Caribbean Entrepreneurs with Businesses Worth Understanding

Jamaica, tourism. Stewart started out selling air conditioners in Kingston through his company Appliance Traders, then bought a run-down hotel in Montego Bay in 1981 and opened the first Sandals. His all-inclusive resorts for couples, where one price covered food, drink and activities, suited visitors wary of spending money in an unfamiliar place, and Sandals spread across the region. He died in 2021.

Jamaica, hotels. Issa, from a Lebanese-Jamaican merchant family, opened the Tower Isle hotel near Ocho Rios in 1949, widely described as Jamaica's first resort open all year rather than only in the winter season. Its success helped open the island's north coast to tourism, and he became the first chairman of the Jamaica Tourist Board. His family later turned Tower Isle into the first Couples resort.

Dominican Republic, tourism and infrastructure. Rainieri began developing Punta Cana in 1969 with American investors, when the eastern tip of the island had no roads, power or airport. To bring visitors in, the group built its own international airport, opened in 1984 and one of the first privately owned international airports in the world. Punta Cana became the busiest tourist destination in the Caribbean.

Cuba, rum. Bacardí, a Catalan wine merchant in Santiago de Cuba, bought a small distillery in 1862 and set out to make rum smoother and lighter, using a cultivated yeast, charcoal filtering and ageing in oak. That changed rum from a rough spirit into one suited to mixing. The company left Cuba after its assets were nationalised in 1960 and kept growing elsewhere.

Cuba, sugar trading. Lobo was the most powerful sugar trader of the mid-twentieth century, owning mills in Cuba and trading on world markets from Havana, at a time when the island was one of the largest sugar exporters. His business shows how dependent a Caribbean economy could become on one commodity. After the revolution, his mills were seized in 1960 and he left Cuba, losing almost everything.

Puerto Rico, cement and industry. Ferré, an engineer from a Ponce industrial family, ran the family's iron works and built Puerto Rico Cement, supplying the concrete for the island's rapid building programme in the mid-twentieth century. He later served as governor from 1969 to 1973 and founded the Museo de Arte de Ponce, showing how one family business could shape an island's economy and civic life.

Jamaica, music and hotels. Blackwell founded Island Records in Jamaica in 1959, recording local ska and selling records to Jamaican communities in Britain from the boot of his car after moving to London. He signed Bob Marley and the Wailers and marketed them as a rock act, taking reggae worldwide. He later built Island Outpost, a group of small hotels including GoldenEye, Ian Fleming's former home.

Jamaica and Canada, finance. Lee-Chin, born in Port Antonio, moved to Canada, bought the small mutual fund manager AIC in 1987 and grew it on a concentrated buy-and-hold strategy. In 2002 he bought control of Jamaica's National Commercial Bank, bringing a large share of the island's banking back under Jamaican-born ownership, and built Portland Holdings around investments in the region.

Barbados, beauty. Rihanna launched Fenty Beauty with LVMH in 2017 with 40 shades of foundation, at a time when many brands offered few options for darker skin. Selling to customers the industry had underserved, rather than relying on her fame alone, made it one of the fastest-growing cosmetics brands, and she followed with the lingerie brand Savage X Fenty.

Jamaica, hospitality and trading. Before her fame as a Crimean War nurse, Seacole ran a boarding house in Kingston and stores and a hotel in Panama serving travellers on the route to the Californian goldfields. In 1855 she financed and built the British Hotel near Balaclava, selling food and supplies to officers and treating the sick. Her career is an early example of Caribbean enterprise following trade routes abroad.