On Becoming a Virtual Entrepreneur

Me and my MacBook at Susie's Cafe

When I looked back these past years, I realised that I’ve never really had a traditional professional life. The starter was that straight out of college – Utech ( previously known as C.A.S.T) I said no to a desk job as Purchasing Manager at the then Telecommunications of Jamaica ( now LIME and from which I won a college scholarship). I went to  work for a startup newspaper The Jamaica Observer as a reporter. I got the full time job even though I sent in a letter as to  the top 5 reasons why they should hire me as a full time columnist.  I just had to choose what felt right for me, even if it meant pissing off my family and taking an initial pay cut.

I never regretted it. I left the Observer with 3 national journalism awards. While there, I was the only reporter who had a beat plus a regular weekly column. I was the first to get a company car even though I was the last one hired. I was one of the first to go on an overseas assignment that I pitched for. I got to cover the Presidential elections in Haiti in 1990s rewarded by being the first Caribbean reporter to score an exclusive with Presidential candidate Jean Bertrand Aristide. Then on my way back had a sweet little layover in Miami with friends spent clubbing, then it was back to Kingston. That was in essence the nature of my first career as investigative reporter and features writer.

I realised very early that I was not going to have a conventional professional life and I welcomed it. I was destined to be a professional free agent and entrepreneur I believe, because I chose it. Over the last 12 years I’ve worked inside 6 startups in various capacities, 1 of them was mine.

The Brand Called You. Read the Article on FastCompany.com

Fast forward to 3 years ago when I was starting up ConnectiMass and founding Kingston Beta, already blogging for two years at SiliconCaribe and it stayed with me – that what I wanted, was to be free to roam the world and still become a US$millionaire doing it. And even though during some tamarind seasons and lifestyle downsizing exercises I didn’t feel like giving up, I just felt that there must be a better way of achieving it,  but at that moment, I just hadn’t found it yet.

Regardless of the bumps and scratches, stops and starts I’ve spent the last 3 years, having moved from an office in Seymour Park to now working from home, at client offices, in my favourite coffee shops, airports, a friend’s loft in New York, a Montego Bay resort, a train from Orlando to Miami and on planes. And I Love it! And thankfully technology and mindsets have changed to make this possible.

Beliefs of a Virtual Entrepreneur

I’ve always wanted a life that matched who I am. I rebelled against simply fall in line with what other said I “should” do or “should” be. I’m A non-conformist to di bone. And the digital age facilitates people like me even more so now. The fresh paradigm shift in the world of work, in how people now do business, also underscores this choice of being a virtual professional, a virtual entrepreneur.

I always wanted my sole focus and constraint to be delivering results and being rewarded very well financially. I believe decisions drive results, not the number of meetings I attend. I believe when you hire well, outsource smartly you don’t need to micromanage. You don’t need to ask “how do I know that the team members are doing their work”. You can set the blueprint, communicate expectations and goals at the outset and give people room to deliver excellently, knowing they will be rewarded or not, based on their results too. I believe you must use the technology and tools available to get the work done and well. Over the years I’ve had clients out of Trinidad, London, Atlanta and Canada whom I’ve never met face-to-face, but with Skype video, Go To Meeting we’ve made decisions, done business and with this beautiful thing called a wire transfer I get paid and on time.

What is “Office” Culture ?

So then people ask, well don’t you need people to come into an office to build a vibe and be part of a company culture. My quick answer…oh hell no! People vibe off the mission of a project – it’s the ideas, the opportunities to do memorable work. That’s what build vibes and a company culture. Plus culture is not grown in a cubicle. Culture is in the personalities and backgrounds of the people you hire, train, how you challenge and treat this talent base, who’s there to help you achieve your business goals. Culture is the how you communicate and collaborate with other to make something unique to your brand. It’s not loads of face time locked in meetings or being interrupted by a flurry of bodies banked behind desks with headphones on just because you need to see them there to feel better. Great Work almost always doesn’t happen “at work”.

The Mantra of a virtual entrepreneur

Work is What you do, Not Where you do it.! That’s the mantra of the virtual entrepreneur. It’s about the idea, the variety, the challenge of creating work you’re proud of and yes for the most part- on your terms. I don’t know about you, but I relish the freedom of movement, time and travel and I must be the only one to determine where, when and why of that. I have no desire or plans to change this. As a virtual entrepreneur, you can get your work done where you want, anytime you want, how you want as long as you have access to the internet. Why would you want a thing else!

How I am doing it

1. Entrepreneurship – I started ConnectiMass – A digital marketing company 3 years ago. I have an ever evolving pool of wicked talent I draw on for projects for the agency side of the business. The events and education side of the business is growing nicely, so much so that I am now finalising a small team and have been approached by potential partners. So being in charge of how you make your money is pivotal.

2. Being Mobile – I’ve always had a MacBook, high speed Internet Access at home; a list of coffee shops, restaurants with free and open wifi and relationships with places that give me codes for free once I am doing lunch. I have my Blackberry Bold Two, my Digital Camera, My FlipVideo Camera always with me in my laptop bag. I make sure too that I always have an updated passport and a working airconditioned car. LOL. Added to that you must have a list of web applications you can use for invoicing, project management ( BaseCamp), video conferencing ( Skype video) or managing clients social media campaigns. Add to that places you can upload and email big files ( YouSend it) and Dropox. And the list goes on.

3. Clients who care and who didn’t care – For the first year of ConnectiMass I was terrified that clients would think less of me now that I was no longer in a nice 1000sq ft office in Seymour Park. I was worried that they’d think I was unstable and unreliable even though at that time, I had over 5 years experience and client braggables in tow. So for a while I faked it by doing things like changing my apt number to a Suite # and making my company seem bigger than it really was. Then I got over myself and decided to be true to myself, to communicate value, not a hot address; to communicate and leverage my experiences, ideas and successes. I only seek clients who care more about what was in my head and say no to those who want to hire an el cheapo negro who has less overheads.

As the agency side of ConnectiMass evolves ( new website in a couple of weeks) I’m more focused on working with fewer clients at higher rates since I sell based on value, not on time and overheads. And, I refuse to work with clients that don’t fully appreciate the value I have to offer. I can make more space in my head to serve clients who do. As for the Kingston Beta and workshop events side of the business – I made sure to focus on growing the event and community first, before getting to where I am now, in seeking strong and meaningful partnerships in sponsors to take things to another level. On the media side of things, I’ve been tweaking the blogs and building a readership,so now I feel good about accepting paid advertisements. I’m also about to launch a video focused blog. ;-).

It has not been easy but it’s been so worth it.

4. Passive Income and investments – This is the next thing for me to achieve. My company is based on services, events and media and its been presenting some cool opportunities to build in passive income to a greater degree. Opportunities that make me money while I sleep even more so and needs my very, very minimal involvement in some respects. I believe I’ll be there in a couple of months.

5. Skills that helped paid the Bills. I’ve learnt ALOT over the last 10 years, especially the last 5. How to buy a domain, set up hosting, maintain a web server, create emails, create, publish and market email newsletters and online magzines; set up a wordpress blog, read and edit HTML code, use Adobe Photo Shop, iMovie editing, planning and executing events, being a keynote speaker, better interviewer and so many other skills.

This is my journey so far. 2011 has set up itself to rock. So if you’re considering the life of a virtual entrepreneur- go for it!