Startup Cuba is a media platform existing to create world-class, digestible Latinx-oriented content that builds bridges.
The Malecón in Havana. Photo credit: Alejandro Rojas

Startup Cuba is a media platform put on the map by its namesake docuseries about Cuba’s cuentapropistas (entrepreneurs). Since that inception, while staying true to our roots, we’ve evolved into a lifestyle content brand for the Cuban American, Puerto Rican and broader Latinx communities. The majority of content we created started as video. All of it focused on building bridges and generating conversation. We also create content for select brand partners.

Before the Coronavirus pandemic ravaged the planet, we depended largely on traveling to create these video stories. As I’m sure you can relate, COVID-19 put a kink in our plans. Seeing our travel grounded, and recognizing our responsibility to restrict our own travel to curb the spread, forced us to quickly rethink our approach. So, we began to accelerate plans we had to add written and photographic content to our mix (Write for Us), in addition to only video. It’s indisputable that the world has changed, and the path we were on with our project needed to pivot to this new world, too.

So, that’s what we’re doing now — bringing people into the fold by creating a collective of storytellers.

Taxing to the terminal after landing in Havana for the first time.

So, what started as a nine-episode online documentary about Cuba’s entrepreneurs has now officially evolved into a this website; a platform to amplify the collective voices in the space between the United States and Cuba and the broader Latinx community. It’s a multi-media mix of content that tells stories to bring us together. 

Related Post: Who Pays Us?

But to set the stage, I want to first take a brief step back and offer a little detail behind the Startup Cuba journey in the time before COVID-19 — often exciting, albeit challenging.

The Startup Cuba docuseries trailer

In early 2017, we went to Cuba to make our docuseries, Startup Cuba, about Cuban entrepreneurs (cuentapropista means literally “self-employed”). Personally, I had never made a documentary. In fact, other than my Canon G7X Point & Shoot, I didn’t even own a camera (true story). I was fortunate enough to have teamed up with my friend Tamara Park who showed me the ropes and listened to my bad jokes.  

startup cuba youtube
Watch Startup Cuba Video Replays Here on YouTube.

For me, this was a very special project: Although a gringo, Cuban-American culture heavily influenced my life growing up in South Florida. I had secretly always wanted to be a filmmaker (but was too scared to put myself out there), and as a lifelong entrepreneur the subject matter was near and dear to me. The project checked off three of the biggest passions of mine all at once – Cuban culture, filmmaking and startups – thus making it a literal opportunity of a lifetime. So, I got on a plane to Havana.

Clandestina’s latest, “actually, estoy en el gao.” Available on their online store. Photo credit: Ken Deckinger

(By the way, you can imagine my wife’s face when I told her, ” I’m going to Cuba to make a documentary.” Yes. We’re still married.) 

My personal ethos is driven by a desire to break down barriers. I want the same thing that I believe most people want: a Cuba that is prosperous and open.

Fast-forward to 2018 and we produced the documentary series. I am incredibly proud of the work that was accomplished by our entire team. And, slowly, the nine-episode series dripped out for the world to watch on Facebook. Twenty-four months later, the series and our social media videos racked up millions of views and we had a following of tens of thousands on social media.  

Spending so much time in Cuba taught me as much about myself as it taught me about cuentapropismo and Cuban people. It also opened my eyes to the idea that Cuba is more complex and multifaceted than most of us have been taught in the US (right-wing propaganda much?). Beyond what we already know about Cuba, Cuba is also…Cuba. It’s home to a people that are creative, loving, open-minded and resilient. It’s a country that is caught in the vice grip of contrasting political ideologies causing disproportionate suffering first and foremost to the lovely people of the island.

I’m not an activist. I’m just a bald guy with a passion and a microphone who believes that we have to break the cycle. I’m convinced at my core that the more we can know each other, and trust each other, the more amazing things we can do together now and for our children. 

Photo credit: Alejandro Rojas

My personal ethos is driven by a desire to break down barriers. I want the same thing that I believe most people want: a Cuba that is prosperous and open. A Cuba that respects people’s rights. A Cuba where parents can see their kids’ dreams come to fruition, on the island. And a Cuba that is actively part of creating its own future. I mean, mira. Whether you believe in engagement or are a hardliner, if you’re a human being with any empathy whatsoever, you want the best for others no matter where they are in the world. 

I believe that continued forced isolation does nothing to move the ball forward. In fact, I have seen first hand how the hardline U.S. policies of the past 60 years have only repressed progress. If you don’t believe me and aren’t willing to go to Cuba yourself, spend some time learning about the Obama era when relations eased up. Not only was there much more engagement between people in the US and Cuba, but countless new and creative —and successful— small businesses popped up as Cubans saw an opportunity to make it, without leaving the island. Then compare that to what’s happening now with the current administration’s restrictions. We’re going backwards and we’re dragging Cuba with us. 

I’m not an activist. I’m just a bald guy with a passion and a microphone who believes that we have to break the cycle. I’m convinced at my core that the more we can know each other, and trust each other, the more amazing things we can do together now and for our children. 

The author at a casa particular in Havana.

And this brings us back to today and the new Startup Cuba that we created while stuck at home. 

There are so many people involved in the space between the US and Cuba. People that I believe collectively can help us get to know each other. They’re in the US and in Cuba and around the world, and they have such beautiful stories to tell. To share, and to play a little role in adding to the narrative. So, that’s what we’re doing now — bringing people into the fold by creating a collective of storytellers. They’re writers, content creators, journalists, filmmakers, academics, photographers, and people who just want to close the space between Key West and Havana by sharing knowledge and experiences. 

So what started as a video platform to make documentaries for social media has shifted today, in the time of COVID-19, into a new multimedia platform. You may not always agree with everything you read (except for my review of El Café — go there in Habana Vieja and try to disagree, I challenge you). But, hopefully you’ll at least have been touched by an additional facet of this complex relationship and be encouraged to give some besos and be inspired to resolver, together.

(In other news, the author loves to give besos and is incredibly frustrated by the restrictions that COVID-19 is imposing on those efforts.)

Besos with @cravingcuba and @cubanochris

P.S. StartupCuba.tv is completely independent and unaffiliated. We do not work with or take money from the government of any country. Nada. Learn more here.

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Ken Deckinger is the co-founder and CEO of Startup Cuba and the executive producer and host of its namesake docuseries. A native of South Florida, Ken has been an entrepreneur for his entire professional career. Previously he was co-founder and CEO of HurryDate, pioneering the global concept of speed dating to 45 cities throughout the US, UK and Canada. HurryDate eventually evolved into online dating and was acquired by Spark Networks, the parent company of ChristianMingle.com and JDate.com. Ken is a graduate of Boston College and the University of Florida, where he was honored with the University’s Alumni Entrepreneur of the Year Under 40 award and sits on the Board for the Center for Entrepreneurship and Innovation. He actively advises entrepreneurs and is a two-time protagonist of a Harvard Business School case study. Ken’s filmmaking and journalistic journey is inspired by a love of travel and authentic connections with other cultures. He believes that the more we know about each other, through stories, the closer we can become — thus the mission of Startup Cuba: to amplify the voices of the people sharing stories in the Latinx space. After living in New York City for 15 years, he encouraged his wife to move their family to Miami to get back to his South Florida roots. Needless to say, it was a short discussion and he and his family now call Boston, where his wife grew up, their home.

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