorary Chairman of St. Patrick’s Foundation, which supports charitable activities in inner-city communities, and as Chairman of the Board of Governors of Hillel Academy in Kingston, Jamaica.

A leader in the business community, Mr. Matalon also holds directorships on a number of other boards including West Indies Home Contractors Limited, WIHCON Properties Limited, Prime Asset Management Limited, Margarita Limited, and The Tony Thwaites Wing of University Hospital of the West Indies.


successful Jamaican entrepreneurs

Gordon “Butch” Stewart

Another of the successful Jamaican entrepreneurs is Gordon ‘Butch’ Stewart.  He started Sandals Resorts, in 1981. This business venture has grown leaps and bounds over the years and he is now the owner and/or Chairman of over two dozen companies throughout the Caribbean, North America and Great Britain.

The business maverick owns and runs 20 resorts under the Sandals umbrella.  These include the original Sandals all-inclusive couples-only resorts, the Beaches resorts for families, and four boutique hotels. Mr Stewart serves as company chairman, while his son Adam, now serves as CEO. Despite his many achievements and unconventional attitude to business, Butch Stewart’s inspirational life story remains widely unknown.

Mr. Stewart started out as a young man when he opened Appliance Traders Limited (ATL). It is said that he started with a rented office, a second-hand car and a second-hand pickup. Today, ATL Group is also in the office equipment business and is the distributor of Honda motorcars. ATL also owns the Jamaica Observer newspaper.


John Issa is a part of the group of successful Jamaica entrepreneurs.

John Issa

John Issa introduced the all-inclusive concept in Jamaica when he created the first all-inclusive hotel on the island in 1976 – Negril Beach Village – which later became Hedonism II in 1981. He revolutionized the resort industry again with the introduction of the Super-Inclusive holiday, promising vacations with no hidden costs.

As a successful Jamaican entrepreneur Mr. Issa left a lasting legacy and after more than 30 years of development, the SuperClubs Super-Inclusive concept continues to grow in the Caribbean and beyond.

There are 11 SuperClubs properties in Jamaica, Curaçao, The Bahamas, the Dominican Republic, and Brazil, which fall under the brand names Breezes, Grand Lido, and Hedonism. In addition, SuperClubs has three Super-Affiliate resorts in Jamaica: Starfish Trelawny Beach Resort, Rooms Ocho Rios, and the Negril Beach Villa.

New properties include the Rooms in Negril, Jamaica, and the Starfish Santa Luzia in Aracaju, Brazil.


Audrey Hinchcliffe one of the top female successful Jamaican entrepreneurs.

Audrey Hinchcliffe

The only female featured in the list of successful Jamaican entrepreneurs is Audrey Hinchcliffe.  She is the head of Manpower and Maintenance Services Ltd.

Ms. Hinchcliffe was invited by former United States Secretary of State Hillary Clinton to join the US Department of State’s International Council on Women’s Business Leadership for a two-year term.

Hinchcliffe is principal of Caribbean Health Management Consultants Limited.


You too can become a successful home-grown Jamaican entrepreneur. There are opportunities available that can allow you to make your dreams reality.

Take a look at what it takes to be a successful entrepreneur and decide if you are willing to take this life-changing.

There is also a program with a community of like-minded people who have been very instrumental in my online career. Come on inside and have a look at this program. You have nothing to lose,it is free to look around and if you want to stay it is very affordable.

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