262: How to Write Killer Email Newsletters

Steli Efti:

Hey everybody, this is Steli Efti.

Hiten Shah:

And this is Hiton Shah. And today we’re going to talk about email newsletters, and  the reason we’re talking about this is both us have email news letters for different  reasons. I probably have, I don’t know how many, but a lot of them. And  a few ones that I’m spending a lot of time on, so this is a  great topic. Let’s give some context though, what kind of email newsletters are we talking  about here Steli?

Steli Efti:

Well that’s the big question right. So the reason I wanted to talk about this  is two fold. One, I feel like almost every startup has one, right? So startups  do this activity where they collect emails and then they send these emails a regular  generic message, a newsletter of sorts. But I’ve also seen that recently, the behaviors of  many startups when it comes to the newsletters has changed. I think that people have  gotten a bit more sophisticated and smart about it. I see a rise in individual  newsletters, like your product habits newsletter started as just an individual curated newsletter. So I  see a lot of changes happening, I see a lot of things happening with people having email lists and sending out newsletters, so I wanted to chat a little bit  about what’s going on today and what we recommend, especially for startups in terms of  how to use a newsletter in a purposeful way that either grows your audience, grows  your engagement, or converts your audience to more customers, not just doing it mindlessly. So  I’ll start with the mindless shit that people were doing in the past, and many  still do today I guess, and then let’s talk a little bit about some of  the things we do that we see other people do that are inspiring or particularly  effective that we think startups should steal and copy and learn from. So I think  the typical newsletter template that everybody has in their mind is this generic email that  is sent to everybody that marketing at a startup has an email on. And it’s  typically this HTML format that here is anything of potential generic interest to people on  this list. So startups will have like here are a few news items about us,  here are some articles we’ve written, here’s some new features we’ve developed, here’s a promotion  we’re running, here’s a little funny thing we’ve done because it’s Christmas season, and here’s  something else. It’s usually pretty long, and it’s super generic, and it just includes a  number of ‘news’ items about the company, hence why probably the name newsletter. Like here’s  everything new about us, everything that could be of interest, and it’s very generic and very long, and it’s send to an incredibly generic list, just everybody. That I think  is how most companies were doing newsletters forever, and I see that changing now, and  in big favor so I wanted to talk about that.

Hiten Shah:

Yeah. People think email is dead, Steli, that’s I think something that comes up every  fricking three months. Someone says “Email is dead,” and I want to shake them and  say “Why would you tell anybody email is dead?” How often do we as Knowledge  workers, if you want to call us that, or people building products, or founders, or anybody on the planet that is doing any work, how often do we use email?  Even Slack cannot kill email with the ubiquity Slack has. Even any of those things,  even text message cannot kill email. And I’m not talking about the Snapchat generation, I’m  not talking about pre millennials, which I think you and I both have, a few  little ones that are pre millennials. I have this great picture I have to post  somewhere of them looking so millennial it’s funny. But anyway, it’s not pre millennial sorry,  post millennial, see I’m even getting that wrong. You and are probably more pre millennials.  Anyways, I’m border line, I was born in 81, so … My point is even  once those folks get in the work place, email is still going to be where  it’s at to a great extent, because they are going to have to interact with  folks that only work through email. And, you know, to me people open your emails  if they are good. I’ll even say it even better, people will continue to open  your emails if they are great. And what does great mean? That to me is  what the discussion is all about. How do you write great email? Not how do  you write good email? Not what tool do I use? It’s how do you write  great email? So Steli my first question for you about this is how do you  write great email?

Steli Efti:

Well, that’s great question. So the way I write great emails, very fundamental, I think  about the user experience, and I think about the user journey with it. So to  me, an email starts in the inbox with the subject line, which is something I  want to … So I first I get into somebody’s inbox. I need to know  who that person is, and hopefully it’s the right person, and the right day and  time to even be in their inbox. Then I want to write a subject line  that will both capture your imagination and make you feel intrigued enough to want to  open the email and read it, and also is honest enough that what I’m promising  you in the subject, I’m delivering in the email. Then, I’m asking myself, I had  the base assumption that people are really, really busy, and so I don’t want to  send large, generic junk. I want to send short, specific, really valuable stuff. So I’m  asking myself how can I make this as short as possible, but not shorter? How  can I make this as valuable to the reader as possible? And how can I  make sure that I’m formatting this in a way that allows the reader to quickly  figure out what is this about? What does Steli want from me? Where can I  get more? What do I do with this? And so for us it meant going  from doing what I described earlier, of sending an email to everybody, like once a  month, that was a nicely formatted HTML thing that just included everything, to really start  segmenting our list and saying okay, here’s the people that we want to send our  best content to … Because we know they really love our content, and they read  it, and they open the emails, let’s send them more emails, right, because they want  to have more of our stuff in their lives. And let’s take some of the  product announcements that we’re going to do, and focus those announcements on the specific users  that care most about them, and need to know more about them, and send them  those very highly targeted messages. And then let’s think about the intersection, the people that  we know have never tried our product, but have been reading and appreciating our content  for a really long time, come from areas in the world that we know we  get lots of customers from. Let’s make a frequent effort, once a month in our  case, to approach these people and tell them hey, we’re sending you all this stuff,  we’re teaching you all these things, you’re getting all this value from us. Did you  know about our product? Here’s a reason you should check it out, and push them and convert them to try us. And just being more segmented, being more focused is  one thing, killing the newsletter, the generic newsletter was another thing. But then from an  individual email point of view, it’s always the same thing. I’m thinking about the journey  that the reader has from seeing the email in their inbox to opening it, to  reading it, to asking themselves the inevitable question, what do I do next? Sometimes I  want them to just think what I do next is click this link so I  can read this entire article on how to negotiate a million dollar deal, or how  to do a cold call, or whatever it is. And sometimes it’s what they want  me to do is hit reply and tell Steli my number one question about sales.  Or what they want me to do is click this link and sign up for  a trial for . Going through the journey, and keeping that in mind that people  receive this, and wondering what their needs are, is I think at the fundamental level  how we approach every single email we write, and why many people like our emails.

Hiten Shah:

I like that. So one of the key tactics there is honestly segmenting a piece  of the list, right?

Steli Efti:

Yeah.

Hiten Shah:

Between customers and non customers, right?

Steli Efti:

Yeah, absolutely.

Hiten Shah:

I think that’s an important thing a lot of people don’t consider. That’s like super  useful and critical. So what I would add to what you’re saying that I’ve learned  over the last couple of years with email especially, which I wish I had known  before, is that if you have an email list, the best thing you can do  is start actually engaging with that email list in whatever way you can. One of  my favorite ways, which I’ve used a few times this year, is I just ask them a question, and I just tell them they can reply to the email. I  don’t make them fill out a survey all the time, I don’t do any of  that, and I just ask a question. And that question that I ask should be  designed around providing them with . And I’ve found that to be one of the  key ways to really understand what their needs are, and what I can do for  them. And that helps me create content over any other thing I’ve ever tried. And  part of the reason is, think of the experience, they’ve signed up for my email  list for some reason or another, and they are receiving my emails, they’re opting in,  and they want something from me. If I don’t know what they want, then I’m  just giving them bullshit that they don’t want. So my key driver of writing great  emails is first and foremost knowing what they want. My second driver is basically making  sure that once I know what they want, I’m actually delivering on it, and it’s  better content for what they want than anything else out there. And that’s a really  high bar, but today, if people are still running around saying email is dead, one  of the reasons they’re saying that is that good email is dead. Great email is  thriving, it’s alive. It gets you everything that you could possibly want, but it takes  so much effort, and so much work, that most people aren’t willing to do it  today.

Steli Efti:

I love that. I have to go back and highlight this to make sure nobody  misses this, right? Email isn’t dead, good email is so rare that if you …

Hiten Shah:

Great email, great email.

Steli Efti:

… Great email.

Hiten Shah:

Good email is dead. Good email is good. Those templates, those images, those ecommerce emails  with sales, those are dead. Those are dead. What you need to do is you  need to write great email, and you cannot do that, sorry Steli, taking your time,  if you cannot write great email, do not do email. Learn how to write great  email, and I just told you how in two steps.

Steli Efti:

I love it. I almost want to just stop here because this is so good,  and I butchered it, I thank you, you saved me actually, you didn’t take my  time. I was thinking great, good email is dead. I was like good email is  good, and you’re like great email, and I’m like oh yes, okay, sorry.

Hiten Shah:

Come on Steli, people read your emails because they’re awesome. People read your content because  it’s awesome, it’s better than anything else they can read today on that topic that  they asked for. And in your case, you guys have turned into a machine of  intuitively knowing what sales people want. But it’s not because you didn’t do any work,  it’s because you spent many years building sales teams for other companies. You know exactly  what this market thinks about all the time, right?

Steli Efti:

Yeah. .

Hiten Shah:

So you didn’t have to ask that question, but you know. Yeah, go ahead.

Steli Efti:

But also I think this is really the obvious truth that everybody will go “Yeah,  I totally get this,” but nobody does, which is we cared about them getting value.  Most people are very selfish in the way they do things, right? They’re like alright,  I want people to open my emails, or I want people to hit reply, or  I want to drive more trials. So since I want this, how can I manipulate  people, into just bullying them, or pushing them to do the thing I want them  to do? I just want to send an email, I’m in the marketing team and  we have a 200,000 email list, and I just want to be sending out 200,000  emails once a month, because that makes me feel excited. Or I really like to  do nice designs for an HTML email, and there’s no other place that’s good than  a newsletter, so I’m fucking around for a whole week designing the most beautiful looking  newsletter with the most generic, useless information in it. Most emails are sent incredibly selfishly  without a single care in the world for whose receiving it, or what their needs  are. I think that’s really the differentiator here, because if you don’t think about the  person receiving your email, and if you do care about what they need, they don’t  care about you, and they don’t give a fuck about what you want, and they  don’t respond to it. And that’s the end of it, right, and you don’t need  to be an expert email … Like every fucking person on earth right now that  has a job and is in a business, and is not like a six year  old, is already an expert in email, in bad email, in good email. Just ask  yourself what are the emails every day that I get that are total bullshit, that  I delete, archive, or that I’m shaking my head in disbelief, why are they sending  me this crap? Or I’m puzzled, what does this person want from me? Any of  these emails are an example for shitty email. Just ask yourself why am I puzzled  about this? Why do I think this is spam? Why do I think this is  dumb? And then don’t do that. And then think about the rare cases, it’s so  rare that you get an email that you think whoa, this is awesome, how many  times does it really happen? Not often, but it happens. When that happens, just ask  yourself what about this email do I like so much? Don’t just respond as the  recipient, also respond, or take the chance to really be a good student of good  email and good communication, and ask yourself why is this great? Like why is this  different? I just got an email yesterday, I get tons of emails every day from  developer shops, out source. Like “Oh, we see you’re hiring developers,” it always starts with  something like this. Either great energy in the subject line, and then I know it’s  a recruiter or it’s a development shop, and it says “Well, we have many great  engineers, and we work really cheaply offshore,” from whatever place in the world. And I  get so many of these crappy emails, and it’s always spam, spam, spam. Yesterday I  got one of these emails, but here’s the differentiator, I don’t remember what the subject  matter was, but I opened the email and his first sentence was “Steli, I know  you’re just seconds away from hitting spam or delete, and I totally get it. Please  just give me two more sentences before you make that decision. Yes, we are a  developer shop, and we do out source engineers,” blah, blah blah. And then he just  continued, and I was like this is actually really good. It doesn’t mean that I’m  a good fit for his service, or that we are going to become a customer,  but this person realized that almost everybody he’s emailing, the first thought they have is  is this another out source developer shop email? And let me go as quickly as  possible to the spam or delete button? And he since he knows that everybody’s thinking  this, he’s addressing it in the email, right. He’s telling me dude, I know you’re  going to delete this in a second, please just for the love of God give  me three more sentences before you make that judgment call. And I was like yeah,  that’s a fair call, that’s a fair ask. I’m intrigued now, I’ll give you three  more sentences. I’ll read on for three more sentences before making a final decision. It’s  these little things that stand out. I’m getting, I don’t know, 30 of these emails  a day, and I can’t think of the last time I got an email that  I read four or five sentences of. And his I did, because he seemed to  care, he seemed to know, he was standing out with his email from all the  other ones that I got. And I assume that he’s getting a lot more success  with it, right? It’s a tough product market, and very competitive, but it’s these little  things. When you get a great email, it stands out. I’ve been on your email  list, it used to be the Hiton Shah newsletter where you curated all the best contented sass. Today it’s product habits. You guys are if you’re not already on it,  got to producthabits.com, and get on the fucking list, because this is one of the  few lists … There’s like two people or so that I’m on their curated list  because I know I’m going to get really fucking great content. If he likes an  article, I know the sheer amount of content that you read Hiton, if you put  it in your newsletter, it’s good. Your summaries at times are often better than the  fucking article, so I’m like , I just read your email. I read it word  for word, I read the summaries of the stuff that you post. I get an  incredible amount of value from it, and it’s one of the few emails that I  open every single week that I get from entity or personal company. Why? Because you’re  putting in the effort to really have amazingly valuable content. You put in the effort  to not just have a link share, like just have here’s the top 10 articles  I read, just the links. Or here’s the top 10 articles I read, here’s the  first two sentences I copy and pasted from the blog post, with like a dot,  dot, dot, and then a click here to read the whole article. No, you actually  put in the work and time to read the fucking thing, and then summarize it  in two or three sentences for your audience. And you do a pretty damn good  job at it. So you’re receiving email every single day. Learn from the mistakes of  people based on your reactions, and learn from the things that people and companies do really well based on your reactions. So study great email by your inbox. It’s the  university for greatness, and for poor examples as well.

Hiten Shah:

Yeah, it just quickly wanted to double click on what you said, which is, you  know, I did my best to not to have to write those thorough summaries, even  if they’re short, they’re thorough, and they’re descriptive. And like you said, sometimes it can  be better than a lot of the content in the introductions, et cetera, in the  content. One I love finding the best links each week, and I have a really  good idea of the audience and what people are looking for. But two, I tried  to lazy it out Steli, and you know what I got? I got replies from  people saying “Can you go back to the old format where you actually describe the  link in your own words?” And I was like damn, I’ve got to spend that  time. Because look, this is the difference between a good email and a great email.  So good email is okay, Hiton’s a good curator, here’s a bunch of links. A  great email is here’s his opinion on each link. And then it’s like you said,  you know I spent the time, more important you wanted to know what I had  to say about it, because you’re signing up for my newsletter, right? And that is  so powerful. And again, good email, dead. Great email, more alive than ever.

Steli Efti:

I love it. All right, we’ll end on this power quote from the legend, the  myth, the man .

Hiten Shah:

You’re the myth, you’re the man, not me.

Steli Efti:

All right, that’s it from us.

Hiten Shah:

All right.

Steli Efti:

We’ll hear from you soon. By the way, do us a favor, if you haven’t  done it yet, if you like the podcast and you appreciate it, we know from  the awesome feedback we get from people that you do, and if you haven’t sent  us an email please do, and if you appreciate the podcast, if you have suggestions  for topic shoot us an email at steli@close.io, or hnshah@gmail.com. And make sure to go  to iTunes, give us five stars, give us a review, it’s going to help us  rank higher, get more people to discover the podcast, and hopefully more people in startups benefit from the things that we’re discussing every single week. That’s our call to action  for today, and that’s it from us, we’ll be here very soon.

Hiten Shah:

Later.

Steli Efti:

Later.