The Vindication of Ask Jeeves

Garrett Gruener, the co-creator of Ask Jeeves, couldn’t beat Google, but he’s feeling just fine about the dawn of the chatbot era.

An illustration of Jeeves from "Ask Jeeves" hatching out of an egg
Matt Chase / The Atlantic. Source: Getty.

It was a simpler time. A friend introduced us, pulling up a static yellow webpage using a shaky dial-up modem. A man stood forth, dressed in a dapper black pinstriped suit with a red-accented tie. He held one hand out, as if carrying an imaginary waiter’s tray. He looked regal and confident and eminently at my service. “Have a Question?” he beckoned. “Just type it in and click Ask!” And ask, I did. Over and over.

With his steady hand, Jeeves helped me make sense of the tangled mess of the early, pre-Google internet. He wasn’t perfect—plenty of context got lost between my inquiries and his responses. Still, my 11-year-old brain always delighted in the idea of a well-coiffed man chauffeuring me down the information superhighway. But things changed. Google arrived, with its clean design and almost magic ability to deliver exactly the answers I wanted. Jeeves and I grew apart. Eventually, in 2006, Ask Jeeves disappeared from the internet altogether and was replaced with the more generic

Many years later, it seems I owe Jeeves an apology: He had the right idea all along. Thanks to advances in artificial intelligence and the stunning popularity of generative-text tools such as ChatGPT, today’s search-engine giants are making huge bets on AI search chatbots. In February, Microsoft revealed its Bing Chatbot, which has thrilled and frightened early users for its ability to scour the internet and answer questions (not always correctly) with convincingly human-sounding language. The same week, Google demoed Bard, the company’s forthcoming attempt at an AI-powered chat-search product. But for all the hype, when I stare at these new chatbots, I can’t help but see the faint reflection of my former besuited internet manservant. In a sense, Bing and Bard are finishing what Ask Jeeves started. What people want when they ask a question is for an all-knowing, machine-powered guide to confidently present them with the right answer in plain language, just as a reliable friend would.

With this in mind, I decided to go back to the source. More than a decade after parting ways, I found myself on the phone with one of the men behind the machine, getting as close to Asking Jeeves as is humanly possible. These days, Garrett Gruener, Ask Jeeves’s co-creator, is a venture capitalist in the Bay Area. He and his former business partner David Warthen eventually sold Ask Jeeves to Barry Diller and IAC for just under $2 billion. Still, I wondered if Gruener had been unsettled by Jeeves’s demise. Did he, like me, see the new chatbots as the final form of his original idea? Did he feel vindicated or haunted by the fact that his creation may have simply been born far too early?

The original conception for Jeeves, Gruener told me, was remarkably similar to what Microsoft and Google are trying to build today. As a student at UC San Diego in the mid-1970s, Gruener—a sci-fi aficionado—got an early glimpse of ARPANET, the pre-browser predecessor to the commercial internet, and fell in love. Just over a decade later, as the web grew and the beginnings of the internet came into view, Gruener realized that people would need a way to find things in the morass of semiconnected servers and networks. “It became clear that the web needed search but that mere mortals without computer-science degrees needed something easy, even conversational,” he said. Inspired by Eliza, the famous chatbot designed by MIT’s Joseph Weizenbaum, Gruener dreamed of a search engine that could converse with people using natural-language processing. Unfortunately, the technology wasn’t sophisticated enough for Gruener to create his ideal conversational search bot.

So Gruener and Warthen tried a work-around. Their code allowed a user to write a statement in English, which was then matched to a preprogrammed vector, which Gruener explained to me as “a canonical snapshot of answers to what the engine thought you were trying to say.” Essentially, they taught the machine to recognize certain words and provide really broad categorical answers. “If you were looking for population stats for a country, the query would see all your words and associated variables and go, Well, this Boolean search seems close, so it’s probably this.” Jeeves would provide the answer, and then you could clarify whether it worked or not.

“We tried to discern what people were trying to say in search, but without actually doing the natural-recognition part of it,” Gruener said. After some brainstorming, they realized that they were essentially building a butler. One of Gruener’s friends mocked up a drawing of the friendly servant, and Jeeves was born.

Pre-Google, Ask Jeeves exploded in popularity, largely because it allowed people to talk with their search engine like a person. Within just two years, the site was handling more than 1 million queries a day. A massive Jeeves balloon floated down Central Park West during Macy’s 1999 Thanksgiving parade. But not long after the butler achieved buoyancy, the site started to lose ground in the search wars. Google’s web-crawling superiority led to hard times for Ask Jeeves. “None of us were very concerned about monetization in the beginning,” Gruener told me. “Everyone in search early on realized, if you got this right, you’d essentially be in the position of being the oracle. If you could be the company to go to in order to ask questions online, you’re going to be paid handsomely.”

Gruener isn’t bitter about losing out to Google. “If anything, I’m really proud of our Jeeves,” he told me. Listening to Gruener explain the history, it’s not hard to see why. In the mid-2000s, Google began to pivot search away from offering only 10 blue links to images, news, maps, and shopping. Eventually, the company began to fulfill parts of the Jeeves promise of answering questions with answer boxes. One way to look at the evolution of big search engines in the 21st century is that all companies are trying their best to create their own intuitive search butlers. Gruener told me that Ask Jeeves’s master plan had two phases, though the company was sold before it could tackle the second. Gruener had hoped that, eventually, Jeeves could act as a digital concierge for users. He’d hoped to employ the same vector technology to get people to ask questions and allow Jeeves to make educated guesses and help users complete all kinds of tasks. “If you look at Amazon’s Alexa, they’re essentially using the same approach we designed for Jeeves, just with voice,” Gruener said. Yesterday’s butler has been rebranded as today’s virtual assistant, and the technology is ubiquitous in many of our home devices and phones. “We were right for the consumer back then, and maybe we’d be right now. But at some point the consumer evolved,” he said.

I’ve been fixated on what might’ve been if Gruener’s vision had come about now. We might all be Jeevesing about the internet for answers to our mundane questions. Perhaps our Jeevesmail inboxes would be overflowing and we’d be getting turn-by-turn directions from an Oxford-educated man with a stiff English accent. Perhaps we’d all be much better off.

Gruener told me about an encounter he’d had during the search wars with one of Google’s founders at a TED conference (he wouldn’t specify which of the two). “I told him that we’re going to learn an enormous amount about the people who are using our platforms, especially as they become more conversational. And I said that it was a potentially dangerous position,” he said. “But he didn’t seem very receptive to my concerns.”

Near the end of our call, I offered an apology for deserting Jeeves like everyone else did. Gruener just laughed. “I find this future fascinating and, if I’m honest, a little validating,” he said. “It’s like, ultimately, as the tech has come around, the big guys have come around to what we were trying to do.”