Driven, intelligent but unknowable: What is Paddy Cosgrave really like?

In the space of one evening, Cianan Brennan tries to get to know the tech multimillionaire Paddy Cosgrave

Web Summit CEO and founder Paddy Cosgrave delivers a speech on the opening day of the Web Summit in Lisbon on  Tuesday. Picture: Patricia De Melo Moreira/AFP via Getty Images

I spent four hours in Paddy Cosgrave’s company this week. Having ruminated on the assignment, I decided the question I wanted to try and answer was: “Is he knowable?” 

That is to say, clearly, the 39-year-old multi-millionaire has a personality — he has a wife and child, a second son on the way next year, and a formidable business empire. But is it possible for the public to know him better? Or does he only give out what he wants to?

One could make the argument he is the best-known businessman in the country, certainly in terms of crossover recognition, most of it via his some-might-say outlandish social media pronouncements, which became particularly noteworthy during the initial stages of Covid lockdown.

But that recognition is notable in two ways: 1) It has little or nothing to do with what he does for a living; and 2) It would be fair to say that many of the opinions of him, certainly on social media in Ireland, are not positive.

During the launch of Cosgrave’s Web Summit — the enormous tech conference he founded, which left Ireland in 2016 — in Lisbon this week, a near-catastrophic camera failure saw the opening night shut down for nearly an hour as a fixture dangled from the roof and needed fixing. I was watching the event in real-time from within the 14,000-capacity Altice Arena.

The replies to the tweets I put up regarding what had happened were almost uniformly derisory. 

“How’s the wifi?” was the most common gambit, a reference to the contretemps Web Summit had with the Irish government over the standard of wireless broadband in the RDS in 2015 — the argument which saw the event move into the welcoming arms of the Portuguese the following year.

The Irish can have long, and not particularly charitable, memories.

“We were literally two minutes from having to evacuate the building,” Cosgrave says the following evening, which is slightly different to the message which was being given in the moment. 

At the time, I had thought he had looked fairly stressed, standing on stage and urging calm among the audience (“it will be worth it, I promise you”). Was he?

“A little bit at the time," he conceded.

But, was it the most stressful situation Web Summit has presented him with to date? 

“Definitely not.” 

We’re sat in the back of a transporter with his small entourage of security and appointment managers.

Immediately following the Web Summit’s daytime end of 5pm, Cosgrave has multiple appointments to keep, dotted around the city.

Before each, he seems genuinely unclear as to where he’s supposed to be going next.

(“That’s my job,” his diary manager tells me. “I cover that part of his brain so he doesn’t have to.” So where does his attention go? “On running the event.”) 

I can well believe that. Not to labour the point, but Web Summit is scarcely believably large. It is, indisputably, an enormous achievement of organisation and presentation. 

There are 70,000 people present and it all runs quite smoothly, bar the opening night dramatics. To pull off an event on that scale certainly requires a degree of resolve and purpose.

For all those, though, that think the Irish government missed a trick in letting the event leave six years ago, it is very hard to imagine how it could have been accommodated in Dublin in its current guise.

Cosgrave agrees — Web Summit won’t be returning home. 

“The infrastructure just isn’t there. But then it’s hard to think of a city other than here [Lisbon] where it is,” he says.

The first stop on the night tour is for the opening of a series of roundtable sessions for high-profile influencers at the Palacio do Grilo, a stunning 400-year-old stone structure. 

The event is hosted by Caspar Lee, a South African YouTuber with nearly 7m subscribers. People wearing the ubiquitous Web Summit lanyards are everywhere. Cosgrave stays maybe five minutes, long enough to make an introductory speech, press some flesh, and then depart.

He has a date at a cocktail party being thrown by the mayor of Lisbon at City Hall.

This must be what living as a campaigning politician is like — diplomacy by bungee cord. It seems exhausting enough in itself, let alone for someone who has been running an event with 70,000 attendees for the better part of the day.

“I’m tired, yeah,” Cosgrave says as we settle back into the van. 

He doesn’t seem fatigued, he’s very fit-looking. He says he has been getting seven hours of sleep a night in Lisbon, which is not bad for a man in his position.

“He has a phenomenal amount of energy,” a fellow journalist told me recently. 

“Anyone would struggle to keep up.” 

This is a repeat observation you hear about Cosgrave when you ask about him. (Another is: “He’s perfectly fine, unless he turns on you.”)

We have never met previously but I find him genial company, but very similar to how he comes across via Twitter.

He likes to pontificate at length on whatever subject you raise. He is clearly highly intelligent and well-read, but also at times it is, frankly, hard to understand what he’s talking about.

Perhaps he’s the Irish Elon Musk. What does he make of the South African billionaire’s takeover of Twitter?

“He’s a marketing genius. Twitter is the ultimate marketplace,” he says. 

I suggest the finances of the €44bn deal appear to make little sense at face value, but Cosgrave smiles and says he doesn’t think he has much more to add to the topic.

This is a recurring theme. When you ask him about Irish politics, something he holds forth on constantly on social, his response is “it really doesn’t affect me”.

But he will offer an opinion anyway. He sees Fianna Fáil and Fine Gael’s stewardship of Ireland’s housing market as “appalling mismanagement”. 

He thinks Sinn Féin will lead the next Government, but while he says many of Sinn Féin’s newer generation of representatives are “very impressive”, he doesn’t name any. 

In fact, the only Irish politician who Cosgrave namechecks as having impressed him is People Before Profit’s Dublin TD Paul Murphy, which he does twice.

But it seems to me to be as important to Cosgrave to dismiss all Fianna Fáil or Fine Gael representatives as “useless” as to talk about who will do a better job.

While he dismisses the various flare-ups and spats in which he has become embroiled as “just good craic”, Cosgrave’s recent history would suggest settling scores matters to him.

Ukraine's first lady Olena Zelenska delivers an address to the Web Summit on Tuesday. 

There is something interesting going on in Lisbon as we chat, and I am not talking about the 500 or so Web Summit-related parties — known as Night Summit — which are taking place across the city, where the majority of deal-making at the event reportedly takes place.

In return for the presence of Ukrainian first lady Olena Zelenska on opening night, Web Summit was forced to rescind the speaking invites for left-wing journalists Max Blumenthal and Aaron Maté, whose writings have been noted as pro-Russian.

This is something which appears to rankle Cosgrave, for the two are still in Lisbon as the Web Summit continues, and attended a Web Summit-sponsored dinner in the city on Wednesday evening, a day after Ms Zelenska addressed the conference.

“They deserve to be here,” Cosgrave says as he acknowledges a “spiky” relationship with the Ukrainian delegation.

A day later he will say that he had been lambasted by “legends of media” for rescinding the invites and that he had no “good answer” when it was put to him that Grayzone has never been deplatformed from social media.

The fact that Blumenthal and Maté remained in the city at Web Summit’s invitation despite Ms Zelenska having stuck to her side of the bargain points to the contradiction at the heart of Cosgrave: Does he really care most about free speech? Does he simply enjoy winding people up? Or does he simply not care about anything at all?

The most animated he becomes throughout the evening is in discussing the commercial court cases outstanding between himself and Web Summit co-founders David Kelly and Daire Hickey, which have been notable for the vitriol expressed in the grounding affidavits from both sides, relationships which are long since beyond repair.

He says the cases will most likely come to a head at the end of next year, and seems, while relaxed, in little mood for conciliation.

While Paddy is detained with Lisbon Mayor Carlos Moedas, a former EU Commissioner and another five-minute speaking engagement, some of those around him describe him in far warmer terms, particularly with regard to the kindness with which he can treat his employees.

What does he think of his reputation at home, I ask?

“He’s passionate about what he believes in, and he doesn’t care what people think about him. He just doesn’t mind,” they say.

So what is he most passionate about?

“Web Summit.” 

From there the entourage makes its way to a private media function, with some eye-opening names in attendance. 

You sometimes forget the circles an event like Web Summit can cause someone to mix in. Perhaps that’s why Paddy Cosgrave has so little concern for how he’s perceived. 

Given what he’s achieved, what the great unwashed think of him probably really doesn’t affect him.

He once more performs his statesman routine with those assembled, but before the event can begin he is gone. He has a family commitment to keep.

So is he knowable then? No, not on the basis of the evening’s events.

I suspect that’s just how he likes it.