MY STARTUPS, A FEW QUESTIONS and MANY LESSONS

I sat down this week thinking about startups, I just joined another one. For the first time I thought about how many I’ve personally been apart of. If I had to count the number of startups I’ve given free advice to, send jobs to, facilitated crucial handshakes, just help in some way, the number would double. I realized that I’ve been personally involved in 10 startups from the start of my career as a journalist 15 years ago until now where I’m a blogger/writer, tech entrepreneur, digital strategy consultant.

Just out of college, I became an investigative reporter and columnist at the upstart startup daily newspaper The Jamaica Observer within 6 months of it opening for business. I left 4 years later to a startup political organization National Democratic Movement, led then by the current Prime Minister Bruce Golding. I was the Press Secretary. I left to form my own company Maverick Media and launched the Caribbean’s first Internet Guide which went on to win an Innovation in Media award and it was the company where I made my official foray into the Internet and Web Development business.

I put Maverick Media on ice when I was recruited to HomeView Media LLc, an American company which hired me as Chief Content Officer, I was fired months before it closed and become dust in the dot com boom and a local controversy. I went to Boston to live and started Passion Fruit Studio a web consulting company focused on Content Development and Strategy.  While in Boston I became an equity rewarded, read free playing Content Development  Goto Person for Caribgreetings.com, the Caribbean’s first online greetings site born out of St Kitts & Nevis. When I came back from being in Boston for about a year, I also got involved with a Barbados-based startup called Caribarts.org which was the first online repository of all things Caribbean arts and launched its first newsletter and created a content blueprint for its first website.

I went on to start with a business partner Dutchpot Interactive, a web development and digital marketing company. Now, I co-own Caribclix, the Caribbean’s first online advertising network with four guys, all tech entrepreneurs with about the same about on years in the Tech business like myself. I’ve also been working as an Independent Internet Marketing Consultant under the moniker Connectimass and then recently I became Vice President of Content & Media for Caribbean Ideas, a year old company with roots in Trinidad and shoots in the United States. The company’s timing I believe is just right given the rise of the Caribbean Web very reminiscent of the dot com boom of the 1990s. I’m also about to launch a niche social network with a partner in Canada.

 The Questions and Lessons

The questions that immediately came to my mind were – Am I addicted to startups and starting things up? What does all this diverse experience with startups mean for me, to me? Is all this experience leading me to something greater and should I even be thinking like that?

I’ve been passionate about doing something even if it means I had to pioneer the project. In fact there were a couple of instances where, being the first was what got me outta bed early and had me up way too late at nights. The journey so far though has been extremely rewarding, fulfilling even at times I wanted to just scream WTF am I doing here again, especially not yet driving my wine red Range Rover Sport? I’ve made a lot of money and lost some too. I’ve traveled a lot and made numerous friendships and relationships at home here in Jamaica, in the Caribbean and globally. And most definitely I’ve learnt so much.

I’ve learnt more about who I am under different circumstances and in varying environments. I’ve learnt what I’m good at, what gets me excited. I’ve learnt about selecting the right partners and managing money; that it’s ok to fire clients and not want to deal with marketing managers who don’t want to get it. I’ve learnt to feel comfortable with tough decisions that may make me unpopular in that moment.

I’ve learnt how to negotiate some things better, what is meant by life and work balance, having weighed my heaviest ever (215 lbs on a 5 ft 9 ” frame) while working for a dot com and losing every unhealthy and unwanted pound and then some.

I’ve learnt that whether it’s a dot com or a brick and mortar company, if you’re building a business, then build a business-work the process, have fun and ohh God yes have a life. I realized that it’s ok, even necessary to experiment, test your ideas, test yourself. I’ve learnt too, to value my ideas yet knowing how to remain detached enough to walk away from the ones that simply are not working or do not make good business sense.

I’ve learnt that failure is really not that big a deal, at least not if you learn the lessons you’re suppose to- it’s all just part  of the process. I’ve learnt that money is not a bad thing, in fact, it’s a very good thing, just not the only thing. I’ve come to realise that there are many, many, many ways to making a successful and profitable business and that no one has THE answer, the blueprint that guarantees.

Along this journey I’ve redefined my personal definition of success and have the fortune to be living much of it now.“Do what you love, surrounded by the people you love, in a place you love and that loves you back.”  Someone said it’s the journey, not the destination, now at age 39, I finally get that now.

My dream has always to live my life on my own terms, to do what I love having faith along with the fulfillment, the  achievement and a knowing, that the money would also follow. I do wished at times though, that it comes much faster. I’ve always wanted to own stakes in profitable, successful and saleable businesses; be a highly paid consultant in what I love to do and do best; to work with brilliant, driven, passionate people; yes to become the Caribbean’s first woman billionaire entrepreneur or as a second prize to be a dot com multimillionaire in US$ or Pound sterling terms since I’ve already achieved that in Jamaican currency(the latter is very easy to achieve); become a best selling writer; all while being healthy, having all the time that I want to spend travelling, spend with myself, my life partner (people still get married?), my friends and family. I’m smiling as I write this, as I just realized that they are only two things not yet achieved on that list. What a journey I’ve been enjoying, it’s going to be interesting to see what kind of story I’d be sharing in another 5 -10 years.