Business Irish

Saturday 17 August 2019

Spoofer turned prophet: the enigma of Paddy Cosgrave

Tech guru with model fiancée seems to have it all

Paddy Cosgrave and Faye Dinsmore
Paddy Cosgrave and Faye Dinsmore
Faye appeared in one of her trademark chunky jumpers at this year's Web Summit
This year's Web Summit attracted 40,000 attendees including Rio Ferdinand and Brian O'Driscoll
Faye Dinsmore is well-known as a fashion model
Nicola Anderson

Nicola Anderson

On his last address to the last Dublin Web Summit, Paddy Cosgrave finally admitted that he was roasting inside the Aran jumper handknitted by his international model fiancée - but that he wasn't going to take it off.

"Because that's the kind of hero I am," he declared, straight faced.

It says much about the 32-year-old entrepreneur that nobody in the crowd knew whether to respond with laughter or not.

With a reputation for being "down to earth and unpretentious" up until relatively recently, a shift appears to have occurred. One of his former staff now believes "Paddy has lost the plot."

A huddle of sheep dyed in violent shades of purple, red and green - the colours of the Web Summit logo - grazed rather miserably in the grounds of the RDS, amid the downpours of the past week. They provided a ready background for zany 'Irishy' selfies. But they were also something of an in-joke about Cosgrave's own background as the son of a wealthy Wicklow farmer - who still likes to wield a pitchfork himself from time to time. Metaphorical or otherwise.


Cosgrave speaks little of his early years but it seems likely that much was expected of him from a young age. He was sent away to board at Glenstal Abbey - which seems to have left its mark; an almost monastic fervour still clings to him.

He previously revealed how his father was one of the earliest adopters of tech in this country and considered it "the silver bullet for getting ahead in life."

"Dad's main ambition for me was probably that I wouldn't end up in farming, so when I showed an interest in the tech side of things he was very open to it," he said.

Cosgrave ended up at Trinity College studying Business, Economics, Political Science and Social Studies.

A flair for networking saw him become President of the University Philosophical Society, or the 'Phil' - a position once held by Bram Stoker.

In an interview with a Trinity publication, Cosgrave said it was the prospect of meeting interesting people that initially attracted him to the debating society.

He also became editor of the satirical newspaper, 'Piranha' - and managed to have it banned during his era.

In addition, he edited the Social and Political Review, and served as Business Manager for Trinity News and The Record.

And in the middle of all this, he remarkably found the time to strike up a relationship with a beautiful student of French and Classics from Co Donegal.

Faye Dinsmore was modelling on the side to pay for her education. Completely disinterested in the fashion world, she prefers more thoughtful pursuits like woodwork and knitting.

The couple got engaged in 2012 but Dinsmore's modelling career has taken her to New York, where she is studying at Harvard.

Cosgrave's trademark jumpers come courtesy of Dinsmore - who has a sideline in promoting Donegal-produced Aran knits.

And in the meantime, Cosgrave still lives student-style, with friends, in a rented house in Dublin 6.

He graduated with a 2.1 degree in 2006. A year later, he came up with the Rock the Vote Ireland campaign and founded the MiCandidate website during the 2009 European elections.

Cosgrave and partner Oisin Hanrahan exited the company after a management buyout. Those ventures ran alongside a three-year spell as a UN "e-leader" for ICT and Youth. But the idea for the Web Summit came along very soon.

In an interview with a tech magazine, Cosgrave said the concept of the Web Summit was born out of a trip to California, where a number of Cosgrave's friends were working for Facebook.

On a night out in Palo Alto, a friend asked Cosgrave to come to a 7am networking breakfast.

Taken aback that they would want to attend after such a late night, Cosgrave was told: "Paddy, Silicon Valley doesn't work because nerds sit behind computer screens 24/7. It works because those nerds are occasionally drawn together by great events and great speakers.

"It's where you discover new ideas. It's where you discover new ideas from new conversations you've started ... That's the eco-system, that's how it all works."

On his return to Dublin - amid the recession - Cosgrave met up with his sister, Anna.

During their conversation, Anna said: "The internet is so big these days: wouldn't it be great if some of the big internet names could come to the student society.'"

After this 'lightbulb moment', it was a matter of cold-calling possible guest speakers from Cosgrave's attic - and using his killer weapon: polite persistence.

In those early days, it was more spoof than genius. But obviously there was something about Paddy.

The first Web Summit was held in 2010 with 400 Irish attendees, co-organised by friends Daire Hickey and David Kelly. The wi-fi didn't work.

The same year, he organised Founders, which was described by Bloomberg as "Davos for Geeks".

But as far back as 2011, Cosgrave had begun to grumble about the absence of Government interest and the IDA. He felt they weren't on board and did not appreciate what he was doing.

"The hardest thing for Irish entrepreneurs and people who work in tech in Ireland is to meet and connect with people who run parts of the sector globally," said one Irish Silicon Valley insider.

"To have this in the back garden was a great thing."

The authorities, on the other hand, assumed that having given Cosgrave early support, the venture needed less and less of their assistance as time went on.

In the five years of the Web Summit, it ballooned. And then the cracks began to show.

It had outgrown its cosy venue at the RDS, that much was clear. But Cosgrave would not just simply admit this and launched a missile at the Government.

In turn they hit back, unveiling a list of ludicrous Web Summit demands. "Does anyone have anything good to say about him?" said one industry observer.

"He claims this is Irish begrudgery - there is an element of truth but their childishness eclipses it."

Cosgrave now has bigger fish to fry. In 2016 Web Summit will be hosting Collision in New Orleans, and RISE in Hong Kong - as well as the Web Summit in Lisbon. But in the meantime, this fervent spoofer-turned-genius feels like a prophet, unrecognised in his own land.

Irish Independent

Also in Business