How to Send Email Like a Startup

6. Don't explain/remind in the email what your product does, because "Squinderly" is such an obvious name.

Yes all part of the cult of "do things that don't scale" [1].

1. Yes I know why this is suggested and yes many times it is the right thing to do do, but finding sucessful approaches that do scale is really, really hard.

So, focusing strictly on the business side of things, you have two user groups:

1) Users who have some interest and may purchase your product.

2) Users who "just briefly want to see what all the fuzz is all about" but "don't want to be treated as a customer already."

User group 1 may very well respond to your emails because they already have some interest in your product and the benefit it could provide them. These users like to read about ways to help themselves, thus probably don't consider email related to the product they are interested in as spam.

User group 2 is not interested in the product. We know that. Therefore few, if any, are ever going to pay you for it.

So, why as a business owner, would you care about annoying people in User group 2 (who could always just opt-out of the emails) at the expense of accelerating people in User group 1 through the funnel and paying you more?

Hi there, I helped put this guide together and this is totally something we have in mind pretty much all the time (when you tell people you work for an email startup, you're kind of forced to.) But this is actually the kind of email we're trying to prevent. I usually refer to it as "The Other Spam."

I've had multiple users of ours talk about how they tried starting newsletters to resurrect dropped users but got more unsubs/spam reports than renewals. Some even got hit up by their ESPs for a spike in spam reports affecting their domain credibility. There should probably be a more prominent section on this, but we do talk about it in our blog a lot.

Here's what I usually say:

1) Always have a separate opt-in for product updates, off by default, ideally with some sense of frequency. Failing that, send product updates only to paying/active customers.

2) If you have an onboarding drip campaign, once it runs its course, if they haven't engaged, let them go.

3) From there on, all other communications should pretty much be transactional, sent to the opt-in group, or based on some pre-qualification that the user is still interested.

These are all things that we try and make really simple in our product and exercise ourselves. Part of sending better email is just not sending the shitty ones.

On the personal side, I also just add tags to my email address when I sign up for something knowing that I'm just poking around so I can easily filter their follow-ups. I also appreciate this from a lead validation angle, because I can filter email addys with a + in them from our funnel metrics.

This is a fine line to walk indeed: you don't want to spam the user, but you also want to stay "top of mind" in the prospect mind.

I think most of app founders view this under the lens of "how can we get this user to use our app?" which I think is a wrong approach.

To me the right approach as always is to start from the user, and not to see yourself (the app maker) as just this app provider. Instead, see yourself as a business coach and help the user solving the business problem (that your product solves).

Brennan Dunn's app (planscope.io) does this quite well. He doesn't just tell you to use his app, by he actively tries to educate you on how to win proposals (and his app is project management app).

Your end goals as a business app provider should be to solve for your customer success. By solving for customer success, you will solve for your product long term success. And this should drive every decision in the business.

So when you think about that email that you send, ask yourself "is this contributing to our customer success? or is it just spamming this user who might need something else at this moment?"

I know this does not help your point for the companies side, but I usually use temporary email adresses (such as http://10minutemail.com/) to avoid that problem.

This is amazing, we never considered making the guide open source/community driven. Many of our other resources already are.

We'll fork your markdown version this weekend and make the guide we host github powered.

Have they lost anything when you do that, though? You weren't really a customer or user anymore anyway, and now they can figure that out.

If they send out that email to 100 people, and 95 inactive users unsubscribe but 5 become active users again, that's a huge net gain for them, right?

Thanks! We get many questions around this topic, and it made sense to us that you track your metrics against a funnel (AARRR usually) you can map your emails to that as well.

Seconded. This is my 5th bookmark of the year. Wonderful resource.

Best tl;dr on the thread. I tolerate quite a bit of email pestering from companies with this approach; the majority of what hits my inbox is dealt with by pressing the "delete" key in less than a second, without reading anything beyond the subject line. For the ones who get too aggressive, I just filter their spam directly to the trash rather than dealing with their usually dishonest "unsubscribe" process. I'm not interested in being "onboarded" or shoved through a "sales funnel."

The Ministry of Statistics thanks you for your contribution. We have noted your click through rate and have added it to our population sample.

You're getting downvotes for the unconstructive snark, but I feel there is a salient point in there.

Unsolicited email = spam; simple as that. And by that association, anything and everything being sold by those emails is suspect. After all, if you had a product or service that people actually wanted to use, why would you resort to spamming?

My hindrance is that no one responds to any form of communication via the internet, targeted to specific people who could benefit from my product. Sure, it's basically relevant spam, individualized for the person receiving it, but for an aggregation service, how else can I know what people think of my product if no one actually sees it (aside from being on Twitter, et al, which also isn't helping much).

Use the dialer in Hangouts (Android's default messaging app), and calls to US and Canada are free. VOIP is the answer to free or nearly free calls with all your customers. You can get an 800 number for ~$2/month to make it toll-free for them.

Skype has unlimited USA and Canada calling for $2.95/month

Twilio is pretty reasonable