I'm pretty sure I'm not allowed to fundraise according to the SEC, so let's just play hypotheticals for the moment... wink wink, nudge nudge.
IF I was a startup looking to raise seed money for development of a project, ooh.... something similar to Path 101 (I think I've settled on having a space there), and raising somewhere between 250-450k, what should the makeup of that round look like?
On one side, not many VCs would even do such a round pre-product, but a few of the would. There are
some smaller, perhaps more specialized funds that do this sort of thing. Either way, these are people that are primarily in the business of investing in startups. To me, the benefit is that they have experience, connections, and they (ideally) have a sense of professionalism around the way they conduct their business. (i.e. They're not going to show up at your door one night demanding their money back.)
The one thing I don't necessarily believe is that it makes them any more likely to invest in an A round. Sure, they've gotten a chance to get to know you, but if a VC is interested, they don't need to put in 200K to do that. They can take you out to a few lunches and hang around the rim enough to see what you're up to. Plus, if you don't wind up coming out with a compelling product, they're free to just walk away from the deal anyway. At least with angels, there isn't an expectation that they're going to participate significantly in an A round, so you won't have egg on your face if it doesn't happen.
As for angels, you're likely to need them at this point, so I think the question becomes more of a question of composition. Friends? Family? Big names? Angel groups? A mix? How many?
If you can, I think its advisable to avoid friends and family, unless you have friends and family in the business that you're going into, whether its tech or something else. You'll need their moral and emotional support and you should let them know that's what's important. You don't want money, or lack of it when the company blows up, getting in the way there. Plus, unsophisticated investors, even if it's your mom, are probably going to be a little bit of a pain in the butt. (Although, Jeff Bezos' parents turned out to be good angels...)
I think a mix should probably be in order.... the professional investors that you know best, and also a few "reach" candidates. If you could get anyone on board--captains of industry, celebrities, etc--who would it be? For me, I think anyone on the founding teams of Monster, Careerbuilder, or Hotjobs would be perfect. Published authors of books like "What Color is Your Parachute?" would be ideal, too.
But I'd like to hear from entrepreneurs. What's been your angel experience? Surprises? Who's been a much better addition than you expected? Who's been a disappointment? VCs in angel/seed rounds?