Going Rogue: Advice for Budding Entrepreneurs

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Last summer, I went rogue when I quit my corporate job and decided to travel and write for a living. I also started this blog to document my adventures – and misadventures – so other people could learn from my experiences. Since then, many people have reached out to ask:

How did you do it, and how can I mirror that success?

This has been a hard lesson to teach, since writing is more an art than a skill. To add to this, many of the ventures readers need advice with require large capital and hiring outside help; whereas I was able to start my writing business with my old laptop and 10 years of professional writing experience.

A few weeks ago, I had the pleasure of speaking with Alexander Powell, a fellow Jamaican entrepreneur. He too believes in the importance of turning our dreams into achievable goals, and making them a reality. But more importantly, he has firsthand knowledge and experience, from building Jamaica’s first social media network from the ground up.

Thus, I know Alexander has much better advice for budding entrepreneurs than I could ever offer. Check out my interview with him below.


They say many entrepreneurs began their first ventures as children. Would you say this is true for you? And if yes, what kind of business ventures did you get into as a child?

Oh boy. I didn’t think of them as ventures then, but my entrepreneurship résumé includes candy retail, grasshopper pet services, remote tech-support, and graphic design consulting. I believed in diversification… and I needed money to buy Yu-Gi-Oh cards.

Did you always want to be a techie entrepreneur as a child? If not, what made you decide to pursue a career in this field?

I’ve always loved technology and dial-up gave me lots of time to think about it as a child. Technology entrepreneurship satisfies my inner detective. Piecing together the clues of customer desire to figure out just what will make their lives better suits me well. I also have a high tolerance for risk, which certainly helps.

How did you find other business partners and employees to help make this techie-dream a reality?

This one was easy. We’ve all been friends since we were 11 years old. We’ve been a team since our time at Jamaica’s Campion College.


What was your biggest struggle while developing and running your business? How did you handle the situation?

There hasn’t been a specific “we’re going to crash, grab your parachute” situation. The biggest challenge has been being underfunded and overworked, while balancing the health of our friendships with the health of the mission. The solution I’ve found is focusing on leveraging healthy friendships in order to support the business.

How did you find the capital to start your business? What methods would you recommend to other people trying to start their own business?

The answer is out-of-pocket. We keep our overhead very low and without outside funding (yet), have been able to move forward in pursuing product-market fit. What I’d say to anyone who asks is look at the full set of options. Everyone is in love with venture capital funding, but depending on who and where you are, loans and bootstrapping can be good girlfriends too.

What kind of personal sacrifices have you made for your business?

You can find me in the AM behind a certain cash register to make cash-flow work, but things like that are minor. The fact that any venture could amount to nothing but an experience, and living in the reality that truth crafts for you creates an everyday emotional rollercoaster. I willingly ride it over and over; which, while fun in its own way, is a sacrifice.

What do you wish you knew before you started your own business?

Working on too many parts of your business at the same time slows down how quickly you can make key elements work. Don’t spend two weeks on selecting your font. Use razor-sharp focus on your key assumptions and customer feedback to either be proven right, and start running forward, or be proven wrong and hit the drawing board (sometimes literally). Taking to heart the phrase, “Fail fast and fail often” is key.


Many people view entrepreneurship as the pinnacle of success – until they get there and see how much of a struggle it can be. Now that you’re an entrepreneur how do you define real success in life?

I’m surprised to hear most people view it that way – most of what I’ve heard is how big a gamble it is and how rarely it works out. Success in life is based on who you are and who you want to be, and decreasing the distance between those two. For everyone it’s different, but striving for continuous improvement is the core.

What lasting effect do you hope your business has on the world, for the better?

I hope nobody intends on lasting effects for the worse. LinkUp aims to create a more connected and engaged Jamaica.  To create little pockets of communities where you can belong and experience what matters. Where you are is key to who you are at any given moment, and we’re trying to be on the cutting edge of technology that understands this, and so much more.


What advice would you give to college students who want to be entrepreneurs?

Do it. You’re gonna need moxie, kid.

Really, you need to understand and embrace uncertainty. Be prepared for the cheers, boos and confused huhs when you announce your intentions; and be prepared for nothing going exactly as planned. A supportive community and a powerful set of experiences are waiting for you when you dive in.

What advice would you give to people looking to quit corporate life and chase their dreams?

Be prepared. Be prepared to define your own direction. Be prepared to have a month where you can’t cut yourself a cheque. Be prepared for real, life-changing adventure.

About Alexander Powell:

Alexander is CEO and COO of LinkUp, Jamaica’s first mobile social media network. When he isn’t going rogue with his revolutionary entrepreneurial ventures, you can find him reminiscing about his time at Cornell University, reading on crazy fringe topics, and catching up with family and friends.

About LinkUp

LinkUp is a social media platform built by Jamaicans for Jamaicans. LinkUp helps users to stay connected with their roots, through community-wide chats, and providing relevant information on Jamaican events, news, and social issues. Connect with Link Up on, TwitterFacebookInstagram, or download the Google Play App.

This post was brought to you by Alexander Powell and LinkUp. If you have an amazing product or service you believe my readers could benefit from, check out my sponsored posts tabs on Alexis Chateau PR for guidelines on pitching.

6 thoughts on “Going Rogue: Advice for Budding Entrepreneurs

  1. I feel that this is sound advice, regardless on what direction you want to move. It may not always be apples to apples, but the principles are sound.

    1. Thanks Wade. Alexander did have some sound advice. Must be that Ivy League schooling haha. He’s a Cornell graduate. In fact, the whole team is made of Jamaicans who graduated from Ivy Leagues. Pretty impressive.

  2. Reblogged this on Godigio and commented:

    Thinking of starting your own business in the tech-industry? This entrepreneur got his start while attending Cornell University, and shares the lessons he learned from starting a business while in college.

  3. I enjoyed reading this and I think I just found the answers I have been looking for! Thanks.

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