002 – Blazing the Tech trail in the Caribbean, with Ingrid Riley

Ingrid Riley is a trailblazer in the field of tech. An Award-winning Blogger, she is the founder of Silicon Caribe and Co-Founder and Chief Digital Strategist at getCONNECTID. She is also the leading lady behind many Meetups+ Pitch events, 3 Caribbean Tech Conferences, 3 Caribbean-wide Hackathons, a few Mobile App Competitions, Online Twitter Chats and  Startup Weekends.

#PeakPerformers, @IngridRiley shares her awesome journey on #TEY #Podcast today! Click To Tweet

Show Notes:


If you were really hungry and really, really sleepy and you had to choose only one, which would you choose? Would it be sleep or would it food?

I’ll definitely do the food. Because the food would probably help me to sleep better because you can’t really sleep well if you’re hungry if your belly is like rumbling.

Who is Ingrid Riley?

Just somebody who is curious, love to experiment, love to get to know people, love to read, love to observe individuals, love to travel. I definitely have a thing for travelling. If I don’t travel, my skin starts to itch.

So now, let’s get a little digital. How were you able to get started in this somewhat predominantly male-oriented field?

I never thought that would—I have no other intention just to simply follow what I was curious and passionate about. I was an investigative journalist. And when I kind of reached as far as I could and having been surrounded by technology. And I just kind of fell in love and fell really hard. Coming from that thought tradition and media background, I was looking at online media. Because of all of that exposure, I started my first company, which was called Maverik Media. 

What were some of the bumps in the road that you encountered?

I’ll choose one from the early days. Because I had this internet guide, it was my then business partner, I said, “Hey, I don’t know how to do this. Can you help me? Let’s put it together.” Because of that, she was also part of Maverick Media and we like doing things like email, newsletters or stuff that we are learning and sending out to people that we knew. We were recruited by this American dot-com called HomeView.com And so we put Maverick Media on ice to go and join this team in the hope of, you know, the whole thing of you joining a team. You get shares. We’re going to go IPO, you know, instant millionaire, right? The dot-com bubble popped. I led myself to be fired and went back to Maverick Media afterwards.

The thing that I learned from that is never put your own company on hold to go and work for somebody else unless you were at the centre of negotiating and really negotiate terms that are actually really good for you. I think we’re just kind of happy to be there, happy to learn, happy to be part of this thing without actually thinking about the business aspect of it carefully and recognise when a shark comes and knock on your door. Don’t put your company on the ice. Learn how to negotiate better. Don’t do things that are against your value system because it’s always going to come and bite you.

The second lesson I’ve learned recently is in this whole process of being involved in kick-starting the Jamaican tech entrepreneurship and startup ecosystem here and the Caribbean as well, I learnt to say no and always take care of myself.

How important is it for entrepreneurs and even persons who are considering entering entrepreneurship to follow their instinct?

It is the number one thing. It comes down to trusting yourself as an entrepreneur who tends to see things differently, tends to see things before others.

Well, let’s look at the flipside note, alright? When you create a product or a service or whatever it is, you become so intimately attached to it and you take it too personal to the extent that you refuse to listen to others. I know what is best for me. That’s the flipside. What do you say to that?

No. I believe that there’s always value in that—success always leaves clues. If you see somebody, you know…is like I keep telling people that I do not take financial or money advice from anybody who isn’t richer than me.

We are living in such an awesome time right now. It’s amazing, the opportunities that are available and sometimes we are looking around waiting for persons to come and present stuff on a platter.

Exactly! We are waiting for someone to hand us when it’s there right in front of us. We have the connection. Now, what do we do with it? How do we spend our time? What are we going to create? What are we going to do with others? How do we want to express ourselves in this world? You have access to this internet through your phone, through a laptop to whatever it is.

Persons may be listening in our community now and are wondering how are some of the ways in which I can monetize online, what are some options?

What are you willing to spend a lot of time on getting to be really really great at. You could say, for instance, somebody is passionate about beaches. That’s all played out. Where can you find a list of a map of top 500 beaches in the Caribbean? What do they look like? What are they? Who goes there? What happens there. You become an authority on these beaches. You have your videos, you have your text, you have your photos. There’s a way to monetize that. 

So as an award-winning blogger for siliconcarib.com Is it only just tech that you blog about?

It’s a technology and digital lifestyle blog. I blog about the people, the product, the places and what we’re doing. We’re embracing technology in the Caribbean and how we are positioning ourselves to be successful in the global digital economy. 

Main Take-Aways:

  • Don’t do things that are against your value system because it’s always going to come and bite you.
  • Find a way to monetize what you’re really good at.
  • never put your own company on hold to go and work for somebody else.



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7 Hindrances to Growth in the Caribbean and How to Overcome Them

In the words of the English Poet, John Donne, “No man is an island no man stands alone”. Click To Tweet

There couldn’t be a statement more on point as it relates to building successful relations in business and in life generally.

Yet sometimes we allow our very delicate egos to get the better of us. These egos, when left uncontrolled, have a tendency to play deceive us into thinking we can accomplish mighty feats without the help of others. This is a lie – and I’ll add, as we say in church circles, ‘from the pit of hell”. Statements such as “we are stronger together”“unity is strength” and “together everyone achieves more” are not just fancy sounding and over-used cliches. Entrepreneurs must be in constant awareness of this to allow for excellence in the pursuit of our passion.

I’ve had several opportunities to work with a number of individuals from within the Caribbean as well as the developed world. While there are no perfect relationships – they are all works in progress -, and that working with persons in the developed world has its fair share of challenges, I’ve witnessed some unfortunate success-inhibiting traits that are evident whilst doing business with some of my Caribbean counterparts.

Suffice it to say, defining the Caribbean in and of itself is a challenge. Although not widely used as a definition, in some instances it is based on geology (Caribbean Plate) i.e. structural features and commonalities which allow for similar tectonic, seismic and volcanic features and processes.

The Caribbean is also defined in terms of geographical location which is surrounded by the Caribbean Sea and is called the Caribbean Basin. This includes most of the islands in the Lesser and Greater Antilles as well mainland Central and North South America such as Venezuela and Colombia.

Then there is the Historical Caribbean which saw the impact of slavery, colonisation by the English, French, Dutch and the Spanish, indentureship and the plantation system. The commonality in this instance is the historical or cultural experiences that these territories shared at one time or another.

Politics also has its say in defining the Caribbean. Some nations are now independent – former colonies that are self-governing, some are Associated states – not independent and enjoy all the rights and privileges of the country that governs it.   Some are still colonial dependencies, governed by other countries but do not enjoy the rights and privileges of those in an Associated state. For the purpose of this discourse, the Caribbean takes into consideration all the factors that help to define it, making it unique relative to the other parts of the world.

To continue, the gains made by Caribbean nationals overtime in our outlook and approach to building effective working relationships should not be discounted. However, there are much more grounds to cover. I am positive we will be able to overcome any remaining barriers to growth, leaving selfishness behind.

Our success-inhibiting traits are sometimes subtle but in some instances, the ‘small island mentality’ is quite overt. If we are not careful, realising our full potential will be an impossible task if we do not take the necessary steps to shift our thought process to get to maturity.

While my observations are not scientific and may very well be applicable to other business folks outside of the Caribbean, for the benefit of this article, I will hold all other factors constant.

Here are 7 of my observations and possible recommendations for dealing with them:

The crab in a barrel phenomenon

Many times I’ve seen where persons could assist others in getting to their next level yet they refused to do so for a number of reasons. One is that they would rather keep that individual where they are thinking if I can’t have it, neither should you. The thought process may very well be that if they help them achieve success then said person receiving assistance may outshine them. Like crabs in a barrel, with every attempt someone makes to move forward, they are being pulled down by others who view them as a threat.

We need to begin to see others as partners rather than competitors. When we start doing this we work to collaborate rather than compete.

Lack of Transparency/Lack of Trust

As Caribbean folks, we tend to keep our ideas close to our chests in the initial stage for fear that someone will steal it. We want to wait until we have attained perfection before making a move. We must remember that ideas are a dime a dozen and it’s the execution that makes the difference.

In order to gain the trust of others, we must be willing to expose ourselves and become vulnerable. There is nothing wrong in making that first move to be transparent and open with others. The liberation that accompanies this action is worth the exposure.

This is how I’ve always done it

The theory of Relativity developed by German Physicist, Albert Einstein has changed life as we know it. But probably the most profound impact he’s had is to posit that “insanity is doing the same thing over and again expecting different results”. Yet so many Caribbean folks are unwilling to unlearn their way of doing things to in order to learn a better way even when their way has not proved any form of fertility. In theory, many persons agree with this but what they practice when the rubber hits the road is another matter.

I like Abraham Maslow’s ‘4 stages of learning’ theory. Unbeknownst to us, many of us are at stage 1 in the learning process unconscious incompetence’. This is where we have no idea that we don’t know. Next is the conscious incompetence were we become aware that we don’t know it all. Then there is the conscious competence where we have become more consciously adept at doing things. It is the fourth and final stage that we aim to reach – the unconscious competence.

In order to get to this stage of second-nature capability, we must have an open mind. It is very liberating when we are at the growth level where we can humbly accept that someone’s idea may be more effective in attaining the desired result than our own.

Superiority Complex

I’ve watched with intrigue how some Caribbean nationals from some countries operate with a preconceived notion that because we are from a particular territory then we are superior to others. This is usually accompanied by a feeling of rights and entitlement.

While some Caribbean countries may have more notoriety than others because of their size, economy, culture or other factors, in the grand scale of things the islands in the Caribbean are just a dot on the globe when compared to the rest of the world.

When we think of competing on a global scale, each country cannot depend on trade within itself to achieve above average level of success.

We must think bigger than we actually are; we must recognise that on our own we can’t make it very far.

Threat of Another Successful Person

Someone once said that “if you are the brightest person in the room then you are in the wrong room”. Yet for some of us, the moment we realise that another person is as equally or more talented than us, we quickly begin to strategize how to victimise and sideline that person.

Each of us is uniquely gifted; there is no need to be jealousy of others, we only need to stay in our individual lanes and watch the magic happens.

This issue is deeply rooted in insecurity. Daily affirmations can serve as confidence boosters. This allows us to channel that energy in affirming who we are rather than spend time feeling threatened by the strengths of others. Do this for a number of days consecutively and watch how a shift in mindset takes place.

Opportunistic/Parasitic Behaviour

This is evident in the way some of us network at business events. The minute we get connected to others, our main interest becomes what can they do for us.

We should consider networking akin to going on a date. Just as there are things you wouldn’t do on a first date, apply this same principle to networking.

We want to aim to find ways to provide value to others. It really is more blessed to give than receive. When we extend our hands to others, they will feel the need to reciprocate.

Let’s aim to become a river rather than a reservoir.

Burning Bridges

Physical bridges are built to facilitate passing over an obstacle with success. We sometimes treat others as bridges to aid in the achievement of our goal. No sooner than they’ve become accomplished, the bridges are burnt.

Before we burn bridges, we must consider that we may want to cross over again. Let’s instead aim to enhance our relationships with others through careful nurturing and sensitivity.

We must make a conscious effort to esteem others as we value ourselves. As we begin to do this, we will also begin to cultivate an attitude of gratitude.

In the final analysis, there is no perfect human being but we must make every effort to be our best selves. As we consciously seek growth, not just in terms of our economic pursuits but in who we are deep inside, our productivity will increase. It is possible for all of us to collaborate and achieve much more than we could ever do on our own.

After the Caribbean is a beautiful place filled with beautiful people which are our greatest asset.

Let’s do it!

Heneka Watkis-Porter is a serial-entrepreneur, IBI Ambassador, cultural ambassador, sociologist, author, speaker, fashion designer and podcaster.  She wakes up every day with a grateful heart as she lives her purpose of “life transformation through inspiration”. She is the leading lady behind Patwa Culcha International, the company that owns the authentic Jamaica clothing brand, Patwa Apparel.