‘Do you Yahoo?’: The monster task of healing the brand that won’t die
Last week Yahoo hired a new chief marketing officer. Josh Line, formerly chief brand guy at Paramount Global, faces one of the toughest gigs imaginable.
The job is to take what is effectively a living fossil and invigorate it. Line must transform Yahoo – a brand synonymous with missed opportunity and decline – into something new and vibrant. He must do that in an environment where even the companies that buried Yahoo two decades ago – Google and Meta – are existentially challenged.
So does Line look back to go forwards? Exactly how much is the right amount of nostalgia? What is the product proposition in a world flooded by AI slop and dominated by the promise of AI agents?
Yahoo CMO Josh Line
The mad fact is that Yahoo is still one of the biggest sites on the internet. The company founded in 1994 as a hand-curated web directory has an annual turnover in the billions and employs thousands of people.
The even madder fact is that Yahoo’s single biggest demographic is 25-34 year olds (according to Similarweb data). In Australia, where Yahoo was never the dominant force it has been in the US, the local version of the portal gets 5-6m visits a month from an older audience (biggest demo is over-50s). This size places it in the zone of a minor news site like theheraldsun.com.au.
But in the US, Yahoo registers three billion monthly visits (again, Similarweb) from just under 250 million people (Comscore), which for December 2024 makes it the second-most popular web property after Google.
Yahoo’s core functionality is email, news and finance. It doesn’t do social networking. It doesn’t do messaging anymore. Its search engine is borrowed from Bing, which is hardly a killer brand. It’s old school World Wide Web, which is exactly where it began in 1994, when the only browser was Mosaic and there were fewer than 1000 sites in the whole world.
Yahoo’s initial explosion in the 1990s was so big that the residual heat is still fuelling the business 30 years later. All the genius – marketing, product – seems to have been contained in those first few years, when everybody knew the Yahoo yodel and that company’s wacky culture and net pioneer status translated into commercial success. The company was valued at $125 billion at the height of the dot.com madness in 2000. It never got so high again. Over the years, Yahoo became famous for its failures: it failed to buy Google (twice), Facebook, and Youtube. A string of CEOs made it feel like a place people just worked at, rather than believed in. The 90s became dated and depressing. The purple, the exclamation mark, the yodel. Awful.
Come 2025, and harking back to the 90s is not such a handicap. According to the numbers, Yahoo’s old school World Wide Web product is just what a sizeable chunk of Millennials and even some Gen Zers want. Yahoo claims that 45% of its US visitors come from those two demos.
This is allegedly being fuelled by the strange phenomenon of nostalgia for a time never experienced. There is an idea for those not alive at the time that the world was simpler back then. This pleasant illusion is Yahoo’s ally as it seeks to rebuild.
Yahoo’s homepage 1995 (Version Museum)
How far does nostalgia take you?
Yahoo’s new CMO Josh Line must know that relying on a fondness for an idealised bygone era is a short term strategy. Yahoo has “almost latent brand love” among consumers as “one of the OGs of the internet,” Line told the Wall Street Journal on landing the job. “A big part of the marketing challenge is to kind of reignite that love and to put the brand back into culture, and, of course, to drive growth of all the products.”
The casual reference to product here is the key. During Yahoo’s first explosion it was a cutting-edge product for a brand-new medium. That combined with great marketing from Yahoo’s pioneering CMO Karen Edwards to create a $125 billion company.
Where is Yahoo’s cutting edge product now? The nostalgia angle of a purely World Wide Web product is almost a direct contradiction to the need to innovate. Line’s fellow Yahoo exec Matt Sanchez has spoken of “layering on AI” in order to reinvigorate the product, which to me sounds more like Microsoft’s Copilot approach than a revolution.
The deep problem
Yahoo’s problem is much deeper than just trying to make the brand cool again or to “layer on” some product features. Yahoo has always been a web company. It was the original portal, the starting point of the internet, and for millions of people that’s still the case. In thirty years it’s moved from darling of the market to something like a utility. There’s no shame in that. The deep problem is that the foundation of the business, the web itself, is under attack.
There are two main fronts in this war on the web: AI slop inundation and knowledge-seeking AI search. To explain each in turn, AI slop is the generic name for the reams of mediocre and flawed content generated by Large Language Models. The ability to automatically build and publish web pages on any topic with no personal knowledge or intervention is an existential threat to the usefulness of the web. What was quaintly once “surfed” and manually indexed by Yahoo employees is a rapidly expanding sea of words, pictures and videos. There will come a time when AI-generated web content outnumbers and then dwarfs the human kind. What began with the 1000 janky sites becomes a near-infinite collection of mirrors. Not that useful.
The other assault on the web is the replacement of knowledge queries by AI. Under the old model, a need for knowledge meant posing a question in Google and then following up on the web. I find myself doing this less and less, instead asking the AI the first question and getting a direct answer. I follow up and fact check on the web if accuracy is important. Often it isn’t. While this isn’t a direct threat to Yahoo – except for its remnant search capacity – the new behaviour makes the open web less and less relevant.
Yahoo may find a way out of its web dependence. Alternatively, Josh Line may decide to double down its original proposition as a human-curated view of the online world, which could make it stand out in the AI-era. But it’s going to take something very special to make Yahoo a bigger business than it is now.
As someone who worked at Y! in the good old days the lack of exclamation marks after the “Yahoo”‘s in this article still triggers me even though it has been more than 20 years.
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