Sunday 25 August 2019

Heat and fire of the Dragon Sean O'Sullivan

An impoverished child who was often cold and hungry, multi-millionaire entrepreneur and philanthropist Sean O'Sullivan drove himself out of the welfare trap and helped improve countless lives

Bright spark: Electrical engineer Sean O'Sullivan pioneered the technology for street mapping and location intelligence software. Photo: Tony Gavin.
Bright spark: Electrical engineer Sean O'Sullivan pioneered the technology for street mapping and location intelligence software. Photo: Tony Gavin.

Andrea Smith

I'm sitting with Sean O'Sullivan at Citywest Hotel, where he has flown in for the EY Entrepreneur of the Year awards, and so far eight people have interrupted the interview to say hello to him. He greets them all warmly but shyly, and it's abundantly clear that he isn't someone who revels in the limelight. What also becomes evident is that he's one of the most extraordinary people I've ever met, and someone who has made a significant difference to the world through his work and philanthropy.

"I was shy as a child, but probably became more introverted later in life," he says. "They say introversion is when you get more energy from your own thoughts and actions, and while I like people, I find myself a little overwhelmed in certain situations. People want more from me now, so maybe that's why I'm so introverted lately."

Twice during our chat, his eyes fill with tears, and on both occasions we're discussing the years he spent living in Iraq. He founded the reconstruction NGO, Jumpstart International, after the US invasion in 2003, and employed 3,500 Iraqis to clear out and rebuild bombed buildings, houses and businesses.

Nobody else was doing that work, so Sean got stuck in during a chaotic, difficult time, operating on his long-held principle that helping people become self-sufficient is the long-term solution to global political and economic instability. He narrowly avoided being killed on one occasion, but his best friend and JumpStart co-founder, Mohaymen Al Safar, 27, who was due to be best man at his wedding, was fatally shot in his car on the way to look at new clearing and cleaning projects.

Sean may be a multi-millionaire entrepreneur, venture capitalist and philanthropist, but the softly-spoken, 51-year-old Irish-American remains heartbroken at the memories of that time. "I saw a lot of things," he says. "We did clean-ups where bombs had gone off and there were bodies still there, and while it didn't affect me when I was there going through it, it hit me afterwards and still bothers me now."

Sean was born eighth of the late Joan and Kieran O'Sullivan's nine children and was raised in the farmlands north of New York. His mother's grandparents came from Cork, and his father's parents were from Kerry - his maternal grandfather, Reginald O'Callaghan, was the guy who introduced Joe Kennedy to Rose Fitzgerald.

"My grandmother on my father's side was a spy in the post office," says Sean. "She had to flee the country and got an award from Eamon de Valera years later."

Sean wasn't a big fan of his late father, who he refers to as "my biological father". He left the family when Sean was three years old and didn't support them. He has no memories of living with his father and never spoke to him, although some older siblings remained in contact. What he does have is a clear memory of being freezing cold every winter and never having a lot to eat, as US welfare was then about a quarter of the Irish rate.

"We would all sleep in the living room because it had a wood stove where we'd burn the wood we cut down," he says. "Even so, we would wake up in the morning and it could be minus 12 or 15 degrees Celsius in the room. My mom was fantastic and a pillar of strength, but it was brutal when you couldn't afford to heat the house. My biological father didn't support us financially, although he was doing well for himself, but something switched off in his head and he decided he didn't need to take care of his responsibilities. My mom couldn't fight a court case and beg for help from lawyers when she was simultaneously raising nine kids, so we were on welfare for years until enough of us were old enough to allow her to go out to work."

When he was in third grade, Sean calculated how much he would make on minimum wage for the rest of his life. He decided there and then that he was going to have to drive himself out of poverty, because he never wanted to be cold again or not have enough to eat. "I weighed 115 pounds when I went to college," he says. "I'm five-eleven and weigh 165 pounds now, which is about where I'm supposed to be."

His mother, Joan, was a "massively productive and extremely religious woman with a very strong heart", and when she got back into the workforce she started a home health aid programme that trained 3,000 people. When she became ill later in life and needed care, Sean and other family members went after their father to get him to pay what he owed her.

"I had to take him through nine different court systems as he kept appealing, but I won and got possession of his house in Manhattan, two blocks from the Empire State Building," he says. "He had apartment buildings in Texas too. The money paid for my mom's healthcare, as she was a lifelong diabetic and was coming down with dementia. Before I made any money from my first company going public, I was able to carve out some time to do the work and go after him."

Sean's beloved mother died at 72, and his father died two years later. He gets along very well with his siblings, but they aren't the tightest bunch as they're scattered throughout the world. He began coding at 12, and chose to study electrical engineering at Rensselaer Polytechnic Institute. It was the most creative outlet he could think of, as he loved the idea of designing real world things that would impact on people's lives. He worked throughout the summers and took out loans for tens of thousands of dollars to pay for the course, along with a bit of a scholarship and some grants.

He graduated in 1985, and has achieved a staggering amount of success. Through his first company, MapInfo, which he founded straight out of college, he pioneered the technology for street mapping and location intelligence software. It was an amazing innovation, as it impacted everything from police work to package delivery to deciding where to install ATMs.

"CD roms containing 660 megabytes of data came out, and I made a list of applications to see what we could possibly do with them that would be useful to people," says Sean. "Putting maps on to computers was suddenly feasible, and I calculated that you could fit all the street maps of the US on to one CD rom. At that time, other technologies were coming out like VGA graphics, and I figured if we could put processing, graphics and memory together for mapping, there was a chance we would be first in the world doing it.

"Being first is a very good thing, as there is no competition, even for a young, start-up company, and if you have something no one else has, you have instant credibility. So we did that and no one else was ever able to catch up - not even the bigger players with hundreds of millions in revenue behind them."

Sean went from obscurity to being on magazine covers when he was 23, with stories running in newspapers in the US about how his technology was helping different industries. His company was worth $200m by the time he was 28, and he coined the term "cloud computing" along with Compaq's George Favaloro.

"Success can make you very arrogant, as you think you're a genius and you're always right," says Sean. "I'm humble now, but that's a lesson I had to learn as my first company was a huge success but my second one wasn't. I didn't need a second company, but I just wanted to prove that I could make anything worth hundreds of millions of dollars. And actually I couldn't, as you need all the right ingredients."

He took a detour by leaving the company in 1993 to start a rock band called Janet Speaks French. They released two CDs, and he co-founded the famous Sonic Recording Stu- dios in Philadelphia. He then started NetCentric, which developed software for faster, more efficient web communications, and decided to enter the film school at the University of Southern California to focus on documentary film-making. This is what took him to Iraq, where he met his wife, Tish Durkin, in 2003, the day after the fall of Baghdad.

From Caldwell, New Jersey, Tish was the Observer's war correspondent, and they bonded while sharing a 14-hour cab ride to the Iraqi capital. By his own admission, Sean was never a ladies' man, as he wasn't confident with the opposite sex. "Tish and I hit it off because I was a nerd and she was kind of a nerd too, but a more glamorous one," he says, laughing. "I loved her capability, her passion and her incredible intellect."

They were married in 2004 and lived in Spain. As soon as they found out they were expecting their first child, they stopped their operations in war zones.

"I was thinking of software ideas and wanted to stay in Europe, and Ireland was in the Eurozone and has a great technology sector," says Sean. "Dublin had mad traffic and congestion and Galway had bad traffic and poor planning, so Cork was the city we chose. We lived in Kinsale for nine years. It's a lovely town, and while it was a culture shock in some ways, the non-violence of Ireland appealed to me."

Sean and Tish have two children, Charlotte, 10, and eight-year-old Matthias, and the entrepreneur says that fatherhood has been a fantastic, life-changing experience. Charlotte is an academically-gifted child who is fluent in Spanish and English, has some Irish and is learning Latin because she has a passion for it. "She wants to rule the world, and for it to go exactly how she wants," says her proud dad. "She gets her own way with everyone as she's so strong-willed and confident, which I am very happy about."

Mathias is a fun-loving child, engaged and affectionate. He also has autism and is unable to communicate verbally. The diagnosis was made officially when he was three-and-a-half, but the family had figured it out over a year earlier and had put some interventions in place. They tried to build an educational programme for Mathias in Cork while working remotely with an advanced institute in the US, but it wasn't effective.

For two years, Tish tried living in New Jersey where Mathias was enrolled in an applied behavioural analysis programme, and Sean looked after Charlotte in Cork. They would commute one week per month, which meant they were spending 25pc of the time with the whole family together as a unit, but with Sean's work commitments it was hit-or-miss, and the situation couldn't continue.

They made the decision to leave Cork in July and relocate to New Jersey as a family. Mathias is flourishing at a wonderful school in Princeton that is doing an incredibly good job at helping him develop his skills.

"He's a very smart kid, but he doesn't speak apart from one-word sentences so he has real challenges," says Sean. "The school is great, and we hope that if we can crack his verbal communication problem, he will be able to go to college. He would have been seen as a severely autistic child, but we're trying to work him up to be moderate, or even to the point where he can be a mainstream student."

As anyone who saw the EY Entrepreneur Of The Year awards ceremony on UTV Ireland will know, Sean didn't win this year. The gong went to Limerick brothers John and Patrick Collison, for their web and mobile payments company, Stripe. Sean thinks the awards programme is fantastic as it promotes and empowers entrepreneurs in growing their businesses in Ireland and around the world. It also provides an invaluable network and business opportunity within a 416-strong alumni community.

Sean now runs SOSV, which employs 46 people in the US, Asia and Cork and invests over €44m a year in start-ups. It backs 130 new companies each year, and has hundreds of mentors and around 500 entrepreneurs annually in its programmes. The secret to success is not relying on investors as much as you rely on customers who love what you do so much that they are willing to pay you for it, he says.

"A lot of entrepreneurs think they need a lot of investment to get started, but the more you do that, the less of the company you are going to own and the less of your future you are going to control," he says. "When you get investment from capitalists, you are setting in motion a ticking time-bomb. You have some time to deliver on your promises and make money, but if you stop delivering, you run out of time and boom - either your company goes up in flames or you do."

Sean feels it's a remarkable gift to be able to support a new generation of entrepreneurs doing wonderful things for efficiencies, health, computing and creating new products that are shaping the world.

"One company has a device that can predict cancer years before any other means, which means it will be more treatable as long as you get frequent blood tests," he says. "We can predict Alzheimer's the same way and slow down that process. The most expensive surgery in the US is spinal surgery, and we have a medical device for fixing that, which will help improve a lot of people's lives. I just think it would be great if a lot of these products end up being successful."

While he's very busy, Sean insists that the 80 hours a week he spends at work is actually time for himself, because he adores what he does. He is excited about all the potential new developments in the companies he supports, but admits that Tish laments that he says yes to far too many things. He is founder of Open Ireland, but while he should never have agreed to being on RTE's Dragons' Den because he was far too busy, he feels that, on balance, the direction it took him in was wonderful. "It gave me a stage to make more of a difference to Ireland," he says. "I was able to have some impact on policy issues regarding entrepreneurship."

Despite his wealth, Sean travels economy class and drives an old car. He spends money on his children's education and going to conferences, such as the TED conference which costs thousands of euro to attend.

"It's ridiculously expensive, but you get to hang out with some great people and have amazing experiences," he says. "It's a massive networking thing, so the payment can be justified. I spend far more on projects like CoderDojo (the free, volunteer-led, community-based programming clubs for young people) or Mathletes, which are great favourites of mine, and I'm glad to help fund them. It's teaching us something about values that it doesn't cost these kids anything to learn and they're willing to give up their own time to mentor other kids."

So, with family commitments and projects bubbling all over the place, how does Sean actually switch off? "I still have the old Late Late Show piano that I took with me, and everyone has played on it, even Elton John, so I sit and play on that for an hour a week," he says. "I also walk to work and do my 10,000 steps a day, but even when I'm walking, I'll still be on the phone working."

Sean feels that while good governments are very important, they're not the solution to all our problems, as technology is giving us a better quality of life, making things more affordable and connected and having an impact on billions of people.

"Enabling people to climb up the ladder through their own will is what will get them out of poverty quicker than any government," says the man who used to go to bed cold and hungry. "We're giving people the tools so they don't just consume, they also create."

For information on the EY Entrepreneur of the Year programme, visit

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