What was your first impression of Kingston?

My first visit to Kingston was 15 years ago. I thought it was stunning. I was born and raised in the United States. I have been in difficult parts of inner cities in the US. I lived in Boston, Washington, New York and Chicago. When I landed in Kingston I stayed at St George’s College on North Street, and I was astonished by the way the city seemed denied of privileges and infrastructure. I had never seen anything like it and that was a long time ago.

What is the most memorable meal you have enjoyed in Kingston?

There were two. In 2001, I was staying at St George’s College and I was on a volunteer trip, and our meal was chicken foot boiled with rice. That’s a memorable meal. The second was a dinner party at Thalia Lyn’s home. I enjoyed the jerk pork and chicken. I love jerk.

What would be your recommendations to a first-time visitor to Kingston?

This is my first trip in three years and what I was struck by this time is how beautiful the airport is — completely renovated. I thought the general character and feeling of downtown was really nice. It felt clean, safe and sprightly. So, I would say come to downtown Kingston and discover it. I think it’s beautiful.

Share the title of the last book you read.

The Imperial Cruise by James Bradley. It’s about the cruise and experiences of William Howard Taft to Asia in the early 20th century as the continent was opening up.

What are you listening to?

I use Pandora. I like American folk music so it’s James Taylor, Jim Croce and Dan Fogelberg, but most of the guys are long gone. I play the guitar and a little piano and am a traditional music person.

What cologne are you splashing?

Ralph Lauren. I don’t usually splash. I take what I have and use intermittently.

Share some places in your black book.

Havana in Cuba — I was there legally as I was working with Catholic Relief Services. Beijing, Zimbabwe, Zambia, London, Brussels, Amsterdam and Paris. I wouldn’t call myself a seasoned traveller. I have been to a lot of places but it’s generally for a purpose. Generally, when I have free time, I go on my boat in the United States and go fishing.

What was your last major splurge?

Watching House of Cards on-demand. My wife and I do these weekends of watching Showtime and Mad Men. Those are the splurges that we do. Watching these mini-series that run consecutively.

Any New Year’s resolution?

Mine was to come back to Jamaica and keep it going.

How do you unwind?

I run marathons. I’ve run four marathons and a bunch of half-marathons. I ran the Boston Marathon in 2010. After that I injured my knee and am not allowed to run marathons anymore even though I am training for one. I also play ice hockey, fish, write and read, and play music.

What are you writing now?

I am writing a book on my own experiences. I would call it a bit of a memoir. I have worked actively at it for a couple of years.

How did you forge the link with the Mustard Seed Communities here in Jamaica?

I came to Kingston in 1999 with a group of alumni from Boston College. I had heard about Gregory Ramkissoon and I wanted to meet him. I went to Mustard Seed and met him and we became instant friends. He asked me to help Mustard Seed in the United States and I joined his board in the US and became chairman for six years. I came back to Jamaica many times and brought many people, and it’s a very important part of my life. I got my two sons involved and they’ve also been to Kingston many times.

Is it important for you to instil a sense of altruism in your children?

It is. My older son was 14 when I brought him to Jamaica 10 years ago. He just graduated from Boston College and he moved to Chicago and has made a two-year commitment to work at an inner-city Jesuit high school in one of the worst neighbourhoods in Chicago. It’s volunteer with a stipend and that’s what he’s doing after college. I feel like in many ways his experience in Jamaica had a lot to do with that.

What has your involvement in charity work meant to you personally?

I believe in something that my friend told me a long time ago that I found to be vividly real — “the heart cannot feel what the eyes have not seen” — and so I think about that every time I come to Jamaica. I never come to Jamaica without coming into Kingston. I won’t go to Ocho Rios or Montego Bay. I have to come to Kingston. That’s what Jamaica means to me — gritty urban city of hope, striving, diversity, and this sort of rhythm to it. [Personally, my charity involvement has meant]… if you have a decent life, you are on the hook to help others have a decent life.

What drove you to pursue a career in media?

Media is by definition a creative enterprise. You start with an idea and you turn it into something. It could be a show, a story, a blog or a video, but it’s inherently something you create. That was the way I thought I was wired and I thought it would be a really good way to spend my life, and I was lucky enough to be successful at it.

Who is your media inspiration?

When I worked for Parade, I worked with S I Newhouse, who is an old man now. He created Condé Nast and his family owns this incredible American media company and they created a thinking about the customer and the reader. It’s a multibillion-dollar enterprise and they thought about it in terms of generations, not quarterly public results. It was a great privilege in my life working for an enterprise like that. They didn’t get all wrapped up in what would happen tomorrow, they thought about the continuum over a long period of time. S I Newhouse was the patriarch of the family, but there is a whole family of Newhouses who are American legends.

You transitioned from being head of a mammoth media company to running your own business — Empirical Media. Clue us in to what you do.

I ran a big media company and now I have a firm. The definition of the word ’empirical’ means based on the evidence, and so what we do is help media companies face the evidence of where they are likely to go. It’s an advisory and consultancy firm and most of our clients are big American print media companies.

And who are your clients?

I can’t say, but you would recognise them all. Print media is in a huge transition and what we help these companies do is very quietly, without fanfare, without boasting, discover the evidence and what to do with it.

What’s your proudest accomplishment in your media journey?

I spent most of my career at Meredith Corporation. Twelve years. It’s one of the most admired media companies. I helped build it and built a great team and a new model. I look back on that with pride.

What is your philosophy?

Never waste potential, whatever it is. Use it on behalf of others, not just yourself.