In 1959, one of the first official acts of a young Fidel Castro was to nationalize private property that resulted in the mass expulsion of foreign companies from Cuba. Fast forward to five decades later, where a diplomatic thaw is underway between the island and the world's largest economy, but businesses are still in the dock awaiting opportunities to profit from the evolving détente.
With Barack Obama preparing to become the first U.S. president in decades to visit the nation this month, the economic blockade — which can only be lifted by Congress — remains in force. That suggests American companies are unlikely to reap the benefits of the new relationship between the two countries — at least not right away, even as the White House has eased restrictions on travel and remittances.
Recent moves by the U.S. to normalize relations with Cuba haven't opened the floodgates for foreign investment, and observers say domestic Cuban businesses are still adapting to the new reality. Beginning in 2010, the island saw a boom in start-ups, which have increased from 150,000 to more than 500,000 in the last five years, according to Cuban government data.
That being said, the state of Cuban entrepreneurs, or "cuentapropistas," as they are called, remains "incipient" due to being suppressed by the Communist government, said Ted Henken, an author and professor at Baruch College in New York.
Owning a business in Cuba is a "struggle," Henken, a sociologist who has written extensively on the Cuban economy, told CNBC in a recent interview.