In the summer of 2022, in the private diningroom of a downtown Toronto restaurant, I found myself standing about a metre away from renowned author Margaret Atwood.
Swallowing my nerves, I approached her to introduce myself and make conversation about the speech she had delivered earlier that evening from the stage of Collision, the North American conference spin-off of Web Summit.
But just as we made eye contact and shook hands, Paddy Cosgrave, appearing directly next to us, told her my name, followed immediately by a description that consisted solely of the phrase “she’s an amazing journalist”.
Over a year later he would level a series of insults at me, then denounce me publicly before ceasing contact altogether. But that night in Toronto, being wined, dined, and meeting one of my heroes, I was at the heart of what Web Summit has sold to the world for over a decade.
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From helping to strengthen Ireland’s reputation as a tech-centred destination to presenting Dublin on a platter as a playground to the rich, the company’s rise was stratospheric.
It managed to secure guests such as Jack Dorsey, Elon Musk, Eva Longoria, Al Gore, Ukraine’s first lady Olena Zelenska, and countless others as it sold tickets to entrepreneurs hopeful of making it big.
Web Summit traversed the globe trying to make it in the unpredictable world of live events, with conferences in Las Vegas, Hong Kong, Toronto, Bangalore, and many other cities.
Staff partied with the world’s richest tech founders and found reasons to make business excursions to places such as Davos and Coachella. There were many glorious highs and plenty of gut-wrenching lows.
Throughout all of this, Web Summit’s ability to make a name for itself often came from Cosgrave’s skill at harnessing the media to serve his business goals. He flung himself headfirst into controversies he had no reason to be in, all to drum up exposure for his business.
Cosgrave found ways to get the company into the headlines or on people’s minds by being loud and aggressive with his views. He played the media by leaning into rows and revelled in storm-in-a-teacup scraps
His love of publicity stunts even extended to real-life situations: to launch a pre-Web Summit start-up in 2009, he proposed setting a door on fire outside Leinster House to illustrate how his company would render obsolete politicians needing to go door to door for election canvassing. Due to fire safety concerns, he settled on having it chopped down with an axe.
[ Web Summit’s ‘ungovernable zaniness’ sets it apartOpens in new window ]
Cosgrave’s book review of Contagious: How to Build Word of Mouth in the Digital Age by Jonah Berger, which was distributed to select staffers in 2014, said: “Mars bars have above average sales when planet Mars is in the news. Why? Mars is top of mind.
“Can we make Ireland, Web Summit or other relevant things top of mind?”
In 2015, when he decided to move Web Summit to Lisbon, he asked some of his closest advisers whether he should release a trove of emails with the then Irish government where he gave out about its abilities. The answer was a resounding no – but in typical Cosgrave fashion, he did it anyway.
I find it fascinating that a tech conference company held such a prominent, and arguably outsized, place in the world of business. I wanted to tell the story of how that happened and I wanted to try to capture the characters involved.
I spoke to 85 people to write a book that chronicles the company’s rise, Cosgrave’s resignation last year, his return and the ugly fallouts with his co-founders.
Web Summit has been a business story no one wanted to tell from the beginning for fear that it would put a target on their back, it seemed to me.
This is because of Cosgrave’s track record of lambasting people he dislikes online, a cohort which has included Irish journalists, business figures, politicians, members of the tech community and former employees.
Since turning against me for allegedly not doing my job well, he has sent me a barrage of angry messages, attacked my integrity online, and instructed legal letters to be sent to my publishers claiming that I have written “unbalanced articles” without elaborating on the article or the content in dispute.
At first the vitriol seemed like another one of his many flippant trolls. In a weird throwback to the axe story, he once tweeted that I was writing a “hatchet job”, before getting into an argument with me on WhatsApp about the difference between a hatchet and an axe. I asked him to stop sending me photos of weapons.
But it eventually turned darker, with aggressive messages when he disliked an article of mine published in the Business Post and a heated argument when I pushed back on a narrative that the story of Web Summit is a story about the long list of people who have allegedly wronged him.
In taking on the task of telling this story, I have knowingly assumed the risk that more attacks will follow, but I hope readers will be left to make up their own mind about the story and its characters. I am also very alive to the nuanced views many people hold about Cosgrave and believe in the importance of telling stories regardless of whether the main character is litigious or not.
While Cosgrave’s antics bolstered Web Summit’s rise in its early and middle years, he also surrounded himself with hundreds of extremely talented people who believed in the company and his vision.
And part of their belief in him stemmed from being told that they were brilliant, talented or amazing. Until, in some cases, he decided they were not.
Cosgrave has “that ability to build you up to the outside world as exceptional, and tear you down to just enough that you lose your sense of worth, but never feel able to leave”.
It wasn’t until I heard these words, spoken by someone who worked with the company for a number of years, that I realised how tactical praise can turn into an endless pursuit of validation.
When I first met Cosgrave in Dublin in early 2022, I told him frankly that I found his tendency to attack people or put them ‘on blast’ offensive, and that I had blocked him on Twitter as a result.
He seemed to enjoy being openly slagged off, because it gave him a chance to rebut allegations, be generally disarming, and revel in his collegiate love of debating.
Cosgrave, who is largely upbeat and spirited in person, regards his online persona to be a different entity, but that does not negate the hurt people have felt at the hands of either character.
Over many years, Cosgrave found ways to get the company into the headlines or on people’s minds by being loud and aggressive with his views. He played the media by leaning into rows and revelled in storm-in-a-teacup scraps that most businesspeople would shy away from. He later became an intense critic of Ireland’s politicians and entire political system, denouncing it as corrupt and fanning the flames of unrest among some of his online followers.
A lot of this is based on a genuine love of fighting, believing his voice is one that can help right the wrongs he perceives in the world. But some of it is manufactured trolling, a way for him to have fun at the expense of others, their feelings or reputations often left in his wake.
As one leading business figure described it to me, his online attacks were personal to the people they were inflicted upon and yet not personal to Cosgrave.
“I think he does it for another purpose, [of] not being serious, but you have to realise that’s incredibly serious for someone,” the person said.
Unsurprisingly, this type of behaviour has burned bridges over the years, especially with tech founders and journalists who once championed the entrepreneur before finding themselves at the receiving end of condemnation.
As a result of his impulsive tendencies having no significant consequences for him professionally, Cosgrave seemed to act with a perceived impunity.
That was until he tweeted critically about Israel in the wake of nearly 1,200 people being killed by Hamas fighters in October 2023.
The fallout for the company was immense, with big-name sponsors and high-profile speakers withdrawing from the event in the days and weeks after his comments. Cosgrave was criticised for taking days to show sympathy to those killed in Israel, where many of the corporates have offices and staff.
A number of those brands, such as Google, Stripe and Intel, have not returned to Web Summit’s website under its list of partners for this year’s flagship event next month. But whether they remain gone forever, or whether enough new ones have appeared to make up for their loss, remains unclear.
[ Google and Meta pull out of Web Summit over Cosgrave’s Israel-Hamas commentsOpens in new window ]
Now, 12 months on, the company faces into another Web Summit conference, albeit amid a very different geopolitical landscape.
Web Summit also faces many more challenges ahead, especially the series of co-founder lawsuits scheduled to go to hearing in the Irish High Court next March.
In 2021 Cosgrave sued David Kelly, his longtime friend and a 12 per cent shareholder; then Kelly sued Paddy; then Daire Hickey, another former friend and a 7 per cent shareholder, sued Paddy. Relations have gone from bad to worse to extremely ugly.
At the heart of the lawsuits are three men who were present during many important moments in each other’s lives, but now only speak through lawyers. They are hurt, angry, and rich – fighting over money, control, and how the past will be remembered for years to come.
For many current and former Web Summit staff that I’ve spoken to, the lawsuits are painful and should have been avoided. Their mere existence is stress-inducing, given some could be called as witnesses if the cases proceed.
Over the course of his career, Cosgrave has led hundreds of people up a mountain with him in a quest for success.
For those who figure out ways to navigate an often-tricky dynamic with the 41-year-old, the journey can be immensely rewarding. For others, it can be damaging.
Cosgrave is not done charging up that mountain, but what cost he faces when he gets to the top remains to be seen.
Drama Drives Interest: The Web Summit Story by Catherine Sanz is published by HarperCollins
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