During the summer season of 2022, I found myself within a metre of celebrated author Margaret Atwood in an exclusive dining area of a popular restaurant located in the heart of Toronto. While mustering up the courage to interact with her and discuss her speech that she had presented earlier at Collision, a North American offshoot of Web Summit, we were interrupted. Paddy Cosgrave, appearing suddenly beside us, introduced me to her by simply stating, “she’s an incredible journalist”. Later, after more than a year, he would hurl a series of derogatory remarks towards me, rebuke me publicly, and then choose to sever all forms of communication with me. This episode, however, was nothing more than a momentary hiccup in an otherwise thrilling evening where I found myself rubbing shoulders with some of my idols.
For more than ten years, Web Summit has been promoting such encounters to the world. From advocating for Ireland to be recognized as a tech-focused hotspot, to showcasing Dublin as a luxurious haven for the wealthy, the brand’s rise has indeed been astronomical. Big-name guests like Jack Dorsey, Elon Musk, Eva Longoria, Al Gore, the first lady of Ukraine-Olena Zelenska, and many others were present at the events, enticing entrepreneurial attendees hoping to attain success.
Web Summit has journeyed across the world with its range of live events, marking its presence in places as diverse as Las Vegas, Hong Kong, Toronto, Bangalore, and more. Its employees have revelled alongside the world’s wealthiest tech moguls and made several business-related trips to destinations like Davos and Coachella, experiencing a roller-coaster of unforgettable highs and crushing lows.
In this saga, it’s worth noting that Web Summit’s illustrious image was often a reflection of Cosgrave’s adept talent for using the media to accomplish his commercial endeavours. Despite having no logical reasons to involve himself in various controversies, he plunged into them head-on, all in the name of garnering publicity for his business.
Cosgrave had a knack for keeping his firm in the spotlight by voicing his strong opinions in a boisterous and assertive manner. He would bask in the media attention through engaging in controversies and enjoying minor rumbles. Furthermore, his proclivity for staging PR stunts extended to actual situations as well: for the inauguration of a pre-Web Summit start-up in 2009, he suggested the idea of setting a door ablaze outside Leinster House, symbolising the obsoleting of politicians having to campaign door to door. Fire safety issues however led him to choose a different approach, dismantling the door using an axe.
In a company-distributed review of the book Contagious: How to Build Word of Mouth in the Digital Age by Jonah Berger, Cosgrave wrote:”Mars bars record higher than average sales whenever planet Mars captures headlines. Why? Because Mars begets attention.
“Can we position Ireland, Web Summit, and other pertinent things at the front of people’s mind?”
In 2015, Cosgrave, while considering relocating Web Summit to Lisbon, sought advice from his closest confidants about publicising his confrontational email exchange with the then Irish Government about its deficiencies. Dissent was the consensus, yet Cosgrave, true to his nature, acted on his plan anyway.
My fascination with the central and somewhat bloated role a tech conference firm held within the business world inspired me to uncover this story. I wanted to portray the personalities involved and reveal the inception and subsequent rise, Cosgrave’s brief retreat last year, his return and the subsequent disastrous split with his co-founders. I consulted with 85 individuals to document this story.
It wasn’t an easy task as it seemed that nobody wanted to narrate the story of Web Summit from its origin, as it risked creating antagonists. And that’s attributed to Cosgrave’s habit of berating individuals who are not to his liking on the internet, a group that includes Irish journalists, businesspeople, politicians, tech industry professionals, and former colleagues.
After publicly criticising my performance, he has launched a storm of irate messages towards me, smeared my reputation virtually and even involved the law by dispatching legal notices to my editors, stating that I’ve penned “biased content” while failing to clarify which article or aspect was the issue.
Initially, his tirade came across as just another casual smear, reminiscent of a previous axe-related disagreement when he tweeted that I was engaging in “character assassination” before initiating a heated exchange over the distinctions between an axe and a hatchet on WhatsApp. I requested him to cease sending weapon images.
However, his annoyance eventually took a darker turn, stemming from his aversion to an article I wrote in the Business Post and an angered debate that ensued when I challenged his notion of the Web Summit narrative that focused on all those who purportedly cheated him.
Knowing that going ahead with such a controversial story could potentially subject me to further hostilities didn’t deter me, as I’d wish for readers to make their own judgement. I’m acutely aware that Cosgrave invokes diverging perspectives, but the relevance of telling stories, regardless of the protagonist’s litigious nature, must not be undermined.
Cosgrave’s eccentric behaviour played a significant role in catapulting Web Summit into prominence during its initial and intermediate stages. Simultaneously, he gathered a team of highly skilled individuals who trusted in the organisation and his ideas.
Their faith was nurtured through constant encouragement regarding their brilliance, skill and extraordinariness, until, in certain instances, he abruptly deemed them unworthy.
Cosgrave possesses the knack to elevate one’s status publicly whilst simultaneously breaking someone down silently leading to a lost sense of dignity, yet creating a situation where leaving seems impossible.
Listening to these words from a seasoned employee made me realise how psychological manipulation can covertly seek to gain acceptance.
When I initially encountered Cosgrave in Dublin in early 2022, I explicitly expressed to him my discomfort with his habit of berating individuals and publically chastising them, which prompted me to block him on Twitter.
His response, however, was quite the contrary, appearing to relish this open criticism as it provided him an opportunity to disprove chargebacks, be congenial and engage in debates, presumably feeding his academic fondness for such exchanges.
Cosgrave, frequently known for his optimistic and lively disposition, recognises a distinct identity for himself in the digital space. However, this doesn’t diminish the emotional harm either of his personas may have caused individuals. For numerous years, Cosgrave leveraged his bold and assertive opinions to command attention and create headlines for his business, a tactic many entrepreneurs might avoid. Simultaneously, he often found joy in causing these uproars, treating them as mere instances of harmless amusement to the detriment of others, and resulting in damaged feelings or marred reputations.
He pursued these activities out of a deep-rooted passion for championing for what he believed was right, utilising his voice as a platform for change. On the other hand, part of it was simply an act of sabotage, enacted for his enjoyment. Although these online affronts were personal to those on the receiving end, they were impersonal to Cosgrave, who often used this online attitude to gain attention.
There was a general agreement among several prominent business figures that whilst he may seem light-hearted in his antics, the effects of his actions can be notably severe for those on the receiving end. Unsurprisingly, his habit of acting upon his whims, without facing any detrimental impacts on his career, have resulted in strained relationships, particularly with tech founders and journalists who previously admired the entrepreneur until falling victim to his harsh criticisms.
However, his perceived invincibility was certainly questioned after his controversial remarks towards Israel following the desath of almost 1,200 people by Hamas fighters in October 2023. The repercussions for Cosgrave’s company were significant, with notable sponsors and acclaimed speakers retracting their support in light of his remarks. Amid the criticism for his delayed response to show condolences for the victims in Israel, it was also noted that many of the corporate entities affected maintain offices and staff in the country.
Several corporate giants, including Google, Stripe and Intel, remain absent from this year’s list of partners for the flagship event next month, as shown on the Web Summit’s website. Whether these companies have permanently severed ties, or whether new partnerships have emerged to compensate for their departure, is yet to be seen.
As the Web Summit conference approaches another year, the company finds itself amidst a notably changed global context. Additionally, numerous hurdles lie ahead for the Web Summit, of particular note are forthcoming co-founder lawsuits scheduled for hearing at the Irish High Court this coming March.
The plaintiffs include Cosgrave, who filed a suit against his longtime friend David Kelly, who owns 12 per cent shares in the company, followed by Kelly returning the favour. Furthermore, a suit was launched against Paddy by Daire Hickey, a previous friend with a 7 per cent shareholding. The friendship has catastrophically degenerated over time, becoming intensely bitter.
At the core of these legal battles are three individuals who have shared enumerable significant events together, however currently their interaction is strictly limited to legal representation. These are financially successful men, gripped by resentment and pain, embroiled in disputes over financial assets, influence and the historical narrative of the past.
Conversations with current and previous Web Summit employees reveal a common sentiment that these legal battles are acutely distressing and could have been prevented. The fact they are taking place is a source of anxiety, particularly since some may be summoned as witnesses in the event the litigation progresses.
Throughout his professional journey, Cosgrave has guided a multitude of individuals up a metaphorical mountain in the pursuit of success. This journey with the 41-year-old Cosgrave can be hugely fruitful for those who manage to negotiate the often challenging relationships. However, it can also be detrimental for others.
Although Cosgrave has every intention to keep scaling that mountain, the aftermath once he reaches the pinnacle is yet to be seen.
The book “Drama Drives Interest: The Web Summit Story” by Catherine Sanz, published by HarperCollins, further details the Web Summit tale.