In the forward to Drama Drives Interest, her history of Web Summit, Catherine Sanz calls the controversial company “the most compelling Irish business story of my generation”. I can’t quite agree. Quibbles aside about what constitutes an “Irish” story, Stripe surely wears the crown. With its €65 billion valuation and an estimated €13 billion in revenue for 2023, plus a pittance of the controversy, the Collison brothers’ fintech colossus dwarfs Web Summit, which Sanz says might reach €100 million in revenue this year.
But Web Summit is easily the most compelling Irish business drama of the past 15 years, primarily due to Paddy Cosgrave, its cofounder and recently restored chief executive. The exasperating, darkly brilliant professional enfant terrible has never met a contentious or outrageous assertion he didn’t like, which has gained him ardent admirers and devoted enemies.
Sanz, who writes for the Business Post, starts near the end, landing her reader in Lisbon last November as Web Summit 2023 is about to open sans Cosgrave. A month earlier he’d made an unsympathetic tweet critical of Israel in the wake of the Hamas attacks of October 7th. Then he made things worse, apologising yet also apparently rejoicing that his comments had increased ticket sales, even if a whole contingent of big sponsors (including Stripe, Intel, Google, Amazon, IBM and Meta) and high-profile keynote speakers had withdrawn in protest. With Web Summit pitching slowly into a company-threatening spiral, Cosgrave resigned.
At the same time his lawyers were setting out their case in an Irish court against another Web Summit founder, Daire Hickey, in the long-running set of legal disputes in which all three original founders (the third is David Kelly) are variously suing each other. The slow-moving legal tumbril rolls steadily on, costing a small fortune in fees and providing a reliable stream of media stories.
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How Cosgrave, Hickey and Kelly got here from Web Summit’s start in 2009 propels the narrative of Drama Drives Interest, though inevitably this is mostly Cosgrave’s story. The title is a comment he once made to Sanz in defence of his regular pugnacious utterances. The tale is an improbable, fascinating, perhaps only-in-Ireland one, and having this kind of structured history and helpful highlighting of key incidents, political and social fisticuffs and legal-battle emails provides an entertaining and informative addition to Irish business history. It is often hard to put down if occasionally tedious in its endless he-said-he-said (rarely she-said) accounts.
These are often unattributed, as if the sources would rather not become Cosgrave’s next social-media target, but relying so heavily on anonymous opinions weakens the story: should we really care what some unidentified anybody said?
Many on-the-record interviews are with individuals familiar to anyone who has spent time on X; they are the handful willing to spar with Cosgrave.
The lack of an index and, especially, of footnotes and attributions also means quotes and references are too often given little to no context, which is surprising from a journalist, especially when writing about dauntingly litigious individuals.
The book misses two formative proto-Web Summit moments. These are, first, a trip Cosgrave made to see friends in Silicon Valley in or around 2008. He somehow was asked to talk informally at Yahoo! to people interested in how Ireland had become such a big tech force. To his incredulity he found a crowd had gathered for the talk, including at least one of Yahoo!’s founders. He gained unexpected contacts and visibility.
The second is the first pre-Web Summit event Cosgrave staged, a talk at Trinity College Dublin by Tim Draper, the third in a famed dynasty of Silicon Valley venture capitalists. I first met Cosgrave in 2009, when I saw the talk advertised. I didn’t know Draper personally, but his family were for a time our California neighbours, and our mothers were friends. I contacted Cosgrave to offer to help publicise the event. A good crowd filled a lecture room, raucous evening drinks were held at Fade Street Social, the nearby restaurant, and by the end Cosgrave had thoroughly charmed Draper – so gaining a big Valley tech contact – made inroads into the Irish tech world and, crucially, set a template for a unique event. Months later, off the back of the talk, he rolled out the first, modest Web Summit, creating what would become a tech-event behemoth like no other.
The book mostly focuses on Web Summit’s business and legal battles, displaying a weaker grasp of its tech context. Probably for that reason, the book glides past one of Web Summit’s more controversial elements: its apparently relentless digital data gathering from attendees. Sanz glancingly suggests that boundaries were likely pushed in advance of what would be disallowed by the later General Data Protection Regulation. Serious questions were raised that such activities were out of line with existing EU data-protection law. Without noting any irony, she mentions Edward Snowden’s Web Summit keynote in 2019, in which he decried state and corporate data surveillance – even though he was speaking at an event that, as she earlier records uncritically, once used ceiling-mounted GoPro cameras to surveil attendees in Dublin. (Cosgrave told me at the time about using cameras to track attendee movements and badge QR codes.)
Sanz is adept at identifying other controversies and hypocrisies, such as Cosgrave’s decision to launch a Web Summit event in Qatar in 2023 despite the country’s well-documented human rights abuses. Noam Chomsky, a hero of Cosgrave’s (and a past Web Summit speaker), noted in a 2022 interview that Qatar’s population is mostly migrants working in “slave conditions” who “built fancy hotels, stadiums and so on where the rich are celebrating. It is a disgusting, disgraceful situation.” But, as Sanz notes, it is also a lucrative Web Summit location. “Where the rich are celebrating” sounds just like Web Summit.
Sanz’s book is somewhat marred by appearing rushed (it mentions events happening as late as August) and weakly edited. It contains quite a few typos and misspellings, as well as some muddled word choices (such as “spurned” when “spawned” was probably meant). And there are a couple of clangers, including referring to the well-known founder of Craigslist, the headline speaker at an early Web Summit, as Chris Newmark. It’s called Craigslist for a reason.
By the end of Drama Drives Interest it still isn’t clear whether all the recent “drama” will have been too much for Web Summit’s ultimate survival. But it probably won’t matter. As Sanz rightly notes, the same companies and individuals who exited Web Summit last year over Cosgrave’s comments had seemed unbothered by earlier years’ verbal assaults on various businesspeople, journalists, companies and politicians. Paddy or no Paddy, they’ll likely be gathering in November in Lisbon for Web Summit 2024.
