From Encouraging Entrepreneurship in Cuba to Forging a New Path as an Entrepreneur of the Cuban Diaspora

Discussing entrepreneurship in Cuba almost always involves describing creativity under pressure, opportunities born from scarcity, and leadership flourishing in difficult circumstances. One outstanding example is Jorge Mandilego, an engineer by training who spent barely three days practicing in his field, and has instead devoted his life to building—and rebuilding—entrepreneurial ventures both on the Island and abroad.

From launching his first printing business in Havana to leading the landmark CubaEmprende project, Jorge has helped hundreds of Cuban entrepreneurs pursue economic independence in a country where private business has long operated under legal uncertainty.

Now based in Miami, he continues to blaze trails: combining his experience selling on Amazon with the launch of Pricepeak AI, a tech startup powered by artificial intelligence that provides practical solutions to e-commerce entrepreneurs.

In this interview, Jorge shares not only his migration journey, the challenges of starting over in a new country, the lessons of navigating complex leadership contexts, but also his honest, hopeful reflections on potential collaboration between the diaspora and Island-based entrepreneurs.

He represents a Cuban who hasn’t given up on his homeland, even when distance—and politics—make that connection difficult.

Origin and Migration Journey

Tell us your story from the beginning and how you emigrated.

“I’m from Regla, Havana, where I was born and raised. I earned a degree in electrical engineering, but worked less than three days as an engineer. I wasn’t comfortable in my assigned work environment, so I quit.  I began my own work project printing t-shirts and posters.  That was my real beginning.

From there, a group of us founded Taller San José, a venture focused on serving one client - the Catholic Church – for which we produced a variety of products over the years.  It was a great experience, as we had to start from nothing. We endured really tough months, where we survived on just two or three dollars.  Fortunately, our parents supported us. 

With determination and a desire to succeed, the business grew to nearly 50 employees. It really was something marvelous. I learned a lot about business, but also got to know my co-workers.  It was a great education on life and entrepreneurship”.

I cannot fail to ask you about the CubaEmprende project, of which you were a founder and the first executive director.  It is a project of great importance for the development of entrepreneurship on the Island.  How were you introduced to the project and what was its special importance to you?

“That was my final major project before leaving Cuba. I wasn’t present at the initial brainstorming for the project.  But, I can share what I learned from those who were.

Various Cuban‑American entrepreneurs associated with the Cuba Study Group approached Cardinal Jaime Ortega to propose a venture supporting nascent Cuban private sector activity.  They proposed working through the Catholic Church, because of its legitimacy in Cuba and its ability to provide necessary infrastructure.

I learned that they had interviewed many in Cuba for the position of project director and almost all said the project was impossible to implement.  When I was asked, I said, ‘Of course this can be done.’  Perhaps my innocent, direct answer and my optimism led to my selection?  

My prior experience was starting a business from scratch and facing challenges with calm resolve. In my view, ‘we just had to do it’, simple as that. Moreover, at that time I was pursuing an MBA at the Universidad Católica de Murcia in Havana, which provided with me with a valuable theoretical base.  All of these factors gave my candidacy a boost.

In short, my practical experience, passion, and some luck resulted in my selection. CubaEmprende became a pivotal project for me and many Cuban entrepreneurs.”

Why leave Cuba while working a successful venture like CubaEmprende?

“I directed CubaEmprende for eight years. Around year six, I realized that staying too long, far from benefiting the project, might actually hold it back from evolving. 

That’s why I made a decided to step aside and make space for others—new voices who could bring fresh perspectives. Otherwise, over time, I feared growing complacent or losing momentum, and the project did not need that. Initially, I intended to step back from the project, without considering a departure from the Island.

The real reason for the subsequent departure was personal. I value family deeply. I have always sought to be close to my family.  Although work often required me to be away, it was essential for me to return home and spend time with my loved ones.

For separate reasons, my children had obtained U.S. visas, visited the U.S. and returned.  Sometime later, my older daughter expressed her firm intention to move to the U.S.  Later, the younger one did the same.  The youngest child, a son, who was not even 18, said he shared his sisters’ goal. 

However, what ultimately accelerated our departure was my wife’s health problem. She fell ill, and although our initial intention was to have her treated in Cuba, her health deteriorated quickly and treatment became more complicated. At the urging of family and friends who kept repeating, ‘Come for now, and just get her some tests,’ we decided to have her evaluated in the U.S.  Just a few weeks later, the pandemic broke out. We realized that our cycle in Cuba had come to an end and that we needed to begin a new chapter here.” 

What were the biggest challenges upon arriving in the U.S.?

“In my opinion, the first major challenge is arriving in a country that isn’t your own. I came to the United States at the age of 48, and although I had visited the country several times and was familiar with certain of its aspects, it’s one thing to come as a visitor and a very different thing to start a life here. It’s a country with a structure very different from that of Cuba, built on a first world economic system, which from arrival places demands on you at various levels.

I arrived in Miami, where I am still living.  It is true that Miami has a strong Cuban presence, which helps, but does not moderate the fact that I was inserting myself in a totally different society.  Although I had some prior knowledge of and advice from people who had already lived and succeeded in the United States, being an immigrant always means facing a series of challenges. You don’t arrive with full command of the cultural codes, and that can take a toll on you.

For example, language is a barrier. Even when you can speak it, there are nuances and expressions that catch you by surprise. And then there are the financial challenges, which were some of the toughest for me.  From a professional standpoint, I came with a solid background: experience in project management, academic training, knowledge of strategic planning, human resources, business plan development... all of which gave me useful tools, but nonetheless, it was in a novel scenario.

A few friends who knew me from our days together in Cuba gave me good advice.  They explained the legal way to insert myself in the workforce given my immigration status.  It was important not just to learn the rules but to comply with them.  I learned that the fundamental thing in the U.S. is to know the law, how things are structured and act accordingly.

For the first time, I felt I wasn’t living in a place where everything was prohibited or illegal, instead I could learn the rules of the game and I could play by clear rules. It was a profound shift in the way I saw life and opportunities.”

The Path to Entrepreneurship

How did your entrepreneurship begin in the U.S.? Was it something you had planned for a while or a response to the situation in which you found yourself?

“I developed a philosophy that I still live by: you shouldn't be afraid to start over from scratch. Things can go well or go badly, but if you cling to what you had before, you won't move forward. You have to learn to let go, to start fresh fearlessly. That mindset helped me a lot when I arrived in the United States.

Running a business is like an addiction: every day brings new challenges, and you're motivated by the need to solve them. So for me, entrepreneurship wasn't just a rational choice — it was an existential need. It's what I know how to do.”

What did you design, and what projects are you working on now?

“After spending some time in the insurance world, I kept looking for something I could do on my own. I explored a lot of ideas online but couldn’t find anything that really convinced me — until I discovered the world of selling on Amazon. What drew me in wasn’t the act of selling itself, but the idea of having my own company, of building something structured without having to sell door to door. Moreover, Amazon’s platform acts as a filter between my business and the customer, which felt both comfortable and challenging.

I took my first course, to learn the “Private Label” model. But it was just as we were emerging from the COVID pandemic, and I realized the supply chain was too long and the cash flow too slow given my limited resources. So I kept researching and eventually found a course by a great group of Mexicans who offered a model that was more beneficial given my situation. That’s how I got started.

The business was going well, but I quickly realized working alone wasn’t for me. I need to work in a team. I learned that during my time at Taller San José and later at CubaEmprende. So I began looking for other Cubans interested in selling on Amazon. That’s how I met two guys from Santiago de Cuba — now good friends — with whom I began to work and from whom I learned a lot.  We continue to support each other to this day.

At the same time, I reconnected with a Cuban I knew from the Island — the founder of KeWelta^[1], and a constant generator of ideas. As we brainstormed, we decided to partner, combining our expertise and launched a new project: Pricepeak AI.

Pricepeak AI is an artificial intelligence (AI) system designed for Amazon sellers. We started with a chat interface that allows sellers to troubleshoot problems through conversation. Behind the scenes, there's a complex system with multiple AI agents trained to offer a wide range of solutions. The potential is huge, especially if we manage to feed the system with relevant data.

What’s needed most is simple: trust and clear rules.”

Today, I’m focused on two fronts:

1. My Amazon store, which remains my main source of income — what I call “the cash cow.”
2. Pricepeak AI, which aims to change the way people start businesses on Amazon. It’s focused on uncovering hidden business opportunities and ensuring data accuracy, which significantly improves operational efficiency and decision-making for our clients.”

Keys to Business Growth

What’s been the biggest factor that has allowed you to keep going and grow your business?

“Without a doubt: persistence. There’s no other way. There's always a high failure rate. But resilience — personal strength — is what keeps you going. It’s very easy to give up and take a regular job that relieves you of stress, but if you truly want to build something, you have to stand your ground.

I don’t know if I’ll be an Amazon seller for the rest of my life. Hopefully yes, because it’s a good business. But the important thing is to keep growing, to turn this into a rising company. And if another opportunity arises tomorrow, I’ll evaluate it and move forward. But the key has always been to persist, even when you're working long hours without seeing results.

It's also important who you walk with. If you do it alone, it's easier to make mistakes without realizing it. In a team, you’re more likely to spot those mistakes in time.”

Do you think Cuban idiosyncrasy has influenced your persistence and your decision to keep going despite the challenges?

“Living in the U.S. teaches you humility. I’ve met Colombians, Venezuelans, Ecuadorians — amazing people, super prepared and hardworking. That makes you realize Cubans not the only ones who “know things.”

Nonetheless, Cuban culture added something interesting: we believe we can do anything. And, while that self-confidence might seem like a flaw, sometimes it’s actually a strength. Because if we were fully aware of how little we really know about the world, it might paralyze us.  That overconfidence drives us to try things one might not try otherwise.

But we have to be careful. Our Cuban education is good, yes — but we’re not the only ones with one. And we not only need self-confidence, but also humility to recognize others' value and not underestimate them.”

Cuba and Private Enterprise

Do you think a business like yours could work in Cuba under a different political context? What would need to happen for that to be possible?

“Even now, people criticize me for not continuing to dream about a business in Cuba. In the current environment, how many people in Cuba could run a successful Amazon-style business? It’s a business that requires little capital to start up: a computer, a phone, and personal time.

You don’t need physical infrastructure, and you never even have to see or touch the product. I’m not the only one saying this — just look at how many Colombians, Venezuelans, and others are operating these businesses from abroad, without ever stepping foot in the U.S.

So yes, there’s knowledge and opportunity for Cubans to do it — this and many other businesses. But in practice, there are barriers. U.S. laws don’t allow it: no Cuban resident on the island can open a U.S. bank account, which is the minimum Amazon requires. Amazon complies with U.S. law, and because Cuba is on the list of state sponsors of terrorism, the law does not allow direct operations from there.

And that’s just the obstacle from the U.S. side. From Cuba’s side, internal laws do not truly allow Cubans to run international businesses, gain real economic empowerment, or operate freely from the island. So Cubans in Cuba are trapped by both sides. The policies of both countries tie their hands. And if someone ever gets too successful, a new law or interpretation of existing law is adopted by the Cuban government to move in and shut down the successful business.”

Looking Ahead

What changes do you think would foster a more productive relationship between the Cuban diaspora and entrepreneurs on the island?

“There are several limiting factors. One is the Cuban government’s resistance to letting outside entrepreneurs invest directly or even collaborate with local businesses.

These barriers are not contained in written rules, but you can sense them. On the other hand, there are the restrictions of the U.S. embargo, which discourage many people from investing or collaborating with businesses in Cuba.

It would be really important to create legal and political conditions that allow for a real connection between the Cuban community abroad — which includes many successful entrepreneurs — and those starting businesses on the island. That could generate a stronger, more creative, and more equitable economic ecosystem for all Cubans.”

What changes would be necessary for people like you to invest in Cuba?

“First, changes are necessary inside Cuba. There’s a clearly restrictive legal framework that limits the development of private enterprise development. That’s not just my opinion — it’s the law. You can read the legislation and see that it places many obstacles to private business growth.

The Constitution defines the state-run socialist enterprise as the driving force of the economy. Beyond ideology, that model has proven to be inefficient in practice. Without outside support — like the Soviet or Venezuelan aid in the past — the system isn’t sustainable. There are economists in Cuba who’ve proposed viable reforms that wouldn’t even take power away from the state over the economy, but sadly, those proposals exist but they haven’t been implemented.

Second, from the U.S. side, there’s also a complex legal and political framework. U.S. laws, as a result of historical and political policies, prevent Cuba from integrating into global trade. There are many arguments for continuing to support the embargo, but the most painful part is that in the interaction between both systems, the one who suffers is the average Cuban — someone who has nothing to do with the political decisions of either government.  That person continues to pay the price.

As for the Cuban diaspora: the Cuban government’s failure to recognize a community of Cubans who’ve succeeded in many countries, who have resources, knowledge, and willingness to help, is a big mistake. Many of them were already successful before the Revolution. Others left with nothing and built large enterprises in new countries.

So in 2025, many of those entrepreneurs ask themselves: “What does Cuba offer me today from a business standpoint?” It’s a country in crisis — no infrastructure, no finance, no real market capacity. How will that investment pay off? Where is the return guarantee? Why invest in Cuba today? The logical answer is: it’s not worth it. But that’s where emotion comes in.”

If there were legal guarantees and respect for entrepreneurs and businesses as legal entities, would you consider investing in Cuba?

“In a way, I already am. Not with a company, but by investing in people. I support projects. I collaborate. Why? Because I’m Cuban. No one can take that away from me. Even those who haven’t set foot on the island in 60 years still feel Cuban. There’s a sense of belonging that goes beyond pragmatism.

I’m still betting on Cuba. I could do business in Venezuela, Guatemala, El Salvador, Colombia… but I choose Cuba because it matters to me. And I know others would too under better conditions — or already are.

But the real question is: how many more would bet on the island today? Because unless the environment changes — and I mean the legal framework, institutional trust, and respect for the rules — it’s going to be hard. Trump, for example, might come back and tighten the embargo again, despite his being limited to a term of four years. The Cuban government, on the other hand, has never changed its economic policies.

Cuba must encourage investment under fair and clear commercial rules. It’s not enough to have a law saying investment is allowed — there must be proof that those guarantees are real, that investors can trust the law. 

[1] Ke Welta is a Cuban technology project founded by Carlos Manuel García Vergara, focused on cultural and advertising outreach in environments with limited connectivity. It emerged in response to the need to share information, events, and announcements within Cuba, where access to the Internet has historically been restricted or expensive.