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My Time With the Castros

Written by Jason Williams
Posted March 6, 2020

So, I had a very interesting adventure this past weekend. I’d planned a business trip several months ago, long before the first cases of coronavirus started popping up in China.

And, since the country I had intended to visit hadn’t had a case (and still has zero confirmed cases), I decided that I’d put my immune system to the test and hop on an international flight.

I was part of a tour group and the official reason for our visit was to support the Cuban national tennis team, a group of kids between 13 and 19 with aspirations of using tennis as a way to improve things for themselves and their families.

But my unofficial purpose was to judge the state of Cuba and the Cuban people’s attitudes towards the U.S., our businesses, and capitalism in general.

At around noon last Thursday, my plane touched down in a place I never thought I’d end up — Havana, Cuba.

The Land that Time Forgot

We touched down just outside the city of Havana and were ushered into a VIP waiting area where we enjoyed Cristal, the preferred beer of the Cuban people, while our bags were screened by customs.

Then we headed outside into the Caribbean heat, an extremely welcome change from February in the Mid-Atlantic, and met our guide for the weekend. He was a charming Cuban named Armando (or, more affectionately, Mandy), who helped us load our things into the taxi and then offered me a cigar as we waited on the rest of our group.

I quit smoking last February, but when in Rome, you do as the Romans. And when in Cuba, you try a Cuban cigar. It was pretty good, but not being a cigar aficionado, I’m really not sure what all the fuss is about.

After gathering the stragglers, we headed off to our accommodations for the weekend. If you’re like me, you’re probably thinking huts or old hotels that were falling apart. But you’d be wrong. While there are some huts and buildings in disrepair, we stayed in beautiful Airbnb-esque homes built in the 1920s–1950s.

Our hosts lived just next door and took immaculate care of their business properties. Hot water wasn’t quite what it is here in the States, but otherwise, we had all the comforts of home.

The architecture in Cuba is something to behold. It’s really a land that time forgot. The buildings were all built before the communist revolution of the 1950s.

old havana

I was able to eat dinner in restaurants that Frank Sinatra visited back when a military government ruled Cuba. I toured Ernest Hemingway’s home and farm, where he wrote For Whom the Bell Tolls (before heading back to America to avoid charges of treason after the revolution). And I shared a cigar with the guys who maintain his beautiful custom fishing boat, Pilar.

I danced with the Buena Vista Social Club at Buena Vista Social Night. I saw a town entirely covered in tile mosaics. And I walked past the former embassy of the USSR (which is allegedly shaped like a sword thrust into the earth, but I think looks more like a vodka bottle towering over the neighborhood).

 fusterlandia cars and cigars

And the cars! Wow, the cars! Willys Jeeps from WWII, Chevy Bel Airs from the '50s, a legit pink Cadillac with fins the size of a small child — all held together with whatever the owners could find that worked. Old American power blocks with newer Russian parts jerry-rigged in but all running smooth and looking like a dream.

And then there are the people. Such incredible people…

Los Cubanos Spectacular

Before I go any further, I want to make sure you’re not thinking that old Jason had his mind changed down in Cuba. I’m not a communist now. And I’m not voting for Bernie, if that’s what you’re thinking.

I consider myself an emissary of capitalism. No matter where I am, I want to make sure I show just how great our economic system is, and Cuba was no different.

But I did have some opinions flipped completely upside down. And the biggest was the assumptions I’d made about the Cuban people themselves.

I went into my trip thinking that Cubans were communists because they wanted it that way; that's not really the case at all. Cubans are communists because their government is communist.

But Cubans are pretty darned capitalistic if you ask me. Everyone has a hustle. Everyone is looking for a way to make things better for themselves and their families. And everyone is looking for hot fashion and electronic trends just like in any other nation.

But despite that constant hustle to make an extra buck, they’re some of the nicest, friendliest people I’ve ever met. I never once felt like I was in danger. And, on one occasion, dropped a very important document only to have a grey-haired man chase me down the block to make sure I got it back.

Over the past few years, Cuba has opened up a lot to the outside world. People from other countries have always been allowed to visit. Americans were the only ones with restrictions, and those came from our government, not theirs.

But recently, Cuba got access to international television networks and the internet, and change is happening fast now. The Cuban people were used to seeing tourists from other countries, but it’s easy to assume that anyone traveling the world must be rich when you come from a relatively poor place.

Now, they can see how everyone lives through their television sets and on their connected devices. And if anyone reading is old enough to remember, that’s where the Soviet Union really started to crumble. Pop culture has always been the West’s best weapon against communism.

When the Soviets got hooked on Dallas, they didn’t really care who shot J.R. They wanted all the nice things they saw Americans had instead of the beet rations they were getting.

Cubans aren’t that different from the rest of us. When we see someone else with something nicer than what we’ve got, we usually want one, too. And that’s exactly what I saw happening.

Support of the Cuban People

Like I said at the start of my trip, my official purpose was to support the Cuban tennis team. My visa literally said “support of the Cuban people.” And I did support the team.

The group I went with, Elite Tennis Travel, founded the Friendship Games Havana Open several years ago to help bring tennis to the people of the island. The founder of the company, Adriana Isaza, is a former professional player. She, her sisters, and many other family members were able to attend college in the U.S. thanks to tennis scholarships.

So, she knows that tennis can be more than just a game or a sport; it can be a ticket to a new life in a better place. Adriana, her sisters Catalina and Lili, her niece Eliana, and numerous other members of their families were able to leave Colombia (during the Narco Wars) and Venezuela (after Chavez took over) and come to the United States thanks to tennis.

Her groups bring donations of rackets, clothing, balls, and other gear the team needs so that it can compete on an international level. And thanks to those groups, the kids have gotten the opportunity to do just that.

They play in tournaments around the world thanks to the donations Adriana and her tour groups bring down. And they repaid us by playing a tournament with us while we were visiting.

cuban tennis team

If that sounds like something you’d be interested in doing — helping some kids make a better life, playing tennis on some beautiful courts, and touristing your way around Habana Vieja — Elite will be doing another trip later this year

Editor’s Note: If this kind of trip sounds fun, but you’re not so sure about Cuba, Elite offers a multitude of additional tennis experiences, including the Barcelona Open in Spain, the French Open in Paris, the Italian Open in Rome, the Rolex Monte Carlo Masters, the U.S. Open in New York, and the Indian Wells in Palm Springs. It also offers packages to other locations like Cartegena, Colombia, the International Tennis Hall of Fame near Newport Beach, and even the Hamptons. Or, you can learn to play like a pro and sip some tropical drinks by attending one of its trips to the Rafa Nadal Training Academy in Cancun, the Sanchez-Casal Academy in Barcelona, the Clijsters Academy in Belgium, or the Mouratoglou Academy in France. Elite will even custom tailor a trip for you and your friends to fit whatever your travel goals might be. No payment came for this plug, I just had a really great time and wanted to share it with you so that you can, too.

You can get all the information and get in contact with Adriana at the company’s website I highly suggest you go. Cuba is a beautiful island. Its architecture is incredible. The cars make you feel like Marty McFly in the original Back to the Future. The people are warm and generous.

And the economic situation and current style of government aren’t going to be around forever…

The Future Looks Bright

While I played with the kids on the Cuban team, I got to talk with them about their lives, their parents, and their dreams. And guess what: They’re not that different from ours.

They want to travel. They want to see the world. They want to help their parents and earn a better life for themselves and their families.

And they might just have that chance; not only because of the generous donations Elite makes but because things in Cuba are ripe for a change. And it could easily come in my lifetime.

That’s what my real purpose in Cuba was. I couldn’t tell them I was coming as a potential investor, and journalists need special permission from the government and (I’m just guessing here) probably have to be escorted everywhere by some official.

So, support for the people it was. And I can get down with that. People are people. It’s our politicians who don’t get along. The more I travel, the more I see we’re all really the same with the same needs and wants and dreams and aspirations.

But really, I wanted to know if this island just a few hundred miles away from Florida could ever be home to American businesses and investors again. Because if you want to make the biggest profits, you’ve got to get there first with the most money.

And while I don’t think Cuba is ready for our investment dollars just yet, I can see that time is coming. And the connections I made while visiting are going to pay off for all of us when it does.

I’ll continue to keep in touch with my new Cuban "comrades," and as soon as it’s safe to start investing, I’ll be the first to let you know when and where.

Until then, it’s completely safe to visit, and I highly suggest you give it a try. Think of yourself as a prophet of profit spreading the good word of Adam Smith and the rest of us capitalists.

The more they see them in action, the more they’re going to want capitalism and democracy for themselves.

To your wealth,


Jason Williams

follow basic@TheReal_JayDubs

After graduating Cum Laude in finance and economics, Jason analyzed complex projects and budgets for the U.S. Army. Then, at Morgan Stanley, he led the assistants' team for the North American repo sales desk, responsible for hundreds of multibillion-dollar trades every day. Jason is the founder of Main Street Ventures and an editor for The Wealth Advisory income stock newsletter. He also contributes regularly to Wealth Daily. To learn more about Jason, click here.

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