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Collision CEO Paddy Cosgrave in Toronto on June 21. Cosgrave says his Collision tech conference is still considering where to host its 2025 event after extending its stay in Toronto to 2024.Christopher Katsarov/The Canadian Press

Paddy Cosgrave built a reputation in tech circles as a particularly outspoken figure in an industry with no shortage of vocal leaders. His swagger helped bring attention to the swanky bashes he hosted for the global business elite.

But now Mr. Cosgrave is paying a heavy price for his unrestrained commentary.

The source of his recent troubles is widespread backlash to social-media posts he made this month about the Israel-Hamas war, in which he criticized Western support for Israel.

He resigned last week as chief executive of Web Summit, one of the world’s largest hosts of tech-focused events, including Toronto’s Collision conference, leaving the company without a leader just weeks before its flagship gathering in Lisbon.

His Web Summit co-founders, David Kelly and Daire Hickey, wrote this week to the company’s board of directors to call for him to give up his stake in the business, citing distractions created by his comments, according to a source with direct knowledge of the matter. The Globe and Mail is not naming the source because they were not authorized to speak publicly about the internal discussion.

In a statement announcing his departure, Mr. Cosgrave addressed his remarks.

“Unfortunately, my personal comments have become a distraction from the event, and our team, our sponsors, our startups and the people who attend,” Mr. Cosgrave said. “I sincerely apologise again for any hurt I have caused.”

Web Summit is looking to appoint a new CEO as soon as possible, its vice-president of communications, Katherine Farrell, said in an interview. She added that the company is now being run by its board.

Mr. Cosgrave has “very much stepped back from everything,” Ms. Farrell said, adding that he will not be present at the Lisbon conference in mid-November, and that he has also stepped down from his position on the board. “We’re really just trying to move forward,” she said.

Mr. Cosgrave has long been the public face of Dublin-based Web Summit, which he founded in 2009. He was known for his ability to lure even the most media-averse tech executives to rostrums, where they would speak to thousands of spectators. Irish court documents show Mr. Cosgrave owns 81 per cent of Web Summit’s parent company, Manders Terrace Ltd.

“It’ll be very hard for them to come back from this,” said Cheryl Kim, managing director of Executive Act, a reputation protection and crisis communications firm. “Even if some people decide that Paddy’s resignation is enough, the damage will be reflected in the attendance for the events this year and possibly the next. This kind of thing leaves a mark.”

The uproar began earlier this month, when Mr. Cosgrave made statements on social media in which he condemned Israel’s siege and bombardment of the Gaza Strip. The Israeli government began the assault after Hamas, the militant group that controls Gaza, carried out a deadly attack on southern Israel.

Mr. Cosgrave criticized Western leaders for their support of Israel. He lauded Ireland, his home country, for its calls on the European Union not to suspend aid to Palestinians, and said that although Israel has a right to defend itself, it should not break international law.

“War crimes are war crimes even when committed by allies, and should be called out for what they are,” Mr. Cosgrave wrote in an Oct. 13 post on X, the platform formerly known as Twitter, where he has more than 91,000 followers.

The remarks drew angry responses from venture capitalists, startup executives, founders with operations in Israel and other tech leaders. Large tech companies – including Google parent company Alphabet Inc. GOOG-NE, Facebook parent Meta Platforms Inc. META-Q, Inc. AMZN-Q, ByteDance Ltd.’s TikTok and Intel Corp. INTC-Q – bowed out of the Web Summit in Lisbon, leading to a larger boycott.

Some high-profile investors pulled their sponsorships from a different Web Summit gathering, which is scheduled to be held in Qatar in late February.

Even so, on Oct. 16, Mr. Cosgrave, in another social-media post, repeated his comments about “war crimes,” this time adding that he would “not relent.”

The next day, in another post, he said tech investors were overreacting to his “perfectly reasonable” and “humane” comments. He accused them of “trying to cancel a truly global gathering that has always stood for peace and prosperity.” Doing this, he said, “is not just naive, it’s counter productive.”

He attached screenshots of supportive messages he had received, redacting the names of the people that had sent them. “I’m proud of what I have repeatedly stated,” he added.

A few hours later, Mr. Cosgrave issued an apology on Web Summit’s website. In the lengthy note, he condemned Hamas’s attack, but also reiterated his earlier comments about Israel’s actions in Gaza. “Web Summit has a long history of partnership with Israel and its tech firms,” he said, “and I am deeply regretful that those friends were hurt by any of what I said.” Mr. Cosgrave has not posted on social media since then.

The company announced his resignation on Oct. 21. He declined requests for an interview.

Ms. Kim, of Executive Act, said any company that relies on “larger-than-life characters who court controversy” might risk finding itself in Web Summit’s position.

“Paddy has been able to garner a very big and influential audience for years. There’s not much that can be done to change the tide with Web Summit,” during the continuing controversy, she said. “We just need to see how long it lasts.”

Before social media became a communications necessity, most executives weren’t expected to make public statements on matters that were unrelated to their businesses. Today, there can be pressure, from both inside and outside a company, for leaders to make an organization’s stance clear.

But this wasn’t the first time Web Summit took a stance on a political issue, nor was it Mr. Cosgrave’s first public quarrel.

Last year, Web Summit prohibited all businesses, government officials and media companies with ties to Russia and Belarus from attending its events in Lisbon and Toronto. The decision, which the company made while Russia was escalating its war in Ukraine, was praised at the time.

Mr. Cosgrave has had spats with media outlets such as tech publication BetaKit, which ran a story earlier this year that said Collision was seeking an increase in the millions of dollars it receives from Destination Toronto, a non-profit tourism organization that is in part publicly funded. Mr. Cosgrave called BetaKit reporters “scumbag ‘journalists’” and “creeps.”

Web Summit’s Ms. Farrell said Collision will be hosted in Toronto in 2024, but would not discuss plans for future years. Destination Toronto, which arranges the contracts for the event, declined to comment on Mr. Cosgrave’s Israel comments, or on any details of Collision’s funding. In a statement, it called Collision a “proven driver of our visitor economy and a catalyst for investment, talent attraction and trade in our region.”

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