Before I started working at my current company all I thought of as "cool" was startups and cutting-edge B2C web services companies. It really expands your horizon when you get the chance to work at an awesome enterprise software company who is solving a real business need..
Business software CAN be cool..
Good one, and definitely some truth. I've spent a bit of time in this field and there's certainly the boring factor with some of it.
However--I'm assuming you'd find it interesting if people took a traditional piece of "enterprise software" (big suites sold to big companies, I guess) and Web 2.0-ified it.
Any comment there?
And while both still sell to large companies, they also reach individuals and smaller firms, too.
Nice to know the company I'm in with regards to my reading material!
I think that it has the potential to be the most interesting software to work on, because a lot of it is about real things, but because of its bespoke nature the only way to get at the really interesting bits is to work for the company that it forms part of the infrastructure for. And once you're in that situation, you're dependent on (probably very risk-averse) management for support for doing "smart" things with the software.
This is the crux of my YC funding application, so I really hope the answer is yes!
From my own experience: unless you're doing something really special (and even then it's not guaranteed), it's tough to convince a large firm to license your product if you're a startup or 2, 3 man firm.
The best way, actually, is through the proverbial "back door", i.e. make versions available on the web or downloadable, and get a critical mass of employees within the company to use it.