I want to create an app (w/ website) that connects subject matter experts to users who need answers over live video. What should I name it?

neither.
Your name is too broad and has no catch. Try writing a user profile. who she or he is, what are they doing in the morning? where do they live? are they married? financial status... type of hurdle, what are they seeking? what's most valuable to them - advice or step by step... based on questions like these you can find a catchy psychological name that triggers your audience interests like - clarity.fm
people here are looking for advice in other words clarity.

Reading between the lines, I'm deducing that your question is about domains: should you go with the tried and true .com (which would require hyphenating the business name) or take a bit of a risk on the newer .expert?

Those are reasonable questions. But as Humberto points out, they're not the questions you should be asking. The real question is: Why are you opting for a generic name -- which could be used by any expert site, not just yours -- instead of crafting a name that highlights what's distinctive about your offering (live video)?

I recommend that you go back to the beginning and write a detailed naming brief. (See this post for tips: http://nancyfriedman.typepad.com/away_with_words/2011/11/how-to-write-a-naming-brief.html) Then put yourself in your hypothetical user's shoes: what makes your app special, memorable, recommendable? See what vocabulary comes up as a result of these exercises.

If you still need help, schedule a Clarity call to talk about the naming brief and creative directions.

One more thing: "Askan" does not look like "ask an." It looks like the name of a distant planet or a made-up language.

Frankly, I'm not keen on either of them. Definitely not the hyphenated version. If you'd like to discuss the reasoning, give me a call. Choosing domain names has been my full-time job for many years.