I'm going to avoid the obvious stuff, like the importance of a sales team and support, and the fact that the decision-makers will never use the product. Those h

I'm going to avoid the obvious stuff, like the importance of a sales team and support, and the fact that the decision-makers will never use the product. Those have already been covered. The worst thing about trying to sell to the Enterprise is that it's mind-bogglingly slow. The feedback cycle is not there. With a consumer app, you can start with a rough demo, A/B test it, roll out new features, and scrap ideas that the market rejects. You don't give a damn about reputation issues because whatever people say about your product will be buried in 3 months. If the market rejects what you are building, it will be merciful enough to do so immediately. Build something else. When you deal with the Enterprise, expect prospective clients to take months to make up their minds. Half a year isn't atypical. Getting paid on time can be difficult, too. You also have to worry about bad-faith clients who'll use their social connections (to nominally "competing" firms) to black-ball you if they don't get what they want. In B2C, that's some idiot mouthing off on Twitter. Who gives a shit? At scale, there's no such thing as bad publicity. In B2B, it can be lights out. I worked for an enterprise startup that failed. One of the most frustrating things was that, at the time, I could not evaluate whether the CEO was making the right decisions. I still can't. "The client needs <X>". Well, then <X> is what we do. I wasn't in the room with that client. When you build for consumers, there's enough consistency in aggregate humanity to get a sense of, if nothing else, whether you're doing a good job. With the Enterprise, the feedback is slow, opaque, and polluted by invisible political forces within the clients, so you never know for sure. This leads into one other thing about the Enterprise. You will hate the word "requirement". It will make you want to throw chairs. Why? Because 90% of so-called requirements are nonsensical features that damage the project's conceptual integrity beyond repair. Ten percent are actually vital, by which I mean you aren't doing your job if you don't address them. Good luck figuring out which are which. Start here: http://steve-yegge.blogspot.com/2008/08/business-requirements-are-bullshit.html http://steve-yegge.blogspot.com/2008/08/business-requirement... I am not saying that the Enterprise is a bad place to be. Clients are probably less obnoxious, on the whole, than investors. The client needs you to solve a problem, while the investor sees you as a social inferior (a poor, a prole, a hustler with a hand out). However, I am going to say that the rapid feedback cycle that you might expect in an entrepreneurial environment is not going to be there. You can wait 6 months on a deal, only to have it fall through because of some external event that had nothing to do with you (such as your contact getting fired, moved, or promoted into a less hands-on role).