Its attitude toward the Internet. (Picture from the Richmond Library childrens' blog, Batavia, NY.)
Stephen Wolfram does not trust the Internet. He doesn't trust its inputs, he doesn't like its outputs. He doesn't like what it has done to "intellectual property." He does not like it, Sam I am.
Notice what I just did there? I alluded to a copyrighted work without attribution. Wolfram wouldn't like that.
Wolfram promises that all Wolfram Alpha results will be "vetted." The freewheeling attitudes of Google or even Wikipedia are forbidden.
It's the site's attitude toward Internet inputs, as opposed to Matt Asay's revelations on Internet outputs, which I am afraid marks Wolfram Alpha for failure.
The Internet, for all its messiness, for all its lies and lying liars, usually does come up with the right answer. Maybe it's not on the first reference, certainly not on every page, but if you page through a dozen good links on a subject, collected objectively, you're going to get around the answer to your question.
Wolfram Alpha takes a different, more proprietary approach. They control their inputs, and their results are essentially reports. Ask about Google vs. Microsoft and you get financial charts. Ask about me and you get nothing. Same with Matt. Same, for that matter, with Palamida.
What Wolfram Alpha wants to build is an authority, and my point is that on the Internet there is no unitary authority, no final answer. Questions on the Internet lead mainly to other questions, or to data, or to opinions, usually all three.
Personally I don't want a cul de sac. I prefer the superhighway. Wolfram Alpha won't ask the Internet for the data it needs and it won't tell you what it hasn't checked. That is not a strength.