Episode 15 – Email Autoresponders with Terry Dean

Terry dropped additional nuggets of sales and marketing goodness in the EXTENDED Interview. Be sure to click here to access all of our great extended interviews, transcripts and more within our Insider's Club.

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Expert Insights on Email Autoresponders

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Terry Dean started his online business from scratch in 1996. He went from delivering pizzas for a living to building a million dollar Internet business, promoted primarily through the Internet. Within a few years, he was also consulting with home based businesses, local companies and million dollar corporations. His original company and websites were sold in 2004, and he founded MyMarketingCoach, LLC, which is dedicated to coaching entrepreneurs in the 10 key principles of success in business and life.

Podcast Transcription

Brian Basilico: All right, everybody, welcome to Mymarketingmagnet.com and I'm your host, Brian Basilico. I am so super pumped to have our guest today, Terry Dean. Terry is an incredible internet marketer who's got a great story and Terry, having you on the show teaching just about autoresponders to me is like having time with Wayne Gretzky, and he only teaches you how to tie up your hockey skates.

Terry Dean: I think it's better than that at least because autoresponders and email in general drive a vast majority of my profits and all of my clients' profits.

Brian: See? I love that. Well, tells us a little about you and your story. How did you get into internet marketing? I understand that you started out as a pizza delivery guy first. Is that right?

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Terry: I did. We're talking way back in the stone age of the internet when dinosaurs run the internet in 1996 and I first heard some stories about people succeeding online and it was really interesting to me because at that point in time I was delivering pizzas for Little Caesars for $8 an hour and I have tried a lot of things, ways to start my own business. I have tried doing direct mail, I have tried door-to-door sales, I was a network marketing failure going somewhere to happen with a bunch of junk in our basement at the time, but still I had a support of life who said, “Yes, you can do this. I know you can do this.” I heard the stories about the internet that went out and bought my first PC at Best Buy. It was like $2,500 for a PC and monitor that was a Pentium 75.

Brian: I remember those days, yes.

Terry: It was that paper weight. I taught myself to use the PC and got online and basically my very beginning of market online was I got a hold of some materials by Jay Abraham and Gary Halbert like some of the real low-cost materials that they had and study basics of direct marketing. I said, “Okay, what do they teach in direct marketing and direct mail? How will I apply it to the internet and what can I do online with it?” So then I got a hold of eight licenses to some VHS videos that were really dating ourselves. There are VHS videos, especially self-help, things like Mark Victor Hansen, things like this and I started marketing online on the old CompuServe Boards and it's kind of funny because I was thinking about this today as I was writing some emails.

In some 1996, I started with content marketing. The method has changed, the [inaudible] have changed, but the overall strategy stayed the same. Back then I posted content gave value on some of the CompuServe Boards and ask them to contact me if they wanted to get a free report, and if they contacted me, I got them on an email list, and began publishing more content, and selling those videos to them. We follow almost the similar process today. We just have a whole lot better tools for it.

Brian: Wow. Well, I got two questions real quick for you. Number one, did the VHSs come in Beta too and I remember you brought me back to the days when they had a Commodore 64 and trying to learn how to program that thing. It's like man, when you're talking about CompuServe, that's way back there.

Terry: It is way back there and no, my videos didn't come in Beta also, but the fact that I know that beats me also.

Brian: There you go. That's awesome. Tell me about the early days of email marketing? What was it like and how do you see it evolving, or how did it evolve over time?

Terry: Well, originally, I had to use old software that was originally used by some of the spammers online who first came on online and were just doing the spam. I had to use some of that software that ran from my own computer. We didn't have autoresponders and I feel like we have walked up till both ways back in those days, but we built a list from this and would email out and I would email out one a week. The first few years is funny. My subject line I kept writing was, “Web gold is here” which is the title of my newsletter, which is a really stupid subject line, but have worked anyway because they built a brand there that I kept sending out the content weekly to my list.

What happened is the same thing that happens now, which is we send out content, we make sales, we run specials and I really started getting a large reputation online. It was a little bit later on, about two years into my business online as when I first started creating a lot of my products of teaching others about internet marketing because I have to sell all those videos. People started saying, “How are you doing this? How are you making a living online?” So it was just natural to start teaching some of that and then you move forward maybe about another two years or up to about 2000, and I got invited to start speaking at a lot of internet conferences; and at the conferences I started issuing a challenge that they would see me at the conference, and then I'll email and I would produce at least $10,000 over the weekend from an email sent to my list.

Brian: Wow.

Terry: I did this at multiple conferences, the biggest one being $96,250 for the weekend that was produced from an email to my list. Those were some exciting emails sent out. I remember one of them that was really funny. It wasn't the big one – I wish it was, but one of the other ones, which was I think we did somewhere in $30,000 range overall for this and I had to send several emails, but I sent an email and I actually misspelled my own domain name on the email that was sent out on Friday. We still had about 100 orders at lunch time from the email from people who figured out that they had to spell it correctly because they knew me and they knew my brand, and then I had to send out another email and that one said, “Hey, okay, I screwed up on the link. Here is the correct link to come purchase.” That's really funny when you're in front of a crowd and you send out a link that's wrong.

Brian: Oh, man. We've all done it. A matter of fact I just sent an email to somebody who spelled their name differently from the normal Nicole and it's like I had to go, “I'm sorry.” I think everybody has done that and gets it.

So from an email standpoint today, what kind of tools do you recommend? What are the de facto tools, or your go-to stuff?

Terry: There are so many good autoresponders systems that I don't want to sit here and say, “Hey, you need to use this autoresponder. You need to use that one.” There's Aweber, there's GetResponse, there's Infusionsoft, there's even systems that run on your own server and which one do you run, I honestly don't care. I have clients who use all of the ones I just named at this point in time and are extremely profitable with them. The key is all of these tools give you the ability to let the entire system run inside the email. All you've got to do is concentrate on producing good order, producing emails and content that goes out to the list. I'm sure we're going to talk about some of the methods I use for that, but it's all about what we're writing, and who we're speaking to.

Brian: Absolutely. I know a lot of people on this podcast and the others, they have a constant contact, or eye contact, email contact, Aweber, whatever it is, they're just using it as a broadcast email system. They don't really understand what an autoresponder is. So, can you talk about why you want to use that and what it does?

Terry: In my system, I end up doing both. So, I do both autoresponders and broadcast. All my clients do the same. The reason we use autoresponders initially in a sequence is you actually create a sequence of emails that when somebody first joins your list, they're going to go through the sequence in order. If they join today, they're going to get email #1, tomorrow they might get email #2, down the road they'll get email #3 all in order. If somebody joins six months from now, they get the same order so they're still going to get the first email, second email, third email. That's very important to install an autoresponder series. I have every single one of my clients, has an autoresponder series even if we do a lot of broadcast. The reason is you want that first sequence to make a connection with the prospect, you wanted to make a connected with you and let them know who you are.

Basically it's almost like we're running the re-runs of they get to know who you are. A good example is in the autoresponder sequence, somewhere in the very first week, I always have every client produce an origin story. So their origin story and the origin story simply means why you're in this business? How did you get started in this business? Why did you choose this business? What are you so passionate about in this business that you have to talk about it? We get that into the first week as an email somewhere to make a connection with the prospect and let them know why we're there and see if we only sent broadcast, that means somebody who'd come into our list would miss out on that personal connection and that plan that we make over those first few weeks or even first few months in the autoresponder sequence.

Brian: So the autoresponder sequence, if somebody signs up for one of your lists, then you set that autoresponder sequence to go in that and not just people that are buying products who are doing certain things. Is that right?

Terry: Yes. Buying goes out to everyone. So, everyone who comes on to the list is going to get the initial autoresponder sequence.

Brian: That's awesome. So, what is a great autoresponder sequence? How many are you doing? How often do you do them? What kind of things?

Terry: A great autoresponder sequence is one that produces sales. That's the best way to define it first.

Brian: Good point.

Terry: I have to make that definition because a lot of people look at other stats and we can use other stats to help gauge our progress and compare one email to another, and some of those stats we might look at are open rates, or click through rates, and things like this, but at the end, the only thing that really matters is are we producing sales or are we not? And are we increasing the sales or not? I don't care if you have an 80% open rate, if you're not making any sales, it doesn't matter. Where like here is a stat that everyone looks at and it's totally wrong to even be thinking about that much and that's the unsubscribe rate.

In many cases, you'll find that good producing autoresponder sequences that make a lot of sales might have a lightly higher unsubscribe rate on those. On those, you might have a little higher unsubscribe rate and it doesn't matter if we're producing buyers. Something I always ask every client if they come back and they're concerned about their unsubscribe rate, ask them, are they buyers that are unsubscribing? Because I'm concerned if we start losing the people who are giving us money, but if they were just people who joined our list and they drop off for whatever reason, they're not passionate about the subject, they're not buyers, then that's just to be assumed because we're sorted and sifting through our leads in choosing the right ones. Now how do we do the sequence and how do we set it up? What you're going to end up doing with most autoresponder sequences is – just to give you a comparison here, I have some clients who are on the short end, the autoresponder sequence might be 10 emails total. Like one of my is 78 emails right this minute.

Brian: Oh my.

Terry: I have a client that we have five years of autoresponder emails in his sequence.

Brian: Wow.

Terry: There's a variation here. What you'll find with this is that with most of these, I start off the autoresponder sequence, it depends on the market that we're in. For most of these markets, we'll start off the autoresponder sequence somewhere around three emails a week on average. That means one email immediately, we'll have two more of that first week and generally on that process starting out, and we might change it around and move. To give you an example, my sequence right now is right at four emails a week. It's not many as you send out because I took it up to it was like to six and I'm seeing the unsubscribe people, the sales weren't doing quite as well, I pulled it back down to four and four was just what seem to fit mine best.

Now, that might be a little too frequent for a business-to-business market of some types, so if we have a real estate agent who is listing it too and say, “My audience does not listen to me four times a week.” Well, that might be true unless they're looking for a house right now, they might want to hear from you a lot. Depending on what market you're in, we might move that back to once a week. So you could say, once a week is the minimum and generally daily is the maximum and we vary it by the market that we're in.

Brian: Dude, that's fabulous. Outstanding stuff. Thank you very, very much.

Terry, what are some of the most common autoresponder mistakes people make?

Terry: Well, some of the common mistakes that they make is let's take about the two big ones, which is falling in a ditch on either side of where they should be. The first ditch that they fall into is they just provide free content. That's all they give away as a lot of value, a lot of content with almost no pitch whatsoever and you would think that, “Hey, that would work well.” But my experience of being called in and paid really nice fees to help, at times is a list like that who's been going like that for years, is the hardest list to get to convert. Those are actually like my nightmare situations where I go in and tell the client beforehand that, “This is going to really suck – what we're going to do. You're going to have a lot of pain over the next month as we try to get this list to buy something.” They're going to tell you that they hate you, they're going to tell you all kinds of nasty things, you're going to have higher unsubscribe rates than you've ever had in your life as we go in and start trying to sell to them because basically, you train them. Then all you do is send the free stuff. The moment you try and sell something, they're going to get upset with you. That's a mistake to only give free content.

Then the other side is to just sell. That's a whole total mistake, too. It's all you're doing is sending sales pieces out. That's going to do the same mistake. Let me give you a description that I like to tell everybody. I like literation and I'm going to give you two different ones here. First one is the 3 Cs. I want you to send out Contrarian content from a confident Character Consistently. I want you to send Contrarian content from a confident Character Consistently. Contrarian content means that we're not just going to send useful content. Yes, the content we send is going to be useful, but it also needs to be different than what they're normally hearing. We need to look for the conflicts and the differences in the market. I'll use it again, that I look for the 3 Ms which are the Mistakes, the Myth and the Misconceptions in my market. What are the mistakes, the myths and the misconceptions in your market that you can talk about and that's what we're going to come up with for our contrarian content. We're going to talk about these in the emails that we send out, that's the content we're going to be providing where it's going to come from a confident character, which means you're going to have a persona even if you're a little shy, even if you're a little laid back.

I'm actually an introvert which people don't see because I've spoken and I do these interviews, I can seem extroverted for a while and as I'm talking to an interview like this, but then I'll go often to my cave and hide for a little bit after an interview or a series of interviews. What you'll do with a confident character means you stand up and you basically position yourself as the authority and I'll review emails regularly from clients you added in what we call “weasel words,” it's your email, we're going to remove this “actually” that you added or “probably.” We're going to remove that, we're going to remove this weak little statement you made here, we're going to make it a nice declarative strong statement and I go through and look for things like this because you need to have a persona that's strong, that's in charge.

A good example of that is I have a friend who's an awesome copywriter named [Doberman Dan] and I always joke with him that he has a person that looks like a drill instructor that's about ready to beat you up at all times and that's the tone he gives that, “You need to do this, or else…” He's a really laid back type person, but that's the persona he puts out and it's the same thing. We all have our positioning that we're doing and who is your confident character, who are you? I almost like to like in this, too. In my own daily life, I'm this mild-manner Clark Kent, but I'm a superhero online and that's the persona that I'm going to have throughout my emails and that we need to be consistent with the content and the message that we're sharing.

Then I told you there was a second set of a literation here, and that's going to be the 3 Es, which is we want to Entertain, Educate and Earn. That means in the emails that I'm sending, I always look for, “Are we doing something that's entertaining?” As a hook, a lot of times for us, these are going to be stories. Are we telling a story? Are we making a connection? Are we having some fun with our emails. If we're not having fun writing our emails, nobody else is having fun reading them, so we try to have a little fun with entertainment, then we do something for educational. In every email, there's something that's going to have value. You could call it the moral of the story. I'm thinking back to when I was young and we watch cartoons all the time, they always have the cartoon and they have this little 30 seconds at the end, “And here is the moral of the story.” Well, that's what we do. We have our story, we have the moral of the story that we tell that's our education and then we have some way that we earn, you make a connection to what we're offering at the end of the email.

So, I just basically gave you several models for creating the email right there.

Brian: That's great. You are so energetic, and so well-versed and the two things that blew me away is in one interview I heard you said you were not good at direct sales, you aren't a good sales person and you tell me that you're an introvert blows me away. It just doesn't sound like who you are. It's amazing. When you turn it on, you turn it on great.

What are some of the best practices that you can give people as far as setting up their autoresponders in doing this? Do you go back and look at them often? Do you do A/B testing? What kind of things are you doing with autoresponders as far as the best practice goes?

Terry: Well for the best practice, again, I keep pushing back to the content side of it. Not as much on the technical. A lot of people will try to get stuck in the technical elements. I do go back and scan through and probably not as often as I should – let's give it another admission here. Do I go back and examine my own email autoresponder sequence as often as I should? No. I probably don't because I'm always coming up with some other new project to work on at the time. I think that's pretty much across the board for entrepreneurs, but should I go back more? I should.

For testing, I do test different subject lines, I do test different approaches for the email. There's kind of a problem with testing emails and that is unless you have an absolute massive list, it's easy to test subject lines. But it's a little difficult to test emails because I find emails almost like a daily contact or an ongoing contact. So the email I sent today might produce sales for me on Wednesday for example. We'll just say it's a Monday and I'm sending out email on Wednesday. The email I sent today might produce the sales on Wednesday, it might continue on. If you kind of like saying that we had a daily radio show, we're going to test which radio show is the absolute best.

But we can see how many people show up, how many people stay on the whole time, we can look at things like that like open rates, and clicks, and sales, and things like that, but it's a little limited on doing too much and thinking that this split testing really works that well for it. But you should do some split testing with subject lines and then they give you some subject lines, concepts that work really well is you want to look at your subject lines and think about benefit plus curiosity, “Am I giving a benefit plus curiosity in my subject line?” That's the easiest test you could ever do on a subject line, is there both a benefit and there's curiosity? Because you want to get people to open up.

Let me just give you some examples of email subjects lines that have done really well for me over just the past six months.

Brian: I'd love that. Thank you.

Terry: Okay, “30-day Guide to Online Profits” appears to be one of the biggest ones just from the last six months; “When to Say Goodbye to Your Boss,” which you'd see that sounds like a little bit of a story there. It's the entertaining concept you can see. We've got “The Millionaire Expert” and you'll notice how short these subject lines are. That's something you'll often notice. If you can get the benefit curiosity in quick, you're usually much better off in that direction, join the business coaching revolution, did extremely well here, how to attract dream clients, but most of them are a benefit-type statement. There is advanced secret to multiplying your profits that did extremely well.

Even “3 Quick Time Management Tips,” those were the top open rates specifically for the emails. Not necessarily the best sales rates, but those are some of the top open rate ones. You can say that they're all short subject lines, they get the benefit in, they get curiosity in some way. Just for example like the last one I read, “3 Quick Time Management Tips,” the benefit obviously is the time management tips and the curiosity is three to it. There's three time management tips. I find numbers often create a little bit of a curiosity factor because people are like, “Hey, I know one or two of those tips. Let's see if I know all three of these.”

Brian: Right. The same thing works in blogging. So how long is an average autoresponder? Are you writing 100 words? A thousand words? What's the sweet spot for that?

Terry: Most of my autoresponder messages are between 300 and 600 words. I actually tell my clients to go on the lower end of that. I'm just kind of wordy. That's not necessarily the best thing to be wordy, but the 300 words and up is [inaudible] because you need enough as you can get a little bit of a story that you can teach them the story. Like I deal one-on-one with my clients also and there are some clients that while I help them with a lot of other things in their business – I can't help them a lot with other things, there are some clients who come to me that all we do with all of our discussions and every time we speak is we help rewrite some of their emails. We've been doing that for years just because they see the success and how much more they make and we do this with their emails.

But what I end up looking for is we end up telling as often as we can some type of story from their life or some type of story connection, and that takes a little bit of time to do for the emails. You're talking maybe 300-500 words. As I said, minor a little bit on the long side, about 500, that's because I usually try to get a little bit more content that's even necessary into my emails. That's kind of the length we're talking about. You might think and say, “300-500? That might take a while.” It doesn't really take that long especially if it's a story you're passionate about. Here's another quick tip for doing autoresponders.

It's kind of difficult to just sit down and say, “Okay, I'm going to write an email now.” That can be a little bit difficult. What works much better and I do this and most of my clients do also, is we keep a notebook of little ideas that we can tell in an email, little stories we can tell in an email. If you just keep that little note, then it makes it very easy when you turn around and write an email. An example of one that I have was like I went to the optometrist and while at the optometrist and I mentioned something about how bad everybody drives around here, and he off-handedly said that we have so many drivers here who are actually legally blind. They come into his office and he won't let them drive until they get glasses. I'm like, “Oh, that is so much an email. I need an email on this.”

Brian: That's awesome.

Terry: I turned it into a subject line of, “Blind drivers and broke gurus” was the subject line.

Brian: I like that.

Terry: “Blind drivers and broke gurus” so I could talk about how the fact that all these blind drivers were going to the optometrist and I said it's the same thing online. We have all these broke gurus because I've met quite a few of them that promote, “Here is my product. Follow me on this product.” And we find out in the background that they're actually broke and don't have any money. So we got “Blind drivers and broke gurus” running around.

Brian: That's great.

Terry: Always be looking for a story and take notes whenever there's a story to tell for it.

Brian: Yes, and I love to use Evernote. I've got it on my phone, my iPad, everywhere. In that way I can gather those things and just slice and dice and put them in. So yes, I hear you. That's awesome stuff.

Now, this is kind of a loaded question, but it's one of those things that I have to ask, is how do you measure success? But let me add this: not everybody is selling online products. They're trying to communicate to potential customers, they're trying to do branding, they're doing different things with this. So, how do you measure success in those various different ways?

Terry: I would push that they want to have something that they're tracking for. If we're making online sales and that's what we're tracking, the online sales, if we're wanting to generate leads for a business, then we're going to track phone calls. We're getting phone calls into the business from our emails that we're sending them. We're getting people who sign up with us or whatever we're doing because you have to remember for the clients, everybody I worked with is trying to produce something in the business like I've worked with a couple of charities. Well, what does a charity track? They track donations. They want donations in the charity, the businesses wants leads or they want sales, they want phone calls, they want the phone to ring.

For example if you're working, anybody who's out there who works with local business owners, another thing that I do is I train business coaches and the business consultants who do local services for business owners and the big thing that I have to teach them is the fact that they have all these things that thinking about, “Why do AdWords?” Or, “I can help them do this.” All a business owner really wants is they want the phone to ring online. That's what we got to do and that's what I would be tracking. In their case is, “Are we getting the phone to ring from our emails? Are they coming in and bringing in the coupon that we might have gave an email? What are we doing for any type of response?”

For branding for it, I hate to look at branding separate because the way I like to define a brand is basically a brand is a shortcut to making a buying decisions. You look at big brands, you look at Coke, you look at Pepsi, you look at any big brand out there, basically all they've done over the years is they've connected good emotional feelings about their product to create a shortcut to a buying decision for you. So you don't have to sit there in front of the store, look at all the different products and say, “Hmm, which one should I buy? I need to read all the information on all these products.” No, that's not what you do. You just have a shortcut to a buying decision.

It's the same thing online. As we're doing these emails, we're going to automatically produce some branding effect. If you have people who have been on your list for six months, a year, you're going to have a portion. Not a large portion, but there's going to be a portion of your list the moment you release a product, the moment you announce something for sale, they're going to jump over and they're going to buy it without reading anything, or watching a new video, or anything else. An example here that you can see – I'm moving out of email but it kind of defines here – is let's say that you run a video sales letter and you run into a cold list, you'll usually do better with a cold list of having the order button pop up somewhere later in the sales video.

If you ran that same video salesletter to your own list, you might just find that you have better success if the order button is there from the very beginning because you have a portion of your own list who's just going to buy immediately without even watching anything. The reason is branding is a shortcut to a buying decision.

Brian: That's some great advice. That's the thing that a lot of people don't think about and what I see is people just create email list and they just are broadcasting one thing to everybody rather than segmenting and thinking about them differently. That's awesome advice. Speaking of which, I know that you have a system that helps people to better understand autoresponders. Can you tell us a little bit about that?

Terry: That's the course Autoresponder Alchemy. This course first of all talk about one of the big bonuses that come with the course and the bonus that comes with the course is what I call the million-dollar emails and I took one of my email sequences, which had 80 emails in it and I actually went through and examined each of the emails and templated it. So why did I do – I basically went back and re-examined why I wrote the email exactly the way I did because I've done this over the years and I said, “Okay, here is the template. Here is why I did this. Here is where we put this. This is why I put this here. This is why I put this information here.” And I basically broke out the entire 80 emails giving you all these different types of emails as templates. There's the original email, there's the template that you follow to give everyone a step-by-step system to model emails.

The reason I've seen that is so important, is when I first started online, is I have really learned copywriting by modeling other people's salesletters. I learned from again Gary Halbert and John Carlton and Jay Abraham – a lot from John Carlton back then and I would sit then to write a headline. How did I write my first headlines? I would pull out really good producing headlines and I've modeled them. I wouldn't copy them word-perword, but I've modeled the concept of it. So I created a whole email sequence that you could do the exact same thing to make your emails much quicker and easier to use by following my templates. So not only can you model them, but you get to see step-bystep why I did them the way I did and even in some cases, it's fill in the blanks, “Here is what I want you to put here. Here is what I want you to write here. Here is the content that you want to put here for this and this is what the content is about and here is how we're going to turn it into a sale.”

Along with that, that's the bonus that comes with the course and in the course itself is a step-by-step system over a total of eight weeks teaching you how to write the entire autoresponder sequence and to do email broadcast, and even to integrate such things as a limited time special inside of an autoresponder because a lot of people don't know that, but you can build a limited time special such as a special that's only good for the next three to four days right inside of an autoresponder sequence itself and it will run correctly for everybody who comes through.

Brian: Wow, that's awesome. So if people want to contact you and get to know you better, what's the best way for them to get a hold of you?

Terry: They could contact me over at Mymarketingcoach.com. Also, which of course there's a nice free gift on the top of that website for that.

Brian: Awesome, Terry. Hey, man, this was so great stuff. It was really educational and that's the only way I could say this. Man, I learned a lot through this and I really appreciate you and your time talking with me and my audience today.

Terry: Excellent. I'm glad to be here. Brian: Wow, that was some amazing stuff on internet marketing. Hope you guys enjoyed it as much as I did. Make sure you check back next week with us because we're going to have another great internet marketing expert interview. Till then. Rock on.

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