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You’ve been hearing that you should be using email to build your brand and market your products, but how exactly do you do that? Where should you get started? How do you even start an email list? How do you take the one you have and supercharge the growth?

In this jam-packed episode, I give you a crash course on email marketing. You’ll learn how to get people to sign up, what to send, when to send, and why using email gets you more than 10x the engagement Twitter does.

We talk about effective ways to incentivize signups without adding spammy popups to your site and whether it matters what type of lead magnet you use.

We answer a ton of questions from the chat, so you’re bound to hear something that resonates with you whether you’re just thinking about using email or if you’ve been marketing for a long time.

Show Notes
  • 04:50 Sean: Why email marketing? Why should you have a newsletter? Why not use social media, isn’t that what everyone is using? Who uses email anymore? Well, you probably do. You probably checked your email before you started listening to this podcast. You probably check it multiple times a day or you’re one of those crazy people with push notifications for your email. People still use email a lot. Even if your open rates are 30%—that’s nothing like the old days—but it’s still many times the amount of engagement you’ll get with Twitter.
  • 05:32 Last year, we talked about the engagement for Twitter being 2.5% but it just keeps going down. Engagement on Instagram is pretty good right now but that’s more visual, you won’t be able to deliver a bunch of written content to people that way. With email, even if you’re at the industry standard open rate of 30%, that’s more than ten times the engagement of Twitter! If you have a tenth of someone’s followers on Twitter in email subscribers, you actually have a more engagement audience.
  • 06:21 Ben: I wonder if email is the most powerful form of communication right now. Mail marketing used to be powerful because people were used to getting their mail and opening everything they received but I think email has become the new standby for people, even with all the new things that are coming out. It’s what people trust because most of the time they’re receiving something important that they need to pay attention to.
  • 07:03 Sean: It’s the fall back. Nothing else has become the de facto standard besides email. If you’re going to get an order receipt from an Amazon order or your plane tickets, it’s always going to email. Even if you get a text notification, they’re never going to just rely on text notifications. It’s always a fallback of email, at least right now. I’m not saying that will never change in the future, though

Email is far from dead and right now, it’s the most effective form of marketing in terms of engagement.

  • 07:40 Ben: I’ve seen some companies push toward text message marketing but I feel like people are more likely to keep an email address for a long period of time vs. keeping a phone number. Peoples’ phone numbers probably change more often than their email addresses do. There’s even more permanence to someone’s email address than there is to their physical address. I don’t know all of the facts behind it but it makes sense that it’s a strong tool for marketing.
  • 08:20 Sean: For anyone on the fence, I’m trying to help them realize they need to be paying attention to email. You can’t just be focused on Facebook, the engagement is terrible for Facebook pages. We’re going to assume that you’re on board with doing some sort of email marketing if you’re listening to this podcast.

Increasing Signups and Growing Your List

  • 08:43 The way you get people on an email list is to have a signup form. You have them opt-in with their email address. A lot of forms will say, “Sign up for our newsletter,” with a name and email field, then a submit button. Now, there’s a few problems with this. In the chat room, Justin asks, “How do you communicate that your newsletter is something people will want to sign up for when you’re just starting out and don’t have something like an e-book to grow it?” He’s talking about a lead magnet here. A lead magnet is something you give away in exchange for someone’s email address. They sign up and they actually get something for that. That’s very different from someone saying, “Sign up for our newsletter,” because that’s seen as an ask. You’re basically wanting to take their email address.

When you give someone a gift for subscribing to your newsletter, you’re exchanging value.

  • 09:55 You’re saying, “Hey, if you give me your email address, I’m going to send you this valuable thing.” You need some form of lead magnet because no one wants to sign up for just another newsletter. Having a newsletter used to be cool and it was enough to just have people sign up for that, but now everyone has a newsletter. It’s not cool anymore. You need to give people a reason for signing up. An email address is special and people try to protect it. They don’t want spam so they don’t give it away to just anyone. You need to give them a reason and you need to provide value. It’s giving vs. taking and, “Sign up for our newsletter,” is seen as taking.
  • 10:41 Ben: Are you suggesting that you do not ask for email addresses from people until you have something of value to provide them in exchange?
  • 10:51 Sean: I believe that’s the best approach. What if I don’t have an ebook? Don’t see this as, “Well, I guess I can’t get started because I don’t have an ebook.” There’s a common misconception that the lead magnet has to be something huge like an ebook, but it doesn’t. I would encourage you to spend 3 hours creating a guide to something that is relevant to your target audience. What are they signing up for? What kind of content are you putting out? What kind of value are you providing? What are people interested in? Create a relevant guide around that topic and give it away as your lead magnet. It could just be a nice looking PDF document. Spend some time on it—spend an hour or two on the content and another hour on layout and design.
  • 11:49 Ben: One of the other questions I hear people asking a lot is, “Should I wait until I have a lead magnet to even start putting out content?” but I would say part of what primes your audience to sign up for your email list is the fact that you’re consistently providing value in other ways, even if you have a lead magnet. If they’re visiting your site, reading your articles, or listening to your podcast and you consistently provide that value, then when you do make an email list signup available and you provide an incentive to sign up, they’re already associating the value they’ve received from you up to that point with the lead magnet. Even if the title you came up with for the lead magnet was terrible, they’ll still say, “This is probably valuable too,” because they’ve seen the value you’ve provided.
  • 12:56 Sean: It’s your existing reputation that the visitors and potential subscribers are going to apply to this lead magnet. It doesn’t have to be 60 to 80 pages long. If it is, that’s great, but there have been tests confirming whether you have a full ebook or a six page guide has little to no effect on the conversion rate.
  • 13:24 Ben: If you’re creating content consistently, you can also curate some of that. You can package the content you’ve already created and use that as your lead magnet.
  • 14:12 Sean: The answer to Justin’s question, “What’s the best way to grow your email list?” is consistency. You need to provide consistent, valuable content, plus a lead magnet. The lead magnet is what pushes them over the edge. It reminds them that you’re providing value and you’re not just trying to take from them. In tests, there’s little to no difference between a short guide and a full-blown ebook on conversion rates. It’s either lead magnet or no lead magnet—that’s where the huge difference is. If you don’t have a lead magnet and you’re just telling people to sign up, your conversion rate is going to be a lot lower. I would also recommend that you don’t ask for a name. Don’t have a name field on your signup form because you’re going to drastically reduce your conversions. That’s one more step for people to do and it’s a hurdle.
  • 15:06 One of our Community members, Kyle Adams, has an autoresponder that goes out two weeks into sending emails. At that point, they’ve received several emails from him and they realize he’s got good stuff to offer. He sends an automated email out that says, “Hey, want to go update your subscription preferences? You can update your name so it will be more personalized.” People know that when you put your name in and the newsletter says, “Hi Ben,” it’s not being written just to you but it still feels more personal. He addresses the elephant in the room and tells people to update their subscription preferences so that way he doesn’t ask for it up front, he’s got a higher conversion rate, and later they can still get it personalized.
  • 16:04 Ben: It seems a little bit sneaky but at the same time, you don’t want people to get in their own way if what you have to offer is truly valuable. It’s like, “I want you to have the value of what I’m offering so much that I’m not going to put a pop-up signup box on my website, but I’m going to make it easy for you to sign up. I’m going to remove as many hurdles as I can so you can get this thing of value, then we’ll get to know each other a little bit more.”
  • 17:12 Sean: I know some people are going to wonder how to do an autoresponder email. That’s going to come down to your email service provider. I know MailChimp does it but you have to be a paid user in order to use autoresponders. They do have a free plan though. I’m pretty sure MailChimp is the only one that does provide a free plan, out of the other email service providers out there. You might just want to bite the bullet there because you’ve got to pay to play.

Welcome Email (What Should Go Inside?)

  • 17:50 Some email service providers have what’s called a welcome email but you could also set up an autoresponder that serves as a welcome email and customize it. I suggest that you do have an email that automatically sends to people when they sign up. Don’t just dump them on a list and start sending them your latest thing. You’ve got to get them accustomed and bring them on board. You need to set expectations—let them know what they can expect—and set the stage: Who are you and why should they listen to you?
  • 18:28 You’ve got to familiarize them with who you are, what you came from, what you do, and why you do it. They want to be able to relate to you and you want them to relate to you so they’ll listen to what you have to say.
  • 18:42 Ben: You might think to yourself, “If they’re signing up to my email list, then they probably already know me to a certain extent,” but you don’t want to assume too much. It’s better to give them more information about yourself than they need—because they can skim over the parts they already feel like they know—than to not give enough of yourself and leave them feeling like they’re not connected with you.
  • 19:09 Sean: Let them know why they should listen to you and then let them know what’s to come. What’s to come could be a number of things—a series laid out in an autoresponder or the type of content you’re going to be sending them. You should let them know what’s to come, at what frequency, and on what days. The key to your welcome email is to let them know what to expect and ask a question. The question you want to ask is more or less, “What are you struggling with when it comes to X?” X being whatever the topic is or the industry you’re in. Figure out what people are struggling with! Say, “Hey, just hit reply on this email and let me know.” That’s going to be gold for you. It will be the source for all of your future content and it will be tailored to them. You have to listen to people. Listen to what people are looking for, then give them what they want. They’ll feel like you’re reading their minds.

If you want to develop content that resonates with people, you have to give them what they want.

The only way to know what they want is by listening to them.

  • 20:34 The only way they’re going to say something you can listen to is by asking questions (Related: e099 How to Read Minds). Ask them what they’re struggling with and then what I would do is set a label in Gmail—which you should be using—with the subject of your welcome email. Use that label and archive it, where you can go and check it later. You can look through those responses to see what people are interested in then write content in response to them.

How to Supercharge Your Autoresponders

  • 21:07 The next thing you want to do is look at the most frequently asked questions. Look at the content you wrote in response to those questions, which ones of those resonated most strongly with people? What was the most shared? What got the most replies or comments? Take those and turn them into an autoresponder series. This is what I meant when I was talking about letting people know if you have a series coming up. Once you have content you put out there you know is resonating with people, turn that into a series. This is something I’m working on but haven’t even done yet! I’m going to be revamping the newsletter to include this. It’s essentially a crash course of the most valuable content I’ve put out. I’m going to rewrite that and send it in the order of the most frequently asked questions. That’s going to result in a large percentage of your subscribers feeling like you’re reading their minds.
  • 22:14 Ben: You’ve already got them on your list, so is the autoresponder series part of a lead magnet? How do you use that to your benefit, or are you doing that just to provide extra value to the people who are subscribed?
  • 22:35 Sean: You could do it either way. Some people like to say, “Hey, I’m going to send you an email course,” which isn’t a bad idea. Sometimes that in and of itself is the lead magnet. You don’t have to acknowledge it even. You could provide a lead magnet and then automatically send five emails that you know, through responses received from people, will be highly relevant to them. You don’t have to call it an email course or acknowledge it as an autoresponder. No one cares what it is, they care if the content is relevant to them. You could go about it either way. If you feel like this series you’ve put together is really cohesive and it’s solving a specific problem, not like, “Here’s 5 popular articles,” then it could serve as a lead magnet.
  • 25:02 Ben: The autoresponder series is a great way to get people to feel like you’re reading their minds but you can also be purposeful about it by seeing it as each one of these interactions serves as a deepening of that relationship.
  • 25:27 Sean: What I’ve realized is without having this kind of a series at the beginning, I’m really just dumping people into whatever I do that happens to come next. I’m saying, “Go in with these other subscribers and I’m going to give you the latest piece of my content whether it’s relevant or not.” That’s not ideal. I would rather bring people along, especially when it comes to the Community. I’m realizing a lot of people subscribe to the Community and they don’t know a lot of the core concepts we’ve talked about. They don’t know about focusing on values, Professionalism, Full Price or Free, the Overlap Technique, or the One Concept Approach. I think it would be better if I brought people through intentionally, like a mini tour for each person because they matter. Instead of just thinking that or saying they matter, I want to show it with my actions.
  • 26:43 Ben: It’s like your email newsletter serves as an ambassador. I’ve got this picture of someone moving to a foreign country where they may have been before but they don’t know much about the culture. When they first step off the plane, there’s a person that can speak their language who says, “I’m your ambassador for this country. I’m going to introduce you to the history and culture of this country. I’ll teach you the customs and the way we do things.” It would be overwhelming to dump all of that on a person at once and it would be equally overwhelming to throw someone into that situation without giving them that context. That ambassador’s job is to pace that person through the process of learning those things in the right order so that by the time they get to their destination, they’re well versed.

Why You Need Regular Content

  • 28:26 Sean: Regular content is a big key, no matter what you’re doing, whether it’s putting out new content every week or content you’ve already made that you’re automating or putting out at certain intervals. I do both versions of this: with the seanwes newsletter I’m putting out new content regularly that people are used to getting at certain times on certain days but with Learn Lettering, I’m not actually making new regular content. I do have an autoresponder series that allows content to trickle out to people at the right time after they sign up. You can do a hybrid by having the autoresponder go and you can bring people into your main area where you’re giving new content. Either way, you’ve got to have regular and consistent content.

Show up consistently, on time, without fail because your reputation is at stake.

  • 29:35 Ben: One thing we didn’t mention about the email list is not only do you need a lead magnet, something to incentivize people to sign up, but you also need to let them know on the sign up form what to expect from you. It’s not just asking them to sign up and then communicating, you should communicate all of that even before they sign up.
  • 30:02 Sean: “Get the new blog post every Friday,” or something like that so people know the frequency up front. Even before they opt-in, they know what to expect. Cory asked, “What is the best way to provide content through an email? Is it better to put an entire blog post, article, or news update in the email, or is it better to include an excerpt and then a link to your website?” There’s multiple ways of thinking about this but I don’t think there’s a wrong way. It depends on what your goals are and how you want to use these tools.
  • 30:46 You might want people to go to your website because you want the traffic and you want people to discover other things there, like products or other articles. Those are all good things and I think you should want to give people a way to get to your website. At the very least, have a link somewhere so people can go to your site if they want to. The second part is whether or not to push people to the content. Say you have a 1,000 word blog post, do you write an excerpt and say to read the blog post through a link or do you give it to them right there?
  • 31:44 Ben: Gary Vaynerchuck answered a question about doing videos on Facebook and instead of linking to his YouTube channel, where he’s collecting subscribers, he’s uploading his videos to Facebook. People asked him why he was doing that when he could be driving traffic to his channel. His answer was that when you upload a video directly to Facebook, using their platform, it gets more visibility because the people are already there and Facebook favors that. What I get from that is that people signed up for your email list for your messages, definitely give them opportunities to go to your website, but the reason they’re there is for your emails. That’s where the bulk of your value should be provided because that’s what they signed up for. The principle there is to let most of the value live in the medium for which people signed up for. If they’re getting value from you, they’ll find ways to get to your website.
  • 33:23 Sean: I agree with you. In the chat room, Justin is saying, “I don’t like it when I’m reading content in an email and have to go to the site. I usually don’t click,” and that’s true for a lot of people. The click rate is going to be lower than the open rate, no matter what. What you’re not going to get is the people who would have read the content in the email that aren’t going to click. Maybe they’re on a plane, they don’t want to wait for something to load, or they’ve got more emails to get to. Gary’s philosophy is to engage with people where they are.
  • 34:09 Ben: If the question is if they’re going to read all of the content in the email but not click something, do I want them to leave with something that’s complete and fully formed, or do I want them to leave with something incomplete? If you’re doing that consistently, you’re spreading the ask too thin. If you’re providing the full version of your value consistently, then when you do make a stronger ask it will be more impactful.
  • 34:58 Sean: This goes over to my Twitter philosophy too. When I tweet something, it’s the opposite of the click bait. Click bait doesn’t give you anything, it just tries to get you to click and there’s even Twitter accounts dedicated to uncovering the click bait answer. They’ll retweet someone else’s link in quotes and within the commentary, they’ll say yes or no. The click bait title might say, “Does the new whatever have this feature?” They answer no and save you a click. I do the opposite of the click bait thing—I give people the takeaway right there. Even if they don’t click on the link, they got the best part of it in that tweet. That actually helps it go a lot further. Think about it with email too, people forward emails to friends. Are they more likely to forward an email that has value or forward a teaser with a button that the recipient also has to click?
  • 36:02 Ben: Maybe you don’t get as much traffic to your site immediately doing it that way but you’re providing a lot of value. It’s your name you’re putting out there and people are associating value with. Over time, that’s going to end up equalling a lot more traffic to your site than if you’re doing it with the shallow approach to getting people to engage with your content. You’re giving as much value as you can and your ask is relatively small, compared to the value you’re giving. What people will take from that is, “name = value,” every time. Eventually, they’re so conditioned to that, they want to find you wherever you are to get that same value from you.

It’s not about the numbers, site traffic, or likes, but the association with your name and the weight that carries.

  • 36:55 Sean: When someone else hears the name—even if they’re not subscribed or maybe they listen to the podcast—some sort of interaction with you has left an impression with them and they’re going to associate quality or value with anything else that has your name on it. That’s why it’s not always obvious how much of an impact something is going to have when you put it out there, like a new course or product.
  • 37:38 You can’t just go by the number of subscribers in an industry average conversion rate or number of followers because it’s so much broader than that. Maybe someone on this platform isn’t on another platform but because you’re consistently providing value there, even if it can’t be measured on the other platform, you know they’re going to buy your thing because they see your name on it and they know it will be valuable to them.
  • 38:20 Ben: I’m going to confess here, in the past when I’ve had a question I wanted people to respond to, I would tell them to contact me and I provided a link that went to the contact form on my site for them to fill out. Looking back, how difficult am I making it for people to reply to me? Part of the reason people sign up for an email list is because of the kind of direct interaction they can have with you. That reply shouldn’t be going through a contact form on your website, it should be a button that allows them to immediately reply within their email browser.

Treat Email Like A Human Would

  • 39:09 Sean: Think about how anyone uses email. Think of someone in your family sending you an email, are they going to say, “Hey Bro, I’ve got this awesome thing I want you to check out. It’s going to be good. You’re going to like it but I’m not going to give it to you here, you’ll have to go somewhere else.” Most people don’t do that, they send an email and say what they have to say. They don’t make you go somewhere else or take another step. They include it right there in the email. You want to treat it like you would write an email to any other person.
  • 39:53 Think of it this way: the content you’re writing is in response to the questions you’re getting. Let’s say someone sends you an email, not through your contact form or as a reply to your newsletter, they compose a new message and say, “Hey, I’ve got this question. I’m really struggling with this. I know you talk about this all the time, so I thought you could help me. You’re the person who came to mind. Do you have any advice about this situation?” When you answer them, are you going to make them go somewhere else to get the answer or are you going to provide value for them right there in the email? Think of it that way because that’s what email is. I would lean towards giving people the value right there in the email. It’s still one person opening an email from one other person.

Even if you’re sending an email to 10,000 people, it’s still a one-on-one interaction.

  • 40:54 Ben: Not just the value but the native ability to reply directly to you so they don’t have to jump through hoops to interact with you on that medium.
  • 41:07 Sean: In the chat room, Keshna says, “I like the way Sean puts everything in his newsletter, that way I don’t have to go to his site to read the articles.” You can also do a hybrid approach, where you give people the value but you also provide a link that says, “Read this post on,” that way if they can go there, copy the link, save it, or tweet it—they have that option. For the podcast newsletter, I give people an excerpt and mention they can listen to the podcast and see the shownotes on my site but I also include it right there in the email for people. Coding HTML newsletters is no small feat, it’s a lot of work but people appreciate it.
  • 41:53 People tell me they never read the shownotes and that’s fine. A lot of times they’ll just scroll through to the bottom to see if there’s anything else but while they’re scrolling they notice the pull-quotes and headers. They’re getting the takeaways. We’re designing this experience for different levels of engagement. Some people want to read through the whole thing and we have deaf people in the audience who get to read it. They can’t experience a podcast so they’re going to read word-for-word. Other people might search the page for something they specifically want and then there’s the skimmers who just look through it really quick. We give them the takeaways. We bold certain phrases and include headers or pull-quotes that give skimmers the best stuff without them having to go through it word for word.
  • 42:58 Ben: Our very own Aaron Dowd, the Podcast Dude, started putting out a newsletter and I signed up for his list. As I was watching a video he produced, I was thinking that there’s a lot of stuff I already know, so it would be neat to have a transcript of it with text hierarchy—the way you do shownotes, Sean—to be able to look through and pick out the new information. I did watch the whole video he put out and I did learn some new things. A lot of the time there are audience members who are familiar with the things you’re sharing. They might already know 50% to 70% of it but that 30% to 50% is value they have yet to receive and they want it. When you go into more detail and share shownotes in outline form, it’s really nice for people to glean the pieces they want and not feel like they have to sift through the entire thing.
  • 44:32 Sean: Romaric says “I’m always annoyed when there’s no web-version of the content because it means I can’t add it to Pocket for me to read on my own time.” First of all, people consume different ways. Some people want to read the content right in their email and if you don’t give it to them in full, they’re not going to read it. Some people might click it but it’s a negative experience for them, which is something you don’t know. You don’t know that it can be seen as a burden that builds on itself and eventually, the person might not want to keep clicking to read your stuff every time.
  • 45:10 Then there’s the people who want to read the web version. They want to read it in a browser because of readability, or because they can share it or use their Chrome extensions. That’s why I say to provide the, “Read on my website,” link. I mentioned to Romaric he can do an email forward and he didn’t know that existed. If you use Instapaper or Pocket and you want to send an email, you can actually go into your account and get a specific email address you can forward emails to. It will convert it and send it to your read-later list. You can even set up an automatic filter for it to go straight to your Instapaper or you can do it selectively.
  • 46:26 In the chat room, Cory says, “I have my own newsletter archive set up that I manually create and share to my newsletter subscribers so they can go back and have a hard copy later on or see previous emails they might have missed before they subscribed.” That’s a great idea! If your emails are automatically going to your blog, people can go view your blog but if you’re not posting all of those emails to a blog, you can do what he does and have an archive of the newsletters on your website. There’s different services you can use, like MailChimp has a past issue archive people can go through, but that’s not native. I like how he puts it on his own domain.

How Many Emails is Too Many?

  • 47:24 Sam asks, “How many emails is too many? How can you keep people engaged without flooding their inbox and forcing them to unsubscribe?” This is a touchy subject. I used to be very wary of sending lots of emails and I was afraid people would unsubscribe. On average, I send three emails a week and I did decide to give people subscription preferences so they can choose to receive the podcast shownote emails or not. The reason I give a preference here is because some people get those shownotes in their feeds or in their app, or they already listen on the website, where the player is right there with the shownotes. Maybe they don’t want those emails and I understand that’s a legitimate case.
  • 48:23 When it comes to something like autoresponders and how often you send emails, you can do it daily. I might even encourage to do daily and I know that sounds crazy because everyone is going to tell you it’s spam and they’ll instantly unsubscribe. Well, that’s fine because those people aren’t my target audience. I just spent $300 on a course on email marketing and normally this course was sent as an autoresponder. Every day it would send you a new installment of the course, but eventually it was changed so you can access it all. I binged through it in a few days but I wanted all of it. I was hungry for it and that’s what you want.
  • 49:21 You want the people that are hungry for it and if you’re targeting the right people, they’re going to want daily emails on a subject they’re interested in. Someone who is interested in lettering wants to be given stuff on lettering every day, because that’s what they’re scouring the internet for. You might as well give it to them. If you’ve got value—free lessons, tutorials, instructions, guides, blog posts, etc.—give it to them! Do you think they’re going to wake up the next day and not consume any content? Do you think they’re not going to get on Twitter, not going to get on Facebook, not going to click links, or check their email?

People are going to be consuming every single day.

Is it going to be your content or someone else’s content?

  • 50:05 With Learn Lettering, I have an autoresponder that sends every single day and I have a 75% open rate, which is very high. Why is it that high? It’s that high because people search for lettering on Google and they click on my site. They browse Pinterest and see my work. They’re interested in lettering and the sign up speaks directly to them. I give them something immediately. I let them know what’s going to come next and I deliver on that. I let them know what’s going to come after that, I deliver on that. Spreading these things out, letting people know what’s to come, and then showing up and delivering is fulfilling a promise. It’s a micro-promise keep. I showed you that I’m true to my word and that I’m here to provide value to you consistently, every single day.
  • 51:02 Ben: People are worried about sending emails too often and having people unsubscribe. If you communicate what to expect up front then people are going to know what to expect going into it.
  • 51:19 Sean: Say you have daily emails on lettering, or whatever it is you’ll be providing, and there’s going to be people that subscribe for that. They’re hungry for it. If you don’t have that much content on a regular basis, that’s fine. Do weekly or twice a week instead. You can do it however much you want.
  • 51:48 Ben: How much is too seldom?
  • 51:55 Sean: Less frequently than once a week is not ideal. I’m not saying it can’t work or that people won’t open your emails because they will, but it’s not the same. People have a weekly cycle that resets every week. They watch shows every week and have routines every week. You’ve got to get inside that cycle if you want to be really effective. Does that mean if you only have something once a month you shouldn’t be doing an email list?
  • 52:23 It doesn’t mean that but there’s no way you only have something once a month, unless you’re just not committed. You can make something once a week. It’s not that hard. Even if you’re not making something new once a week, you can spend a bunch of time making a ton of valuable content you know will resonate with people because you’ve been listening to their questions, and then set up an autoresponder that sends it at whatever interval you want to do. There’s ways to do it if you really want to. I prefer not to cater to, “Well, can I do it monthly?”

Make it a goal to put out content weekly at the very least.

  • 53:04 Ben: Spend a week writing 52 email posts and set up an autoresponder with a reply option so people can respond to your questions. Put that out there and then you don’t have to do anything for a whole year.
  • 53:22 Sean: “Ben, I don’t have time to take a week and write 50 emails. That’s about 10 a day or so. I could probably do it if I really buckled down and spent a week but I don’t have time to.” Do you have time to make five figures a month? Because that’s what those emails are doing for me. I made something valuable and now I’m selling it by sending out automated emails I took time to write. Now, I’m going to be taking the time to go back and write all of them again—time I don’t have but time I’m making because it’s worth it.
  • 54:00 Ben: It’s important to think about any time you spend on an email responder series, or even on setting up your email list the right way, as an investment in your future. Those are returns that are going to come to you eventually.

HMTL vs. Plaintext

  • 54:31 Sean: Cory says, “What are your thoughts on plain text vs. HTML markup? If someone isn’t an expert in HTML, is it better to send plain text or to get something pretty good up?” I like HTML. A lot of email marketers will say you’ve got to do plaintext because it converts better but I say it depends on your brand. People know me for design and HTML works for my audience. I like HTML emails, they’re nice looking. It’s not tricking anyone when you do plaintext and say, “Hi, [Name].” They know it’s automated and not going just to them.
  • 55:12 You’re not tricking anyone so you might as well make it look nice. Make it reflect your brand if design is a core element to whatever you’re doing. If it’s not, test it out. See what kind of engagement you get with plaintext vs. HTML. To answer Cory’s question, if you’re not an expert in HTML, there’s a lot of great templates you can use. It doesn’t take much to customize a template. If you want to do something more advanced and you’re finding that it looks bad, or things are inconsistent, maybe revert to plaintext until you can do it well. A plaintext email is better than a poor looking, messy, or broken HTML email.
  • 55:58 Ben: Hiring a developer to help you with that is also an option as an investment.
  • 56:28 Sean: Cory asks, “How many different autoresponders should you have set up? Should you have one for the main page subscribe link, a blog subscription link, and so on for different targeting and analytics?” Yes, as much as possible. As much as you can technically accomplish or your email service provider can do. You want to be hyper-targeted and hyper-segmented. I’m switching from MailChimp to Infusionsoft, which has tagging and tagging is huge. The way MailChimp works is you have to have separate lists, if you want to do the things I want to do. They don’t even encourage using separate list but I have to, which means people are duplicated across lists and you’re paying for them multiple times.
  • 57:20 It’s rough but Infusionsoft has one database of contacts and everyone has tags. You send out emails based on tags—it’s brilliant. If you have an autoresponder campaign for something going, you can say, “Are you interested in the podcast? Click here,” and even if they’re not on the podcast list, you could tag them as, “Interested in the podcast.” Then, you can start sending them related stuff. You can have thousands of tags with Infusionsoft and you can categorize those tags. Every single action—“Signed up from this page,” “Is interested in this,” “Bought this,” “Bought more than [a certain amount]” “Clicked on this link,” “Clicked on all of these links”—can be hyper-tagged.
  • 58:11 These tags can trigger actions. For instance, someone can be tagged based on clinking a link or signing up and you could put them through a campaign. If they’re getting regular newsletters about something, you can put that on pause and send them through an automated campaign that gives them hyper-relevant information and then puts them back onto the normal newsletter sequence.
  • 58:44 Ben: That sounds incredibly value and incredible complicated. Sean, when are you going to come out with a course for Infusionsoft?
  • 58:59 Sean: I was actually planning on eventually coming out with a course on email marketing with MailChimp because they have a free plan and then it’s pretty inexpensive to start. Infusionsoft is $300 a month and up, depending on the size of your list and that’s a huge investment. It’s pretty much for pro-users. With MailChimp you can do some types of automation. There’s some segmenting you can do but not very much.
  • 59:33 Basically, I’m thinking about doing a course at some point in the future that shows you how to segment within MailChimp and run automated campaigns that are based on whether or not someone has bought something. MailChimp has eCommerce 360 integrated, which will integrate with a bunch of different eCommerce platforms. I actually had a custom plug-in developed especially for my usage case and the guy who developed it has turned it into a plug-in you can now buy.
  • 1:00:22 If you use WooCommerce on WordPress, which is an eCommerce plug-in, you can have it say if someone buys a product in this category, add them to this list. I have Learn Lettering courses and physical products in my store, like shirts, prints, and mugs, and I also have the Community, which is a membership subscription. Here’s how this normally works: if you get the basic WordPress MailChimp plug-in, you can have it set up to when someone buys something on the store, you can say, “Do you want to subscribe to the newsletter?” and it will add them to a list. That’s not very segmented though, so this plug-in will help you segment it.
  • 1:01:17 It will transmit the eCommerce data, even if they don’t subscribe to the newsletter. If you buy a product and you don’t check the subscribe box, the eCommerce 360 data isn’t transmitted to MailChimp, which means you can’t segment based on if someone has bought, unless they check that box. This custom plug-in allows you to bypass that. This is what it allows me to do right now: when someone signs up for Learn Lettering, they’re automatically added to an automation where they get a series of autoresponders. Now, let’s say there’s five emails and on the second email they think, “I loved this free lesson, I want to buy this course,” and they go buy the course.
  • 1:02:07 They start going through the course and they start getting more emails every day that’s directing them to the course but they’ve already bought it! That becomes a terrible experience. This plug-in allows it to tell it to send this to people who haven’t bought from this category and regardless of whether or not they checked a box, I have that data. All that to say, you can do some great stuff with MailChimp, WooCommerce, and eCommerce 360 without paying $300 a month for Infusionsoft. The course I’m considering doing would be on that very specific usage case.

How to Handle Responsive Email Design

  • 1:03:13 Stephanie asks, “What about how to handle responsive email design and which services handle it in the best way?” I’m going to have to give a shout out to MailChimp here. They do a phenomenal job with their user interface and they have such a high focus on design. I’ve heard good things about Campaign Monitor, although I don’t use them. Aweber can do more powerful things than MailChimp but it’s going to be a little less focused on design. If you’re a designer you might cringe a little bit. Infusionsoft is even more powerful but you’ll still miss things from MailChimp like drag-and-drop features where it will automatically create plaintext. I’m going to miss the polish and the kind of quality I love with anything but MailChimp, and I say this as someone switching away from it out of necessity!
  • 1:04:32 As far as HTML email, on the bright side, Mobile Gmail has finally updated to at least be optimized. It’s not fully responsive, but it’s optimized so it will recognize when the text size isn’t big enough and will make it bigger. It will respect some of the responsive stuff you have if you’re coding things manually. If you’re coding things manually, make sure to set explicit font sizes in different sections. If you use em units instead of pixel units, you’ll run into problems on different things. Also, if you use P tags instead of break tags, you’ll run into problems on different platforms so just use break tags. If you don’t know what any of this is and you don’t want to, MailChimp is your best bet for responsive email design.
  • 1:05:30 Ben: For the person who’s thinking, “Most of this is over my head, maybe I shouldn’t even get started,” the bottom line is there are so many great tools you can use to make the best possible experience for the end user but you’ve got to move forward with providing value in the medium for which someone is signing up. If someone wants to sign up for an email list, your first and most important task is interacting with them on that medium. If that means you can’t manage all of that other stuff right now, that’s ok. At least get started.

What to Avoid in Your Emails

  • 1:06:20 Sean: Cory asked, “Are there any sleazy tactics to 100% avoid? What should never ever be part of the emails you send?” We could go down an endless list of what you shouldn’t include but I would rather focus on the right things and that will rule some stuff out for you. Relationship Marketing—you want to provide value and then give people a way to compensate you. Do the same thing with your email. Provide value and be there for people when they want to buy from you. That’s the time where you can close the sale. Don’t try to close the sale right up front. When someone comes onto your email list, that’s like walking into a store. They’ve heard good things about it and they think it looks pretty nice so they want to try it out. They haven’t committed to anything, they’re just checking it out.
  • 1:07:40 If you go into Journey’s Footwear, looking for a specific shoe from there, and you walk in, that’s like signing up to an email list. When you try to close the sale right there and push people to buy, that’s like someone coming up to you as soon as you walk in the door and saying, “Hey, I want you to buy this shoe right now! Come over here. I’ll check you out right now. We’ll take your credit card right now and we’ll close this sale. The shoe will be fine for you. We don’t need to know anything about you or you life. This shoe right here is what I want you to buy.” That’s the equivalent! Instead, you should get to know that person.

You should figure out what someone signs up wondering and answer those questions preemptively.

  • 1:09:02 Say, “Hey, a lot of times people come in here looking for this or this, what interests you? What kind of questions can I answer?” You can start answering the most common questions and lead them through a story. Figure out what fits them best.
  • 1:09:25 Ben: If you see someone pick up a shoe and, after looking down at their feet and determining they’re an 11.5, you can grab a few pairs of that shoe in sizes 11 through 12 from the back for them.
  • 1:08:52 Sean: I want to illustrate the difference between something like MailChimp and Infusionsoft here. With MailChimp, the guy pulls a size 11.5 shoe box off the shelf, MailChimp then goes, “I can do automation! I can bring you the size nine box and right after that I can bring you the size 10, then the size 11. Eventually, we’re going to get to your size and something will fit you, so you’ll close the sale.” Infusionsoft sees you pull an 11.5 size box off the shelf and immediately you have another 11.5 in a different color next to you. Then, after you leave the store, you get something in the mail that says, “Would you like us to send you this 11.5 sized pair of shoes?” That’s the difference in power.
  • 1:10:46 Ben: If someone is willing to invest $300+ for Infusionsoft, how much do you think they’d be willing to invest in learning to do it right?
  • 1:11:02 Sean: They actually have a required $2,000 kick-off training course, that’s how intense it is. It’s so advanced, you could have half a dozen full-time people managing your Infusionsoft account. They don’t want you to be so overwhelmed you can’t even use it, so they actually require that training, then there’s consultants beyond that.

What Do You Do With “Unengaged” Subscribers?

  • 1:11:37 Another question from Cory here, “How do you handle the ‘unengaged’ audience? If there is a significant number of subscribers who don’t even open the emails, you’re likely paying for those subscribers. How often should you prune your lists, and how would you go about doing that?” You can’t always know who are the “unengaged” people because it’s based on open rates, which aren’t always accurately displayed. Not every email client triggers an open, as far as how the clients track it. People can be reading your emails and it might not show up in your open rate. You want to be really careful of automatically deleting people that haven’t opened emails because maybe they actually have, and their client isn’t registering an open. Look at that open rate and know it’s a guess. You can be sure that a click will always trigger an open. If someone clicks a link, obviously they had to open the email.
  • 1:12:43 If someone hasn’t opened an email in six months, they also haven’t clicked anything in six months so they’re less engaged but it’s just something to be aware of. First of all, if you have a large list—50,000 to 100,000 subscribers—it’s not worth your time because, in theory, you’re probably doing something right and making money. Those are at least potential people. Even if they haven’t opened anything in months but maybe they do and they buy something, is it really worth saving that half penny on that one person? If you’re really trying to keep costs down, every six months to a year segment out the people who haven’t opened anything in the last six months.
  • 1:13:34 Send a campaign to them and say, “Hey, I’m cleaning up and I’ve noticed you haven’t opened anything. A lot of times this can be falsely measured so I want to make sure. If you really do want to keep receiving this stuff, click the link below and I’ll keep you on the list.” That link can just be a button that goes to an unlinked page that says, “Thank you! I’ll make sure to keep you on the list.” All you’ve got to do is look at the results of that campaign, segment those that clicked the link, put them back on the list, and get rid of the rest. I cleaned out about 5,000 people this way. I sent a campaign out to 5,000 “unengaged” people—who supposedly didn’t open any emails for six months—and 5% of them still stayed on. I saved a little bit of money doing that.

What Should You Focus On?

  • 1:14:34 Samuel says, “Can we rotate the purpose of the newsletter from announcing new products, teaching the fellow artist, sharing the process of your work/product, and other things? Should we try to stick with one focus area of communication with our subscriber list?” That also affects what kind of content you’re putting out anywhere, not just email. It affects how targeted you are with your blog, what you share, what you tweet, and what you make videos about or put on your podcast. What is your focus? Consistency is the most important thing. If you’re doing a few things, at least make them consistent. For example: every Wednesday you put out a video, every Friday you put out a podcast, and every Sunday there’s a blog post. It just needs to have some level of consistency, no matter how you’re doing it. Keep an eye on not getting too fragmented, in a general sense.
  • 1:15:30 Ben: The purpose determines what you’re putting out too. If your end-game is to sell a course, you might want steer it in that direction or create a new segment. Create a new place for people, who may already be on your main list, to go and sign up. I feel like you’ve done that with Value-Based Pricing. A lot of people that have signed up for Value-Based Pricing are probably already on your main list but because they want that specific information from you, they now get content that’s catered specifically to what they signed up for.

What About Popup Boxes for Email Signups?

  • 1:16:28 Sean: Matt asks, “Should you use pop-ups for your email opt-in on your website?” Pop-ups on a mobile device is a terrible experience. I will acknowledge that the conversion rate is unarguable. If you put pop-ups on your site with an email box, you will get more signups. Before someone has consumed the theoretically valuable content on your site is the wrong time to take.
  • 1:17:44 It’s like we talked about before: giving vs. taking. When is the right time to ask? When you land on a website, you’re making an immediate judgement. You’re noticing a number of things but what it really boils down to is: is this a giving page or a taking page? A pop-up is a take. It’s the Rule of Reciprocity 101:

The right time to ask for an email address is after you’ve already given.

  • 1:18:11 You should give first and pop-ups do it wrong. The visitor hasn’t even had a chance to read your content and yet, you’re asking something of them. You’re trying to take. Are you going to get signups because people want your lead magnet? Yes. Will you get signups from clueless people who don’t even know there’s such a thing as closing a pop-up? Yes, you will.
  • 1:18:37 Will you get people who enter spam addresses? Yes, you will. What are you going to see? Numbers, conversions, and metrics that tell you what you want to see and what you want to hear. It will show you this is worth doing because that’s what you’re looking for, but what do you not see? The people who closed your pop-up and read your article but they had their experience colored by an obtrusive initial model over their reading experience. What do you not hear? The people who left before they ever read your article because of the pop-ups even though your analytics showed them as a view on your page. You don’t learn that, over time, their perception of your brand has diminished imperceptibly.
  • 1:19:47 The only way to really recognize that is a decline in your engagement or sales possibly years down the line. What I’m talking about is something you can’t really measure, which goes back to the weight of your name and what people associate with your name. Am I going to get quality and value from this name? That’s not obvious and it’s not something you have metrics on that you can track. If your sales decline years from now maybe you can attribute it to that but you’re not going to know. Maybe your metrics stay the same but what you’re not going to know how much better it would have been if people would have associated quality with your name over the long-run?
  • 1:20:37 Ben: I don’t purposefully go to many websites but the ones I purposefully go to don’t have pop-ups. What if I do see a pop-up and I sign up for their email list, the next time I go back to their website, am I going to have to see that again? Is it somehow going to magically check if I’m on the list before asking me? If I feel like I’m going to have that experience every time, I’m not going to go back there. They’re interacting with you through that medium, so provide value through that medium. Don’t hustle them of to some other medium right away. You want them to leave your website feeling like they got something really valuable there and they’ll keep coming back.

The more people associate your name with value, the more they’re going to look for other ways to connect with you.

  • 1:21:41 Sean: Stop thinking about the numbers. you’ve got to stop worrying that your list has 1,000 subscribers and other people have 10,000. It doesn’t matter! Having the right kind of people is what matters. People that aren’t going to unsubscribe.
  • 1:21:56 Ben: One person who is completely loyal is worth 100 people who happen to fill out your pop-up email list and that you’re paying for. You’re paying for every single one of those people.

Train Your Audience to Take Action

  • 1:22:18 Sean: Cory was on fire today. He asks, “Should your weekly newsletter always include a call-to-action, and if so, how do you structure the email to avoid sounding just like another salesperson?” You should be training people to take some kind of action on your emails. You should do this from the beginning. You don’t want to obscure everything and not provide value in the email by saying, “Click here, click here!” The way you avoid sounding like just another sales person is by providing value every single time someone clicks. If you reward the click, they’re going to keep clicking. You want to provide value upfront and then provide value when someone clicks.
  • 23:24 I provide value in the form of podcasts or blogposts and then provide more value when people sign up. They sign up for the Community and I overwhelm them with value. Don’t hold all of that back and make people have to jump through hoops to get it. For example, if I send out an email with a lesson on lettering, maybe I talk about it in the email, but I provide a video. They can click and they get a whole lesson. Provide a tutorial or some kind of overview of something—teach them something—and say, “If you want a template of this, download it here.”

Train people to expect value every time they click and then deliver on that.

  • 1:24:27 Ben: I like that because the focus is on giving away value. People worry that if they give away that much value, they won’t see that much value come back to them, but the reality is you see value come back to you by giving it away. It comes back to you by many factors. The more you give away, the more you’re going to get back. You have to get out of the mindset of, “If I give too much away here, I’m going to spread myself too thin. I’m not going to get a good return on my investment,” and think of it in terms of the long-term value of your name. What is that going to be worth five or 10 years from now? When you’ve been consistently providing value and giving it way, that’s going to come back to you.