I've written before about how the very first email to an angel investor really matters, or at least to this angel investor. It's very easy to get thrown in a bucket of wannabes or bad first-timers. Here are a few of those red flags from my perspective.
Sending an email through a service.
My email is really easy to find. Yet you'd be surprised how many people write me cold messages through Facebook, LinkedIn and Twitter. Yes, I'm easy to find there too, but I prefer email, and I think most people do too. If you send me a message through a service, I have to either find your email or reply through that service, both of which are pretty annoying as they require me to leave my inbox. So already, despite the content of the message, you've irritated me a bit, which is just not a good way to start.
Founders should send emails to investors. Financial consultants (people helping you raise money) should not send them. In fact, for seed rounds, engaging anyone like that is a red flag to begin with.
Really long messages.
When I see a wall of text I scroll down and just sigh because I know this is going to take a while to process. Really, the shorter the better. Pique my interest and then let me ask follow-up questions. In fact, the goal should be to get that conversation started.
You need more than an idea to ask for investment. I can't stress that enough. If you're asking for mentorship, that's a slightly different story, but the answer is probably the same. You need to go out and build something. Otherwise you just don't seem serious.
Not having links ready to go.
If I'm intrigued by your email, I'm going to want to investigate a bit on my own. If there is a demo, I want to see it. If there is a slide deck, I'm going to want to flip through it. I will want to see your twitter, linkedin, etc. If those things aren't up to date (or non-existent), that is a red flag. But you also shouldn't make me work to find them. Send a good short message with the links at the bottom and then let me go from there. (Note: I'm not saying you need a Twitter/LinkedIn/anything specific, but I would expect if you're starting an Internet company you have an online presence somewhere.)
I appreciate what it takes to get something off the ground and how most startups are movements. Saying otherwise makes me very skeptical, like I'm the next Facebook or this will be a billion dollar company. Don't get me wrong -- I think big vision is necessary and to be rewarded. It's more of a tone thing.
Not being able to describe what it is.
If you can't describe it to me then how are you going to describe it to customers? You should have an explanatory sentence down. This is sort of a corllary to the long email thing. It shouldn't take several paragraphs to tell me what you're doing. Your personal history is a different thing, however. That I'd like to hear about.
Not in my target areas.
I've made my criteria as detailed as I can, and yet I get stuff all over the place, e.g. non-US. There are a ton of angel investors. Concentrate on the ones that are most likely to fund you. You want someone to click immediately with your story, which generally means they have to be pretty aligned with what you're doing in one way or another.
Obviously not personalized.
If it feels like a form email... But really, like the last one, if you are going to click with me you need to relate your story to me, individually. I've written a lot of blog posts on a lot of different startup subjects. I'm sure you can find something to relate to! A related red flag is asking me a question or mentioning something that I've obviously addressed in a blog post.
This may be just me but I don't like to be pressured, e.g. we're closing out this round in two weeks and would really like you in. Generally I want to know people ahead of time, take my time, etc. The pressure really pushes me out of my comfort zone and is a bit turnoff. Even if it is true, don't mention it right away.