Denis O’Brien

Denis O’Brien’s business education didn’t start in a classroom in college, it came from joining his father—who sold equine products across Europe, the U.S. and Asia — on business trips when he was a kid. His mother, at the same time, distilled in him a deep compassion for the developing world at a young age. Thanks to them, Today O’Brien is a successful entrepreneur who has started multiple telecommunications companies and funds a range of philanthropic initiatives devoted to education, humanitarian efforts, special needs and sustainability.

O’Brien is the founder and Chairman of Digicel, a telecommunications company serving 32 countries across the Caribbean, Central America and Pacific. He’s also the owner of Beacon Hospital in Dublin, Ireland. In addition, O’Brien founded the Digicel Foundation, which gives back to the communities Digicel operates in; he is co-founder of Front Line Defenders and serves as the group’s Chairman; sits on the boards of Special Olympics Ireland and Concern Worldwide US; and is the founder of the Iris O’Brien Foundation.

He holds a bachelor’s degree in Politics and History from the University College Dublin and an MBA from Boston College in the U.S.

Where did the idea for Digicel come from?

I saw an advert in the Financial Times in early 2001 advertising the auction of two mobile phone licences by the Jamaican Government.

I had just sold Esat Telecom Plc — a NASDAQ quoted cellular and business solutions provider that we had built to become the number two telecommunications company in Ireland — to British Telecom Plc.

When our team looked at the cellular opportunity in Jamaica, we found a monopoly market where customers suffered poor service and high prices.

Our goal was to democratize communications, initially in Jamaica, and ensure that everyone, everywhere could benefit from the cellular communications revolution. Our business plan was to reach 100,000 customers in our first year in Jamaica; we did that in our first 100 days. Today, Digicel operates in 32 countries across the Caribbean, Central America and Pacific.

What does your typical day look like and how do you make it productive?

I try to break the day into parts. Early morning, from 7 a.m. onwards, I am on the phone with our Pacific operations – and again late at night. When the Caribbean and Central America wake up at 7:30 a.m., it’s calls and video calls right through to about 8 or 9 at night.

How do you bring ideas to life?

By creating small teams to develop the idea, polish the idea and create a plan around it. Then a team is put together to implement the plan; it could be the same team or possibly another separate team, but they need to be strong on execution.

What’s one trend that excites you?

I think the communications business has become a much bigger opportunity, particularly in digital, data, entertainment and content. I think certainly these are the next waves of growth for us. There’s also a big opportunity in mobile money and Fintech.

What is one habit of yours that makes you more productive as an entrepreneur?

I keep reminders of my conversations with all of our CEOs and my teams so that I can ask them knowledgeably when I meet them what happened and ensure that we achieved what we set out to do. I have weekly conversations with all our market CEOs.

What advice would you give your younger self?

Don’t stay in an industry that’s dead. A lot of talented people waste time in a sunset industry that’s going nowhere or is in decline. You need to find a business that has really high growth potential and latch on to it, learn everything about it and exploit it.

Tell us something that’s true that almost nobody agrees with you on.

Facebook has a very corrosive impact on society in every country in the world. When we look back on this period, they will be seen as even more damaging than the rise of fascism in Europe in the 1930s. They have destroyed democracy in many countries and fueled hatred between humans. They are a publisher in every sense but deny it. The game is up for them.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Keep questioning your business model, keep questioning whether you have the right people, and keep questioning if you are bringing the business in the right direction. We all need to keep reinventing ourselves, almost on a yearly basis!

What is one strategy that has helped you grow your business?

Looking at each country that we invest in individually. We look at all of Digicel’s 32 countries as separate markets and businesses and create a plan around each country because every country is different. A consumer in Haiti is different from a consumer in Papua New Guinea.

What is one failure you had as an entrepreneur, and how did you overcome it?

I have made investments that maybe didn’t work out well, but if you get two-thirds of your investments right and some of them really come home, it’s a result. You can make investments that initially don’t work out, but over a period of time, you can turn them into good investments. Sometimes donkeys can become thoroughbreds. That’s the nature of a portfolio approach to investing.

What is one business idea that you’re willing to give away to our readers?

I’m not going to share my best business idea with anybody!!!

What is the best $100 you recently spent? What and why?

I don’t buy books from Amazon. They’re a horrible employer with their zero-hour contracts. I mostly buy books from a bookstore in Donnybrook in Dublin. I regularly spend more than $100 on my reading for the next two months. I’m reading a book at the moment on Boris Johnson by Tim Bower. I have another book on Toussaint Louverture, the founder of Haiti, and one called Silent Invasion: China’s Influence in Australia by Clive Hamilton.

What is one piece of software or a web service that helps you be productive?

Bluejeans. I think it’s the best of all of the video conferencing services. Zoom is hit or miss, but I think Bluejeans by Verizon is a terrific product.

What is the one book that you recommend our community should read and why?

There is an alarming book on Facebook: “Zucked; Waking Up to the Facebook Catastrophe” by Roger McNamee. He was one of the early investors in Facebook and he called it out and he said “we’re going down a very bad path”. He asked Zuckerberg and Sheryl to adjust the Facebook business model and they refused and he lost two great friendships because they were not prepared to listen in any way.

What is your favorite quote?

“Keep going”.

Key Learnings:

• It’s all about:
  -constant reinvention
  -moving ahead
  -looking ahead
  -and giving back.
• Vital to this approach is that as you operate and make a profit in a country, you do what you can to help that country to move forward.