I absolutely think it can be. I think it mainly depends on who you work with at the enterprise software company. Its exciting to work around smart and highly motivated people, even if the product is a seemingly "boring" B2B application to us web hacker types.

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..

PG: I laughed along with most everyone else at Startup School after your line about (paraphrasing) "if you're not smart then develop enterprise software, since it's a sales business, not a technology business."

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?

I think there is probably a lot of opportunity for smart little startups to compete with enterprise software in the way microcomputers competed with mainframes. Just make something good that everyone can use, and eventually businesses will realize they can use it too.

That's right out of a "disruptive innovation" paper I read recently.

Nice to know the company I'm in with regards to my reading material!

Both Zimbra and SalesForce.com are doing it, i.e. taking an "enterprise" product and making it web-available to anyone.

And while both still sell to large companies, they also reach individuals and smaller firms, too.

There you go. I think maybe that's the key--take an existing segment which is back in the early 90s in its usability, put it on the web with the latest UI, usability, etc., and you then go right up against the existing suites. I've actually seen NetSuite do this for ERP, and their UI isn't even any good.

The sad thing is that web2.0 is a sales business too, rather than a technology business.

The problem with enterprise software (at least as I understand it) is that it's frequently bespoke data processing software, written in-house -- it's not the sort of thing that you can do once and sell to multiple clients, it's the sort of thing that needs to be customized for each client.

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.

Absolutely it is; I spent a long time this year working with a small real estate company that uses very primitive software and analog techniques to track very complex business processes. Existing software that would help them is too cumbersome or requires too much training; they can't afford to hire a consultant to sort it all out for them.

This is the crux of my YC funding application, so I really hope the answer is yes!

"Enterprise" software is a market distinction, not a functional class of software, right? Are you asking if the enterprise software market is interesting if you're somehow smart about it?

Enterprise software has a bad rap because it's such a jaded business; decisions almost never get made for the right reasons, and the level of politics and bs is absurd.

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.

I absolutely agree. I used to work for a big enterprise software company, and it took me a while to get used to the fact that we're selling crappy software for millions of $ a piece. I think the problem is that large enterprises trust other large organizations to solve their problems. You can't really get ahead in a large enterprise and become a manager with a budget to spend on software solutions unless you have that kind of organizational mindset. You fear change and fear failure, and so you'd rather spend tons of cash on a crappy solution from someone "trustworthy" - so they can't blame you if the software you bought sucks, than on a small startup's product that no one else in your industry is using. BTW, Crossing the Chasm is a good book on the subject. I recommend it to anyone considering going into enterprise software.

Yeah, that's pretty much it. Asking really for clarification on Paul's comment about enterprise software in his speech. I sometimes think we've gone a bit too much B2C lately, and we're missing out on a lot of opportunities to Make Something People Want, with the People in this case working at big companies in traditional enterprise functions.