Nothing impedes business like uncertainty; therefore it's not surprising that many U.S. business owners still have more questions than answers about how they can do business in Cuba. The questions first arose in a substantive way on Dec. 17, 2014, when the Obama administration and the Cuban government announced they were taking steps to reestablish diplomatic and greater commercial relations between the two countries.

The news was a radical change to the more than half a century policy of isolation pursued by the U.S. government. While Cuba is just 11 million people with a state-run economy of about $80 billion, many U.S. business leaders wanted to leverage what they perceived as a great opportunity to enter a new market. Now, after more than two-and-a-half years and the election of President Donald J. Trump, we see how complicated the answer to the question of how to do business in Cuba can be for U.S. companies.

The initial steps to take

So far, the reality of doing business with Cuba has been an exercise in patience, frustration and hope for American companies. As a first step, most American ventures in Cuba will require approval from the U.S. government. The process can be lengthy, often taking months—if not years, due to a range of factors, including an intensive inter-agency review process and the high number of requests being reviewed by the main regulatory agency, the Treasury Department's Office of Foreign Assets Control, which also oversees U.S. sanctions programs against a number of other countries, entities and individuals. The licensing process is lengthy, as OFAC and the other U.S. agencies overseeing the Cuban embargo are staffed by professionals who must operate pursuant to established regulations.