My dearly departed father schooled me in being oriented around achievement from a young age, particularly academic, and he had a pretty good carrot incentive system of tying successes to keeping up with my social life. Funny how wanting to get to the fun social stuff is a great carrot for studying for some..

But that helped get me going on wanting to achieve, and pretty soon it became clear to me that one of the biggest areas of achievement I ultimately wanted, was to be an entrepreneur..

And not just any old entrepreneur. One who positively impacted the Caribbean World at large and would also represent Caribbean people on the world stage eventually.

I’ve had a winding path thus far. From a business degree in Toronto, followed by an MBA in Boston, and big company stops at Ernst and Young, and Microsoft, I’ve been following the entrepreneurial / startup path since then. I’m a co-founder of a digital agency based in Trinidad and Tobago called Caribbean Ideas, which I ran full-time for about 5 years, followed by my current time running marketing for cloud software startup SkyKick.

WHAT’S WITH THE WHOLE CARIBBEAN MAVERICK THING?

So where did this whole maverick thing come from? It’s not exactly like Caribbean people exactly associate themselves with the Cowboy life is it?  Picture this story.

Being this academically minded / accustomed to doing well at stuff / super competitive guy that I am, I always remember the performance review that most got under my skin in my “before entrepreneurship” career.

It was my last manager at Microsoft telling me in July 2010 that what he wasn’t getting from me was that I wasn’t enough of a maverick. Just doing all sorts of unpredictable stuff to move the business forward.

The irony at least in my eyes?

That unknown to him, I’d been balancing a day job at Microsoft, while moonlighting and running a young digital startup 5,000km and 3 time zones away.

And I kind of had to just swallow it and not say anything, believing myself to be exactly what he wanted, yet recognizing that splitting my time between two things meant that he wouldn’t always see it in my day job, and I wasn’t exactly ready at the time to share my upcoming plans to leave the company in a few months.

So when it came to naming this blog, I thought about my persona and who I am and who I want this blog to be for, and that review conversation popped into my head.

And looking at the definition for a maverick (unorthodox, independent person), it just fit.

There’s an amazing new generation of Caribbean entrepreneurs and leaders of sales and marketing who are focused on building more successful, customer-centric companies that thrive in the digital-era. This is a blog for that next generation.

I am a Caribbean Maverick, and if you are too, then this is a blog for you.

(Please note, all thoughts on this blog are my own)