For the 1%, which has more to do with connections than net worth by the way, it's incredibly easy and any idiot can do it. So, many idiots do.
The difficult part can be what happens after raising money. Some investors are hadns-off and some will micromanage. Some will add and others will detract. Since your investors will determine whether you can get future funding, and will probably make the introductions that lead to partnerships and clients (if you're a service company) you want to make them happy enough that their resources are deployed to your benefit.
The one bit of good news is that "free ride" investors are a minority. Most have too much ego, which can be a force for good (if they help you succeed) or bad (if they try to manage you). They exist, but they're not common. They do seem to be more common in New York than in the Bay Area.
I wonder how does the career of Kevin Rose fit into this. Perhaps I don't know something, but I've got a feeling that despite he didn't create anything successful since Digg, he enjoys a nice career. I'm not suggesting that he is a free-rider, but his example suggests that SV decisions aren't that optimal.