How To Get Your Emails Delivered With Greg Kraios of 250ok

Greg Kraios of 250ok talks about how you can ensure your emails get delivered. He covers the myths and evolution in email deliverability. Most importantly for you startup, he teaches you how not to be a spammer. Being a spammer might seem to have short term gains, but it can’t compete with having an email campaign and list where your customers love to get your emails.

Smartups August 2014 How Not To Be A Spammer with Greg Kraios of 250ok by Smartups on Mixcloud

Full Transcript After The Jump.

Thanks, Tim, for the introduction and opportunity to talk to you guys. As Tim mentioned, my name is Greg Kraios. I’m the founder and CEO of 250ok. I’m going to give you guys a little bit of background on myself, how I got into e-mail, and 250ok, what it is, what we do, lessons I’ve learned along the way, and then we’ll talk a little bit about e-mail marketing and answer some questions if you guys have them.

So how I got into e-mail was about 15 years ago my best friend was the original architect of ExactTarget. So I had an opportunity to sit in his living room, watch the first lines of code get written, and watch three guys with an idea stand over his shoulder and ask him to put a button here, make it do this, make it to do that.

It was really exciting for me because I was around at a time where they weren’t popular, nobody would give them money, didn’t understand what they were doing. They were way ahead of the curve. So as they kind of grew a little bit I was close to my friend and got to go in their office, hang out, see them grow, and from that around 2003 they had a job for a deliverability analyst.

I looked at it. I didn’t really know anything about e-mail. I knew the founders and had kind of a tech background and so my buddy turned in my resume and next thing I know I was the first person they hired to really manage deliverability.

So what that really meant was they just gave me a desk and said, “Go figure this out.” And literally I had to be kind of a sysadmin on the mail servers, figure out what an antispam policy should look like, police our customers that were doing things that were either malicious or just because they didn’t know any better.

From that as well I also had to be the bad guy to those customers and sometimes shut them down. Our sales team would routinely call me “the deal killer.” So I said, “Yeah, those guys are spammers. We can’t really have them around,” but needless to say it was kind of a young point in the company where we had to take on some risky business.

So in addition to all that I also served as our face and voice in the antispam community and got a chance to work with a lot of great people at ISP’s and other places all over the world. So getting to interact with people like AOL, Google, Hotmail, Yahoo, and figuring out kind of what the challenges they are up against in terms of putting mail in the inbox that people want and seeing spam filtering evolve over time.

So from that I stayed at ExactTarget about three years. Around the end of 2006, beginning of 2007 I realized that my time was probably up and I stumbled into the world of consulting. Got a chance to work with a lot of ExactTarget competitors, helping them with deliverability challenges, companies, brands, you name it. So did that for about another five years. It was really good, but I was always inspired by Scott Dorsey and other people with an entrepreneurial spirit.

So I decided one day that I wanted to swing the bat and start my own company and with that 250ok was born. So technically 250ok was founded in 2010, although we didn’t really start until 2011. Essentially in 2010 we filed the paperwork, had a guy who was going to be my partner who backed out, and about a year later I teamed up with Dave Caster who was kind of co-founder of Speakeasy here. And said, “Hey, Dave, I’m an e-mail nerd; I don’t know first thing about raising money, starting a company, operating agreements, legal stuff, just over my head. I don’t get it, whatever.”

So Dave said, “No problem. I can help you with all that, but I want to first see that you have a product that works and that there’s a market opportunity.” So luckily we had an alpha version of our first product and had a paying customer, so that was easy, and with that Dave helped me with everything else. So our total capital raise we did a seed round of about 200k from friends, family, local entrepreneurs. ExactTarget executives were heavily invested in our business.

That lasted up until I would say early this year and we took about another 200k, but that was really cash and services. Since we started the company we’ve had about 5X revenue growth every year, still continues this year. Haven’t really done any marketing. I know that really goes against everything that you guys are here for, but being in the industry for 10, 11 years I have a pretty good rolodex and luckily all my clients have been people I’ve worked with either as a consultant or referrals or things of that nature.

So our goal this year was we have one major competitor in our space. They do about $80 million a year in revenue. They’re kind of the big guerilla that a lot of people don’t like. So we’re kind of the disrupter to them and it serves us pretty well so far. So our goal this year and build out our technology, get a more parallel platform to them so that next year we can really crank up the marketing engine and hopefully keep that 5X growth again next year.

Things I’ve learned along the way: I make a lot of mistakes and I’m not afraid to make them. I learn from them. I try to surround myself number one with people I trust. So people I know that are going to be hard on me, critical of me, give me the best advice even when I don’t want to hear it. See a lot of people who like to surround themselves with “yes” men or people that say all the right things.

I’m not one of those people, so I love to surround myself with people that are smarter than me, better than me, and can tell me, “This isn’t what you should do” or “We think you should do that,” but as you’ll find out when you start any company everybody’s an armchair quarterback. Everybody knows what’s best for your business and they’re going to tell you. I just usually don’t listen.

So second thing I would say is I try to just stay true to myself and everybody else. So I follow my instincts, do what I think is right at the end of the day. I’m responsible for other people’s money and that’s important to me. So I have to make the hard decisions. They’re not easy. I’ve had to – lost what I thought were friends along the way, maybe they were, maybe they weren’t, but regardless I just try to stay true to myself and do what I feel is right.

And the last thing is I try to play into my strengths and work on my weaknesses. So when I first started the company as I said I went to Dave and said, “Hey, Dave, I’m an e-mail nerd. This is what I know. I’m the subject matter expert. I know e-mail inside and out. I’ve forgotten more about e-mail than most people would or should know.” So I said, “I just don’t know all the other stuff,” and really for the first year of our business I was continuously pushed into roles that I had no business being in and I didn’t know how to say “no.”

I didn’t know how to say, “That’s not what I should be doing. Here’s what I’m good at. I told you what I’m good at. This is where I think I should be for us to succeed.” And as the company’s grown and as I’ve grown I’ve learned pick and choose my battles, to play to my strengths, to bring people in to help me where I’m weak, and it’s served us really well.

So just some simple – I know they sound obvious and easy, but when you’re in this storm of being an entrepreneur at a company that’s growing at a fairly decent rate and everybody’s trying to give you their advice it’s kind of hard to get lost from these core things. So I would say if you’re starting a business or want to start a business, you’re involved in an early stage company, I think these are, for me as I thought about this, the most important things that I’ve realized and the things that I’ll probably use to move forward. So I guess we can talk about 250ok. If you guys have questions on anything along in my journey, things that you guys might be facing, I’d be happy to answer those if anybody has any.

[ Inaudible Question]

Great question. So when two e-mail servers communicate and you get a positive response and the message is received you get a 250ok. So there’s a little bit of nerd – e-mail nerd meaning in there, but it was also a really short domain name that people could remember. So I liked that too. My first original business partner that didn’t – that helped me file the paperwork, we were sitting at lunch trying to think of names and if you’ve ever tried to do that it can be an incredibly difficult, painful exercise.

And we were just talking through different terms of e-mail and said, “Yeah, well, when two e-mail servers communicate – holy crap,” and I’m immediately looking for the domain. Of course some squatter in China had it and we had to pay $1,000.00 for it, but we got it and the nerds in the e-mail world love it. Marketers tend to go, “What,” but it’s a great conversation starter I guess.

Anyone else? So with that said, again, I wanted this to be interactive, so I didn’t really put a lot of slides together, but just some basic e-mail marketing tips that I can tell you that I’ve seen to – and use with clients that I work with and help. Number one is to always obtain explicit permission. How many people in here have e-mailed a friend or a colleague and next thing you know you’re on their mailing list for something?

You didn’t ask for it, you didn’t really want it. You ignore it. You delete it. If you’re me, I’m kind of not nice about it and I mark you as spam because that’s what it is to me and I’m like, “If I want it I’d ask for it.” But I see people constantly trying to cheat this rule and use implicit permission. So you go to a store, you give them your e-mail address, you buy something, and they just add you to their list.

There’s a lot of short term game in that people always ask me, “Why is there spam?” I’m like, “Because it’s profitable. It works. If it didn’t make money people wouldn’t do it.” It’s pretty much that simple. They’d move on to other things. Typically I see a lot of problems originate from the fact that people don’t have explicit permission.

The second thing I would say is collect actionable data. So in the world of e-mail today you want your messages to be personal and targeted and highly relevant to the subscriber. I hate the word “blast.” So if you guys work somewhere and somebody says, “We’re going to send out an e-mail blast,” please freak out on them for me. I don’t want to be blasted by anything, e-mail, water balloons, I don’t care. None of that is good for me. So I would say collect actionable data.

I see people all the time that just collect an e-mail address. I can’t tell you the first thing about a subscriber to know how they could personalize a message. They’re just sending out generic content to everybody. They treat everybody the same and they can’t figure out why their ROI is terrible or they have delivery problems or whatever it may be.

The opposite side of that are people tend to throw out the phishing net and catch everything and they ask you 40 things about yourself. Well, that’s not very helpful either if you don’t know how to make it actionable. So I see people with huge amounts of data and they think, “Oh, God. I’ve got all this data and I’m going to do something cool with it someday.” Well, that someday never happens ‘cause they don’t know what to do with it. So I would say that’s the second piece.

[Inaudible Question] 

It’s just knowing your business, right? So early on at ExactTarget Scotts was a customer and what Scotts did really well is they would ask you for your ZIP code ‘cause they could tell from your ZIP code probably what type of grass you had and what type of treatments that grass is going to need throughout the year. They just knew what they were trying to achieve with their e-mail program.

Again, most people are still thinking it’s a volume game. They think that they don’t know what they’re trying to achieve with the e-mail. They have no goal. They have no – without that they have no way to know what’s actionable.

So just a simple ZIP code for them turned their program from very broad and – to very actionable and very personalized and people would get these different messages. Conversely we had – and Doug Karr is here. Doug and I worked alongside each other at ExactTarget, but we would constantly have customers that would say, like a hardware store, and they’d want to send you lawn mower specials in November. Why?

And then they can’t figure out, “Well, nobody’s opening it.” “Yeah. Genius, I can’t imagine why that would happen,” but that’s kind of the two spectrums of it, right? So there’s no right and there’s no wrong. I think it’s just knowing your business, knowing what you want to achieve with e-mail, deciding what some of those actionable points are, collecting them and then making good use of them. So that’s the other thing.

I think it’s also important to talk about e-mail deliverability. So we would routinely hear at ExactTarget and other companies, people want to talk about their delivery rate, and when you use an ESP of any kind whether it’s ExactTarget, Delivra, MailChimp – there’s hundreds of them out there today – when they report your delivery they’re reporting server to server.

So they’re really just looking at you sent X amount of messages to Yahoo and Yahoo’s server accepted Y amount of them and that’s your delivery rate. What they don’t really tell you is what’s that last mile. What happened after that server took the message? Did they put it in the inbox? Did they put it in the spam folder? Did they delete it?

Sometimes they do delete it and the prime example I give for that is how many people have gotten an e-mail from a friend or family member with a link to it and like, “What is this link? I don’t know.” They click on it. Typically it goes to a malware site. Now you’re part of a botnet or you just got phished. They have some of your personal information.

They put up a really nice landing page. You think it’s Bank of America or whoever it is and you give them your information. You just don’t know any better. Well, even when the ISP’s get it right and Yahoo would put it in the spam folder their users would go in the spam folder and think, “Oh, well, those dummies at Yahoo, they don’t know what they’re doing. They screwed it up again. I’m going to put it back in my inbox. I’m going to click that link,” and they go out and bad stuff happens and then they’re mad at Yahoo. “Oh, Yahoo, why didn’t you protect me from this?”

So Yahoo realizing that users aren’t probably as savvy as they should be decided, “You know what? It’s better for us to delete it and protect these people and never let them see it because even when we get it right the people still get it wrong.” So if you ever get a chance to, and this might be a good thing for another topic, but when you talk to somebody at an ISP they’re under attack 24 hours a day, 7 days a week by really, really bad stuff, and I mean again, the malware, the phishing, the people that are trying to do extremely bad things to you.

To also that gray area, marketing mail, and that’s where they really have a problem ‘cause they don’t know, “Did you really ask for this? Do you really want this?” They have to guess like, “Are you opening it? Are you clicking on things? Are you replying to it?”

That’s another good point. Don’t ever use “no reply.” I hate seeing that. It should be a conversation. It shouldn’t be a broadcast. It shouldn’t be a one way thing. You want customers and people that are on your list to be able to reply. Now I understand that’s hard to do at scale if you’re sending it out millions and millions of e-mails, but the people that can do it do it really well because they have a response center where those messages or replies will come back in, they know how to sort them and pass them off to different groups or whatever it may be.

But I get e-mails all the time from “no reply at some company,” and I’m like, “Well, that just tells me you don’t care about me. You could care less about this.” “Oh well, call us” or “Use another method of communication.” “Well, no. You e-mailed me. I want to e-mail you back.” So I see that all the time and – but knowing that and knowing that replies can actually help get your e-mail delivered are things that most people don’t think about.

So at 250ok one of our tools is called Inbox Informant. I kind of talked about how e-mail server providers measure your delivery. What Inbox Informant does is we help you measure that last mile. So what you can do is we provide a list of addresses. You come into your application, you download that list of addresses, you send your campaign to it like you would your list or with your list, and we’ll help report that last mile metrics.

So we control those mailboxes. So we’ll tell you did it go to the inbox, did it go to the spam folder, is it missing, and then you can use that to figure out what’s happening with your campaign. Typically people don’t figure it out until they go, “My opens are way down” or “My clicks are way down. I don’t know why.” They don’t even know they have a problem until it’s generally too late and by that time how much revenue have you lost? How many potential contacts are no longer interested or haven’t gotten your message or don’t even know that you’re trying to reach them?

I don’t know about you guys, but I check my spam folders maybe once a week. I just don’t have time and every time I go in there I’m always surprised like, “Oh, there was something from somebody I knew” or a purchase receipt or something in there that I should have gotten in my inbox, but spam filterings are really, really hard and that’s why deliverability’s such a challenge. So little shameless plug there at the end to say use 250ok as part of your strategy.

When I was consultant, before I even started this, I would always recommend that people use tools like that. So regardless if it’s my company or someone else’s it should be part of your strategy.

Question: Why are there very large companies that are using the no reply? Why are they still using it if there’s –

Yeah. Mainly for them it’s a scale issue. They just don’t know how to deal with, “Well, what if 200,000 people reply? What would we do?” They honestly – they just figure they just want to shut that channel down because they’re not prepared to staff or to deal with it. I personally don’t like it. We recommend against it all the time. Does it hurt their delivery? Not really, but replies do help.

So in e-mail just try to give a high level overview of spam filtering. So ten years ago at ExactTarget when I started everything was content filter and based. Everybody was worried about words like “free,” exclamation points, “Viagra,” whatever they wanted to put in there and that’s how it worked.

Well, content filtering was very easy to game the system and spammers were always way ahead of it. The ISP’s couldn’t keep up. So the ISP’s then said, “You know what? Maybe it shouldn’t be about what’s in the message, but it should be about who the message is from.” So they started looking at reputation and reputation was tied to an IP address.

I don’t know how many people – I’ll try not to be too nerdy, but reputation was tied to an IP address because they realized there are brands like Pfizer that want to promote Viagra legitimately. “How can we allow them to do that?”

So it became more about the, “If I can trust – if Tim is the source of the message I don’t necessarily care too much what’s in the content. I still have to care because Tim’s mail server could get hacked and he could send out e-mail with those links in it to malware sites or whatever and not know it,” but it’s more about the source. We should consider the source of the message more important than we do the content of the message.

Well, as you can imagine, spammers doing what they do figure out ways to beat that too. So they got ahead of that. So now it comes down to even more which is reputation and engagement and what they’re really looking at is how many of those people on your list are engaged. Are they opening? Are they clicking? Are they forwarding? Are they replying? ‘Cause if you look at the statistics of some of that same stuff on a personal mail stream one to one, we all open e-mails from friends.

We all reply to them. We forward them. We do things with them, but if you look at most marketing mail you probably read the subject line. If it doesn’t seem to relate to you, you just delete it ‘cause you get so much of it and people just don’t interact with it.

So now they’re looking at engagements trying to figure out what to you really want, ‘cause I know you’re just inundated with mail and you get way too much of it and I have no idea what I should put in front of you. So they want you to tell them.

The two biggest things are really marking messages as spam and taking mail that’s in the spam folder and marking it as not spam. They really want that user feedback and interaction to help them drive their decisions. When you see things like “No reply,” I’m like, “You just missed a great opportunity to help your reputation. You just missed a great opportunity to interact with your subscribers.”

There’s plenty of push broadcasting mediums out there where people can’t reply or have a voice and I don’t think e-mail should be one of them. Any questions about any…

Question: So who’s doing it well, in your opinion?

Company wise?

Question: Yeah. What companies are doing it well?

This is where I have to say I’m probably pretty bad because I don’t really sign up for a lot of stuff. I’m just buried in work. So I’m probably like the worst person to ask, but I just think anybody that’s doing it well are the people that are paying attention to my preferences, that asking the right things and giving me the right stuff.

I’m always surprised when I think I signed up for something and they’re pretty clear about what I’m going to get and then they start sliding in all the other stuff slowly but surely or you signed up for one thing and you start getting other stuff. You go to “unsubscribe,” you go to their preference center and they’ve got you checked for like five different content things or even worse, they do co registration and share your address with other companies.

It’s a nightmare. And the companies I work with, especially younger companies, they’re looking to get their message out, they want to broadcast to a ton of people and they think the way to do that is to go buy a list. Would you share your customer list with anybody ever? I’ll take it if you guys are.

So my point is that it just doesn’t work and often times those addresses are either now invalid, which count against your reputation. They could be filled with what they call “spam traps.” So what ISP’s will do is sometimes they set up addresses that have never been used by a human being and the only way they can get on your list is if they’re scraped off the Internet and they know they’re really bad ‘cause these have never been used.

So people send mail to them and they’re like, “There’s no way that you had permission to mail these addresses because we set that up to catch you,” and there’s blacklists and other folks out there that are doing the exact same things. So I don’t care. I know Salesforce has a product. Everybody wants to sell you e-mail addresses and promise they’re all opt in, they’re great, they’re this demographic. “I promise you’re going to get this kind of return.” No. It doesn’t work. It’s too good to be true.

What I always tell people is if that’s the case try to find a partner company who’s in your space who you think might be – have a subscriber base who might benefit from what you’re trying to do and get them to – sometimes you can pay to do this. Sometimes they’ll do it because they just want to help other companies, but get them to promote you in their newsletter, push those people to a landing page and get the permission yourself for them to be on your e-mailing list.

The other thing I would say that’s not up here is track your sources of data. That’s also extremely important because people go to trade shows. They put their business card in a fish bowl. They wanted to win your iPad. They don’t care about your company. They could care less. Now you can maybe send them one e-mail or two saying, “Hey, thank you for stopping by. I would love to tell you more about our business. Sign up for our newsletter.”

But people that don’t track those sources, number one, can’t tell what the highest performing source is and where they should reinvest energy and efforts, but number two, they also can’t tell you where abuse comes from. So again, if those people are marking you as spam and saying, “Hey, I don’t want this mail,” did you know that they came from that trade show? Did you know if they came from your website? Did you know if they came from a partner? Which partner?

If you have multiple partners promoting what you’re doing how do you know who are the best and who are the worst? But again, these are just very simple things that people don’t think about or even realize they should be doing until it’s either (A) too late and they have a big problem or (B) just trying to grow their programs and trying to figure out where to spend limited resources. So I see that all the time as well. Either I’m really good or I’m really boring [laughs]. There’s like no questions.

[Inaudible Question]

Target pay per click ads and e-mail? Again, I think it just depends on the relationship that people have with their subscribers. I see – I think that can work. I think it’s dangerous too though because then you almost promote people to spam and they see it as a volume game and that’s not what it is. So I call that behavior like “spammernomics.”

Everybody thinks that if I have a list of 100,000 people and I make – I don’t know – $20,000.00, if I had a list of 200,000 people I’d make $40,000.00. I’m like, “No. It doesn’t work that way,” but – and I always see people focusing still on the wrong things like, “Well, I don’t want to put ‘free’ in the subject line.” I’m like, “That is the least of your problems and that does not even matter in today’s world. People aren’t filtering based on that.”

Spend half the energy that you’re worried about on your content and “free” or exclamation points in the subject line or whatever it is people are focused on. If you would spend half that energy on again, knowing what your goals are for an e-mail program, collecting all the things you can do to send personal, relevant, targeted content, all that stuff will take you a hell of lot farther than “free” in the subject line.

But again, I think a lot of it still is just an education issue that if you’re a digital marketer today you’re overwhelmed. You don’t know where to spend money. You’re just throwing it out there and seeing what comes back, right? Whether it’s Facebook ads, LinkedIn stuff, Twitter, e-mail, people are just overwhelmed and so it’s really hard to get people to focus on data driven decisions and really analyzing that data and figuring out a strategy.

Question: I have a web app that people sign up for looking for advertising opportunities, looking for advertising partners for their website that they want to work with. And the way I’m managing e-mail right now is if I have an advertiser that I think 100 people that signed up for my web app would want to work with I send a mail merge through Gmail but it’s just riddled with words like advertising and ad and would seem very, very, very spammy. What are Gmail’s restrictions and is engagement the thing that I should most be concerned about rather than trying to curb my terminology?

Yeah. So Gmail is probably at the forefront of spam filtering technology. The reason is they just have more data than anyone else, they have more users. There’s a reason that Gmail gives you the storage they do selfishly, right? They don’t want you to ever delete an e-mail. They want to categorize and store that and analyze you down to everything that you could possibly do or imagine.

So that said, they also have probably the world’s largest and biggest computing network. So they’re able to do like super crazy real time algorithms that nobody else can do because they just don’t have the scale to do that. It’s Google. So what they do is they are really – they’re the leader now in engagement. So if you look at Gmail, what they openly tell you is they first built a learning machine that goes out and takes all these millions of data points and tries to figure out what you want and what you don’t want. So when doing that they’re really doing it at the mailbox level.

So everybody in this room could sign up for the same e-mail from the same sender and depending on how you interacted with it that’ll determine whether Gmail – Gmail may put mine in the spam folder, maybe it put one out of four in the spam folder for me to see, “Okay, if I put one in the spam folder is he going to dig it out? Is he going to mark it as not spam? Is he going to reply to it? Is he going to do anything with it?” They’re looking for those interactions to figure that out. Now they also can openly tell you that they can’t fix a delivery problem.

So I can’t go to the engineers I know on the Gmail team and say, “Hey, this customer’s having a problem.” It doesn’t matter if it’s Joe’s Barber Shop or Home Depot, they don’t care. They’re like, “We built a machine learning algorithm that we can’t really influence like that. It just learns and grows and gets smatter and better,” and I always argue with them because we use Google apps at 250ok to host our mail and they routinely put messages from themselves which are transactional admin messages like when we do something on our network into the spam folder on their own network.

So I’m like, “You take your own transactional mail and classify it as spam,” but other than that they generally do a pretty good job, but yeah. They’re probably the most strict out of anybody to get mail into.

Question: I think you started to answer the question that I was going to go with next, but the powers that be at my office are convinced that lists are the way to go and that they can find the perfect goldmine of lists. But in the event that you do acquire lists and they’re unsuccessful ones and they all go to spam, is there a way to essentially rehabilitate an email program?

Yes, but it just takes time and again, it really depends on who you’re sending that through. So a lot of people think that they can jump from e-mail service provider to e-mail service provider. So for example – I meant to do that. At ExactTarget we’d routinely see people come to us from another e-mail service provider where they dirtied up an IP address or had a terrible reputation.

They think they could come to us. ISP’s are really, really, really smart. Just let me tell you, they’re looking at data sets that are bigger than anyone in here could possibly imagine. Whether you jump around or not, they know how to finger print a message, look at a bunch of different things and say, “Even though you’re sending it now from over here, I still know it’s you and I can still punish you.”

Where it gets tougher is really in the B2B space, right? So if you’re sending e-mail to a lot of companies that have their own spam filters, their own networks, their own things, you’re kind of a little bit more invisible there, but the landscape’s changing. More companies now are hosting at Google, hosting at Rackspace, hosting other places. They’re not going down to their local hosting company and putting up a box to run Exchange and some spam filter. So all that’s changing now.

There’s also less spam filtering companies. So it’s just making them easier for them to identify bad people, but it’s going to take time and people want – they expect, “Okay, well, I quit doing that.” It’s kind of an analogy I’ll use is like if you smoked for ten years you’re not going to get immediately better if you don’t smoke tomorrow. It’s going to take time and you’re going to have to keep doing all the right things.

You’re going to have to get some of those subscribers to help you by digging mail out of the spam folder, clicking it as not spam, replying to it, forwarding it, doing actions. Sometimes you can have them – you can reward them for that. I’ve seen people successfully do strictly reply campaigns at Gmail saying, “Hey, if you want $10.00 off your next order reply to this message,” because they’re trying to help their reputation.

They’re trying to dig themselves out of a hole, but ISP’s also look at things over time and trending patterns and everything else. So I’ve been really fortunate to get to work with them on a pretty inside level that most people don’t get to see and it’s just amazing to me how smart these people are with data and the things that they look at and they think about things and look at things you can’t possibly imagine on a scale that is so ridiculous it’s mind-boggling. So trying to beat that or thinking that you’re smarter than them or “I can get around that,” good luck. Then you come pay a guy like me a whole bunch of money to fix it and thank you [laughs].

Question: At what point do people need to really be concerned with their deliverability? If you have 1,000 subscribers on your list, with billions going out every single week, are you under the radar or is there a certain threshold?

No, ‘cause even then – so ISP’s are smart enough to really look at things like percentages and so they know what percentages are acceptable, but just like anything, there has to be a minimum – for any data set you have to have a minimum volume level for that data set to be meaningful. So, for example, if I mail 50 people at AOL and 2 people complain, a lot of people will be like, “Oh well, that’s only 2 people.”

Well, it’s four percent. So ISP’s are smart and they know how to figure that out. So they’ll start looking at things like trending, but I think it’s never too early to be concerned about delivery because what is one missed message potentially cost you? I know that’s different for every program or everything whether it’s – whether you’re sending out e-mail for monetary purposes or not, every opportunity that you have to reach someone if you’re not getting it to the inbox all that work you’ve done doesn’t mean anything.

So routinely at ExactTarget I would joke ‘cause we’d always build all these features and functionality and we’re going to integrate with this and do all that and again, that’s really great, but if nobody sees it does it matter? I can put a billboard up in the middle of a corn field and who cares, but everybody wants it to be downtown where people see it and they get the most traction. So delivery is like your bottom line, if it’s not getting there all that work is for naught.

Question: Is there any sort of metric or score or test that you can do to check your delivery health, your domain authority so to speak for your e-mail?

So our biggest competitor return path has a – it’s not even really a product. It’s – they try to create an algorithm that you plug into your IP address and it’ll tell you your sender score. Well, here’s the problem is that I routinely work with companies who are blocked at various places because they have a limited source of data and they’ll say, “Your sender score is 99,” and the company – the first thing they would call me when they consult, they’re like, “Well, I can’t get my mail to Yahoo and some of these other places, but my sender’s score is 99.”

I’m like, “How that’s working for ya?” Right? So anybody can – I was like, “I can write a program that spits out some number that’s meaningless and tell you it’s whatever, 75, 99, who cares.” I think using tools like ours where you send a test and you see where that’s going and you compare that with your other data, your opens, your clicks, conversions if you’re tracking that stuff as well, that all tells the story of what you need to know because they don’t have your sending data.

You have your sending data. So you can tell again looking at things like your bounces, your unsubscribes, your complaints, all those things are things you should measure and track and pay attention to. And if people are unsubscribing, why? Was it a particular campaign? Again, what was the source of those people that unsubscribed, the story’s in your own data if you know what to look for and what you’re trying to figure out.

Question: What about frequency? Is that something you should manage a little closer nowadays, how often you’re sending messages?

Yeah, and there’s no right or wrong. I think it’s just about setting the expectation. If you tell people they’re going to get a weekly newsletter, you should send them a weekly newsletter. If you tell them they’re going to get a quarterly newsletter, they’re going to expect that. Now come the month of December I think we all get mail bombed and that’s because all these companies have that spammernomic mentality and the CEO’s sitting over the e-mail marketing guy’s shoulder going, “Hey, how much did we make on that last campaign? Oh, half a million? Well, hit the button again. I need to make more money. We’re behind on our numbers. Let’s hit the button.”

Right? So I equate that to monkey and the banana. Hit button, make money. Hit button, make money. Well, the problem is is like a lot of brand degradation, unsubscribes go up, complaints go up, they may have delivery issues. They’re really playing with fire at that point, but for them it’s just they know every time they hit that button they can count X amount of revenue coming in the door.

So if you’re Best Buy why wouldn’t you send more? It’s December. You’re trying to push everything you can through the door and make as much money as you can. They’ll deal with the rest in January. They don’t care. So yeah. Frequency’s just something you should pay attention to. You should ask your subscribers, give them options. I’ll point out Doug as a good example.

I like the monthly digest I get from Doug. I can’t keep up with the weekly newsletter. I’m too busy, but I do want to see what’s going on out there. I do like getting it in my e-mail. I just want it monthly. I don’t want it weekly and he gives me that option to do that. So giving your subscribers options, ‘cause not everybody’s the same. They all want to consume things differently, but as long as you set that expectation and deliver on it you’ll probably be in good shape.

Question: So I’ve noticed for newsletters that I am signed up to, nine out of ten of them will go to my promotions folder or spam folder or something, but then every once in a while I’ll get one in my inbox. Are they doing something differently?

To get to the inbox you mean instead of promotions? No, because again, Gmail’s really good, but the machine isn’t perfect. Machine was built by man. It’s going to learn, it’s going to have flaws, it’s going to make mistakes, but technically that’s still the inbox even though it’s promotions folder. I consider everything that’s not the spam folder, the inbox, whether it doesn’t matter what tab it is really, but it’s fairly trivial for Gmail to know what’s a marketing message because if you look at the mail headers and all the data that’s in there, it’s very easy to see it’s from an e-mail service provider nine times out of ten.

The content, very easy for them to know. Again, they have enough data they can know pretty easy what’s going on, but occasionally one slips through and they get a little bit wrong, but all in all they’re pretty good at it. So they want people to do that because that’s the experience people want. They don’t want to log in their inbox and just see 100 messages every time they’re due.

Let me ask this. How many people used to have before promotion tabs and Gmail roll out tabs, two e-mail addresses to sign up for stuff? And when you go to a website and they’re like, “Oh, I need an e-mail address,” you’re like, “Ha-ha, yeah. You get this one.” Right? And you may log in once a week, you may log in whenever and you don’t care about that mailbox. It’s not your primary mailbox. Well, Gmail wanted to stop that. They’re like, “Yeah, we don’t really like that. We want everybody using their personal address and we want to help them protect that a little bit better and just make the user experience better.”

So if you think about from their side too, Yahoo, Google, and Microsoft are really in a three way arms race for e-mail dominance. And so with Microsoft it’s now is what they’re trying to push. Cleaner interface, they’re trying to battle Gmail, they want those users just because they sell ad space and ad space is more expensive when they have more eyeballs versus less. So nowadays if you want to – I used to call it “the big four ISP’s” including AOL, but now it’s like three and a half ‘cause not many people still use AOL, but the point is is that AOL used to be like the biggest and the best and they fell off. Now what AOL will charge you to run an ad inside their mail UI versus what Gmail will charge you, it’s completely different.

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