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Phil O’Brien: “Any startup or entrepreneur will make mistakes”

Digital advances have helped society immensely — the ability to call a car from anywhere, order your dinner, even find a date — but I would like to see a movement back to true connection — talking to people IRL — and spending our downtime reading magazines and books. I think mental health in our communities would improve dramatically as a result. I’m […]


Digital advances have helped society immensely — the ability to call a car from anywhere, order your dinner, even find a date — but I would like to see a movement back to true connection — talking to people IRL — and spending our downtime reading magazines and books. I think mental health in our communities would improve dramatically as a result. I’m a catalyst for change and a passionate connector. My movement would be to encourage more people to be open to connection. Find time to talk to a stranger, as they don’t need to be strange. You never know where worlds collide and great things start.


I had the pleasure to interview Phil O’Brien. Phil is a global entrepreneur and Publisher of W42ST Magazine, a media brand founded in 2014 that connects readers to the New York City experience. With a print magazine and vibrant online presence, W42ST is a popular resource for locals and visitors alike to discover the incredible stories, venues, products and people that make Manhattan’s Hell’s Kitchen neighborhood and New York City so unique and exciting. In his previous career, Phil was a press photographer capturing images of The Queen, Princess Diana, Pope John Paul II, Mother Teresa, Nelson Mandela, Freddie Mercury, Ayrton Senna, and more. At 22, he started his own business, EMPICS, which went on to develop a new technology product and become the world’s largest independently-owned sports photography agency. It was acquired by the Press Association in 2004. Before launching W42ST Magazine, his various roles included being a strategic advisor to the Duchess of Rutland and founding a charitable trust for children. Phil attended St. Francis Xavier’s College in Liverpool and studied photo journalism at Richmond College of Further Education.


Thank you so much for joining us Phil! Can you share a story about what brought you to this particular career path?

I’m passionate about storytelling, media and creating great consumer experiences. My vision is to transform the current media landscape into one of true connection and authentic experience.

My career path has been fortuitous: I got my start in photography as a teenager, and this was long before everyone had a camera on their phone. I was able to turn it into a successful business with luck and hard work. I got into the right field at the right time.

When I was first starting out, I lived in a council house — or public housing — in Liverpool, England and had very supportive parents, although I might not have thought so at the time.

By the age of 18, I was sick and tired of academic life — and just wanted to get on and work. I was the only student not to apply to University. I had the grades to take a traditional path, but I followed my heart and enrolled in a year-long course in Press Photography. Before that, I’d had to make some “difficult decisions.” I had a large model railway set and thought a career as an engineer might be interesting. Tempered with that, I had a keen interest in photography. Luckily, I decided to sell my model railway set and buy a better camera! That was the start of my career in storytelling and media.

Can you share the most interesting story that occurred to you in the course of your career?

Over the course of more than three decades, I’ve met incredible people and witnessed amazing things. One of the standout moments was when I was assigned to photograph the return to international sport of South Africa in 1991, after the end of apartheid and the release of Nelson Mandela.

For one of their first games, I accompanied the South African cricket team to India. We arrived late at night in Calcutta. We had a long time in immigration, where they took a particular interest in all the equipment we were bringing into the country (as well as the wire transmitters and colour processing kit — cricket requires very large telephoto lenses and supporting tripods). After that, the ride of a lifetime. There is nothing more exhilarating or terrifying than a ride in a Calcutta taxi late at night. The streets were chaos, and we breathed a sigh of relief as we entered the gates of the Oberoi Grand Hotel.

The next morning, the team were heading for a photo-call at Mother Teresa’s Calcutta convent. The press bus pushed through the packed streets and we arrived a few minutes before the team. The place was thronged with people and I tried to push through the crowd so I could find out what was happening. As I went, a little hand tugged at me. I turned and looked down and a small lady said “can I give you my business card?”. It was Mother Teresa — and she was handing me a small prayer card. It was a wonderful gift, which I still have.

What was the biggest challenge you faced in your journey to becoming a publisher? How did you overcome it? Can you share a story about that that other aspiring writers can learn from?

Publishing a magazine is truly a dream job because it gives me the incredible opportunity to help small businesses and large companies reach and connect with customers, and of course, create amazing original content for readers.

I still feel that I am a trainee publisher. I’m an experienced entrepreneur, which makes me feel that I can learn about and tackle anything, but in the publishing world I still learn every day. I thought the journey would instantly make me feel like Rupert Murdoch or William Randolph Hearst, but I am a few years off that yet. From selling a successful sports photography business, I had the capital available for the initial investment, and now it’s all bootstrapping, hard work and filling the need for a high-quality, local New York City publication.

One thing we learned early on in the development of W42ST was that storytelling is the key — telling the stories of people that our readers identify with. We are not about finding an “out of reach” celebrity and publishing an interview that our readers can aspire to. We interview and get writers to talk about real New York stories of their life, challenges and victories.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Any startup or entrepreneur will make mistakes; the most important thing is how we react, course correct and find solutions.

The original team was myself and the launch editor, Simon Kirrane. He took so much time choosing the wonderful paper stock, working with our designer for the look and feel of the magazine and making sure we had an amazing, visually beautiful magazine at launch. When the 15,000 copies of the first issue arrived, I asked him, as the launch expert, “What do we do with them now? How do we distribute them?” He said, “Phil, I am a launch EDITOR! I don’t know!” We spent the next month learning our way in. Over the last 5 years we now have a super slick way to reach over 100 luxury properties, 600+ Hell’s Kitchen businesses and are now available in the street boxes of Grand Central, Bryant Park and 34th Street Partnerships. Our passion is getting the magazine in the hands of our readers, giving them valuable time away from their phone, and helping them feel less isolated in one of the busiest, most exciting cities on the planet.

What are some of the most interesting or exciting projects you are working on now?

Over the last two years we have built a wonderful partnership with Intrepid Sea, Air & Space Museum. I lived overlooking the ship for nearly three years before I visited; the museum found that was very typical of their engagement with local residents. They have an amazing reputation for tourists, as TripAdvisor just put them in the Top 10 US Attractions. They wanted to build a relationship with locals and that’s where we came in: we developed with them the concept of WestsideEATS, a food festival with local vendors and residents. We had 25 vendors in our first year and 10,000 attendees. This year we hope to make that a three-day festival with 50 vendors. Last year, we helped them launch a monthly Free Friday program. We hosted VIP events each month which brought in locals, 50% of whom had never visited Intrepid. We staged events on the hottest summer evening on the river underneath Concorde and launched our Heroes issue in the Space Shuttle Pavilion. It has been a very fruitful partnership and we are honored to have helped them and other outstanding local businesses meet and exceed their goals.

Can you share the most interesting story that you have recently come across in your publication?

Every issue and every story are like our children. My particular favorite has been following the story of George Hahn, a New York City personality who worked in finance, design and now runs a men’s blog. We featured George in our first year, and his deep connection with the neighborhood was salient. Later on we shared his difficult decision to say farewell to Hell’s Kitchen and head to his hometown of Cleveland. I’m delighted to say that in the latest issue we reported that he is returning this month to New York. That makes me very happy on many levels. Hell’s Kitchen and New York City aren’t just neighborhoods; the people living here are family and the connections run deep.

What is the main empowering lesson you want your readers to take away after finishing your magazine?

Part of our mission at W42ST Magazine is to create community and provide authentic connection between and among readers in our city. Our interviews are both empowering and inspiring. We also provide interesting event ideas — and host some of our own. Pick up an issue, free and available at fine retailers across Manhattan, or you can check us out online at www.w42st.com.

Always remember: you are not alone. In this big, busy, impersonal city, there is the chance of true connection. You can find your best life through people like you. Don’t get dragged into the FOMO!

Based on your experience, what are the “5 Things You Need to Know to Become a Great Writer”? Please share a story or example for each.

While I record in images more than words, I am passionate about great journalism, literature and writing. Here are my top five tips:

  • Be curious. I hardly ever wear headphones in the city. I am far too nosey to miss a second of the New York experience. Anything can happen.
  • Take note. Whether it be writing in a notebook, snapping a picture on your phone camera or making a note in your phone — I use Google Keep for that — documenting what you see can create new meaning in your day.
  • Listen. Everyone has a story, it just takes a little time to understand it. Asking great questions is a real skill; but listening, following a thread will often help the discovery of the most amazing stories.
  • Connect. Don’t allow meeting people to become a transaction. People know people. I love the Granovetter theory on the Strength of Weak Ties. It’s been proven time and time again that the best opportunities come from the most random meetings with interesting people.
  • Ask, is this remarkable? Is the story you are telling, the picture you are sharing something that people will tell their friends about? Will they say to a friend over drinks “I read this the other day”? Will they take the time to share personally with enthusiasm (that doesn’t mean retweeting or liking). You want to be telling that story.

What is the one habit you believe contributed the most to you becoming a great writer? (i.e. perseverance, discipline, play, craft study). Can you share a story or example?

Look for a different or new point of view. This quotation from Alan Kay, the Xerox researcher who pioneered personal computing, always resonates with me: “Point of view is worth 80 IQ points.” It even relates to my press photography training: arrive late/leave early, shoot high/shoot low, move in close/take an overview. Always look for an angle that’s not the obvious one.

Which literature do you draw inspiration from? Why?

My curiosity means that I will read anything. Although it’s become less of a habit, leafing through every section of a Sunday newspaper (preferably the UK Sunday Times) would help me learn more about different aspects of the world. I don’t have a car, don’t want a car, but I’m happy to get snippets from the Car section. I’m not into fashion, but gee, what’s that article about? I have a natural curiosity which has helped me gain a deep knowledge about a lot of things.

I recently re-read Netherlands by Joseph O’Neill. It’s a wonderful book that manages to mix a story about cricket in New York, a body found in the Gowanus Canal, 9/11 and The Chelsea Hotel. Don’t just trust me; our former President Obama praised the book too.

You are a person of enormous influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

Digital advances have helped society immensely — the ability to call a car from anywhere, order your dinner, even find a date — but I would like to see a movement back to true connection — talking to people IRL — and spending our downtime reading magazines and books. I think mental health in our communities would improve dramatically as a result.

I’m a catalyst for change and a passionate connector. My movement would be to encourage more people to be open to connection. Find time to talk to a stranger, as they don’t need to be strange. You never know where worlds collide and great things start.

How can our readers follow you on social media?

Absolutely! Readers can follow @W42ST on any platform for the magazine and @philobr for me.

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