Why All these eyes on the Caribbean Startup Ecosystem Now?

Like Africa, Miami, parts of Eastern Europe, the Caribbean’s Startup Ecosystem is nascent and growing. At the moment, Jamaica, Trinidad, Barbados, and Dominican Republic has been getting alot of attention, because of the level of tech entrepreneurial activity, that’s been bubbling up there. And yes Jamaica has been leading the pack, primarily based on its level of community growth, event activities (the movement kickstarted in 2007) and the work of government/development agencies and corporate champions. Yet over the past 2.5 years, the attention in our neck of the woods has been getting heated.

I’ve been personally contacted at least twice a month, this past year, by people and organisations from the United States and Europe mainly, wanting to get a sense of what’s happening in Jamaica and the Caribbean, to judge whether or not its worth their time and money, to get involved on various levels.

Some may ask for referrals to investible startups; people to contact to sell their entrepreneurship training programmes or to be hired to consult on programmes; others want a mini report on who’s who on the ground and an insider’s view to the politics behind the headlines and events. It’s been pretty interesting,  as having been one of the pioneers in this Startup Ecosystem building game as head of ConnectiMass for just over 8 years now, it has gotten easier for me to the fake from the great. I can now spot the snake oil salesmen/women, the I’m-from-the-first-world-coming-to-help-you-third-worlders-know-it-alls, the passionate do-gooders and the knowledgeable and right thinking ones. It’s all part of the Startup Ecosystem development process.

So, why this spike in interest, these last 2 years particularly? Here’s how I see it

1. The pioneering work and early successes by early adopter tech entrepreneurs, community leaders and entrepreneur-led non-profits, that started from the mid 2000s and still continues across the Caribbean. They are the one who have been the pathfinders that raised the visibility of what was going on, who’s been doing it and have set the foundation and continue to do so in the region. See some Caribbean Internet History via previous blog post SiliconCaribe.com’s Top Caribbean Startups to Watch in 2015

2. Entities such as the Governments, heavily aided by international development agencies like the World Bank, IDB are helping to fuel capacity building events and partnerships, with community leaders who know what’s happening on the ground. Initiatives like Digital Jam and now Startup Jamaica accelerator, started in Jamaica first in 2012 and now IDB and UNESCO are coming in with their programmes also.

3. There aren’t that many places left  in the world for investors (Venture Capital and Angel Capital) to tap for great talent and investible ideas, so emerging markets are hot at the moment, especially ones with good talent and startups seeking to solve problems exportable to large global markets of 50—200 million people. I got those numbers from Dave McClure of 500startups in a short Twitter chat.

4. We still have LOTS of work to do to build out our Caribbean Startup Ecosystem where it yields not only the tech equivalent of Usain Bolt and Bob Marley level of greatness (unicorns), but also the greater flow of small to medium startups, that are profitable and creating jobs in their countries.  If we are to accept the blueprint and approach detailed in Brad Feld’s book “Startup Communities: Building an Entrepreneurial Ecosystem in Your City” we have about 12 more years to go to see major deal flow from the region. He said it takes about 20 years to build a robust Startup Ecosystem. He said it takes about 20 years to build a robust Startup Ecosystem. I think we can cut that time in half. I believe in Jamaica, in the Caribbean.

This book which I recommend every one involved in our ecosystem read twice, shows that there is a clear role for everyone – for communities and the entrepreneurs who start and lead them, private sector, universities and government. It’s needed because what I’ve been seeing over the past 3 years, certain players have been overstepping their boundaries and making a mess of things, but more on that in another post. Added to that too, the buzzwords Entrepreneurship, Startups, Innovation have  reached tipping point globally and the Caribbean is right there too with that trend.

How can aspiring and current Caribbean tech entrepreneurs take advantage of all this?

1. Join in and get busy inside the Community.

Get to know who is doing what, where and why. Go to the meetups, drink ups and join the many online community groups that span the region and many interests – for developers, entrepreneurs, creatives and animators. Being a part of a startup community and contributing to that community is one of the best things you can do for yourself. You will get inspired, connected and find potential co-founders, business partners, friends to WhatsApp your ideas to at night and people to curse and cry with, when you get your ass kicked in some inevitable way.

This is also an excellent way to make yourself known to potential investors, corporate clients, sponsors and government and academic champions. It is the best way to build a unique and supportive network similar to that of the renowned Paypal Posse. So say it with me…community, community, community. join it and contribute to it.

2. Take advantage of workshops, but be selective about competitions you enter.

When the private sector, government/development agencies and education institutions get involved, there is usually a rash of workshops a.k.a capacity building events being produced.  Add yourself to mailing lists, read blogs and attend as many of them that are relevant to your idea or startup. Learn as much as you can, especially on topics such as lean startup methodology, business model development, growth hacking, sales, being investor ready, digital content, social media for entrepreneurs and marketing etc.

However, be selective about the competitions you enter – they can be like a designer being asked to bid on a job and do speculative work – potentially alot of effort and little reward, even when you are being flown to exciting new places. Look for competitions ( hackathons, mobile apps etc ) that have a workshop component delivered by diverse and passionate experts, who’ve actually been taking hits in the startup arena themselves. Look for those competitions too, that have a pipeline to a global platform for funding, more learning and even better network building. And if you win one, for God’s sake spend 85% of the money on your startup and the rest 15%, on partying if you must. Notice the recommended ratio there?!

3. Learn the rules of the games being played and know the players.

Just in case you haven’t figured it out as yet, there is a global race on to find the next big things wherever they are. So since you may have created one of them, heads up! No one does anything solely out of the goodness of their heart, no-one, even Oprah has known business objectives while she helps people to live their best lives along the way. Do you think she can power that OWN Television Network with Namaste and a smile?! Homegirl needs ad dollars and powerful content partners too.

Know that, people are always tuned in to their Whats-In-it-For-Me  station and so should you- and there is nothing wrong with that. Mutually beneficial/ mutual self-interest type of relationships are the best ones but of course. How beneficial they are to you, boils down to how informed, connected you are and if you are the better negotiator. I did tell you it’s a game right.

So I’m talking about everyone from your co-founders, first employees, investors, sponsors, mentors, government/development agency champions or academic partner – everyone is playing a game – your job is to know what kind, if you want to play, what role you want to play, who are your partners if any and what you want to win from it all. And of course, if you don’t like the current games being played, we now live in an era where you go create your own playing field, with your own rules for your own game and tell others to kiss your ass. #yeahIsaidthat That said, not everyone is out to get you, but just be aware and prepared.


But Please Don’t
get caught up in the hype of being a media darling for something you are about to do or hope to do. Of course PR can be a valid strategy that can make you look great and it does share your story so as to inspire others and potentially win funding- but, you know what I mean. If you know you ain’t got shit – no users, no revenue and you just used the last lick of prize money from a competition to fly to Miami, you really can’t ask us to take you seriously.

You simply must know, that nothing has greater impact than the number of real users of your product/ service, that has solved a real problem for them and they are giving you real cash for it. So save the PR tactics for when you have real things to report and seek to be in the news, when it can give your startup a bump in what really makes a tech startup matter….traction.

get all starry eyed and be wetting your lips for an ass kissing, just because you are in the presence of potential investors or more successful entrepreneurs who “just want to hear and see what you are working on (code and all).  Now I’m not saying to be paranoid and ask every smaddy to sign your NDA, what I am saying is…know your worth, make people answer your questions, business date and get to know people, their values and track record, do your due diligence before you drop your digital trow and lay yourself bare. There is no rule that says you have to become someone’s bitch, because they supposedly know more than you, flew in from overseas or have more money than you!  The best thing you can do is trust your instincts, if it feels wrong, it is.

Added to that, if you have been screwed over and frankly, it’s par for the entrepreneurial journey, don’t be embarassed and keep it to yourself, share that info generously with the community and its leaders, so that that others may learn from your experience and a bad apple charlatan, can get named, shamed and thrown out. This leads me to this other point…please don’t…

get Columbus’d. This Christopher Columbus Syndrome as I call it, is happening alot in nascent entrepreneurial ecosystems like the Caribbean and Africa and goes something like this. You’ll see them, they smile, cosy up to you like you’re a long lost friend, they may want to interview you for a research project, a blog, a book, or they are consultants working on a large project in your country and are seeking your help to get information on this, introduced to that person and to be shown (code and all) what you working on.

So invariably, they meetup with local startups struggling with liquidity, knowledge and resource issues and make keen note of that. Then months later, they emerge as the well funded founder who while in your country, stumbled on stunning data, your idea or someone else’s and went on to raise funds for it. Soon thereafter they come back to your country or not, with a bag of cash, you read about them on Techcrunch and they are hitting the social enterprise conference circuit, patting themselves on the back as the saviour of the Caribbean this and African that.

That said, always be open to share and collaborate – but with the right people who share your values in the way you treat others and do business. Also, while I am one of those too, who says ideas are cheap as execution is everything, it doesn’t mean that you must drop your digital trow like a virginal gladiss  (Jamaican word for people pleaser) for every person that comes knocking. Be smart about it. Now go on, go rock your Caribbean startup, the world is waiting on you.


Recommended Reading

“Startup Communities: Building an Entrepreneurial Ecosystem in Your City” by Brad Feld

Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld by Brad Feld (Author), Jason Mendelson (Author), Dick Costolo (Foreword)


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  • Hi Teddy, Well it depends on what kind of entrepreneur one wants to be…it can be solo or with a team depending on your idea and you desire to scale. That said whatever one chooses, there is no need to try to do everything yourself I’ve found that there is always someone willing to help and share what they know. Plus there is always google, so many blogs which amazing How to and How I did it content. Good to hear from you.

    PS When are you launching PriceWhirl.com? Keep us posted. Is there a BETA we can jump in on?

  • I also believe as entrepreneurs we have to change our mind set from going at it alone, and hiding our work, to one of being willing to share “know how” to help others, and give up equity in order to get persons with the right skills on board early.