A Startup CEO Visits Cuba in Transition


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have been unable to replace or repair. Cuba is lacking a lot of basic infrastructure: cars (perhaps 2 percent of Cubans have them, and the 1950s American cars seem to be for wealthy tourists only), consistent running water in public toilets, and basic supplies for students. We visited two children’s programs: one for circus training, and one for after-school activities. Their paucity of supplies was…humbling to the point of tears. A music troupe who played for us used a kazoo in lieu of a trumpet, and a C-clamp with bubble wrap in lieu of a capo.

6. Happiness. We know from Ben-Shahar’s book that wealth and happiness are not correlated, and common experience shows that beyond a certain level of well being, wealthier people often seem less happy. I went running off the beaten path, and saw children playing soccer in bare feet; soldiers hitchhiking; and stores with nearly empty shelves. Yet people seemed genuinely happy.

Photo courtesy of Matt Bencke

Photo courtesy of Matt Bencke

7. Isolation. Cuba is an island unto itself—literally. There is almost no Internet, and where there is, it is heavily censored. I could not access any e-commerce sites, or even Evite. The $5-per-hour WiFi scratch cards in our hotel were like the lottery. Roughly one fourth of the time they worked, and then irregularly, slowly and at the whim of censors. Some people pirate satellite dishes, which they hide in fake water towers. Cubans pay $1-2 to have a black market seller sideload a thumb drive with new content from Hollywood and the news. We saw a flash mob of hundreds of people, and discovered that a hot spot had popped up. Lots of people have smartphones; very few have laptops. Computer labs in schools from elementary to the top university were depressing: filled with heavily utilized, ancient textbooks, CRTs, Windows 95 and XP, and, again, no Internet. A lot of young people are rushing to get out: our talented local tour guide said he was one of three recent graduates who did NOT emigrate to the U.S. from his class—out of 24. More Cubans are trying to escape to the U.S., seeking citizenship.

8. Americans are not the American Government. Literally every local with whom I interacted seemed genuinely eager to chat. They love America, and Americans. They asked me about Obama, and Trump. They all know that they suffer under the embargo, but they don’t seem to blame us. In fact, they are thrilled that the embargo is loosening. Propaganda is ubiquitous. Cubans are quick to cite the many assassination attempts on Castro, and other acts against their citizens (e.g., Cubana flight 455 in 1976). After I asked our guide at the Marti monument about the Cuban government’s relationship with the Catholic church (a rocky one, at best), she cut the tour short (“the elevator to the top is broken”).

9. Window of Optimism? Frankly, I’m not so sure the U.S. and Cuba are on the brink of a meaningful reconciliation. The Obama administration is opening, but only Congress and the White House, working together, can truly change the game. Cubans are still haunted by the “Special Time” when the Soviet Union collapsed, and Russia abandoned the billions of dollars that propped up the economy. People ate cats to survive (dogs are sacrosanct). Venezuela filled the void to some extent, but with that country imploding, people are palpably nervous. While we were there, there were rolling power outages, and the rumors immediately swarmed that another dark era may be upon them. Cuba today reminds me of Russia in the early 1990s: promises of integration, peace, and wealth, which were followed, in that case, by disappointment, disruption and revanchism.

10. Ambivalence. It was pretty easy to get to Cuba, with the help of a travel agent. But Paypal froze one of our accounts for labeling a friend-to-friend transfer, and several of us had our Facebook ad accounts frozen. Officially, it is okay to visit Cuba, but there are restrictions and apparent bureaucratic ambivalence.

I’m glad I got to visit Cuba during this unusual transition. But it remains to be seen, what the next phase brings. There are twelve million educated citizens 90 miles southeast of Florida, yet barely interacting with the United States. That’s an unstable equilibrium, and a fascinating anachronism. I’d love to hear from others, especially those with more context than me.

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