Data Sheet—Friday, May 27, 2016 by Heather Clancy @FortuneMagazine May 27, 2016, 8:55 AM EDT E-mail Tweet Facebook Linkedin Share icons About 10 years ago, I went to Cuba. (No, I didn’t go illegally—I have dual citizenship so I used my non-American passport, which I’m pretty sure was kosher). It was a bittersweet experience, visiting a country that was both idyllic and repressive. Now, with small signs of change in Cuba and our government finally easing up travel restrictions, the doors between the two countries are starting to open. And U.S. CEOs like Airbnb’s Brian Chesky are happy to step right in—the small island nation is now the vacation rental site’s fastest-growing market. A very different kind of company also sees opportunity in Cuba’s crumbling buildings. Doug Oberhelman, the chief executive of construction equipment maker Caterpillar, recently made the pilgrimage to the once-forbidden country too. “I’m 63 years old and for my entire lifetime Cuba has been a topic of discussion,” Oberhelman told me in a recent phone conversation following his trip. “We’ve said for a long time that the embargo should end.” President Barack Obama has called on Congress to lift the decades-long embargo, and Oberhelman is convinced it will happen within the next year or two. In the meantime, he’s already inked a deal with a distribution partner, Rimco, headquartered in nearby Puerto Rico, to sell to Cuba once trade restrictions are over. “It’s not a China nor an India, obviously,” Oberhelman said. “But it’s an opportunity for virtually every product this company makes. They just need so much infrastructure and it’s going to happen, with or without the Americans.” When I was in Cuba, I was struck by the crumbling architecture and the broken-down classic American cars. But I was even more taken by how scrappy and resourceful and, well, innately capitalist the people were. Everywhere you turned someone was running an “underground” business behind the watchful eye of their government. There was the guy with the fishing pole and bucket who gave us a tour of the old town (we had to pay him in secrecy), and the unsanctioned restaurants run in private homes.Who knows what the opportunities in Cuba hold for tech companies, construction equipment manufacturers, and any other industry, or how far the country’s own government will go toward normalizing relations and—gasp—being more friendly to business. (It should go without saying that I don’t see all iterations of democracy and capitalism as a force for good.) It’s hard to believe that next time I go, I can stay in an Airbnb in Havana. And, just maybe, see Caterpillar-made machinery in action. As Oberhelman told me, there are plenty of roads that need to be paved in Cuba. Michal Lev-Ram is a senior writer at Fortune. Follow her on Twitter or reach her via email. Share this essay: http://for.tn/1XW1Hgl. Find past editions of Data Sheet.