Email Introduction Etiquette

Here's a simplified view of my email life: I have a couple hundred people (the intermediaries) I have worked with before or am friends with who each work with or talk to many entreprenuers. Each of these people knows dozens of investors. When they like an entrepreneur, they try to decide which investors would be interested in that entrepreneur. This isn't easy because angel investors change what types of things they are looking for and whether they are looking for anything at all all the time (based on what they have already invested in, on how much time and money they currently have to invest, etc.) They then send out intros to many investors. I get about a thousand of these a year.

Now, there are two types of intros. The most common is "[Founder] is looking for an investor for his company, which looks like [company]." The second is "[Founder] asked to be specifically introduced to you." If the latter, I always take the introduction. If the former I filter for only the stuff I might actually invest in. This saves me time because--since I have a pre-existing relationship with the intermediary--I can say something like "I don't invest in companies like [company], I am looking for [thesis] right now." This takes 30 seconds. If I was to reply to the founder, it would take a lot longer not to be rude. Rudeness is discouraging (I know, I raised money for my own company, lots of investors were rude), and it burns bridges. If an entrepreneur told an intermediary she thought I was rude in my reply, that intermediary may no longer send me anything. I know I, when I've been the intermediary, have stopped sending people stuff because the feedback from the entrepreneur was that they were rude.

Also, the whole point of the intermediary is to save the entrepreneur time. The intermediary sends out a score of emails asking who is interested, and some smaller number reply. The intermediary then makes the connection. Now the entrepreneur only has to deal with the people who have self-qualified as potentially interested. This saves them time (and also puts them in a slightly better negotiating position.)

The only negative to this process is the time it takes for the intermediary. I am an intermediary as much as, or more than, I am a recipient of these intros. It takes time. I've often thought about how to automate much of this introducing work: deciding which people would be most likely to want the intro, sending the emails, tracking replies, making the intros, and tracking which intros worked to feed back into the process. I suppose this is what software like Salesforce does for salespeople, but I've never found a personal CRM that can do this for me. Would love to have one.

Either way, it will be awkward, and checking in with someone to see if they can be introduced just adds another e-mail to the chain.

Maybe I'm just overly choosy with who I introduce, but I have never had someone not respond, or say "No, I don't want to be introduced to that person." It just always seems to add an unnecessary step.