Reflections on Web Summit: Out of the frying pan, and out of the fire?

“What controversy?” said the journalist from a global mainstream television outlet to me at the Web Summit Media Dinner, earlier this month in Lisbon.

For all the heat and light, the gnashing of teeth, the tearing of clothes and the clutching of pearls, the big technology conference had seemingly managed to pull itself out of the fire. After the deeply divisive public statements against Israel made by founder Paddy Cosgrave led to several boycotts from tech figures large and small, and Cosgrave stepping down as chairman and CEO (while cannily retaining a controlling financial stake), the event soldiered on. Something of a late-stage startup itself, Web Summit appeared to have staved-off its catastrophic down-round at the last minute.

The Summit, which this year attracted more than 70,000 visitors, programs hundreds of speakers and designates a “Forum” for the latter group to schmooze in, creating a kind of networking event within the event in itself.

The consensus amongst those I spoke to while walking this vast, speakers-only space indicated an approving thumbs-up for Katherine Maher, the new CEO, who gave a speech on the opening night full of high-minded phrases about Web Summit’s role being “more urgent now than ever,” to rapturous applause. Just as well. “We worked VERY hard on that speech…” whispered a Web Summit source to me, afterwards.

Maher had previously been chair of the board at Signal Foundation and the former CEO of the Wikimedia Foundation — two credentials that make for excellent optics, especially in 2023’s divisive political atmosphere. “She appears to have been grown in a lab for this job,” one attendee quipped to me, rather cheekily. Whatever her appearances, she clearly brings a wealth of experience dealing inside the crucible of contentious issues.

But outside the “inside baseball” chatter and gossip among the speakers, founders and investors, the fireball that blew up in Cosgrave’s face went largely unnoticed by the attendees. With the vast majority of visitors coming from small, early-stage startups — or even more unformed than that: individuals that fancy themselves founders but are still getting ideas and more off the ground — most were far more focused on hunting down investors and their first, elusive angel rounds than talking politics.

As the years have passed, Web Summit has become rather like the “Borg Cube” of Star Trek. You can fire a few photon torpedoes at it, but the missiles largely bounce off and the vessel itself seems to gain more energy as a result.

Indeed, Cosgrave is no stranger to controversial topics, and he has sometimes been accused of engineering some of those torpedoes in the first place. It was only a year ago that he’d tried to invite both the Ukraine-sceptical Grayzone publication AND Volodymyr Zelenskyy’s wife to the same event. Needless to say, Olena won that battle and the Grayzone was hastily uninvited.

In fact, controversy has been par for the course for the event since its earliest days, when it was a much smaller event in Dublin and got called out for clogging up Dublin’s roads while booking out the luxury Shelbourne Hotel.

Warming to the Irish angle on Paddy’s Israel/Palestine tweets, my Dublin-based contacts provided extra context, over G&Ts, at the so-called “secret party” for speakers set in a David Lynchian setting for an “intimate” 300 guest list.

Cosgrave, they reminded me, had become so obsessed with Ireland’s internecine political wars over the last couple of years that he even went to the lengths of co-founding and funding “The Ditch,” an investigative journalism unit almost purpose-built to shine light on the underbelly of Irish politics.

“Israel?!” spluttered the long-time Irish founder, to me. “Paddy probably thought he just was tweeting to about 200 people that obsessively follow Irish politics!” Of course, whatever was going through Cosgrave’s mind or his ultimate intentions, in signaling to his Irish audience his views about Israel, Cosgrave had signaled his views to the entire world.

Was it really just a little idle chatter to a small group of people that went out of control? Was it to spin up some controversy for the event that spectacularly backfired? Was it a reflection of his actual political views? Or perhaps his future political ambitions? Could it — some wags have implied — have been related to Cosgrave’s planning of an upcoming tech conference in Qatar?

Whichever of these it was (or wasn’t), it’s clear that Web Summit now stands in a different place. Now under new leadership, the event may be tempted to eschew controversy in favor of more vanilla topics to suit corporate sponsors. That might be better for its bank account, but it would definitely move it even further from the edgier aspects of startup culture.

If the event’s organizers have enthusiastically boasted that the week was just as strong as ever, those attending did admit it was quieter, but in an oddly positive way. “With less celebs and VCs around, I actually had more time to walk the halls and actually talk to startups,” one high-level networker said to me in the Forum.

No doubt Maher hopes Web Summit won’t lose its edge. But where Cosgrave would, in the old days, have plied the bars of his aforementioned secret party, Maher was conspicuously absent.*

Perhaps it was a blessing. In an echo of the brief stumbling into the world’s spotlight that was Cosgrave’s tweets, everyone at Web Summit thought they *might* have to have an opinion about *that* controversial subject. In the end, most of the opinions were about the event itself, and what the Chattering Digerati got out of it.

That was a pity. The advocates of Israel who’d publicly announced their non-participation were no longer there to state their case in public; there were no obvious public outcries onstage, as there was over Trump’s election, a few years ago.

Instead the conversations were more conventional. Did you meet some amazing people? Were there quality startups? How was *your* side-event/dinner/secret party? Darling, mine was fabulous!

So in the end, the dying embers of the fire lit on social media were consumed by only the most mundane of subjects.

* Web Summit later clarified that Maher had briefly attended the party.