I have long considered Ask.com to be the little search engine that could. They didn't have the legacy audience of Yahoo, the endless budget of MSN (or Live if you prefer), nor did they have the technology and overall popularity of Google. What they did have was an urge to innovate. Ask incorporated an all-in-one search format, binoculars to preview websites, a map system that in my opinion surpasses even Google Maps in terms of usability and neat features, and special current events callout boxes on results pages. All of this should have lead to an expanding user base. But there was a problem.
Ask's marketing strategy has been questionable for quite a while now. Ask used to be called Ask Jeeves. In early 2006 the Jeeves character "retired" perhaps in an attempt to shed the goofy cartoon image of a butler serving you search results. I thought the butler was a nice touch, but in any case. "The Algorithm" became the new marketing focus for Ask, which touted a new and intelligent system to produce search results for users. Billboards went up around the country, some of which drew the wrong kind of attention.

Invoking the name of someone like the Unabomber is perhaps not the best idea when advertising a website. Ask then put a series of TV commercials out, the most notorious two being focused on Kato Kaelin and "chicks with swords". The attempt to be wacky and memorable backfired as search discussion blogs exploded with negative reactions and Ask apologists were left "searching" for answers. For a search engine with less than 5% market share Ask seemed to be making bizarre decisions.
The most recent misstep was an Associated Press Announcement that Ask was firing 8% of their staff and was re-tooling to be a site tailored specifically to married women in the Southeast and Midwest. The next day Ask apparently refuted the claim and said they would not sacrifice general users to appeal to a specific subset. The main problem is that in this internet age news spreads like wildfire. I read the story of Ask's restructuring on more than 10 websites, but only found the supposed retraction on one. With all the buzz and discussion of the validity of these stories, Ask has produced no official position on their blog or in a press release. Even if the story was a mistake, the impact of a splashy headline all over the internet has done its damage.
If we can learn anything from the rocky marketing history of Ask it is that reputation management is of paramount importance on the net. With the constant rush of information users are presented with you might only get one chance to change someone's mind. Make it count.