2017 Was My Best Year Yet! What Did I Do Differently?

No year has ended on a higher note for me yet and I think that reflecting on what I did differently then sharing it might benefit someone so here I am sharing.

The goals that I accomplished are not relevant (or even applicable to most people) but my thought process and the eventual outcomes relative to the expectations are.

  1. Narrow Focus

This time last year I was in California with my family and driving back after a helpful few weeks of clearing my mind while trying to figure out what to do next, having worked on the Clinton Presidential Campaign. I could try my hand at another investment firm, having failed the first time around or I could accept a part-time job offer with a Black-owned hedge fund in Chicago where I would focus on establishing their presence in Florida. I could also focus my energy on the film company I owned in Jamaica that was starting to take off with equipment rental. I knew that I could not do them all.

After 15 years of entrepreneurship, my father challenged me to reflect on all my failures, write down the causes and look at the commonalities. Every single one came down to not having enough money, spending too quickly, depending on the wrong people and stretching myself too thin.

The first order of business was to make time for what really mattered if I was going to accomplish my goals and that meant mercilessly culling things that were timesucks.

I chose to take the part-time job since it allowed me time to work on launching a new investment firm while giving me added credibility and a stable paycheck with upside potential. I also resigned from two non-profit boards that were costing me money and time, of which I had precious little. Lastly, I gave complete autonomy over the film company to my partner and only checked in monthly, letting him tell me what he needed me to do to help. He eventually won a film competition in Jamaica and is shooting the film this month.

2. Rethink Social Media Use

Ever since my wife signed me up for Facebook I saw it as a great marketing and personal branding tool. Social media to me is not about where I am going, pictures of my family, vibrant discussions or keeping up with my friends’ lives. That is too time consuming and the ones I need to keep up-to-date on speak via phone, email and text regularly.

I wrote down my personal brand refresh plan, including a dress code for three kinds of scenarios that would reflect my new position: day to day, business and black tie events. I looked at examples of profiles and pages so that I could modify my own page and slowed down on the personal profile use (I’ve previously temporarily disabled my Facebook Profile twice for more than a year each time). I decided what kinds of content I would post and the hashtags to use.

Most importantly, I disabled social media apps on my phone from having access to data so that I had to manually turn each one on if I was going to post when I was not on wi-fi. This kept me from posting often and getting sucked into what others posted. Consumption of social media is a real timesuck and I hate going down that rabbit hole.

It simply came down to what impression would I want someone to form about me from checking any of my social media profiles? Was I inspiring anyone?

3. Find The Right People

We often hear that we are the 5 people that we spend the most time with. Fewer of us hear that we will be worth the average of the 5 people we spend the most time with.

I resolved to focus most of my time on people that were supportive instead of pessimistic, that would be happy for me instead of envious, that would make me better through discussions, sharing knowledge and book suggestions, as well as people who would open doors for me, Sponsors as my friend Maxeme Tuchman rightly puts it. Mentors are good but I needed Sponsors, people who would make helpful introductions because they trusted me and believed in what I was working on.

This meant a drastically different approach to existing relationships and a clear-eyed approach to new ones. I only invested in relationships where the other party clearly wanted to spend as much time with me as I with them. I also opened doors once trust was built, without expecting anything in return, believing that the Universe always comes full circle.

Most of those people opened unbelievable doors and treated me to some amazing experiences just as expected. Some fell off the wagon just as quickly as they appeared but I was not going to chase anyone down. It would be their loss, not mine.

I also learnt the hard way that some people are so small-minded and ungrateful that even after asking for your help and getting it for free, would not want you to take credit for giving that help. Good riddance.

4. Be Present

The Presidential campaign took me away from my family for 3 months so 2017 was primarily about being there for my 2 sons, Luke — 5 and Liam — 4. I also needed to be the best husband that I could be because my wife had sacrificed a tremendous amount to allow me to work on the campaign trying to protect her rights.

By narrowing my focus, I was able to be more present at home. The hedge fund job had me in Miami for 1 week each month but I controlled the travel. We wrote down some goals together and got to work on them.

For meetings, I was notorious in the past for multi-tasking a.k.a. using my phone or iPad when someone was speaking to me whether in a meeting or out for drinks. 2017 was the year I would try to cut that out and show people that I was paying attention.

5. Try New Things

I never took up golf after a few lessons years ago and definitely had never played in a tournament. I had volunteered with a Rotary Club in Jamaica but never joined because I knew I wasn’t going to live there.

2017 was the year that I chose to try these new things. It didn’t hurt that I had an actual golf budget from the hedge fund and they paid for my lessons. I entered 2 tournaments, both for charity, and my team tied for 1st place in DJ Irie’s Celebrity Golf Tournament in Miami which my brother attended with me to cheer me on.

I regularly attended Rotary Meetings and joined the Windermere Rotary Club, presenting at the meeting and helping to bring down the average age of the club just a little (they especially love my thoughts on how the club can better use social media). I attended a few VentureCafe events at C.I.C. Ventures in Miami, brought friends and got to see the Microsoft Hololens, learn about VR, AR and Cryptocurrencies along with much more. I also made some great contacts.

I made time to help a few friends with their businesses, got back into tennis and finally launched my personal website with the goal of inspiring young people.

6. Write It Down

In 2017, I was meticulous with my to do lists, splitting them into Short-Term To Do and Today, moving items from the former to the latter as the appropriate day arrived and checking my list at the end of a day.

I also created a book list that I shared with my brother, co-worker and a potential business partner, constantly adding to it as books were recommended to me.

I wrote out a clear set of goals based on what needed to be accomplished by the end of the year, figuring out whose help I needed (being vague such as “lawyer” if necessary) and kept track of it by having a friend keep me accountable with weekly calls.

I was tired of being seen as an “ideas guy” and wanted to be seen as an “execution guy.”

7. Stop Caring So Much About The Opinions Of Others

As a marketer, I was always very cognizant of how other people perceived me. I never wanted to give the wrong impression or make it seem like I was faking it until I made it. The politician side of me was extra cautious about my personal brand but a new friend was out playing golf one day when I took a picture and said that I would not post it because it was my second time playing golf for the week.

This multimillionaire asked me “So what? Why do you care what other people think about how you spend your time or your money? Are they helping you to make money? Do they control your access to money?”

That was eye-opening!

I changed my approach but wanted to make sure that it never looked like showing off or humble-bragging (that one is super hard). I know that I did not succeed 100% but it was freeing to just be completely authentic and people could take it or leave it.

8. Say No More Often

I previously tried to say “yes” to everything and figure out how to execute after but that obviously failed. This time I would say no by default and only say yes to the things that I could do well, on my own timeline. If I said yes and realized that I could not execute well then I would apologize and politely back out.

Yes, it made some people upset and even ruined some friendships but I was in a rebuilding phase and could only give so much of myself without my own situation not being secure. It’s harsh but that’s reality: It takes cash to care and I needed to build up my cash and pay down some debt. If that broke a friendship then they weren’t really a friend in the first place.

9. Always Offer To Pay

Some months I barely had any money but if I went out, I always reached for the check and offered to pay. Many people refused to let me pay so the next time around I snuck the payment before they got a chance. Some of it would be reimbursed by the hedge fund so it was only fair but some of it was purely personal. I did not want to come across as a taker and never a giver.

When things were tight I was honest and upfront about it before accepting the invite. Everyone was happy to treat me that time and the next one would be on me. That transparency was a weight off my shoulders and made interactions much easier.

10. Make A Debt Repayment Plan

After the failure of my last venture, I was stuck with a few debts as it had been my turn to risk my credit (my brother and I take turns making the personal guarantees whenever we launch a new venture). That had ruined my credit which was both a good thing and bad thing.

The good thing was that I could not get into any more debt because no one would give me a credit card or a line of credit.

The bad thing was that I had to use my limited cash to cover certain business expenses until I got reimbursed.

It was extreme budgeting but it also taught me that when you don’t pay for 30 days, you feel bad and creditors hound you for all the money. When you don’t pay for 90 days, they are willing to do a deal at 50-60 cents on the dollar.

Amazing things happen when you don’t care about your credit and focus on the daily things that actually impact your life. I got over the American narrative that your credit score was the most important thing. I worked, saved, spent time putting together a business plan and then raised more than enough money to pay off the most troublesome debts by calling, asking for 50% off and willing to pay right then and there. All but one creditor took the deal.

The last creditor did a deal for 55 cents on the dollar the following week after everyone else was paid off. My credit score has only gone up since.

11. Treat Yourself Once In A While

As the year progressed and things kept improving, I would treat myself to things that I felt would help me keep the momentum or be more productive. Sometimes I treated myself to things I just wanted because I had no idea how long I had on this planet.

Videogames, Disney Annual Passes renewed for the family, a nice suit, a vacation, an Apple Watch and new iPhone X (that also help me test the RunLive app we are launching) all contributed to mental health and productivity.

A few galas to network and donating to charity yielded some major investment commitments for 2018 and putting aside my ego allowed me to come on board with RunLive and begin securing investors for a huge deal to be announced this year.

Everyone who spoke to me was amazed at how positive and happy I sounded, especially those who know the depths of hell we had to pass through to reach this point.

That low point had given me perspective and appreciation. This time would be different.

12. Just Do It

Instead of waiting for nicer cameras and the perfect set to start my video series I decided to just shoot on my phone after seeing the quality of video on the new iPhone X and using the Clips app to create the intro.

It was also authentically me because I was the one who shot a documentary on the Jamaican railway on iPhones specifically to drive home the idea of using what you have and starting where you are rather than waiting on some idea of a perfect set of circumstances.

The positive feedback has been energizing and getting to test Facebook and Instagram boosted posts has been eye-opening. That knowledge is now being used to help my brother’s early childhood education charity raise money for scholarships and refurbishment.

My “daddy belly” started to show because I had stopped playing football (soccer) so I got back into it every Sunday morning and started playing tennis twice per week. My dad beat me at table tennis twice so I started practicing again so that I can clobber him this year!

I took up running just to test RunLive and asked a friend to keep me accountable (I’ve been horrible but I am getting the beta-testing done).


2017 is my most successful year to date both personally and in business because of the above things that I did different. Some of it sounds selfish but if you don’t take care of yourself, you won’t be able to take care of anyone else.

Amazing seeds were planted for 2018 and it will certainly blow past 2017 in just the first quarter but I am not going back to the way I did things.

Hopefully you benefit from my lessons and even one change will help you positively this year.

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