Nice service. Back in 2002 we were doing something like this when I was consulting at Flytecomm. We would suck up people's trip confirmations and parse them (just a whole bunch of regexps in Perl) and spit out detailed information about the trip. Since we had real time flight information (since we had an FAA feed) we could match the reservation to flight legs and do cool stuff like realize your flight is going to be late arriving and that you are missing your connection; then we'd look up alternate flights and send you an SMS message with details. Happy days.
I am, for a startup called SmarterReviews.com. It actually parses consumer reviews and quantifies what people are saying about a product (e.g., an IPhone has great screen but bad battery life). I'm very pleased with how it's turning out.
TripIt failed to recognized my itinerary (I suspect discount travel site screwup), but I just used YAPTA and their customer service has blown me away. They took my record locator and harassed the airline twice about getting me a refund in the space of 2 hours. _Every_ startup should blow their customers away like that.
No idea, but I can certainly see how they could make money - context sensitive ads in their e-mails. You know where the person is going, for how long and how frequently they make trips, amongst other things.