During our recent trip to San Jose, I was lucky enough to be the receipient of a dinner with the folks from Ask.com, including Gary Price, Robyn DeuPree, Paul Vallez, Erik Collier and two very nice gentlemen from the Ask public relations team. From the search industry side, I was accompanied by Jennifer Laycock, Lee Odden, Matt Bailey, Andy Beal, Loren Baker and Gillian Muessig (of SEOmoz).

During the dinner, we spent quite a bit of time talking about Ask's efforts to penetrate the search market and grow their share. Erik Collier (who leads Ask's engineering team) and I had the following discussion (note that I'm doing this from memory):

Rand: I think Ask's biggest problem right now is their index size - when techies run ego searches, they expect the same kinds of results they get at Google and when that doesn't happen, there's a disconnect that manifests itself in dissapointment.

Erik: I can't stand that! I see referrals from bloggers who say bad things about Ask, just because they've done a search for their little site or tiny project and didn't find the right results. The actuality is that on 80% or more of the queries that come to us, we're delivering excellent results, that are often more complete, direct and efficient than the results you get at Google.

Rand: But those 20% are the tech-geeks, the influencers, the "tippers." Those are the same people who helped Google to grow out of a techy, geeky service into one of the biggest brands in the world. You're ignoring your most important market and the one that can help you to really have an impact on the web.

Erik: That long tail of search queries is a big challenge to get right - it isn't just about the index size.

Rand: I'm just saying - make the geeks and the techies happy and you'll see a lot more positive press in the blogosphere, which I think will eventually translate into a greater market share.

I don't know if my conversation is going to influence anyone, but if I could talk to Barry Diller, I'd tell him to take the money he's investing in promotion and TV ads and re-invest in the technology basics. Here's a few samples of why Ask.com looks so small to many bloggers:

• SEO Site:SEOmoz.org - first, off a little ego search that shows Ask has indexed only 13 pages from SEOmoz
• Techmeme site:Techmeme.com - Poor Gabe isn't feeling the Ask love either
• Kayak site:kayak.com - Appears they haven't indexed it at all (compare to Google's 700K+ pages)
• Legendary site:legendarypictures.com - The producers of Batman, Superman & Lady in the Water launched a new site a few months back, but Ask hasn't found it, yet.

Now compare those with the excellent results we can get for searches like:

• Gary Price - love the photo and bio
• Piddidle - Obscure reference, but the first few results are dead on
• 40th US President - A perfect match and a very nice instant answer
• Nick Drake Pink Moon - Very solid results and the encouraging binoc tools on many sites
• Digital Camera Reviews - Looks a lot like Google's results, but I love the products ahead of the ads - very classy.

These are probably more in tune with what the "average" searcher is looking for, but I might argue that those average searchers don't have the ability to influence as far and as fast as early-adopter technology types, particularly in a field like web search.

There's no doubt that Ask has some amazing features, and products like their maps and blog search are actually considerably better than what the competition offers. Bloglines is a phenomenal product, and I was inspired by Robyn's passion - she's a terrific evangelist and leader for them. I really hope that Ask can make something great happen in the near future - a four search engine world would be a fun one to play in.