Barry Diller likes long shots. He’s built a career betting on the long shot. Climbing from the mail room of the William Morris agency to network exec was business as usual for Diller. Taking ABC from a perpetual also-ran to challenge the dominance of CBS and NBC was not out of the realm of the doable. And Diller’s Fox is the once impossible fourth network. So, don’t be too quick to bet against him.

Today, Diller is stacking his chips for a run at the lucrative search market, and he’s betting that history can repeat itself. Fresh from killing off his venerable butler, Jeeves, Diller showcased the new Ask.com at the New York Search Engine Strategies show.

In a keynote conversation with Danny Sullivan that opened the show, Diller made it clear that’s he’s in this for the long haul. Diller knows it will take time and significant improvements in the user experience to wrestle market share from the Google Juggernaut. And Ask.com just might have the goods to add another underdog win to Diller’s already impressive CV.

Good Core Functionality

Behind the Ask interface lies some pretty impressive technology. The Teoma back end that Ask purchased in 2001 is arguably every bit as good as Google’s vaulted relevancy algorithms, and many industry insiders argue that their core concept of expert communities or hubs is actually a step ahead of Google’s link based approach.

But good relevancy is just the price you have to pay to play in this game. It should be a given. Relevancy algorithms won the game once (for Google) but the playing field has evened. The next step is an improved user experience, and it’s here where Ask has a couple of significant advantages that might give it a shot at taking on Google, Yahoo and MSN.

Deeply Vertical

The search engines are moving to deeper vertical experiences. They are trying to interpret intent based on the search query, and delivering a richer set of results in the appropriate category. So, if the search engine knows your query is local in nature (because of the inclusion of a city or zip code) it will try to deliver local search results, complete with addresses and maps showing the location. It’s a closer match to what your intent is, which is to locate a local business. The goal of the search engine is to get you closer to the information you want, and minimize the number of clicks you have to take to get there.

Diller’s IAC includes some well established vertical properties, including CitySearch, Hotels.com and Match.com. It makes tremendous sense to use Ask as the portal into these vertical experiences. Already, the new Ask features CitySearch ratings on many local results. Diller indicated that increased verticalization is likely in the future, but it has to be integrated in a way that makes sense, “We have an enormous amount of vertical data, but we’re never going to give a bad user experience.”

Betting Big when You Have Nothing to Lose

Perhaps Ask’s biggest advantage is the fact that they have nothing to loose. Their market share sits at about 2.5% (according to Nielsen NetRatings). They can afford to fine tune an interface.

Google is no longer the brash newcomer in the search biz. When you have 50% plus market share and your entire revenue channel is dependent on maintaining that share, you have to step very carefully. This is not usually the corporate climate that fosters discontinuous innovation. And discontinuous innovation is the only thing that’s going to unseat the leaders in the search space. As Diller said in his keynote address, “We’re not looking for Ask to be another search engine, we’re looking for it to be an alternative to the other engines.”

Ask has already introduced some interesting new features to the search experience. Their “Narrow” and “Expand Your Search” suggestions usually prove helpful. The new Ask also features an editable tool palette on the home page that immediately adds new and deep functionality, such as local, maps, shopping, dictionary and encyclopedia, images, news and weather. Desktop search has also been incorporated. When I attempted to take some of the features for a test drive, the results were mixed. I was told a number of times that the volume of searches being done prevented Ask from delivering local results.

Search and Tools Don’t Mix

When the tools worked, they did seem to deliver pretty good results and some impressive new functionality. Perhaps moving this to the home page will encourage more people to try them. But based on our observations of search user behavior, few of us want to take one second longer than necessary to fine tune our searches. This has been shown by the anemic percentage of users that have historically taken advantage of existing advanced search features. With Ask, to launch a local search, you have to hit the tab, which introduces another search box where you add the city or zip. Sound’s pretty simple right? But users are notoriously lazy when it comes to search. Add one more click, just one, and you seem to eliminate the majority of the audience. Ask’s features are simple and intuitive, but time will tell whether users embrace the additional functionality.

I think Ask is heading in the right direction, but the first version of Ask show tweaks to the accepted search paradigm, not the shake up that’s required for the big win. Perhaps Diller and his search team have more surprises up their sleeve.

Barry gets the Last Word

Diller also shared some more philosophical moments in his conversation with Danny Sullivan. “I’ve spent my whole life telling stories in the narrative. I’m fascinated by the interactivity of online, by what’s possible in a screen. I’m still curious about the potential of this radical revolution.” He also took the opportunity to take some shots at his main rival, Google. “The whole idea of ‘don’t be evil’ is a little pretentious. I don’t believe the vast majority of corporations are out there setting up evil empires.”

One thing that was interesting to note on the floors of SES was the continuing shift in attitude towards Google. Resentment towards their domination of search is growing and becoming more vocal. We want more competition in the search space, and many attendees would like to see Google’s gargantuan corporate ego get knocked down a few notches. It seems that MSN is stumbling in their efforts to get the job done, so perhaps it’s time for the guy who’s always placed his money on the long shot.