I few weeks ago someone asked me how early does a decision start to form about whether I would make an angel investment or not. Thinking back and looking at prior nos and yeses I have to say a lot happens when reading that very first email.
Of course there are a ton of nos and hardly any yeses, so it is a different kind of decision than many. Nevertheless, at least for me, it isn't just that I'm looking for ways to say no. If that were the case you should shoot for being as short and vague as possible to get the next meeting.
The goal is still to progress, but you have to do more than that to do so (at least with me). I've come around to the advice I've received many times from more experienced investors that you have to pretty much love everything about the founders and the company or you shouldn't do the investment.
In other words, if I don't have a strong positive reaction to that first email, I might as well stop there. And that's not an easy task given I don't get excited easily!
Vagueness can push you into the meh category. But to actually get into the positive category takes some creativity and resourcefulness.
I was already thinking of this topic yesterday when I read Paul Graham's latest essay on resourcefulness. He highlights that those that have it vs those that don't can often be categorized by their communication skills, which he calls conversational resourcefulness.
Paul writes "all you have to do is give the right sort of founder a one line intro to a VC, and he'll chase down the money." I believe that's what I'm seeing as well in these first emails, especially cold ones.
The good founders have fully researched me and place their startup (and email) completely in my context. The worst are clearly sending form emails. In-between are either walls of text that make it easy to say no right away or paragraphs that I just don't connect with.
In one sense, everyone knows that first impressions matter. But for something like an angel investment, one would expect that they could matter less, especially for investors who invest in lines not dots, which I try to do.
Perhaps if I was less busy or less weird or had a different angel investment process this first email would matter less. But given my day-to-day, most of my first interactions happen over email. While certainly engaging less senses, email is still essentially an infinite space, and initial emails do vary a lot. It may be hard for you to appreciate if you don't receive a lot of unsolicited email, but know that they vary widely.
Having recently raised money myself, I realize how time consuming the process really can be. Crafting a good first email seems like it just adds to that time, but in reality it doesn't. The resourceful founders will make sure they deliver the best first interactions (including warm intros). If you do that you can actually spend less time in the whole process because you can a) contact less total people and b) the sub-processes (with each individual investor) will move faster.
In retrospect, I should have probably trusted my gut more on these first interactions, and will try to do so more in the future. It may seem like I'm shooting myself in the foot here by writing this post and revealing some of the internals of my process. But in reality I think it's the opposite.
I should also point out like I often do that traction trumps everything. If you have it, you can often get away with that short and sweet first email coupled with a good intro. But you see, that is still being resourceful. You got the traction. You did all the legwork to know that I already know about you. So when it comes to write that email you don't have to write much because you know I'm probably already excited. Nevertheless, I appreciate the personal touch.