A surreal encounter with Jimmy Wales

Wikipedia, wine, and the waning dream of a connected tech utopia

Jimmy Wales tells your humble servant that the future is bright, 2010

In the earlier years of the new century, Wikipedia seemed to confirm the most inspiring of propositions: that you could let loose our troubled species upon an online encyclopedia, allowing everyone to contribute, and the result, the sum total of the effort, would not be bullshit but something rather good.

Within just a few years, Wikipedia had become so dependable that even news organizations were quietly dropping the ban on using it for research (though citing it formally has never quite taken hold). Even as more and more people were claiming to distrust the news, they were positively flocking to Wikipedia, making it one of the world’s top sites. So I jumped at the chance to discuss this weirdness with founder and eminence Jimmy Wales.

It didn’t hurt that this would be happening over fine wine on the shores of Italy’s Lake Como, in the shadow of the opulent Villa d’Este. Originally constructed in 1568 as a Renaissance home for Cardinal Tolomeo Gallio, it has evolved over centuries into one of the most prestigious hotels in the world. Even without George Clooney being a stone’s throw away, one could live a lifetime and never come this close to entering a novel by Stefan Zweig. How we came to be there is a story about the intersection of the news business and fascinating racket of highfalutin geopolitical consultancies.

It began a few weeks earlier, at one of those exquisite, oak-lined gentlemen’s clubs in St. James. I had been invited for a drink by Valerio De Molli, the grand chieftain of The European House – Ambrosetti, a high-level consulting firm with massive ambitions to shape policy. The dash in the name is a giveaway.

Every year, toward the end of summer, he hosts the Ambrosetti Forum at Villa d’Este, bringing together grand thinkers, titans of industry, and political leaders for three days of intense discussion about the issues of the day. The event is aimed to drive top clients to the consultancy that’s able to summon such a crowd. Therefore must be publicized, but in the right way.

The discussions are supposedly off the record, which has many good effects — encouraging openness, creating a satisfying cloak of conspiracy, conferring a sense of privilege. But publicity it is not. De Molli needed a journalist who could thread the political needle, cajole the assembled into interviews on the sidelines, avoid scandal with the Lavazzas and Ferraris, and get published (ideally by a major news agency so that everyone sees the copy).

“You will be as a regular delegate to the Ambrosetti Forum,” Valerio said with a flourish as he reclined in squeaking leather. “Able to assist and participate in all the conversations. And, of course, we would be very happy if you would every now and then send a news dispatch.”

“I would like to lead a panel,” I replied.

“We will absolutely see about you leading a panel,” he said, appearing at once both laser-focused and somehow lost in deep reflection. “It is quite possible, however, that all the panels have been set. Unfortunately.”

Not quite realizing the leverage I had, nor anticipating the extent of the mockery I would absorb from colleagues at AP, I agreed to this proposal. Moreover I insisted that I cover my own expenses, for AP accepts no junkets. Valerio did not quibble about this.

And so I found myself at Villa d’Este, about a week before the global financial meltdown of 2008, talking in the lobby to one of the most respected and senior figures in global finance. I asked whether the "credit crunch" people were nervous about (which in March had caused Bear Stearns to crash) might become a truly major event.

“Absolutely not,” the man replied. “It’s just a subprime mortgage crisis limited mainly to America and to certain sectors. The media is pretty funny — you guys all just learned a new word, ‘contagion,’ and you love to use it now. I wouldn’t worry about contagion so much. It’ll all blow over.”

I cannot identify the man, both because the conversation was not for attribution — and because exactly one week later, on Sept. 15, 2008, Lehman Brothers collapsed, so the statement is embarrassing to a completely unreasonable degree. Soon enough a global financial meltdown collapsed equity markets and caused a panic so huge that a black man who seemed to understand it actually got himself elected president of the United States.

I became an annual fixture at the Ambrosetti Forum — and even got to lead some panels. I made interesting acquaintances, including the late American uber-diplomat Richard Holbrooke, who had brought a measure of peace to the former Yugoslavia, an area I covered in the early 1990s.

Holbrooke

I made an amazing discovery as well, one which troubles me to this day: The Italian tycoons inside the guarded perimeter of Villa d’Este were almost a head taller, on average, than the ordinary people on the streets of Cernobbio village just outside. The sample size was large enough so as to leave me in no doubt. It is one of the most disorienting things to observe and experience, and I figure it’s a harbinger of the coming age of genetic engineering.

In 2010, technology was indeed the major theme of the event. I was especially excited to meet Tim Berners-Lee, credited with inventing the World Wide Web while at CERN in 1989. As a former computer science student and early adopter of Internet precursors like the Arpanet and Bitnet, I considered him a superstar at the Bruce Springsteen level. But the crusty Brit refused to exchange even a pleasantry. “I’m terribly sorry,” he said. “No time.”

I have a theory about people who say they have no time: It’s a half-truth. The whole truth is that they have no time for you. If you were Nelson Mandela or Sofia Loren, let’s just agree that they’d manage to fine time. I spared Berners-Lee this theory of mine, primarily because swiftly he was gone.

Jimmy Wales proved a far more accommodating fellow, agreeing to an an actual interview, just as Valerio had hoped. And in this discussion, he was inspiringly upbeat about the already beleaguered news media industry. Given the state of the news media 15 years later, it seems fair to say that Wales was somewhat less wrong than the man who was sanguine about the credit crunch — but not, alas, by much.

Wales predicted that the increasing use of mobile internet and for-pay apps that run on smartphones and other gadgets might give news providers what they'd been searching for: a way to charge for digital content.

“The apps model — the iPad app, the Kindle — does provide new and interesting opportunities for newspapers,” he said. “If I just click on my iPad, and it's billed on my normal bill, that micropayment model makes it possible for people to have an impulse purchase. I'm not going to pull out my credit card out of my wallet. It's way too much trouble. But if I have a way of just clicking and I get it and I pay a little, it's worth it.”

Of course, newspaper and magazine publishers had already been charging on a subscription basis for years, in most cases with limited success. For every New York Times or Economist that charged a fortune and got millions to pay, there were countless more publications that struggled to get anyone to fork over a peso. The high end is quite successful by now; many more went bust.

In the final analysis, or at least what can be said at present, this model certainly did emerge as viable. Some people pay for journalism. Some of my favorite people on earth pay for Ask Questions Later. But this has not been enough to save hundreds and thousands of publications around the world.

Since 2010, the global news industry has faced a severe contraction, marked by mass layoffs, bankruptcies, and widespread closures. In the U.S., over 2,500 newspapers have shut down, leaving many communities in "news deserts" with little or no local coverage. Chains like Gannett and McClatchy have slashed newsrooms, while digital outlets like Vice and BuzzFeed News have folded or downsized. Print ad revenues have collapsed, and digital ads are dominated by Google and Meta, draining resources from journalism. Globally, the picture is similar, with weakened business models and growing state or oligarch control threatening press freedom and the public's access to reliable information. Big players like the Washington Post and indeed AP have carried out large-scale buyouts, culling staff and diminishing the product.

Perhaps inspired by Jimmy Wales, I was for a time involved in a startup that tried to promote a micropayment system for publishers — charging by issue or by article or vertical or writer. That went nowhere, either. Publishers were just too clueless, and they basically still are, and now much of journalism has moved to Substack and other new platforms and models.

By the way, dear reader, would you like to upgrade to a paid subscription? You’d be proving Jimmy right, albeit 15 years after the fact. That would be good enough for me. Just click on the handy button here:

But back in 2010 at Villa d’Este, Jimmy said he expected newsprint and books to survive longer than the doomsayers predicted. “Print is a pretty amazing technology, really. It's very cheap, lightweight, disposable, batteries don't go dead,” he said — adding that he was taking a book to the beach because an e-reader would be destroyed by the sand.

I think he’s basically right about the books. People like them as decorations and trophies, if you will. Which is great.

Jimmy insisted that despite the online gold rush, Wikipedia, a nonprofit, would remain open and ad-free — a zone of the internet not even trying to monetize. “I don't think it's right for Wikipedia, but I think it's perfectly fine in other contexts,” he said. “When you go to Wikipedia, you should be there to learn, reflect, think, contribute in a positive way. We don't need to commercialize it.”

And he was true to his word. He never got preposterously rich off it, nowhere near the Bezos or Zuckerberg level, even though Wikipedia today is one of the most visited websites in the world, regularly placing in the top five or 10, right on the heels of Google, YouTube and Facebook. It still has no ads, and is basically not about the money.

The English-language edition hosts more than 7 million articles, and 500 new ones are added daily. Anyone can try to edit, and the edits are policed by an army of editors. But the good-news story about human nature has become harder to maintain. Wikipedia has become a battleground in today’s narrative wars. Accusations are rampant — especially since the Gaza conflict — that coordinated pro-Palestinian groups are scrubbing pages to suppress the Zionist perspective, distorting both historical context and current events. The dream of a neutral, crowd-sourced truth is under strain. The openness that once made Wikipedia miraculous is now also what makes it vulnerable.

And this is part of a broader unraveling of the utopian hopes we still held in 2010. The internet that once promised democratization now often delivers cacophony. The network effect, once hailed as a unifying force, has birthed monopolies. Social media, meant to connect us, now runs on algorithms that amplify outrage because rage fuels engagement. AI, once touted for its promise of unprecedented efficiency, is now unsettling the very idea of what truth is. The digital world that once felt so full of promise now feels far messier, more contested, and harder to trust.

I bet Jimmy knows all this, and I bet it makes him sad. I sat next to him at dinner a few years later, at the World Economic Forum in Davos, Switzerland. He remembered our earlier discussion, but was strangely less upbeat. Perhaps it was the freezing cold.