Back in the 90’s Ask Jeeves was a “question answering service” and not a search engine. They had teams of human editors that would curate answers for popular questions. During the dot com boom of the late 90’s they realized they needed to automate that system so they started buying other small startups that were doing more with search technologies. They acquired one search company in New Jersey called Teoma and another in Massachusetts called Direct Hit.

The executives at Jeeves at the time were not very smart though. They were very hands on with these technologies they didn’t fully understand and made some stupid decisions. For example, Direct Hit had a simple advertising platform they had developed where anybody could sign up and bid for ad placement on search results pages. It was largely automated and generated a lot of revenue. The Jeeves CEO said “we’re not in the business of advertising so get rid of it”, so it was sold off. It was sold to that scrappy little startup you mentioned and transformed into AdWords. Jeeves squandered other tech advantages in similar ways.

In a similar vein, they had a huge internal project for many months to create an adult (porn) search engine that they were going to co-brand alongside the Jeeves character they used to use. They planned to call it “Ask Mimi” and had registered domains, created a French maid character to go along with the Jeeves butler character, etc. After a huge push the company decided they didn’t want to tarnish their image with porn and dropped it all pretty much overnight. There used to be an article about all this archived on CNet’s news.com site but I can’t find it anymore thanks to their terrible search engine….

Source: I worked for one of those startups that Jeeves acquired.