The Web Summit scheduled an event at its headquarters in Dublin last Wednesday evening entitled 'Runway to Web Summit'.
It was billed as a chance to meet some of the start-ups heading to next month’s event in Lisbon.
But just weeks out from the opening of the four-day tech conference, instead of being primed for take-off, Web Summit is now in crisis as a result of comments made by its co-founder and chief executive about Israel's conflict with Palestine.
It all began this day last week, when Paddy Cosgrave wrote in a post on the social media platform X that he was "shocked at the rhetoric and actions of so many Western leaders & governments, with the exception in particular of Ireland’s government, who for once are doing the right thing".
"War crimes are war crimes even when committed by allies and should be called out for what they are."
His post immediately met with a strong response by a range of tech figures and others, including the former Chief Executive of PayPal David Marcus.
The high-profile tech leader said he was saddened by the "ill-informed stance" and the long-term supporter of the conference vowed to never attend, sponsor or speak at any of Web Summit’s events again.
Mr Cosgrave later posted another message saying "what Hamas did is outrageous and disgusting. It is by every measure an act of monstrous evil".
"Israel has a right to defend itself, but it does not, as I have already stated, have a right to break international law."
The comments though prompted the Israeli Ambassador to Portugal to take to social media himself on Monday, where he said his country would also not be participating in the event, arising from Mr Cosgrave’s comments.
Dor Shapira said he had written to the Mayor of Lisbon informing him of the decision, blaming what he described as "outrageous statements" made by Mr Cosgrave related to the current Israel-Palestine conflict.
"Even during these difficult times, he is unable to set aside his extreme political views and denounce the Hamas terrorist activities against innocent people," he said.
"Dozens of companies have already cancelled their participation in this conference, and we encourage more to do so."
Mr Cosgrave initially appeared to double down and continued to post in defence of his comments.
He also claimed that while nine investors had cancelled their participation in the event, 35 new ones had registered and that more tickets had been sold on Monday than on any other Monday this year.
But within 24 hours, Mr Cosgrave had done a U-turn, issuing an apology on Tuesday to anyone who had been hurt by the comments.
He said he understood that what he had said, the timing of it and the way it has been presented has caused profound hurt to many.
"To anyone who was hurt by my words, I apologise deeply," he wrote.
"What is needed at this time is compassion, and I did not convey that. My aim is and always has been to strive for peace."
"Ultimately, I hope with all my heart that this can be achieved."
But the mea culpa has failed to stem the bleeding and, since then, a steady stream of attendees, as well as high-profile corporate and individual participant speakers listed to take part, said they no longer intend being involved in Web Summit 2023.
Garry Tan, the President and CEO of the prestigious Y Combinator Accelerator was among those well-known personalities who said he wasn’t going to attend.
Also pulling out were actress Gillian Anderson and comedian Amy Poehler.
Yesterday, tech giants Intel and Siemens added their names to the list.
While today, Google, Meta and senior executives from the Collison brothers’ Stripe also withdrew.
Paddy Cosgrave is well-known for being an outspoken entrepreneur, with strongly held, often controversial views and opinions that he is not shy about sharing.
Doing so has in the past led him into high-profile spats from which he has rarely shied away.
But this time, his forthrightness has brought him to a new place, one where the Web Summit brand and its main event that he has spent his working life building is at risk of serious damage, unless he can find a way of quickly putting things right.