Note: Names and some identifying features have been changed.

José Martí airport in Havana is, like much of the city, pleasantly antiquated—at least to the privileged traveler. To the rest, it’s probably just antiquated. When passengers disembark onto the tarmac, they find themselves surrounded by ravishing rainforest, engulfed in a silencing humidity. The customs area smells like an old bowling alley; In lieu of welcome mats, travelers wipe their feet on cardboard Havana Club Rum boxes. After grabbing their luggage from an airy baggage claim with green and orange walls, they sit in a bar and order beers while they wait for an air-conditioned bus to arrive. Members of the Exeter Center for Entrepreneurs followed this pattern to a T when they arrived in Havana in early October.[1] The Center, which is founded and run by Val Exeter, acts as a multi-faceted advising tool for high growth entrepreneurs. They hold CEO roundtables—seminars led by Val in which executives discuss common problems they face—act as an investment bank to the companies, and organize educational retreats such as the one that brought thirty some-odd innovators to Cuba. They had left their hotel in Miami a little before five o’clock in the morning for a nine AM flight, mostly because of an unrealized fear of bureaucratic red tape delaying them.

“Where you were when the west was won?”

The first stop in Havana for the sleep-deprived group was the headquarters of On Cuba magazine, the first American publication to have a full-time office in the country. Run by Hugo Cancio, a charismatic Cuban-American from Miami, On Cuba has grown from a single in-flight magazine to a budding dynasty that includes periodicals on art and real estate. With his square jaw and broad shoulders—accentuated by a sharply cut blazer—Hugo seems built to be the gravitational center of a room. After a short speech that explained the magazine and how he thought Cuba would progress over the next decade, he took questions from the entrepreneurs. The first was whether the government had ever censored him. He explained that they hadn’t; though the magazine had published articles that the Cuban leadership wasn’t happy with, nothing more than a cordial lunch meeting ever came of it. The second question was from someone the group eventually took to calling Military Man Stan. He had wispy white hair and a Marlboro permanently attached to his cracked lower lip. Wearing a red polo under a tan fishing vest—a variation of the uniform he would rock every day of the trip—he stood up and stated that when the Internet arrives in Cuba, the country will collapse because everyone will leave. Slightly flustered at the lack of a question to respond to, Hugo pointed out that when the group arrived all the people around the office were on Facebook. Though slow, Cuba has Internet. Stan refused to accept this response, insisting that since Adam Smith said everyone acts in his or her own self-interest, everyone will abandon Cuba. He compared Internet in Cuba to “getting in on the ground floor of Apple in 1995.” Apple’s market cap in 1995 was a shade under five billion dollars.

The View from On Cuba’s Headquarters (Photo Courtesy of Kaete Erskine)

“To the victor go the spoils”

The Hotel Nacional is a grand building; it was built by Robber Barons trying to imitate aristocracy. Opened in 1930, the firm that designed it also built the old Penn Station and The American Academy in Rome. The entrance sat perpendicular to a long hallway that made up the lobby. To the left, a stylized drawing of Castro rallying the rebels stared at a gift shop. The concierge and elevators were on the right. Dead ahead were two glass doors that opened up to a massive courtyard. Most of the entrepreneurs spent their late nights there, ordering drinks from one of the two bars, lounging on the sofas near the entrance or talking around tables that overlook the ocean and smoking cigars. A ten-foot cliff marks the end of the property. Below this sat the Malecón, a four-lane road that contoured to the smiling shape of the seaside. On Friday and Saturday nights, thousands of Cubans gather along the wall to listen to music, talk, laugh, and drink.

On the second night of the trip, a few of the drunker entrepreneurs left the comfy confines of the courtyard to join the locals. Upon arrival, they began to take photos in front of the seemingly limitless ocean. A local approached Leila, a nineteen year-old country music singer from rural Tennessee, and asked, “Podemos tener un poco de su ron?” The entrepreneurs stared, confused. He repeated the question. Leila began to stammer out, “no hablo ingles.” Val’s son Nate and I both understood Spanish, and interrupted her to translate. “He’s asking if they can have some of your rum.” She shook her head and responded, “no no no.” Still flustered and slightly fearful, she pulled out a solitary cigarette and held it out to him; nodding as if to say, “have this instead.” He accepted it with a “gracias” and returned to his group. As she watched him, she commented, “I didn’t want them to think Americans are selfish.” Several times during the trip, she mentioned she was not opposed to voting for Donald Trump.

As the scene unraveled, a few of the entrepreneurs got restless. To their right, the sidewalk was empty for thirty yards—a constant spray of seawater from the waves breaking on the wall kept the sane away. Chris, the founder of a personal finance company that focuses on investing with integrity, decided to walk down the drenched patch of concrete to see if any water would land on him. Swigging añejo rum straight from the bottle, he insisted that it wouldn’t, that it’d be “a reverse Jesus” situation. He walked through and back unscathed. As the other entrepreneurs laughed in amazement, he explained that though there was constantly water splashing, the probability that it did so at the exact point and time he was walking through was low. A form of statistical logic backed his drunken bravado.

The night before, people hit the hay early. They had been up since 4:00 in the morning, and most snuck off to their rooms to clandestinely check email before collapsing. Only a few members lounged around the courtyard, sampling the mixed drinks and exchanging stories in two distinct groups. As the numbers dwindled, the two cliques merged, six people sitting on a few couches as waiters swept the floors and the live band packed up their guitars. Among the group was Dana, the granddaughter of an entrepreneur who founded a major fried chicken fast food chain and then opened the first health food restaurant in Atlanta. With long black hair and oversized sunglasses, she drew comparisons from members of the coterie to Jackie Onassis Kennedy. Soon, she began telling the group about her humanitarian trips to Haiti, how she “spread the good word of the gospel” for only $1500 a trip. Her main job there was making connections. She insisted that all Haitian men loved her and all Haitian women were frigid. She felt she made a difference convincing young women and girls forced into prostitution to run away from their pimps, though she always saw them back on the street when she returned months later. The girls really inspired her; when she got back, she “swore to give up [her] five dollar lattes, but [she] always found herself back at Neiman Marcus four weeks later.” She used the trips to work on her Creole, “you know, bonjour, rapido, rapido.” (Rapido is not creole.) When asked about voodoo, her eyes widened. “No, no. They’d take my eyes. They like our eyes,” she explained when asked if she had seen a ceremony. “The houses they use for it are painted.” They don’t try to convert those houses. Her fate was sealed. For the rest of the trip, a subset of the group referred to her as “White Savior Girl.”

The Hotel Nacional Courtyard (Photo Courtesy of Kaete Erskine)

“Desperate Times Call for Desperate Slogans”

A meeting with an economics professor from the University of Havana the second day went much like the conversation with Hugo, down to Military Man Stan raising the specter of Adam Smith. At lunch afterwards, an orthodontist named Dede stood up to give a toast. She’d just sold a portion of her practice and was in a relationship with Val. As the waiters scrolled through Facebook on their phones and the entrepreneurs pondered the veracity of the professor’s insistence that he’d been able to teach classic economics—“[Milton] Friedman, [Friedrich] Hayek, and Adam Smith”—since the ‘70’s with no reprimands, she loudly announced “how inspiring it’s been to see all these incredibly oppressed people struggle vainly but bravely.” As she pontificated, Nate rolled his eyes and melodramatically downed the remainder of his Cristal, a Cuban light beer. She’s the apotheosis of everything he, and supposedly his father, hates. She dresses like a pre-adolescent who’s just discovered floral prints at Forever 21; she’s rabidly right wing and (more damningly to Nate) never fails to announce as much. She’s entrepreneur in name only; most orthodontists start their own practice at some point. As he did this, she stared him down with a botoxed frown; he was well used it by now. Having sucked down the last drop of the tawny, translucent beer, Nate returned the can to the table, where a small ring had developed on the tablecloth.

“Then Says Cain, ‘I did it once brother, and I’d do it again. Look Out’”

Tucked away in the back corner of the Hotel Nacional courtyard, nearly hidden from view, sat a small museum dedicated to the Cuban Missile Crisis. The main room was a bunker constructed after the Bay of Pigs invasion. Underneath the tourists’ feet, trenches and underground passages created a labyrinthine structure that held various artifacts from the two weeks the world spent on the brink of nuclear winter. The posters in the main bunker gave a quick overview of the Bay of Pigs and the Missile Crisis in Spanish, English, French, and Russian. In Spanish, the Americans were described as “imperialist Yankee Americans.” In English, they were just Americans. Sitting in the corner of the main bunker was an eighty-four year old retiree. He had worked at the Nacional for several decades, and during the Missile Crisis was stationed as a volunteer in the dugout where he now sat. Over the course of the weekend, individual members of the group wandered into the bunker and accepted the man’s offer of a tour. On the third day, four of the members who had gathered in the courtyard for a morning beer discussed their impressions.

Military Man Stan was not impressed. He was annoyed because the man was shorter than him, which meant, when combined with the stoop of age, that he easily slipped under hanging edges that Stan nearly busted his head upon. Besides, he felt claustrophobic in the small tunnels. He barely had room to swing his backpack around without it hitting a rock wall. Dana, on the other hand, had no such issues. She was enamored with the volunteer who gave the tour. He was “just the sweetest thing. And it’s his birthday today! He’s 84!” She barely noticed the history lesson on the wall, and dismissed the vast differences in wording between the translations, “As something that happens in languages, ya know?” Expressing her dismay that the man probably receives very little pension-wise from the government, she said she wished she could help him more. I asked if she tipped him for the tour. A look of utter confusion gripped her face as she stared at me. No, why would she do that?

Chris had spent the longest on the tour. Though he spoke no Spanish and the guide spoke little English, he felt that there wasn’t a real language barrier. Standing in front a piece of the downed U2 plane, somewhere between the industrious waves of the Atlantic and the soft lounge chairs of the courtyard, he seemed to have an understanding with the man. Chris learned the reason the man volunteered is because he wanted to make sure no one ever forgets how close we were to nuclear annihilation; he emphasized that the U.S. and Cuba weren’t too different, yet were willing to end it all nonetheless. At one point, the two approached the uniform worn by members of the militia who volunteered to protect Cuba during the crisis. The old man smiled and pointed. “moй.” “‘Mine’ in Russian” Chris explained to us after. Chris had spent over a year in the former Soviet Union, and realized that the two could probably hold a conversation in Russian. As they continued walking, passing a periscope on their left, the old man switched back to Spanish. When Chris had a question, he asked in English.

“Oh Abel, Cleaning all the crumbs from the family table”

At dinner that evening, Val handed out awards to the group. They ranged from serious (fastest growing entrepreneur) to aspirational (top entrepreneurial student) to sarcastic (The Lindsay Lohan award for Biggest Hot Mess). In between two of the awards, Military Man Stan stood up to give a speech. While the members drank wine, snuck sips from the rum they had brought in, and laughed merrily, Stan told the story of how he met Val and explained why his wife had to cancel accompanying him at the last-minute. She had developed breast cancer and though it looked like she would be okay, she couldn’t risk leaving the United States at the moment. As he told the story, the room quieted. He finished, and as Val patted him on the back, he walked outside for a smoke. I followed him out, ready to extend my sympathies. He graciously accepted them, then shook his head and bemoaned the fact that Cuba will certainly collapse when the Internet arrives. He was confident that doctors and other highly educated members of society (which is nearly everyone in Cuba), would abandon the island upon the Internet’s arrival, and he wouldn’t have any protestations that the Internet already existed there. At this point, I was stuck, unable to return to the party inside. His ire then turned to Obamacare. Dinner arrived at the tables indoors. I suggested that the bevy of doctors on the trip seem to support the legislation. He shook his head; “Doctors hate it. It’s ruining them. And it’ll ruin America.” Inside, an ear, nose, and throat doctor lit up a $25 cigar.

“Dinner is getting cold.” I pointed out, attempting to extricate myself.

“I don’t give a damn.” He stamped out his cig. “Let me ask you a question.”

“Shoot.” I eyed inside for help.

“Have you read a man named Adam Smith? The Wealth of Nations. Read it. He said—” the recipient of the Lohan Award had made her way outside.

“Talk inside, so you can eat.” She said, shepherding us in and giving me a knowing wink.

“Gotta sneak something or you’re bound to get bored”

On the bus ride back to the hotel, the joke awards continued. “The Hemingway award, for best young, drunk writer… Here’s a fedora in commemoration.” As the group laughed, Stan once again grabbed the microphone, causing moans to reverberate through the tail end of the bus. He told a story about his son, who as a child adored the all you could eat caviar at the hotel they would stay at in Seaside, Florida. While working for Enterprise car rental, the son was hit by a trucker and killed. Almost exactly a year later, Stan was in a hotel eating breakfast when a bowl of caviar he had not ordered arrived at his table. He took it as a sign that his son was happy in heaven. As he told the story, concentrated laughter emanated from the rear. There was a bottle of booze being passed around the back of the bus, leaving Stan to stew alone.

“Then says Cain: ‘Am I my brother’s keeper or just a vagabond again?’”

The final morning, the bus was quiet. Later, while sitting in the airport, several joked about catching a cab back to the hotel, bemoaning a return to the ceaseless grind of 24/7 connectedness. Eventually, the boarding call for the flight to Miami was announced. The group got up and trudged forward—past the green and orange walls and over the soggy Havana Club Boxes that slid across the linoleum. Each heavy step brought them ever closer to the land of perpetual texts and unceasing email. Behind them, the barkeep scrolled through Facebook.

 

 

 

[1] Not even the fact that it was only a tick past ten could prevent a mass migration to the bar as they waited for the bus.