Bill McCloskey on Email Marketing Best Practices, Creating Passion Groups, Jazz Clubs and Dolphins
Susan Bratton

Episode 88 - Bill McCloskey on Email Marketing Best Practices, Creating Passion Groups, Jazz Clubs and Dolphins

Bill McCloskey sits in the celestial cockpit above the world's commercial email traffic at Email Data Source. His company collects competitive intelligence on over 40,000 email marketing campaigns a day (1 million a month).

Hear Bill's analysis of the latest trends savvy marketers are using to get you to buy. Learn the #1 idea you can model from the country's best marketers to increase your success. Find out what clever techniques Harley Davidson and Stoli Vodka are using to increase the 'bond' to their brand.

Bill gives his expert opinion on the leading email services; his POV on single vs. double opt-in and the always classic question of "text vs. html?" His answers will surprise you.

Bill and Suz talk about channeling inspiratoin, the muse and the original meaning of a demon. A very creative man, Bill has personally launched myriad of special interest groups and exclusive online forums. Find out why they are a salve for his shyness and what you need to know to effectively launch your own passion group. Yes you can.

Now imagine a dolphin sipping a martini at a jazz bar. Why? Listen to this interview from an email maestro to find out.



Susan Bratton: Welcome to Dishymix I’m your host Susan Bratton and on today’s show you’re going to get to meet Bill McCloskey. Bill is the chairman, co-founder and chief evangelist at Email Datasource. I’ve known Bill for a dozen years. We grew up in the internet marketing world together and he really has an interesting perspective on the world of email marketing and he’s going to give us a lot of very insightful tips and techniques that we can apply to our business today. We’re also going to meet him just in general because you know this is Dishymix and Bill is just a neat wonderful guy who has actually don’t so much to help the industry that I think he might provide some inspiration for you and some things that you might do to take yourself and our industry to the next level. So let’s welcome Bill on the show. Welcome Bill 

Bill McCloskey: Thank you Susan it’s great to be here

Susan: I am so happy to have you here Bill. Thank you so much and the first thing that I wanted to let our listeners know about is your business because it’s interesting and there’s a free trial that anyone listening can try which I am signing up for. So tell us about Email Datasource

Bill: Sure, it’s a company that I started back in 2003 to sort of fulfill a need that existed out there which was really a lack of actionable intelligence around email, and so what we did was to start archiving everyones email marketing campaigns and seeing if we could draw trends and ideas out of that data and we now have the largest repository of email marketing in the world and our clients use it to learn about what their competitors are up to, who they are partnered with and even monitor themselves to see how they are appearing in email and it’s a great resource to actually see the power of how my email works in driving traffic and you mentioned the free trial we have a new product called “alerts” which is just like google alerts and you can sign up to be notified every time an email matches some criteria that you set up and I’m sure that we’ll provide a link so that people can go and sign up if they like

Susan: Definitely, Give us a tip, when we set up our free email alerts, What’s the best way to do it? We’re going to track our competition; we’re going to see what our #1 competitor is doing as far as sending email out to their customers right?

Bill: Absolutely and there are a number of ways that you can set it up. You could set it up so that I want to receive all of the emails that are going to a particular website. That would include all the partners all the in-house lists any mention that has a link any email going to a particular domain you could monitor all of that or you just might want to monitor a keyword you may want to monitor your own brand so you could monitor at any time a particular keyword a phrase a name a brand is being mentioned in an email and I think that one of the most powerful aspects of it is to be able to monitor your IP address and all of the IP addresses around yours. IP addresses can be blocked even if you have a great reputation maybe someone who is emailing from the IP address just down the block from you has not such a great reputation. An ISP might block all of those email addresses and this tool allows you to monitor that entire block of IP addresses.

Susan: Wow that’s something I would have never thought of thank you. So you get to look at a lot of email and you are

Bill: yeah about 40 thousand everyday

Susan: *laughs* Personally. Here is what I want to know what is the #1 piece of advice you can give us if we are doing email marketing what is something that you think is a really good best practice that maybe we all haven’t figured out yet that could fundamentally increase our success rate in terms of driving revenue

Bill: I can sum that up in one phrase, A good welcome letter. So many marketers forget that the #1 email that is opened by people that sign up for their lists is the first email that you send and if you provide a great welcome letter you can begin to brand yourself , you can explain how you can begin that relationship. You can make it an insider’s club that they are excited to receive and you can provide all sorts of ways to do posts list segmentation or signup segmentation. So a great welcome letter is the #1 thing that you ought to be doing.

Susan: Text vs html where do you land on that?

Bill: Well, things have changed and the answer that I would have given you a few years ago is not the answer that I would give you today. So many browsers have the graphics turned off by default these days, so it’s not really text vs html right now it’s really making sure that if those graphics are turned off that your email looks good anyway. You have to be able to do both in the same email so you design a good html email but you have to look at it as if those graphics were turned off and it’s still got to be compelling and it’s still got to look good both ways. So you really need to design for no graphics, assume that no one will see the graphics and still create a compelling message.

Susan: Is there a tool that allows you to do that well?

Bill: Well there is a number of different tools out there will certainly allow you to see what your email will look like in various environments, “Pivotal Veracity” is probably the leader in that space so you could
Susan: What’s it called “Pivotal Veracity”?

Bill: “Pivotal Veracity” They have a tool that lets you look and see what your email will look like in AOL in Yahoo even on a blackberry and it allows you to really see how your clients are going to see that email and it may be surprising to you when you finally see the results of that.

Susan: I noticed that big brands use very well formatted email and small companies or individuals or information product marketers use text is there one that’s right? Like if you’re trying to just sell your product online maybe with a landing page and some auto-responders, is there a better way to do that? Is text the default because they are not sophisticated or is it the default because it works better because it has a more personalized feeling? This is more attitudinal I think a question too isn’t it?

Bill: well its also a matter of what audience you are trying to reach. If you are trying to reach a technical for the most part they don’t like to see a lot of graphics and things like that. They like a plain simple message so if you are trying to reach that audience you really need to use text and text is going to be a lot more effective for you. If you are trying to sell a luxury brand a Lexus car, you want to sell some great retail items like a fur coat or even just jeans that look good, well graphics will make a much more important statement when you are dealing with an audience that is interested in retail products. So you first have to look at who you are trying to address and what they are going to be interested in, but there is nothing per se that says graphics or html is better than text. It’s what the message is, how compelling it is and that can be a great text message or it can be a great html message.

Susan: what about email copywriting, what’s the latest and greatest in your personal analysis of what makes good email copy.

Bill: Well its funny that you mention that because I can tell you that one of the things that bothers me is when we as an industry assume that our clients understand the inside baseball language that we use and a great example of that is the term “Cyber-Monday”. We all talk about Cyber-Monday and I think that that’s a general term everyone out there knows so I was very curious to monitor the email campaigns that came out promoting a Cyber-Monday sale and in almost every case anyone who put the term Cyber-Monday in their subject line received almost no traffic. Its almost as if the term scared people away.

Susan: I’ve never heard it and I don’t know what it means.

Bill: Well Cyber-Monday was the great retail term which is “Black-Friday”

Susan: Yeah

Bill: Which is the day after thanksgiving because that is when retailers went from the red to the black traditionally, so it became known as Black Friday. What they found was that especially at a time when most people accessed high speed internet at work the Monday following Black-Friday, it was often the big spike day for internet businesses and so that became known as Cyber-Monday. Black-Friday and Cyber-Monday and you’re exactly right, you didn’t know what that meant. Well so many people don’t know what that means and yet so many retailers are so convinced that everyone is aware of that term that they used it as a way of promoting an email campaign. None of those messages worked; everyone who had instead promoted a simple one day sale on the Monday after thanksgiving did much better.

Susan: what else works in copywriting? What gets people to take action?

Bill: Well, I can tell you some of the emails that I’ve looked at recently that drive huge spikes in traffic are just what you’d think they would be 50% off deals, one day sales, and special year end clearance. Things that are very simple and especially today go to peoples bottom line dollars. People want to save money. It was interesting to note that traditionally around the holiday season we see large amounts of people going to websites at the early part of Christmas or at the early part of December into the second week and then slowly slowing down until the 25th and then there is often a modest spike afterwards as people want to pick up bargains. This year there was almost no traffic up until the 26th and the 26th was the biggest traffic day on the internet and people who took advantage of that idea that people were looking for bargains did extremely well, people right now are hunting for bargains and they are hunting for ways of saving money. So things that play into that idea do extremely well in email.

Susan: What about if you are not interested in discounting your product but you are following up trying to get someone who has expressed interest to actually make a purchase?

Bill: Well, the thing that works really well and we’ve seen this in some recent (?bodgads?) and some other campaigns, Harley Davidson for instance did a six part mini-series campaign. All of these things were geared to making people feel like they were part of a private club, that you are inside the store, that you are going to learn about things that happen before anyone else does. You want to make your inbox seem like it’s the first place that you are going to hear about new things. And if you can create that sense of an inside community, a private list, a private club and make it exclusive where there are offers that are only offered in the email campaigns that are not offered anywhere else you will find tremendous loyalty and a lot of people that are looking for those emails to come into their inbox every week.

Susan: Thank you for that, and I have another question about, I guess it’s not really deliverability it’s about opt-in. I noticed that there are a lot of email marketing services out there, if you have any recommendations for services that you think do a really good job I’d like to hear that first and then I have a question that follows that about opt in.

Bill: sure, well certainly the big areas that people need help in is in the delivery of their email.

Susan: Right, its funny because I almost asked the deliverability thing and waiting until we talked about this to bring that on.

Bill: Yeah, and so you know that’s one of the #1 things that people look at when they are trying to find an email service provider to help them. You know people when they first start out with some of the lower end products or try to do it themselves even through their outlook, but pretty soon that becomes unmanageable. You need to manage the opt-out process, you need to make sure you are CAN-SPAM compliant, a lot of rules and regulations and a lot of bounce processing hat you need to take care of and its much easier to find a third party that is going to handle all of that automatically for you, So when you’re out there searching for a good company to partner with, you want to look at what is their deliverability, How well do they get into the inbox, do they have additional services that will help you as you grow or are they just a very simple service so you may start with one service and as your needs grow and your need for strategy and more handholding increases you may find that some of the other services are more appropriate for what you need, but you can get started with companies like  “icontact” and “Constantcontact” as low as $10 a month and then there are other great services that play more into the small or medium sized businesses like “Exact Target” and “Silverpop” and other people out there so a lot of it depends on where you are with your company and where you are with your lists and you need to sort of evolve as your list evolves.

Susan: Got it, all brands that I’m very familiar with and get a lot of in my inbox so thank you for that. The single versus double opt-in, I’ve noticed that a lot of these companies that you mentioned maybe the “iconact”s’ or the “Aweber”s’ if you are starting out and you are trying to do email marketing, and you have a list you have a database already. You actually can’t put that database into that email system, you have to send an email out and get them to opt-in, double opt-in again where the email goes to their inbox and they have to click on it and confirm again. Do you have to go through all of that are there better ways? What are your thought on this whole opt-in or double opt-in?

Bill: well that’s funny that you would mention that because this week I started a major controversy around that whole very subject.

Susan: Wow, I didn’t even know.

Bill: So I just wrote an article for “ClickZ”, the title of it is “ You Really Really Want to Receive My Information?”. Its basically stating that a single opt in is the way things should go, double opt in is an unnecessary burden and will definitely decrease the number of clients that you are reaching out to. I also delivered that in a debate at the recent “Email Experience Council” meeting this week in Phoenix and I think that the vast majority in that audience agreed with me that the single opt in is certainly the way to go. The kinds of things that double opt in is supposed to do can be handled very well in a welcome letter, making sure that the people know that they have been signed up and if for any reason they didn’t sign up then they could click here to unsubscribe from that list. The fact remains that if you do a double opt-in your list going to suffer there are so many ways that that double opt in message may not be seen or received and the people that are sending out double opt-in emails often do a very poor job of it. I’ve shown one example where the double opt-in message never even showed whet the list was, it just said “someone opted in to my list Click here if you really want to be on it” and never a mention of who they were, so not only do people do the double opt-in poorly but as far as I’m concerned they shouldn’t do it at all

Susan: We’re going to go to a break so I want to get one more good thing out of you before we go. I really liked that #1 thin that some marketers are doing really well but most people are doing poorly and that was the welcome letter. What’s the #2 thing that you see as a best practice that more people should adopt?

Bill: Well, I’d go back to something that I talked about earlier. Its making the inbox a special place that’s really the #1 thing you can do to have a successful email campaign. You need to put thought into yur campaign it cant be just a reiteration of just your print ad or anything like that if you want to have people respond to your emails, if you want to have people read those emails then you need to make those emails special and you need to make the unique against any other marketing channel that you are using. People have to know that they are going to receive something in their inbox that is special that is early and that is just for them. If you do that then you create that kind of insider’s club, I think that’s really the #1 key to e successful in email marketing.

Susan: Are there any particular styles or language patterns or ways that you can convey this insider connection?

Bill: Oh sure, I mentioned some of the interesting campaigns that I’ve looked at recently. There is a “Stoli” Vodka campaign where you receive a private invitation to a hotel, so they set up this Stoli hotel which is only done on a short period of time and you are only notified of it through your email account. You show up and you get to try all of the latest brands, only you get to show up because you’ve known about it since you were smart enough to sign up for their newsletter. I’ll repeat the Harley Davidson example of a 6 part email campaign; it’s like a little mini-series, so you sign up just specifically to receive 6 emails that will walk you through all of the various Harley brands and pricing and special offers. You know all of these types of things are people that have really thought through their email campaigns and look at it is a special channel as its own unique channel, that’s what you really need to do

Susan: that’s helpful thank you, we’re going to go to a break and when we come back I’d like to talk to you about all of these associations and organizations and groups that you’ve founded because I find it very inspiring and I know that my listeners not only will also find it interesting but they are exactly the kind of people that could model you behavior and create greatness for themselves in their industries so I really want to come back and talk about that, I want to talk about John Cage, I want to talk about Jazz clubs I want talk about dolphins, I’ve got a lot of things to talk about that are a lot of fun , so we are going to g to a break to thank my Dishymix sponsors. You are getting to know Bill McCloskey, bill is the chairman co-founder and chief evangelist at Email Datasource and don’t forget to go there and sign up for your free alert, I’m your host Susan Bratton and we’ll be right back.


Susan: Welcome back I’m your host Susan Bratton and you’re listening to Dishymix and you are getting to know Bill McCloskey of Email Datasource. So bill before we left I mentioned that you have done a lot of gosh philanthropic evangelical extracurricular group oriented association positive work in the industry over the last dozen years. Some of the things that I remember are that you started the first rich media special interest group, one of the people that actually coined that term “rich media”. You worked with the IAB on the flash advertising alliance and the rich media standards. You have started discussion groups like the “100 club” that I participated in another group called “Inbox insiders”. You’ve even founded events like the…what was the email one called again?

Bill: The advertising road show

Susan: The advertising road show that was it and then the email insiders summit you also did that

Bill: That’s correct

Susan: Right, so you have spawned al lot of ways that you can bring people together, and one of the things that you told me that I thought was very interesting about you and very surprising was that because you feel like you are more shy person, which I would have never guessed, you feel more comfortable being in front of 100 people than 10 people and I wonder if those 2 things are connected where you want to commune but you want to get a larger group of people so you start all of these groups. Do you think that is connected?

Bill: I think that that is a good insight. I definitely am a shy person and people often when they see me at events, I was a theatre and I always felt comfortable on a stage in front of a lot of people. I never had any kind of shyness against being on stage and talking , making jokes and trying to evangelize whatever I was talking about at the time but if I’m in a small situation with a group of 2 or 3 people it’s a much different situation, so I’ve often felt I’ve started a lot of these organizations, sort of so that everyone would know who I am and I didn’t have to introduce myself. It was a way of meeting people so that they would come up and say “oh hi bill I saw you here or there”. Then it was a way for me to meet people without having to introduce myself.

Susan: Its very interesting, What would you recommend for people who might be like you or people who like to be part of a group or a collective. How would you encourage someone, Like Bill who the hell are you to start a group like, you could have said that to yourself like “who am I to start a group I’m just Bill”. How did you get the confidence and courage to do it and what was it that made those groups successful? What advice could you give to someone who thinks, you know I’m passionate about whatever this thing is and I want to create a group, tell us that.

Bill: well, I can tell you specifically how I started the rich media sig and it actually was the thing that, it was a great realization for me. It’s the person that raises their hand and says I’ll do it and you will find that if you do that everyone will come and say can I help. People just don’t like to put themselves out front but they are more than willing to help anyone who says they’ll start it. I literally read a post on a online blog somewhere it was before blogs so it was an online forum. Someone who didn’t understand rich media and I was so incensed by what I had read, it was clear that he didn’t understand the technology that I said you know I’m going to start an organization called the rich media sig to help explain these technologies to marketers and advertisers and the moment I posted that I had 5 pot with people that said I’ll help you design the website, I’ll help you organize events. About a week later I had a 10 thousand sponsorship from Intel and we launched. It was really a matter of just saying I’ll be the one to do it and literally everyone else came in and did the hard work, they did all the heavy lifting for me.  I was able to take all of the credit and let everyone else do all of the work, but I found that with everything that I’ve done, if I just say that I’m going to do it everyone else is more than happy to support that and help out and actually make it a reality.

Susan: Well then you did it in the time before “Eventful” and “Meetup” and all of the tools “Yahoo Groups”, you know all those tools are available to us today.

Bill: That’s absolutely true anybody can be a media star today which is amazing.

Susan: Do you think that’s a good thing or a bad thing that anyone can be a media star?

Bill: well you know you still have to resonate with people and you have to do something that is meaningful to them. We run a private list and what makes our private list, a lot of people have started private lists that have gone nowhere, nobody sponsored them and nobody posts. The trick to doing a private list that makes it successful is making sure that first of all its exclusive, only the crème de la crème get in and are personally invited and the second thing that, this goes back to the idea of making a private club. The second thing that is important is, I could throw anyone out that does not post in the course of a year, if you haven’t said something significant on that list in one year you are purged at the end of the year and so that makes people want to post and the more people that post the more people want to post and the third thing that I did was make it very private. If you are ever caught taking anything that is said on the list and posting that somewhere else you are thrown off of the list. So, privacy, exclusivity and the rule that you must post there are no lurkers allowed is the key to starting a successful list like that.

Susan: That is helpful thank you and I know I got thrown off of OHC because I never post, I just like to read. Lets see, one of the other things that I thought was a really interesting conversation that I wanted to have with you , you are a very creative person. You just throw off ideas and you always have and you told me that you get your ideas in powerful waves that take you over, and I’m sure you haven’t watched this yet and I want to encourage you and anyone else listening to watch a TED talk. I just got back from the TED conference and my favorite speech of the whole conference was Liz Gilbert who wrote a very popular book that mostly women read called “Eat Pray Love”.  She sold millions of copies and now she’s at this point where she’s not sure that she can right another best seller you know, do I have more of this creativity in me? What is my next thing going to be? And she just had this beautiful 18 minute articulate speech about the history of humanity and how we thought that creativity was sourced from “Daemons” and the Greeks called them “Daemons” or how there was this concept of the “muse(genius)” how people feel like creativity just literally walks through their bodies and they have to grab it and hold on to it and remember what it is, and then I read you telling me that your creativity comes in powerful waves that take you over and it dovetailed so specifically with what she was saying about her experience with creativity that I wonder if you could even get more specific and tangible and finite for us about how you invoke creativity harness it. What’s your experience with it?

Bill: well. In my experience the thing that helps me find those waves is to really not think about it too much. I am a daydreamer I love listening to music and love and I’m not the kind of person who is always thinking of a particular plan or thinking of my next business move. I love having time to just unwind and think and let my mind wander and it’s at those time that you are at your most creative its at those time that you are open I think to those creative ideas. When they do come, at least for me they come fully formed, I get an entire business idea almost in one shot it isn’t like a little piece comes here or a little piece comes there it comes as a gigantic wave where the thing is almost fully formed. I recently came up with a business idea which I haven’t been able to implement yet, but I someday hope to and I can tell you exactly where I was. I was between 59th street and 72nd street on the Westside highway driving to work and I was looking out at the river and I had some music playing an I would say it was a wave of this business fully formed what it needed to be how it needed to be successful and how I thought it would change the world. That idea never left the power of it just got stronger, and so for me I get those powerful inspirations and then I start talking to people about them, what do you think about this? What do you think about that? And they will give me even better ideas. One of the things that I think is important is to not worry about talking about your ideas with people because most people won’t do them, but they will give you great ideas and so I always talk to people about all of the ideas that I have because it helps me to find out if they are good or not.

Susan: Me too, and It also helps me to express them and organize them better when I do talk about them. You know, I want to ask you what would you be doing today if you weren’t collecting all the world’s competitive intelligence about email marketing. Where would we find you? What would be another career?

Bill: That’s a good question. It changes from day to day, my ideal career, if I had all the money to lose I would open up a jazz bar somewhere, a place to nurture jazz musicians and make it a place where people could be exposed to music. When I was a kid there was a great club called “the main point” just outside of Philadelphia and I saw all of the great folk acts of that time and was exposed to people like Bonnie Raitt and Dave Van Ronk. All of these great musicians in a very intimate setting and there really isn’t a place like that for a high school kid to go  to learn about jazz music or other types of music other than the current popular music that’s out there. If I had a lot of money that I could waste and not worry about how much it was losing that’s what I’d do.

Susan: I think there are a lot of people that are listening to this show that have never heard Bonnie Raitt. I love her and I’ve been listening to her for years, we’re old people. What do you think was her best album ever.

Bill: Well, you know I loved her first album

Susan: Me too, give it up

Bill: she was just playing slide guitar and she had lots of people playing with her

Susan: Yes

Bill: and I used to see her when she was just playing solo guitar with a bass player

Susan: Who was that marvelous oboe player that used to rock it out with her?

Bill: Oh I don’t know I missed that one

Susan: But I do love Bonnie Raitt’s give it up album it was raw, it felt so alive they just had a blast creating that album and every song is solid isn’t it?

Bill: oh absolutely

Susan: That is a classic, that’s one of the world’s top classic albums ever I think. It’s funny that you thought the same one. So I’m going to end the show with the funniest most delightful thing that you came up with. I love this question, I love to ask people .If you were reincarnated what would you be reincarnated as? And I loved your answer tell us.

Bill: I think I said a dolphin.

Susan: You did you said a dolphin!

Bill: I can think of nothing better they’re smart they’re fun they seem to have a great time and they’ve got the whole ocean to swim in. what a world to live in and seem to have no cares whatsoever so .

Susan: Whatever I may have thought in the past that I might have wanted to be reincarnated into I’m changing it to a dolphin because I didn’t come up with that I just thought oh yeah I want to be a dolphin. I took my daughter on a whale watching trip one time out off the coast of Monterey and we saw some whales fairly far away but we had a pod of I think maybe more than 1000 dolphins run alongside our boat for 5 minutes and they were just so beautiful jumping in and out of the water and so happy and so gorgeous. There is just something about the dolphin that is so happy; it’s pure happiness isn’t it?

Bill: its happiness its intelligence its spirituality, it’s a great animal; I can’t think of another animal that I’d like to be.

Susan: It’s funny a friend of mine, and you might know him David Herscott. He was one of the founders of MEA Digital and he recently moved to Philadelphia of all places and is the CMO of a company called Evanta and he has a little daughter named Reesie and he just sent me a picture they took, they went to Mexico and Reesie got to swim with the dolphins and my screensaver for the last couple of weeks has been his daughter getting kissed by a dolphin. I mean I had David’s child on my computer because this dolphin had the most precious face and her face was in so much delight having gotten this kiss from this dolphin. *laughs* you know it all sounds like butterflies and you know hello kitty, we’re in hello kitty land in marshmallows right now but I don’t know dolphins are great aren’t they? *laughs*

Bill: Yes they are

Susan: well listen I have had a terrific time getting to know you better you cornet playing dolphin loving email marketing man

Bill: Well thank you so much Susan this has been fantastic I had a great time

Susan: we learned a lot Bill thank you for that and I hope and I will encourage everyone to get a trial to the Email Datasource product because I am definitely going to do that. It’s like what am I going to do if I only get one freebie what am I going to burn it on , it’s almost like I can’t decide. I won’t do it because I need 20.

Bill: Well I could sell you 20, but we’ll give you one for free at and there is a link right on the front page for your free alert.

Susan: we’ll do it; we’ll get our free alert Bill thank you so much. You’ve gotten to know Bill McCloskey of Email Datasource I’m your host Susan Bratton I hope you had a great time with us today and that you’ll tune in next week have a great day.

Find more great shows like this on