How Ask Jeeves blew it

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Upon hearing of a celebrity’s death, have you ever been startled to realize that they hadn’t left us long ago? That happened to me last weekend. Except the dearly departed in question wasn’t a person, but a company: Ask.com, the web property forever better known by its original brand, Ask Jeeves.

For years, I wrote about Ask quite regularly. But when its owner, media conglomerate IAC (which is in the process of changing its own name to People Inc.), announced it had shut down the site as of May 1, it was its first time in the news in more than 15 years. The last time before that was in November 2010, when IAC gave up on Ask being a general-purpose search engine and turned it into a user-generated Q&A site. At some point in between those two moments, Ask had morphed into a bottom-feeding portal for articles so out of date that “10 Best Documentaries of 2022—So Far” was one of the headlines on its homepage when IAC pulled the plug.

In other words, it’s been a long time since Ask.com mattered. And yet its demise inspired a flurry of nostalgic reveries, focused on its early days, original name, and cartoon butler mascot. That residual fondness reminded me that once upon a time, the company really had something. But instead of capitalizing on what it had created, it gave up—just before it might have been able to fulfill its vision.

Ask Jeeves debuted in 1997, a moment of great expectations for the nascent field of internet search. As the web exploded with content, Ask Jeeves was one of a bevy of startups that emerged to organize it. Yahoo and AltaVista were the big dogs, but others included Excite, Lycos, HotBot, LookSmart, Northern Light, and WebCrawler.

Meanwhile, a couple of Stanford graduate students, Larry Page and Sergey Brin, were working on their own search algorithm. When Google launched in 2008, its results were clearly the best in the business, and its ascent was rapid. In 2001, Ask Jeeves responded by buying a startup called Teoma, whose relevance-ranking algorithm was a credible rival to Google’s PageRank. The move certainly felt like a sizable whoop at the time. Or at least it wasn’t yet a given that Google’s momentum was unstoppable.

In 2003, however, Google overtook Yahoo as the dominant search site. After that, there was never a moment when Ask Jeeves, or anyone else, was poised to catch up. Google’s market share steamrolled to 90%-plus, leaving its rivals squabbling over what little remained.

But even after IAC took control of Ask Jeeves—the conglomerate bought it for $2 billion in July 2005 and quickly eliminated the “Jeeves” from its name—you couldn’t accuse the site of doing too little in search of success. Instead, it was all over the place, flinging new ideas at the wall and barely waiting to see if they stuck before moving on to new ones. In June 2007, it released an all-new design that offered tons of useful features Google lacked at the time. By October of the following year, however, it had dumped many of them in favor of an experience that felt like warmed-over Google.

As an IAC property, Ask advertised constantly on TV, but never landed on a brand promise that stuck. At one point, its commercials positioned the site as being for serious searchers who craved advanced tools. Then they claimed it offered “instant getification.” Sometimes they didn’t offer any reason to try it beyond the fact that it wasn’t Google.

All along, I rooted for Ask, simply because even hapless competition for Google served consumers better than no competition at all. But it floundered so publicly that it wasn’t surprising when IAC downsized it to a mundane Q&A platform almost 16 years ago.

Okay, back to 2026 and the eulogies inspired by Ask.com’s shuttering. As far as I can tell, nobody ever cherished that brand. But boy, did Ask Jeeves and its butler lodge themselves in people’s brains. The vast majority of headlines mentioned both, more than 20 years after they putatively entered retirement. (IAC did bring back Jeeves in the U.K. in 2009, in a more dynamic computer-rendered version who bore an eerie resemblance to its chairman, Barry Diller—or at least I thought so at the time.)

In its pre-IAC period, Ask Jeeves bet big on the appeal of its affable, balding mascot, who it maintained was unrelated to writer P. G. Wodehouse’s legendarily capable manservant, though it added a credit to its homepage after the Wodehouse estate complained. A company representative told Salon’s David McDonough that it wanted to make the character as familiar as Popeye. In 1999, Jeeves rode on a float in the Macy’s Thanksgiving Day Parade; the following year, he was upgraded to full balloon status.

If you’d compiled a list of the internet’s most familiar fictional characters around the turn of the century, Jeeves would have been on it, along with the dancing baby, the Pets.com sock puppet, and BonzaiBuddy. Apparently IAC preferred a more modern, less whimsical image for its search engine. Still, when it did away with Jeeves, it torched a massive amount of brand equity.

Ask also failed to build on its original potential in a more fundamental way. Ask Jeeves’s very name suggested that it wasn’t about searching the World Wide Web so much as getting answers to questions. Back then, it was a fuzzy distinction, since the answers you sought were generally scattered across the web. But even as IAC was exiting the search business, Google was working on a technology called the knowledge graph. When it appeared, in 2012, it dramatically increased the percentage of questions the search engine could answer without routing users to other sites. Ask Jeeves could have offered similar features had it remained in the game.

If the site had held on as a search engine all the way into the generative AI age, it might have become the product it always aspired to be: an engaging, hyper-knowledgeable assistant with an uncanny ability to field questions on any topic. Today, Jeeves could also help us manage our calendars, buy stuff, and take care of personal and professional business far outside the realm of 1990s search engines. He could be the ultimate AI agent—and being personified as a cartoon butler would make perfect sense. (In 2023, Ask Jeeves cofounder Garrett Gruener told The Atlantic’s Charlie Warzel that he was proud of the product’s prescience and didn’t feel too bad about losing the search wars to Google.)

As I was mulling over what might have been, it dawned on me that even if IAC failed to seize the opportunity to infuse Jeeves with AI, I could. Chatbots are adept at role-playing, a fact that is often disturbing. But their willingness to take on a persona let me whip up a prompt to turn any bot into a butler.

Voilà:

“Until I request otherwise, take on the role of Jeeves, an experienced, helpful, extraordinarily competent British butler. Respond to my prompts in a dignified, slightly reserved manner that is deferential but not obsequious. Behave as if you are a salaried employee but also sincerely concerned about looking out for me. Use information you know about my interests and habits to facilitate efficient and thoughtful responses. Decline to undertake any requests that are inappropriate.”

Plugging in these instructions to ChatGPT, Claude, Gemini, and Copilot got me entertaining results—especially in the case of Claude, whose stock personality is crisp and professional in the first place. I don’t plan to use them forever, but resuscitating Jeeves for a few days seems like an appropriate way to mourn one of the 20th-century internet’s true giants. If you’re similarly inclined, give them a try in your favorite chatbot, and let me know what you think.

You’ve been reading Plugged In, Fast Company’s weekly tech newsletter from me, global technology editor Harry McCracken. If a friend or colleague forwarded this edition to you—or if you’re reading it on fastcompany.com—you can check out previous issues and sign up to get it yourself every Friday morning. I love hearing from you: Ping me at hmccracken@fastcompany.com with your feedback and ideas for future newsletters. I’m also on Bluesky, Mastodon, and Threads, and you can follow Plugged In on Flipboard.

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