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email cat

(Editor’s note: Jason Cohen is an angel investor and the founder of Smart Bear Software. This story originally appeared on his blog.)

I get a constant stream of requests to look at new startups or to announce something that a startup just did.

As you’d guess, I can’t do it, as much as I love to chat about startups, by which I mean swapping wisdom with fellow entrepreneurs, by which I mean stoke my ego by telling strangers what to do with neither repercussion nor responsibility.

Most of the email is truly spam. But even for the legit stuff, the problem is time. The joke is:

How much time does a startup take?

All of it.

Running WP Engine takes all my time. Also I value my family time. How much time does a 3-year-old and loving wife take?  All of it, as well.

Which leaves no time for “can I pick your brain for 15 minutes” or “can I get your feedback on my pitch deck” and especially “can you spread the word on your blog.”

Some are incredulous that I can’t afford to have a pricking of the brain for a measly little 15 minutes, but the reason has been covered by folks like Paul Graham explaining how one small meeting blows away a day’s worth of productivity and Dharmesh Shah on how his inbox is overwhelmed he has no choice but to say “no” to everything.

But still, one occasionally makes it through. How do those exceptions pierce my fearsome firewall?

I was curious myself, so I inspected a variety of recent email to see which never had a chance, which could have worked but didn’t, and which I actually engaged with. Here’s what I found.


Anything longer than 150 words means you’ve assigned me a project. I’m racing gazelle-like through an inbox bristling with questions and information actually related to my Real Job, and you’ve thrown up a roadblock. It’s not only the time it takes to read, but surely this treatise is explaining something complicated — telling a story, painting context, articulating details, etc.. In the same way it takes special energy to grok source code you didn’t write, I don’t have the special energy to engage.

To force the issue, the email address I publish on my “About me” page goes to aShortmail account, which prevents messages longer than 500 characters.  Still, I’ll get emails complaining about how they couldn’t possibly pen their missive inside this ridiculous limitation, demanding that I provide an alternate email address, all while forgetting to say anything about who they are or what they were going to tell me.

Those get marked as spam.

Plausible, Interesting Call to Action

I get 5-10 emails daily asking if I will “help spread the word” about something.

The following is an actual email I just received, and in fact prompted me to write this post.  I’ve removed details because I have no desire to call anyone out. It’s typical:

Dear Jason,
COMPANY has just completed its first startup accelerator program. I
had emailed you in August before we first started the program and I wanted
to invite you to take a look at some of these new tech-businesses in our
I would love for you to join us and would greatly appreciate if you could
share the news on your blog or Twitter.

There are two calls to action here: (A) Look at a handful of new businesses; (B) Share the news.

The call-to-action is giving me a job to do, and one thing I don’t need is another job, so it has to be clear, sensible, and something that I plausibly would agree to do.

This email fails in both regards, for different reasons.

On (A), I don’t know what “take a look at means.” Scan overviews? Meet founders? Provide advice? Be pitched at? How many companies? Where’s a link?

There’s no way I can even evaluate what I’m being asked to do, and my general (asshole) attitude is that if they can’t articulate why I should be interested, then I’m not interested.

The correct way to have done this is to figure out what would make me personally interested. Like, pick the company most similar to a company I’ve built or that I’ve talked about before or that I advise or have invested in (checkAngelList). Then you can say something like, “Company XYZ does PDQ which is similar to ABC which I know you’re deep in, so I wonder whether you’d be interested in help these guys with some strategic and tactical questions. Since you’re familiar with the space, 15 minutes might go a long way.”

Or: “I know you do a podcast with startup advice.  I have 7 companies here I think you’d find interesting, and they all need advice! Could we schedule a podcast episode just for our accelerator group?  It would take two hours, but I think it would be fun for everyone.”

I’d do that in a heartbeat. It would be fun!

But instead it was “I’d like to invite you to take a look at some of these new tech-businesses.”

On (B), this is the easiest one to remedy. Let’s suppose I do want to spread the word on Twitter.  What would I do next?

I would open my Twitter client and type…. what exactly? I have nothing to go on.  I don’t have a pithy, interesting grabber.  I don’t have their Twitter account.  I don’t have a link.

So effectively I’m being asked to research all of that, condense it into 140 characters (or 110 so there’s room for RT) and then go tweet it.  That’s way too big of a job to give me when you’re already asking a favor from a stranger!

This is so easy to fix. Just paste an example Tweet into the email, which I can copy/paste and then modify only if I want. Or: Add a link to an existing Tweet which I can re-tweet.

Here’s more on that.

Finally, one of the best kinds of calls-to-action are specific questions. Asking for “15 minutes of advice” is almost never possible. Ask a very specific question around a metric or a financial model or how to validate a specific idea or how toprice something or whether to hire a first employee or anything like that is likely to pique my interest and make it possible for me to help.

Appropriate for me

My next mental filter determines whether I’m going to mark it as spam or not, on the basis of whether the request is something that makes sense for me, specifically.

Going back to the suggestion from the previous example that I “share the news on your blog,” it would be clear to any actual reader of my blog that I don’t share “news” like this on my blog. Ever. I barely even announce things that I’m doing myself. Suggesting that I announce a product release or business launch on this blog means you’re spamming me, so I immediately mark it as spam.

Even spreading the “news” on Twitter isn’t what I normally do on Twitter. Although that’s a better request because it can take just a click or two and there’s very little commitment on my part.

But still, why would I personally endorse a startup or news article that I know nothing about?

If you’re committed to being a stranger and not actually developing a relationship, the solution is to explain why it’s in my selfish interest to do this for another stranger.  Typically there’s no benefit for me to promote a stranger’s thingy. It’s not honest and it’s noise. If the only thing I am to you is a megaphone for your crap, it’s spam, and I’m going to respond like an asshole and say “what’s in it for me?”

There can be a reason. For example, maybe you mentioned a blog post of mine in an article of yours, and then you’re wondering whether I’ll also tweet about your post. I will almost always do that. Especially if you disagree with me! Because I like taking a stand on a topic but then giving voice to the opposing viewpoints.

But the better solution is to not be a stranger. When I get email from someone I recognize from blog comments or Twitter interactions, I almost always help out with advice, spreading the word, anything. Because we’re engaged.  We talk about stuff.  We agree and disagree about things, and I know that. That’s all it takes to flip me from “asshole what’s-in-it-for-me” mode into “Oh hey, yeah I remember you” mode.

Unique / Interesting

Here’s another email I got today:

Dear Jason,
Based on your commitment to innovation, I’d like to introduce my web startup to you.
PRODUCT is an early stage web application that enables content creators
to playfully combine multimedia from anywhere on the web through a shared,
virtual whiteboard.
We’ve just started a crowdfunding campaign, and already passed 10% in a
single day. You can find our video and details here:
If you share our vision, help us spreading the word. Thank you!

I can already tell this is spam, because there’s nothing unique to me in this email.  ”Based on your commitment to innovation” is generic and clearly isn’t aimed at me. In fact, I’m specifically not committed to innovation and I avoid words like that.

But also there’s nothing unique or interesting in the concept. There’s 1000 startups that mash up stuff online; it’s OK to build the 1001st, but tell me why I should care about it. The fact that you’re crowd-funding is neither interesting nor novel; maybe if you articulated why people are funding it, that would get me excited too, but whatever that is, it’s not in this email, and no you can’t assign me a job to watch a video to find out. I should “help us spreading the word” (can’t be bothered to use correct grammar?) if I “share our vision,” but what’s the vision exactly?

If you can’t get me excited, I’m not going to dig around to find the gold.

An easy way to get me automatically more excited is to dovetail whatever you’re doing with whatever I’m doing. For example, I do an audio podcast where I help founders on the spot. If you suggest that we do that, I’m interested, because I want to do more episodes. As another example, I do the same thing in a series called the Mailbag.

Examples of doing it right

Here’s some concepts I’ve been emailed about recently which I have indeed supported by advice or spreading the word.

  • A WordPress-related startup, contacted me because of WP Engine, and indicated in the first email why it was a new idea, and why, if he were successful, we might end up wanting to do business together. He was right, so I was interested in at least chatting. The fact is it’s unlikely his startup would ever be able to generate enough revenue for it to be interesting for us at WP Engine (I told him why), but it’s still relevant to me and my space, and therefore I’m interested.
  • A hosting-related startup, not related to WordPress, contacted me because he wanted to build “WP Engine but for XYZ,” and had specific questions around it. Here’s a place I could help a lot in a short amount of time, and there was a reason he was asking me.
  • An accelerator, asking about lessons-learned at Capital Factory, while offering some lessons they learned in their first year.
  • A startup with revenue, deciding between raising money or not raising money, and willing to do a Smart Bear Live podcast about it.
  • A blogger asking to interview me on a new podcast; he admitted the viewership is small but he’ll promote it on his front page for a while.
  • A startup with an unusual pricing question, and willing to do a Mailbag postabout it.
  • A startup founder who previously had written a blog post disagreeing with one of my articles, now interested in my opinion on a specific matter.
  • A blogger submitting a guest-post, which started out inadequate but was willing to iterate until it was excellent; I published it.
  • A group promoting women-owned startups trying to get attention so they can help more women become founders.

As final example of doing this well, here’s yet another email from today, and since I’m complementing instead berating, I won’t anonymize. See, there’s another way to get into this blog!

Hello Jason,
I am starting a business and I’ve decided to video document the steps I take along the way. Jason Fried wrote about doing something similar in his book Rework. Your feedback is more than welcome. I’ve decided not be paranoia about keeping my soon to be unique selling point a secret, in accordance with your advice in one of your recent blog entries.
So here’s the start of the series, Youtube:
Kind regards,
Elian Krosse

Video documentation is sort of interesting. He is clearly a subscriber and is thoughtful about the advice. He’s committed to transparency and taking a risk, which is intrinsically interesting. This isn’t spam, it’s a person trying to something genuine, with some sort of twist.

I hope I don’t come off as even more of an asshole than I actually am. I really do want to hear about interesting things, and I want to help founders who are being genuine. It’s just hard to cull those from the torrent of human-spam, so as a legitimate person trying to reach me, you’ll have to work that much harder to stand out from the noise.

I’m pretty sure the lessons above are more or less true for anyone with a significant web presence.  Hopefully these tips will help you unlock conversations with everyone you want to reach.

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