Why you should care

Because you need a middleman to do business in Cuba.

Everyone on the commuter ferry to the tiny coastal village of Gezaulole in Tanzania recognized Michael Laverty. Not only was he one of a few foreigners living in the rural settlement, but Laverty’s thrill-seeking demeanor had caught people’s attention too. He had taught himself to ride a motorbike on the streets in full view of the community. “I was probably the only person in Tanzania with a Japanese motorcycle,” he says.

Laverty, a die-hard adventurer, has spent close to a decade launching and managing businesses at the farthest edges of the investment universe. In Dar es Salaam, Laverty designed a research study to help antimalarial medicines reach the country’s outermost villages. And in the midst of a civil war in the South Sudanese capital, Juba, he ran a logistics business and oversaw a downstream petroleum company with $5 million a week in turnover. His next challenge: fraught, difficult Cuba.

This island nation, which for more than 50 years has been separated from the U.S. by just a 90-minute flight (and 90 miles of ocean), now holds the promise of opportunity in the globalized economy. Laverty, 34, has become an intermediary, sought after by the increasing number of Americans — investors, companies, politicians, even Hollywood stars — who are licking their chops, and not over rice and beans. He founded Havana Strategies with his brother, Collin, 33, last year, a company that acts as middleman for U.S. companies that want to move in on the Cuban market.

Though Cuba remains lined with 1950s cars, it’s also seen an explosion of private enterprises since Obama and Castro kissed and made up.

They organize fact-finding missions and meetings with Cuban officials, help companies get government approval and brainstorm media strategy. Laverty’s advised at least 15 different companies, half of them Fortune 500 firms, across the hospitality, aviation, technology and logistics industries. When Netflix held its company retreat and meeting (seriously) in Havana this April, all 285 employees were in the Laverty’s hands. When Airbnb headed in, they called Havana Strategies; same with Facebook. (Neither Netflix nor Facebook wanted to comment; an Airbnb spokeswoman said the company’s faced no major issues in setting up shop there.) The brothers, led by Collin at his sister business, helped arrange the logistics for a concert headlined by electronic music king Diplo.

Though Cuba remains lined with 1950s cars and its majority works for the state, living on ration books, it’s also seen an explosion of private enterprises since December 17, the day President Barack Obama and his Cuban counterpart, Raúl Castro, kissed and made up. Or at least approached frenemy status. The excitement of the brave new world reminds Laverty of the same thrill in South Sudan, post independence. He recalls his global business history with a tinge of cheekiness.

Still, huge barriers remain in Laverty’s mission, like a wide-ranging economic and political embargo that’s prevented most U.S. companies from doing business. Despite the excitement, American investment remains essentially notional — it was only in 2014 that the Department of Commerce approved $4.3 billion worth of business transactions; before that, details rarely saw the sun. Naturally, Laverty is careful to hedge his bets, saying he won’t overpromise. The long timeline — two to five years to set up manufacturing, for instance — is a deterrent for some companies, who simply “move on,” he says.

But Havana Strategies is overwhelmed with requests anyway, he says. The Denver-born Fordham alumnus and MIT Zaragoza graduate landed here thanks to a snap decision when his brother, a Cuba expert who’s run the successful Cuba Educational Travel company since 2012, said he needed help managing an onslaught of new clients seeking to enter the island’s market. “I had just got back from Africa, and I was tired and frustrated,” Laverty says. But the fraternal call beckoned; he booked a flight the next day. Don’t let the sprightly decisions cause you to call him an amateur. “It’s not his first time to the rodeo,” says Augusto Maxwell, Cuba Practice chair at Akerman, a U.S. law firm that, he says, helped Laverty with the Airbnb deal. Maxwell says Laverty’s experience in other developing nations shows.

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A rooftop swimming pool at the Hotel Saratoga, Havana, Cuba.

Source Walter Bibikow / Getty Images

A son of former “ski bums in Colorado,” Laverty began his career adventure working for MIT Zaragoza’s international logistics program, focusing on malaria in Tanzania, where he crossed paths with his future wife, 33-year-old Megumi Gordon, then deputy director of the malaria control team at the Clinton Health Access Initiative. So began a love affair between a development-sector power couple. Their marriage caused him to settle down, and in the two years since, he’s briefly muffled his wanderlust. But one wonders what his itchy feet really look like since he travels back and forth from San Francisco to Havana every month. He’s made about 30 trips so far.

But now comes the hard work. Laverty says several companies are still waiting for approval from the government … and fully normalizing economic relations with Cuba will fall to the next U.S. president. Cue the Trump drumroll. Even then, it will take several additional rounds of negotiations before fully lifting the embargo is a possibility. “You’ve got kind of a Cuba bubble right now,” says Andrew Otazo, the executive director at Washington D.C.-based Cuba Study Group. “There’s an exuberance.” But American-Cuban relations remain tense. (Representatives from both the American and Cuban government declined comment.)

Laverty’s ever the optimist. “We’re lucky to be doing stuff in a place that is so sexy and sought after right now,” he says. He points to the breadth of people drooling over the island as proof, from Diplo to the White House.

An earlier version of this article incorrectly stated that Akerman is a Cuban law firm and misstated who was responsible for a Diplo concert.

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