Paddy Cosgrave’s Web Summit second act as the tech giants return

With Web Summit’s co-founder and majority shareholder Paddy Cosgrave back in the driver’s seat after his short-lived resignation, pressure is mounting on the CEO to regain trust after comments he made last year that sent Web Summit into a spiral.

Just as the spotlight shines on Elon Musk when Tesla or SpaceX make the news, so is the case with Paddy Cosgrave and Web Summit, making one inseparable from the other. So when the event co-founder tweeted critically about Israel in the wake of the October 7th attacks last year, it was the summit that suffered.

“I’m shocked at the rhetoric and actions of so many Western leaders and governments, with the exception in particular of Ireland’s government, who for once are doing the right thing,” Cosgrave wrote in the week after October 7th.

“War crimes are war crimes even when committed by allies, and should be called out for what they are.” The fallout from his remarks were extensive, with the CEO heavily criticised for not immediately sympathising with those killed in Israel, a tech hub where many of Web Summit’s top partners have offices.

Summit exodus

The comments led to some of the largest tech giants pulling out just weeks before the event, including Meta, Google, Stripe, Intel and Siemens along with several high-profile speakers such as US comedian Amy Poehler, actress Gillian Anderson and actor Joseph Gordon-Levitt.

The controversy ultimately led to Cosgrave’s resignation as chief executive, with the event founder admitting that his personal comments had “become a distraction to the event, and our team, our sponsors, our startups and the people who attend.”

Former CEO of Wikipedia Katherine Maher took over the top job but stepped down just a few months later to become to head National Public Radio, opening the floor for Cosgrave to return as chief executive just six months after his initial resignation.

“When I stepped back last year, it was the first time I had taken time off in 15 years”, Mr Cosgrave wrote.

“I took the time to reconnect with old Web Summit friends and I listened to what they had to say and what they wanted from Web Summit.”

Cosgrave’s partial time off seems to have largely paid off, with Meta and a number of high-profile speakers back in the fold now that he has been reinstated as CEO. While other companies have yet to return and seem in no rush to do so, his time away has largely acted as a lifeline for him to get the tech roadshow back on track.

Amongst the key speakers this year are:

Paddy Cosgrave remains a controversial figure. Known for his provocative and unfiltered approach to social media, the Web Summit CEO is no stranger to controversy and has built a reputation for engaging often times combatively with both fans and critics alike.

Cosgrave has repeatedly called out journalists, politicians, and former business partners, taking aim at what he considers cronyism, corruption and criminality among those in positions of power.

In the last week alone, Cosgrave has zeroed in on Tánaiste Micheál Martin, disputing claims the Fianna Fáil leader has made regarding his father being a busman, with Cosgrave claiming that he was instead a “well paid CIE inspector.. who owned two properties.”

In another post from this week, the Web Summit CEO called out RTÉ, saying the state broadcaster runs a “propaganda, largely by emission, operation,” citing interviews with former Taoiseach Bertie Aherne where he says RTÉ asked “soft ball questions.”

Cosgrave’s laissez-faire approach to social media has landed him in trouble more than once, with the true impact of his combative style set to be laid bare early next year as he joins fellow Web Summit co-founders Daire Hickey and David Kelly in the high court in March.

Legal battles

Cosgrave maintains an 81% shareholding in Web Summit, with Mr Kelly owning a 12% stake in the company while Mr Hickey owns 7%.

The court will hear the details of a series of lawsuits, with Cosgrave suing David Kelly for allegedly breaching his duty to the company by attempting to secretly use Web Summit’s resources to set up an investment fund for his own personal gain.

David Kelly and Daire Hickey have also separately sued Web Summit and Cosgrave, alleging oppression of their minority shareholders’ rights.

The minority shareholders have also individually sued the company and Cosgrave, claiming a breach of an alleged profit-share agreement.

All of the allegations in each of the cases are denied.

Also at the forefront of attendees’ minds arriving in Lisbon next week will be the new book released by author and journalist Catherine Sanz which dives into the evolution of Web Summit, it’s rise to global prominence, the controversies, the public relation crises and legal battles among its co-founders.

Drama Drives Interest: The Web Summit Storythe title for which is a direct quote from Cosgrave according to Ms Sanz, explores the CEO’s life from growing up on a farm in Wicklow to his time in Trinity College Dublin, his many business ventures, broken friendships and the public feuds he has found himself in the middle of, all the way up to where he is now, back in the top role of one of the world’s largest tech conferences.

The past twelve months has been nothing short of a rollercoaster for Cosgrave. Web Summit partners have withdrawn and come back, resignations have turned into reinstatements and costly legal battles await, but one thing remains unchanged: Cosgrave himself.

Despite it all, the Web Summit CEO embodies the same combative, unfiltered and controversial persona that got him in trouble in the first place. Will Cosgrave put Web Summit at risk once more or have the events of the past twelve months prompted him to turn a new leaf? That is a question only Paddy can answer.