Actually, I'll give him props for asking. As evidenced by all the technically sound start-ups out there with names so dumb and hard to spell that I'd have to TRY to come up with something worse, being smart and being able to build a good product doesn't mean you can pick a good name. He's putting some thought into the process, which is a lot more than I can say for a lot of other companies out there. If he can't come up with the name on his own, I don't see what the big deal is.
Were I being cynical (it's a hobby:-), I would say that he's asking you to put some thought into the process. He should offer some kind of prize, even if it's not really a big deal... a blurb on the new site, a t-shirt, a bottle of wine... something like that.
I tried offering prizes, paying $50 to a name-choosing service, asking everyone I could, spending many hours myself. All results sucked.
For my latest startup I spent just a few minutes on it will resist all urges spend more. I'm not allowing myself to get pulled into that time-sink black hole again.
Want it to be easy? Simple. Have $2000 to $10000 to blow on some squatter scum. Or just choose an uncommon topic area. Probably both are unreasonable for most of us.
