Crashing Into Cuba
THE FRIDAY BEFORE HALLOWEEN, Josh Weinstein was set to take his first trip to Cuba: bags packed, visa in hand, leased Beechcraft turboprop booked for Sunday pickup at Sarasota Bradenton International. Then the dispatcher called. We have verbal approval to fly to Havana, he told Weinstein, but we’re still waiting on one last stamp from the Cuban government. Don’t worry, he explained—this happens all the time. Unfortunately, the government offices were now closed for the Tweekend. “We’ll keep pushing,” he promised.
Weinstein is president of Witzco Challenger, a $12 million family business that builds heavy-haul trailers in Sarasota, Florida, and ships them all over the world. Witzco lost about half its sales in ’08 and ’09 during the Great Recession. That was not long after Weinstein, former treasurer of his local stagehands union and grandson of Witzco’s founder, took over the company from his aunt and uncle, and he’s been scrambling to recover ever since. Exports are a big part of his business, about 35 percent, but they’ve been slipping lately. The stronger dollar hasn’t helped.
His unlikely solution: Cuba. The forbidden market less than an hour’s direct flight from Witzco’s central Florida factory is suddenly bursting with pent-up demand. Tourism in Cuba is soaring, on pace to exceed 2015’s record 3.5 million visitors, including a growing number of Americans who find a way to qualify for one of 12 exceptions to the Treasury Department’s limits on travel. (U.S. tourism is technically still banned.) Weinstein’s betting on a construction boom, spurred by the Cuban government’s plan to double the number of hotel rooms in the country by 2020, in pursuit of economic growth. “The first thing they’re going to have to do is infrastructure,” Weinstein says excitedly. “Water, septic, cable, electricity, communications. They’re going to need heavy equipment. My trailer moves the heavy equipment.” Not exactly a Cuba expert, Weinstein wants to see for himself. “I don’t really know the market, only what I’ve been able to Google,” he says. So he booked a booth at Cuba’s international trade show, slated for the fall.
Sunday night, the stamp came through. Monday morning, he was on his way, a day later than hoped. (The first lesson anyone learns when dealing with Cuba: It’ll happen when it happens.) Forty-five minutes across the Everglades to Miami to top off the tank—gas is much cheaper in the U.S.—and then another 45 minutes across the Straits of Florida to Havana. Upon landing at
