At the dawn of digital, when cell phones were new and culture dominated by cable television, most of my friends and family considered me an ‘early adopter.’ I was usually the first of my crew to engage with any new digital device or service – the Mac, email, the web, search, wifi, even nascent social sites like Friendster, Orkut, and LinkedIn. I was one of the very first people on Instagram, back when it was just a photo site. I was the guy friends and family called when they had a computer problem, and later, when their smart phone acted up. It wasn’t that I was particularly adept at coding or solving IT problems. I was just the guy who everyone knew had spent the most time in the digital world. You know, the Wired guy.
For nearly three decades, I stayed current with all things digital. But about ten years ago, I started pulling back. At first it was more of a vibe – I didn’t like how the digital world was starting to feel. Insistent, needy, demanding. I’d worked for most of my life inside digital spaces, but before the web went world wide, digital was more of a solo act. You, the “user,” were in charge. You decided which applications to pay attention to, which documents to read or write, which sites to visit. That was starting to change, and it didn’t feel right.
All year long I monitor my annual predictions, taking note when events either make me a fool or a sage. 2025 marked perhaps the most unpredictable and frustrating year of them all – and that’s not nothing, given I started prognosticating in 2003. But then again, I did expect an odd one – from my 2025 post: “This isn’t going to be a normal year. 2025 will be strange, frenetic, and full of surprises.”
I titled my post “Tech Takes the Power Position.” While I didn’t make that sentiment one of my specifically numbered predictions, it did provide the context for how I was thinking about the year ahead. “We’re not accustomed to the tech industry having this much raw power. The finance industry? Sure…But this year, for the first time ever, Big Tech has leap-frogged finance in the pantheon of political influence…the subset of Big Tech bros who’ve bought their way into the Oval are evangelists for an untested and downright strange brand of magical thinking best summed up as “techno optimism.” …for better or for worse, 2025 is going to be the year when the loudest voices in the room are all adherents of the Great Man Theory, and they all happen to have direct access to the Oval Office.”
As is his want, last week Fred Wilson wrote a provocative post I’ve been thinking about for the past few days. Titled “Netscape and Microsoft Redux?“, Fred notes the parallels between the browser wars of the late 1990s and the present-day battle for dominance in the consumer AI market. And he asks a prescient question: What new, world-defining product might we be missing by focusing on AI chatbots?
In the early days of the Web, everyone thought the most important new product to emerge from the Internet was the browser. Netscape, a startup with just a few months of operating history, defined the market for those browsers in 1994, then dominated it for several years thereafter. But by the late 1990s, the lumbering incumbent Microsoft had stolen Netscape’s lead by leveraging distribution and pricing advantages inherent to its massive Windows monopoly.
I’ve written a lot about AI lately, and I’ll admit, most of it is critical. Plenty of you have asked me why I’m so down on the sector. The crux of it is this: I think we’re approaching AI without considering history’s lessons, and because of that we’re failing to ask the questions that will matter as the technology becomes inextricably embedded in our culture.
Perhaps the most important question is metaphorical – what’s the best metaphor for how we interact with AI? We’ve got plenty of examples to chose from. Will our interactions with AI end up being like the PC – a personal device that we own and control? Or will it instead end up like social media or search (or worse, television) – a centralized service that is owned and controlled by large corporations?
Finance has always leveraged technology – at Wired in the early 1990s, we were fond of saying that technology’s twin engines of innovation were money and sex – but the most interesting story was always money. Care to understand the future of internet infrastructure? Bone up on how hedge funds optimize network latency. Want to peer into the future of online consumer services back when the Web was a glint in Marc Andreessen’s eye? Start with online banking.
(This piece is cross-posted from Signal360, where it first appeared)
OK, Google, What’s The Business Model?
“How did you go bankrupt?” Bill asked.
“Two ways,” Mike said. “Gradually and then suddenly.” -Ernest Hemingway, The Sun Also Rises
If you work in marketing, Hemingway’s famous passage about bankruptcy will likely resonate. The launch of ChatGPT in 2022 prompted dire predictions that search’s role as a reliable driver of traffic and sales was coming to a close. For the past three years, however, those predictions seemed overwrought. Despite a slight dip in January, which proved temporary, Google has maintained a steady grip on 90 percent of search activity, and continues to direct a firehose of leads and commerce across the web.
But rather suddenly — in the past two months, in fact — it seems everything has changed. Google announced and immediately shipped “AI Mode,” its answer to OpenAI’s ChatGPT. The company had already implemented “AI Overviews” in 2024, essentially an evolution to its “One Box” feature that provides AI summaries for queries above Google’s familiar list of blue links. According to one study, those summaries are already responsible for a nearly 35 percent decline in outbound clicks — the lifeblood of traditional search engine marketing.
Google knows the question is no longer if AI is replacing search, but rather how quickly. Industry analyst Mary Meeker has an answer: AI adoption, she asserts, represents the fastest change in consumer behavior in the history of digital technology.
With AI Mode, Google has decided to push all in. The company understands that consumers are finding AI chatbots a superior search experience. One recent study found that “more than a quarter of Americans (27%) now use AI chatbots like ChatGPT instead of traditional search engines.” And consulting giant Bain found that “about 80 percent of consumers now rely on “zero-click” results in at least 40 percent of their searches.”
Google knows it’s taking a risk by moving quickly, but no matter what, it must keep its grip on the information-gathering habits of its billions of consumers. That leaves a major question unanswered: If search as we knew it is going away, what will replace search marketing as we knew it? What will supplant the time-honored practices of “SEO” and “SEM”?
If you’ve been exploring this question, you are most likely overwhelmed by a slew of firms, from early stage startups to massive agencies and consulting firms, all claiming an intuitive and familiar answer: “SEO, but for answer engines.”
Some call it “GEO,” short for “generative engine optimization,” and others have dubbed their solution “AEO,” for answer engine optimization. Regardless of nomenclature, the goal is the same: a set of best practices that position a product, service or brand to succeed in the brave new world of AI chatbots.
Chatbots “have been a huge wake up call,” says Pete Blackshaw, CEO of BrandRank.ai, a startup that helps brands adapt to what it calls the “answer economy.” “The trillion-dollar brand marketing industry is being severely disrupted by AI search, and marketers don’t know how to measure it, where to start, or how to win.”
It’s still early, but what’s already clear is that “winning” in AI search means playing a very different game. AI chatbots are the ultimate black boxes – even the companies that run them have no idea how the technology chooses its answers. That means marketers accustomed to precise dashboards of SEM and SEO-driven results must go back to basics. Blackshaw advises his clients to focus on understanding the content ecosystem that informs answer engines’ inputs. The often neglected brand website, for example, “is a fueling station for an AI chatbot,” he says.
Along with similar offerings from companies like Anvil and Profound, BrandRank offers dashboards to help clients understand how their brands are performing inside various answer engines like Perplexity, Claude, ChatGPT, and Google. Once you understand where you stand, you can get to work building out content strategies that might improve your brand’s performance overall.
If that sounds squishy, that’s because in an age of chatbots, it’s harder for brands to hide behind paid marketing. Answer engines scour a massive corpus of data to source their answers, and seem to favor community forums like Reddit or authoritative sites like Wikipedia — neither of which are particularly easy for marketers to influence.
“You can’t control how or when you’re going to be mentioned” in AI answer results, observes Bill Gross, the fabled inventor of paid search, now CEO of ProRata.ai. “There’s no statistics, no reporting.” Gross believes he has a solution: ProRata has developed a platform that builds AI-generated ad units that are contextual to the content of a particular chat. In short, Gross is building AdSense for AI – an approach that allows marketers to buy their way into the AI conversation. But it’s still early days — ProRata has yet to sign a major client like Claude or Perplexity.
In the end, what matters most will be how Google adapts its world-beating advertising services to the emerging experiences of AI chat. For now, Google is treating the various “surfaces” of its AI products as just another channel for its massive AdWords and AdSense businesses. But sometime soon, the company will be compelled to roll out AI-specific advertising units that are purpose built for AI conversations.
What might that look like? On that question, Google has so far remained mute. “Everyone thinks we know the answer to that question,” one source inside Google told me. “We might know more than many,” my source continued, but when it comes to what an AI version of AdWords might look like, an admission: “We don’t have a clue.”
Regardless of whether or not Google has a plan to pivot its $350 billion advertising business toward AI, the fact remains that hundreds of millions of consumers – in particular younger generations – now deploy AI-powered chatbots like OpenAI’s ChatGPT and Anthropic’s Claude to do everything from work-related research to more traditional search behaviors like comparing product reviews or finding new restaurants to visit. Oh, and on the horizon? AI agents that do the searching and possibly even the purchasing on behalf of consumers.
Given the pace and complexity of change, seasoned experts in search advise brand managers to move to a wartime footing. The rise of AI is likely to be “more impactful than the introduction of the Web in the mid 1990s,” said GoFundMe CEO Tim Cadogan, an industry veteran who ran search at Overture and Yahoo, then helmed OpenX during the rise of programmatic advertising. To win the day, marketers must be “extremely observant and agile,” he continued. “I don’t think any of us know what is going to happen. Whatever happens will happen very quickly. We have to be prepared to throw out the old ways of doing things.”
Every so often I have the chance to catch up with Gordon Crovitz and Steve Brill, the founders of NewsGuard. I was an advisor to their company for several years, and we keep in touch, as we share something of an obsession around the decline of journalism and the related erosion of fact-based information online. Both Crovitz and Brill have long and storied careers in “traditional” media – Brill started American Lawyer and CourtTV and authored countless pieces of long form reporting, and Crovitz was the former publisher of The Wall Street Journal.
NewsGuard launched as something of a bullshit detector during the ascendence of social media eight years ago. The company’s first product created “reliability ratings” of news and information-based websites. Not surprisingly, the company immediately became a target of the far right media ecosystem, and remains one today.
Cloudflare founders Matthew Prince and Michelle Zatlyn from a 2015 SXSW presentation (image)
There are precious few companies in the tech world that are willing to stick their necks out and “do the right thing,” and even fewer who both operate at Internet scale and enjoy Wall Street’s unabashed fandom.
In fact, I can only think of one: Cloudflare. And today, the $65 billion public company* announced a new policy that has the potential to tilt the balance of the Internet back toward the little guys. Starting this morning, Cloudflare will automatically block AI crawlers from copying the content of every website the company protects. And it’s doing it for free.
If you ever have a hit on your hands, my advice is to take notes. Living in the whirlwind of blinding success is a little like experiencing your own wedding – everyone tells you to enjoy it, to remember every detail. But decades later, all you can recall is leaving the reception, relieved that everyone seemed to have a good time.
Capture.
Every so often I have the chance to catch up with Gordon Crovitz and Steve Brill, the founders of 
