I've started to take a more serious interest in startups and the entrepreneurial world lately. As such it's hard not to stumple upon Y Combinator and Paul Grahams's essays. One thing that resonated with me from the essay How To Start a Startup was the part on niche markets. He argues that a startup has bigger odds of making it in niche markets:
Start by writing software for smaller companies, because it's easier to sell to them. It's worth so much to sell stuff to big companies that the people selling them the crap they currently use spend a lot of time and money to do it. And while you can outhack Oracle with one frontal lobe tied behind your back, you can't outsell an Oracle salesman. So if you want to win through better technology, aim at smaller customers.
One category of software that I've never heard even a singel word of praise for are financial systems, especially the time reporting modules. I've always had an itch to create something that was a pleasure to use rather than to worst thing on the planet. But as Paul writes, there is simply no winning over an IFS, AX Dynamics, Agda, Agresso sales person (those are the ones I've used here in Sweden). So this is probably a dead end.