All that aside, the whole point of the talk was that one can live very well off one's web application even if it's only moderately successful. I think the example he gave was 2,000 small business users at $40/month ~= $1,000,000/year in gross revenue. Or 400 users at the same rate if you don't mind only grossing $200,000 a year.
His argument was that you don't need to stress about investors, 12-hour days, and viral loops as long as you're willing to "settle" for a pleasant, financially viable, and capital efficient business with a niche of users who really appreciate your approach to solving their problems. That's the irony of making fun of an app in this thread for only having several hundred users.
You probably would enjoy the video; I certainly did.
(Incidentally, GitHub and Lighthouse didn't require massive capital investments [1] and I'm pretty sure that they're hosted "for free" on Engine Yard. Having a few hundred users would practically guarantee that they're cashflow positive.)
[1] http://www.akitaonrails.com/2008/4/21/chatting-with-chris-wa...