Answers to the 3 Biggest Email Marketing Questions We Get

I asked two pros to come on and spill their best advice on the three biggest email marketing questions we get here at Copyblogger.

DJ Waldow joins me and Sonia Simone to discuss:

  • The best way to build an email list
  • The 2 reasons why people open an email
  • The most important element of an email that sells
  • How to write emails that get opened
  • How to stay out of your reader’s spam filters
  • Sonia’s secret weapon of email marketing that works

This one’s fast and useful, so keep your ears on …

Hit the flash player below to listen now:


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Please note that this transcript has been lightly edited for clarity and grammar.


Robert Bruce: This is Internet Marketing for Smart People Radio, I am Robert Bruce and we are talking email marketing on the show today. Specifically we’ll be handing you six solid tips on three big questions from two distinguished guests. If you’re into email, stick around. Joining me is Sonia Simone chief marketing officer of Copyblogger Media and DJ Waldow founder and CEO of Waldow Social — Sonia how are you doing today?

Sonia Simone: I am bursting with enthusiasm, is how I am today.

Robert Bruce: Sounds like it – I’m glad to have you on today. DJ thanks for coming on, too. Are you ready to talk email?

DJ Waldow: I’m always ready to talk email, as my bio often says I eat, breathe dream, sleep, and daydream email. So I’m ready to go and I’m excited to be part of this where I would now call this, the six three two right?

Robert Bruce: The six three two show, right. And Sonia is obviously from the sound of her voice a tornado over there. A veritable hurricane of energy and wisdom, so watch yourself, DJ, is my advice for you.

Sonia Simone: I’m just excited because DJ may be a bigger dork about email than I am, which is like beyond my wildest dreams. I’m so excited. So DJ it’s super to have you.

DJ Waldow: I take that as a compliment, Sonia.

Sonia Simone: No, you should!

DJ Waldow: I like that.

Robert Bruce: Alright, so I have got three big email marketing questions that we get over and over and over here at Copyblogger. And I’m going to ask that you guys give me your top tips for each of these three questions. The very best you’ve got. This is kind of like a game show, kind of has the game show feel to it. But, we’ll keep it simple. Sonia you’re up first. What are your top tips for writing an email that actually gets opened?

How to write emails that get opened

Sonia Simone: My top tip for getting an email – writing an email that actually gets opened is – we open mail form people we know. We file mail that we get from companies, so I have a folder in my Gmail and probably other people have this – it’s called something like shopping, because I’m one of those people that’s addicted to online shopping. And it’s got like a thousand unread messages in it. I just sort of throw them in there and if I want to look for something on sale I go in there.

Email, I get from a handful of people running a business who are sending email that feels like it’s from someone I know – those I read. And so my top tip is – create a personal identity; write from a personal identity, so it feels like email from a person, not a company. It’s about voice, it’s about writing an email that doesn’t look like an ad, it looks like an email somebody cool would send you about something you’re interested in. As opposed to a coupon – there’s nothing wrong with coupons or other commercial things but as soon as it looks and smells like an ad people treat it like an ad and that does not put it at the top of their “to-open” list.

Robert Bruce: DJ, what’s your top tip for writing an email that actually gets opened?

DJ Waldow: I want to be clear – we’re going back and forth so I get to take the lead on the next question, right? Cause Sonia of course –

Sonia Simone: Stole your answer? Sorry.

The two reasons people open an email

DJ Waldow: Stole my answer, and this is proof that we did not plan exactly or share our secrets up front. I think Sonia’s first one is – I’m actually going to build on that a little bit. I’m a big believer that people open- and forget being an internet marketer for a second, think of yourself as Sonia just described, as a consumer of email. People open email based really on two factors and two factors alone. Who it’s from and what the subject line is.

And if you think about this – that makes a lot of sense, because it’s the only way you actually look at your inbox unless you’ve got this big old preview pane, it’s all you really see, who it’s from and what it says, and what the subject line says. Really building on what Sonia said – that from name, who the email is from is oh so critical.

And so, I’ll give you an example of – let’s talk about Copyblogger for example – Copyblogger can send an email from Copyblogger or from Sonia or from Brian or from a handful of other people there, and you’re going to get a different response based on who the email is from.

And I’m not making a judgment on Brian or Sonia or anything like that. What I mean is – Copyblogger is a trusted brand. It is a well known name. I know when I get an email from Copyblogger what to expect and I trust it.

That’s much different than getting an email from a person and so I always find it interesting when brands toy with that, and I think — hopefully they’re testing it, trying this idea of — is it from the brand name or the company name or the person or a combination of the two? Because I think what’s really, really critical is – if I get an email from somebody I recognize and trust I’m that much more likely to open it than from a random person.

Sonia Simone: Yeah, absolutely. And I get emails from people I know are going to sell me something – like I get emails from Frank Kern. I always open emails from Frank Kern. I know it’s going to be a pitch from the first letter to the last punctuation mark. But I also know it’s going to be entertaining, I know it’s going to be interesting, I know it’s going to be funny.

And so, it’s not that you shouldn’t sell – it’s okay to sell, it’s okay to pitch, it depends what your audience is therefore. But be entertaining, be interesting, be a person — don’t be a stiff. Unless you have an awesome coupon. If you’re Groupon, you can do things a little differently because people are opening the mail to get the coupons. So it depends on what your audience is there for.

DJ Waldow: But Sonia, it’s an interesting point you bring up Groupon because I’ve had a lot of discussion about this recently. Groupon does something – Groupon actually proves my second point – a subject line that’s compelling because I’m guessing you, like me, don’t open every Groupon email.

You read the subject line – first you see it’s from Groupon and you say okay, I’ve purchased from them before, I trust them, I like them etc., etc., – hopefully. And then the second piece you say, well, it’s for a massage, well you know what, I’ve had four massages already this week, I probably shouldn’t buy another one. I’m going to go ahead and delete that email without even reading it.

Sonia Simone: Yeah.

DJ Waldow: Right. So the subject line in that case says – setting you up to either – it’s basically telling you what’s going to be in the email whether or not you’re going to open it or not.

Robert Bruce: Yeah, that’s good. DJ, let’s get into your second one here. The subject line – the headline you know essentially is what we’re talking about. How important is that to getting the email opened?

DJ Waldow: Well, I started by saying there’s two factors. The “from” name, and the subject line. They can be mutually exclusive. In other words – I cannot recognize the sender or not trust the sender necessarily and have just a totally amazing subject line that is compelling and I just have to open it. That’s one way. But I really do think the two of them combined are the absolutely the most powerful thing, a trusted sender and a compelling subject line.

But to me, it’s the subject line that gives me something – either like a Groupon, I know exactly what I’m going to get when I open it, or it leaves something to be desired. Something – you know – and the winner is dot, dot, dot. Or something where I’m going to – just like you would talk about in general copywriting- something that catches the reader’s attention because you know I’m scanning my inbox and I’m probably like most people in the morning I’m going on my phone and I go and scan and hit delete, delete, delete, and all of a sudden something jumps out at me, and I open it.

Robert Bruce: Same thing with a blog post, I mean if they don’t read your headline, they’re not reading you. Sonia, you want to close us out with your final tip on how to get our emails opened.

Sonia Simone: This one kind of underlies everything, which is don’t send people crap. If the message disappoints the reader when they open it, they’re not going to open the next one. So you don’t just want to write one email that gets opened. You actually want to write emails that get opened consistently.

So first of all don’t have misleading subject headers because A) it’s against the law, and B) it frustrates people and then they open it and they’re kind of disappointed and they have a little bad feeling in their stomach and they won’t open the next one. Actually have something worth reading when you open the email, is sort of the mega tip.

DJ Waldow: Quickly if I could just clarify one thing because I don’t want to imply that using something catchy or something to lead somebody in the email – I agree with Sonia -it is illegal and you don’t want to do anything misleading. I think I’m merely stating that you want to say something that gets them at least excited about opening the email, right?

Sonia Simone: Yeah

DJ Waldow: Without being misleading.

Robert Bruce: Yeah, I know. Thank you for that. We are definitely not in the hype business over here. Let’s move on to our second question. DJ this might be a bit of a shorter answer because this is a little of a technical thing – or can be, at least. How do we keep our emails that we’re sending out of spam filters?

How to stay out of your reader’s spam filters

DJ Waldow: Easy! Send timely, targeted, relevant, valuable emails to people who have asked for them.

Robert Bruce: Wait a minute, is that – one tip or is that like five tips?

DJ Waldow: That’s one long tip. But let me expand on that briefly.

Robert Bruce: Yeah, please.

DJ Waldow: I think – you know I actually got a really interesting email from a mutual colleague friend of ours – Chris Brogan – today. Apparently he had sent an email the day before that ended up in a bunch of peoples spam filters, and he apologized for it and he said – hey, I’m sorry you may want to dig it out of your spam filter. And he said, apparently the email gods don’t like the word free in the subject line.

Sonia will appreciate this as an email geek, I jumped all over that email and let Chris know that actually it’s not. It used to be the case that if you put “free” or used all caps in subject lines that those were going to get caught up in spam filters. It’s not really the case anymore. I mean, certainly some internet service providers or ISPs are marking emails as spam based on subject lines and content. But really, for the most part it has more to do now with reputation.

And I don’t mean reputation like – I was trying to think of a celebrity’s reputation but – I don’t mean that kind of reputation. I mean the reputation of the IP address that you’re sending from or the domain you’re sending from. In other words, if you are someone who is viewed by the ISPs as sending a lot of unsolicited mail or mail that people mark as spam often, your reputation as a domain or as an IP address that you’re sending from will go down.

That’s really more important than anything else, than what the content or the subject line reads to be. And I’ll pause on that for a second because I think Sonia probably has some thoughts on that as well.

Robert Bruce: Yeah, I know Sonia hates spam probably more than anybody I know. And hates to land in spam filters. But you do that the least of anybody I know as well. Sonia, what’s your tips for staying out of these spam filters.

Sonia’s secret to email marketing that works

Sonia Simone: I have a kind of a couple of tips. First of all, you know, everything DJ said. If you get marked as a spammer, then you can be sending people the collected wit and wisdom of Mother Teresa and you’re going to get in the spam filter because you’re a spammer. If you spam people then your reputation is going to suffer, or if it feels like you’re spamming people, if it feels like you’re violating the relationship the person thought they had when you’re signing up.

So be clear about, you know, if you’re selling and you’re a business, don’t try and pretend you’re not a business. Because again, you’re going to create an expectation mismatch, and that’s going to get you marked as a spammer which is going to be a problem. My kind of secret – it’s like so secret right, no one’s ever heard of this – my secret weapon – your readers really need to want to get your mail.

Because if they want it badly enough they will white list you, they will go find it in the spam filter, they will use a different email address. You know, there are some email addresses that are really hard to get into. AOL is hard; Earth Link I’ve always found can be tricky. And also a lot of the small business email addresses.

If you have a small company, hundred people or less, and they have an IT guy. That IT guy has that email server locked down so tight you can’t send in, you know, anything. Sometimes it’s not locked down in a very sophisticated way. Like “?oh, this is bulk email, I’ll throw it away.” You know, it was sent by a bulk sender.

If they really want what you’re sending, they find a way to get the email through.

So you put the burden on the person who’s reading, rather than trying to open a path up on your side. Now I totally believe in doing things to keep your email out of spam filters. I’m kind of increasingly leaning toward text emails rather than HTML, because I do find that I get more clicks, which suggests to me I’m getting more deliverability. It may just be that it looks more like, you know, email that people are used to getting.

The underlying principle for me is, if you give them a really good reason to sign up – like you have this really cool content – which by the way, if you build an autoresponder which is a sequence of emails, you can get a copywriter to create this astonishingly awesome autoresponder content for you. If writing is not your thing, if the content is good enough, if they want it badly enough, they will find a way to clear the path.

DJ Waldow: But, you know, it’s interesting when I first started email marketing I worked at Bronto, it was almost seven years ago now when I started, and I used to be more of that purist. You know, that person who said you have to do it this way. You can’t send text only messages with links here and there. That’s ugly and no one will ever open those or click. We all want these pretty HTML emails and – over the years I’ve matured – well, I should use that term loosely.

I think I’ve matured a little bit to now believe that, hey you can break some of those rules and actually find success. But I think it all goes back, Sonia, to your point; if you have that trust, if you have compelling content. You know we talk about blog posts a lot. You know, the makeup of a blog, and what it should look like and should it have this or two columns or three columns or one column.

Copyblogger, I’m sure you guys can appreciate this. Copy usually trumps all of that stuff. If you have good compelling content, it doesn’t matter as much what your emails looks like or if you have an HTML or text only. If you’re testing it and you’re finding that sending a more personalized email – shorter copy with a couple links of, click here, buy this now, join us for this webinar, and it’s working, then roll with that. That’s what I think. Roll with it.

Robert Bruce: I’ll tell you one thing that should be in everybody’s inbox. That is the Internet Marketing for Smart People email course, your online marketing course that we deliver straight to your email inbox. The short version of this is that it is the very best of Copyblogger wrapped up into twenty emails that Sonia has put together. Extremely readable, extremely useful. Those emails are dripped out to you about once a week.

And when you sign up for this course you’re getting over six years of Copyblogger teaching, tactics and wisdom kind of wrapped up into one place. To get this – it’s totally free – if you want in, you just head over to, scroll down a little bit to about the middle of the home page and you’ll see the headline, “Grab our free twenty-part internet marketing course”. All you have to do is drop your email address into the little box there and we will take care of the rest.

Okay, we have saved the mother of all email marketing questions for last you guys. This is the one that everyone wants to know all the time. Sonia, what’s your tip for how to build an email list.

The best way to build an email list

Sonia Simone: This is sort of a gigantic question so I’m just going to be tactical and short. The good answer to this used to be a pop up form. So you have a blog and there was a little pop up that pops up and says, hey you want to sign up for the email list, which I loathe and detest, and we could never stomach putting them on our blog. But they would very often double or triple sign up or more. So, you know we always knew we were leaving some readers on the table there.

There’s a new kind of a mini trend. The first time I saw it was over at Derek Halpern’s blog, Social Triggers, which is to make the sign up box for your email list, like ridiculously prominent. So he put it in the middle of the screen, not off to the side. It’s not in the side bar, so mobile readers will see it. It’s so big, it feels a little weird.

You know, it’s like wow, that’s really giant. But what you’re doing is asking for the email sign up in a way that can’t be missed, but you’re not popping up on the screen and getting in the way when people are trying to read, and so it’s sort of a hybrid. Chris Brogan tried it over at his blog and, instantly saw a really pretty remarkable increase in the number of email sign ups. We implemented it on our home page,, we instantly, I mean within the hour started to see a sharp increase in sign ups.

Again, getting to that double or triple rate. So, that’s kind of my latest trendy way to do it. Over at Studio Press we actually created a whole WordPress theme that bakes that in called Generate, and it just puts the sign up box – when you first look at it you feel like, wow that’s intense. Like there’s this huge thing in the middle of the screen. But, it’s a good compromise between irritating people with a pop up, but also making sure that you’ve put the opportunity in front of them, because a lot of people that like your content and want to sign up to hear more about what you have to say, they just didn’t see it.

Robert Bruce: I should apologize because this is way too big of a question for a tip so thank you Sonia, that was incredibly useful. And of course, what we’re talking about for people just kind of just joining us and maybe just kind of coming into this conversation for the first time. This is on top of a whole strategy of content creation, building trust, building authority with an audience, you know, through the open web, on your website that you own .

But what you’re saying, in relation to that, Sonia, is basically is that you’re making a conscious choice about the most valuable real estate on your website. Is a big part of this, right?

Sonia Simone: Right, you’re putting it front and center. And frankly, I’d rather see you do that, than have some kind of admittedly nice looking graphic header for your business that says absolutely nothing about what you do and does nothing to build your business.

Robert Bruce: That’s great, yup. DJ?

DJ Waldow: So Robert I thought once again that when you were apologizing I thought you were going to apologize for having Sonia go first – and once again.

Robert Bruce: Why would I do that DJ? It’s worked out well so far.

The importance of social proof and WIFM

DJ Waldow: Stealing! Stealing my idea. Exactly right, it’s so funny that you mention Derek’s blog. You know, I thought of the same one and how he makes it very, very prominent. I actually think you guys at Copyblogger do a really nice job also. I mean I know it’s part way down, you scroll a little bit, but there’s a big old sign up box there.

And to build on what Sonia said. I think it’s also important to do two things within that sign up box. It’s not just asking people to sign up and making it obvious, and clear and easy. But there’s two pieces to this – I’m looking to the Copyblogger site right now. There’s a little bit of the social proof there. So, you have “join over 63,000 smart people today.” Well, I’m saying to myself, 63,000 thousand people, what the heck am I missing, why am I not one of those people?

Sonia Simone: Yeah.

DJ Waldow: So, there is the social proof, and there’s a reason to sign up. And you all do this, and Derrick does this on Social Triggers also, but you tell me why I should sign up. Not just an email box and say please sign up for free updates – what’s in it for me? The WIFM. What am I going to get? What can I expect? So that’s the first one.

And the second one that builds into this too is – again Copyblogger does this – I’m looking at another site right now. Chris Garrett’s This is another trend I’m seeing more and more, putting some kind of incentive. So, again.

Copyblogger, you guys do it where you say, get this 20 part series. Chris Garrett is giving away two eBooks, in order to get an email address. He’s also making it very, very prominent on the site. But tell me what’s in it for me. What am I going to get? Why should I give you my email address?

Sonia Simone: Absolutely. And I will add – that’s a really good point. You know, the language we use on Copyblogger is, “here’s what we’ve got for you.” And that’s a good way to think about it. You might use that language yourself, you might not. But you know, what do you have for the people, what do they get out of it? Hint: it can’t just be access to your ads.

That’s not very interesting. But yeah, focus on the benefits. Make sure people understand what they’ve got for you. There has to be some reason they’re giving you this email address. We ask for people’s time and attention, like somehow that’s less valuable than asking for their money. We have it totally backwards. I can’t make any more time than I have.

If I give you five minutes, and your content is lousy, it’s five minutes I can’t earn back where I suppose, you know if I buy a five dollar sandwich and it sucks, it’s like let’s just make five more dollars, it’s not really a big deal. So think about what you’re asking for when you’re asking somebody for their time and attention. It’s a pretty big deal. You need to be able to deliver on your side.

Robert Bruce: Alright guys, let’s get out of here, let’s wrap this thing up. Sonia, thank you so much. DJ Waldow, where can people find you out there on the web.

DJ Waldow: I have the blessing and the curse of having a unique name like DJ Waldow. So, I’ve wrapped up every single handle that is DJ Waldow, so you can find me on Twitter, on Facebook, on LinkedIn. You can go to , you can go to my personal blog Social Butterfly Guy, and if you can’t find me by going to Google, there’s another DJ Waldow out there impersonating me.

Robert Bruce: Well thanks for listening everybody. As always if this show has done something to you, or for you, we would love it if you got over to iTunes and left a comment or a rating there.

That is one way that kind of spreads the word what we’re doing on this little radio show. We’d really appreciate it. And, Sonia, DJ, thanks a ton for your expertise today. We will be back.

Sonia Simone: Awesome, Robert. Thank you.

DJ Waldow: Thanks, Robert.


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About the Author: Robert Bruce is Copyblogger Media’s Chief Copywriter and Resident Recluse.