Yahoo, the platform once adored by Gen Xers and millennials alike, turned 30 last year with little to no fanfare. But like any addled millennial starting to stare down middle age, it has sprinted into its fourth decade determined to become cool again.
The company spent 2024 upgrading just about everything in its arsenal. Yahoo Mail got AI updates to help search, summarize, and write emails. The Yahoo Fantasy app was redesigned, and Yahoo saw a record number of players this football season. The company acquired Artifact, the Apple News competitor built by Instagram’s founders, and used it to revamp Yahoo News with more personalized recommendations. And a new AI-augmented Yahoo homepage customized for each user is set to be out soon.
But amid all this modernizing, Yahoo is also hearkening back to the ye olden days when it ruled the internet. Since this past fall, the company has been on a nostalgia-washing blitz, making memes about AIM and using dial-up-internet sounds and Microsoft WordArt in unhinged posts on Instagram and TikTok. The company also released a purple button that plays the iconic Yahooooooooo yodel, which quickly sold out on TikTok Shop.
Turn-of-the-millennium nostalgia runs high across the culture, with low-rise jeans, point-and-shoot digital cameras, and even flip phones resurfacing. It’s an era romanticized by Gen Z, who knew little of a time when interactions online were more fleeting, anonymous, and, frankly, more fun. For Yahoo, it’s an eye-catching way to win over eyes and hearts in an era when more people are fed up with the ways Big Tech has encroached on our lives.
But it’s also a great test for a company attempting to reclaim its place in Big Tech’s Mount Rushmore. “Yahoo was the original internet pioneer,” says Matt Sanchez, president and general manager of Yahoo Home Ecosystem, in which he oversees platforms including Yahoo.com, Yahoo News, Yahoo Mail, and Yahoo Search. In 2025, he says, Yahoo is thinking about: “How do you draw from the past and all the great things that people relied on Yahoo for 30 years, but how do you also start to layer on AI and all these other capabilities that start to supercharge that?”
Nostalgia for certain jeans in the ever-cyclical fashion industry is one thing; nostalgia for a more wholesome internet in the ever-accelerating tech industry is another. Ultimately, Yahoo will need more than memories of better days on the interwebs to keep people hanging around.
So far, this “modern-vintage” strategy seems to be working for Yahoo. For the past decade, emails with an @yahoo domain have raised eyebrows. But after revamping Yahoo Mail in the summer, the company said it saw a 125% increase in new users connecting their Gmail accounts to Yahoo Mail on their desktops. The number of Yahoo Mail monthly active users on iOS has been growing by double digits year over year for the past several months. Traffic on Yahoo News on mobile is up 10% year over year, according to Comscore data provided by Yahoo, and Similarweb ranks Yahoo as the top news and media destination in the US.
Yahoo is one of the few companies to survive the dot-com bubble and continue to thrive. Back then, the internet “was a place where you could freely make mistakes,” says Amanda Brennan, an internet librarian who worked as Tumblr’s head of content until 2021. People in their 30s and up feel “nostalgia for this internet that didn’t have all this heaviness” and where more anonymous interactions dominated over virality and cancel culture, she adds. With its campaign, Yahoo is also reaching younger people and “selling the idea of what the internet was to people who cannot grasp the idea of what actually existed,” Brennan says. As people are increasingly interested in setting boundaries around their social media and screen time, Yahoo is playing up the good old days with its fun, purple, cartoonish design scheme on its site and app, and some webpages load with an oversize cursor reminiscent of early browsing designs. On Yahoo’s info page, the company touts itself as “a nice place to stay on the internet.”
Yahoo’s nostalgia strategy has another thing going for it: backlash against its competitors.
Cultural monoliths are disappearing as the media landscape fractures. In calling back tech’s early days, the company is leveraging a rare “connection point for multiple generations,” says Juan Pellerano-Rendón, the chief marketing officer at the e-commerce-software company Swap. By referencing a more adored internet of the recent past, he adds, the company is saying, “Hey, Gen Z, look at this cool thing. And hey, millennials and Gen X, remember this old thing?”
This also seems to be effective: Despite the fact that Gen Z users didn’t come online until after Google had become synonymous with search, millennials and Gen Zers combined make up more than 45% of visitors to Yahoo in the US, and Yahoo Finance is the top destination for financial information among the two generations, Comscore data provided by Yahoo shows.
Several other brands have been deploying this tactic. UScellular last year put out an ad featuring Alanis Morissette that played on her hit song “Ironic” and focused on using phones less; Levi’s got Beyoncé to recreate an ad spot from the 1980s. This nostalgia-washing could be great for engagement, but it’s a fleeting microtrend, particularly in tech, Pellerano-Rendón says, rather than a long-term brand-ethos strategy. If “part of your brand is talking about the past and that’s what’s bringing people in, I don’t think investors are going to stand behind a lot of these brands” if that’s all they have going, he says. While we may long for the days of a more freewheeling internet, that’s not what pays the bills for Big Tech. People may buy old, colorful iPod Nanos and Shuffles, Apple isn’t leaning heavily back into the products. The relaunch of the Motorola Razr generated viral hype, but you probably don’t know anyone who bought one.
That said, Yahoo’s strategy has another thing going for it: backlash against its competitors.
This isn’t the first time Yahoo has tried to take back its cool. In the early 2010s, Yahoo redid its logo to be what then-CEO Marissa Mayer called “whimsical, yet sophisticated.” It also made several big swings that ultimately fizzled: Yahoo bought Tumblr for $1 billion and tried to get into streaming with Yahoo Screen. But a series of high-profile missteps caught up with the company. In its early years, Yahoo passed up a chance to buy Google and missed a shot to acquire Facebook in deals that would have cost pennies on the dollar compared with what those companies are now worth. In 2013, all 3 billion Yahoo accounts were hit by a security breach. The company was too late to adapt to mobile, a move that some declared the death knell of Yahoo. In 2016, Verizon bought Yahoo for less than $5 billion and took it private. In 2021, Yahoo was bought by the private-equity firm Apollo. By then, Yahoo’s relevance had long been eclipsed by Meta and Google.
But now it’s Meta, Google, and several other Big Tech companies that are losing their cool. Meta’s big bid to transform the social web into the metaverse has flopped, leaving the company to scramble in pivots toward glasses as the future of computing. Google’s push to compete in the AI realm has led the company to torpedo its search results in favor of telling people to put glue on pizza or that water will freeze at 32 degrees but not 27. Elon Musk has remade Twitter in his image. Apple added artificial intelligence to its iPhone 16, which was met with a shrug from consumers. As all these companies push for the future, Yahoo is marketing itself as a relic of a time when the internet was fun and full of opportunities for discovery but also signaling that it wants to be part of a generative-AI future. That’s its challenge: “In this very fragmented world where the algorithms maybe pushed everyone deeper into the things that they’re reacting to most, how do you bring back the best of the internet and find those serendipitous or delightful moments mixed in with the stuff that we know you need to know or we know are going to help you accomplish your goals today?” Sanchez says.
After pioneering the early days of the internet, Yahoo became a media company more than a tech company. While everyone is doubling down on building their own AI, Yahoo’s approach is different. Its tools are built on large language models from OpenAI and Google, as well as other open-source LLMs, Sanchez tells me, while Google, Meta, and even Musk’s xAI are building LLMs. The idea is to “supercharge” Yahoo’s functions, he says, by using AI to summarize sporting events or organize unwieldy inboxes. That could be a boon to the company. “Yahoo can be cool by making its search engine more conversational, assistive, and agentic,” Nikhil Lai, a senior analyst at Forrester Research, says in an email. More than one-third of people are using these conversational features to search “whenever they can,” Lai says, citing data from Forrester’s Market Research Online Community. In addition to traditional search, Yahoo’s search has an AI-powered chatbot designed to work much like ChatGPT or Perplexity.
To date the platform, and myself, I probably last used my Yahoo email to apply to colleges in 2012, and it’s since become a repository for promotional emails from companies I rarely shop from. For all the nostalgia Yahoo is playing up, it’s still a company moving to add AI into its various apps, tech that has a lot of hype with yet-to-be-realized returns. The nudges to the ’90s don’t mean the company is actually moving backward to a young internet many long for. Those who come for the memories are going to find a very different Yahoo from the one they remember from 2005. But in the Big Tech landscape of 2025, Yahoo might not need to be cool to succeed — it just needs to be useful.
Amanda Hoover is a senior correspondent at Business Insider covering the tech industry. She writes about the biggest tech companies and trends.
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