Episode #50 – Brendan Dubbels on Ninja Tricks to Skip the Waiting List and Get Your Emails Prioritized

by John McIntyre

Do you use Gmail?

News flash:

Your prospects do.

That means that your emails might be getting BURIED in the Gmail “Promotions” tab.

Or worse –

…not delivered at all.

That’s helluva problem.

It’s the difference between selling like hotcakes in your prospect’s Inbox, next to “hey honey” from Mom –

…or getting tossed in with the Viagra Spam.

Where do you stand?

(HINT: in this episode, you’ll learn how to quickly check.)

Fortunately, there are a few tiny “smoke signals” you can bake into your autoresponder.

Do these, and your emails get ushered past the velvet rope…

…and waltz STRAIGHT into the profit club.

So what are these tweaks?

And how can you take advantage?

Meet Brendan Dubbels.

Brendan is the Post Master at Ontraport.

The guy gets PAID to deliver emails.

(And keep marketers like you profitable).

In this episode, Brendan shows you how to get your emails prioritized.

That means more CA$H.

From emails you’re already sending.

Curious what % of your emails actually get seen?

Want to skip to the front of the line?

Would you like to impress clients and partners with high-impact email marketing advice?

Then listen carefully to this episode.

Welcome to the VIP club.

In this episode, you’ll discover:

  • how to guarantee prospects see your emails
  • why IPs and the technical stuff is becoming less important…and the exciting trend on the horizon
  • a benchmark open rate for your emails (how do you measure up?)
  • Google’s little-known Gmail algorithm, public online
  • when unsubscribes are a GOOD thing
  • the 30-second trick that turns your autoresponder into a profit machine (do this today)
  • 2 scary metrics that Gmail tracks when you read your emails
  • how to protect against DANGER to your identity (this is a must if your biz is growing)
  • how to skip right past the Promotions tab
  • why you don’t need to be clever in your email subject lines

Email Marketing Podcast Episode 1


Get a free 30-min consultation with Brendan on your email deliverability as a listener of the podcast! Email him at [email protected]

Intro and outro backing music: Forever More by CREO

Raw transcript:

Download PDF transcript here.

John: It’s John McIntyre, the Autoresponder Guy. I’m here Brendan Dubbels, a deliverability expert, I think the deliverability man at Ontraport, an Office Order Pilot. He’s in charge of making sure customers get their emails, as far as they get their emails into their customers inboxes.

I actually saw him on Quora. I was clicking around on Quora, which is a great site, by the way, quora.com. People ask these crazy- these very intellectual questions. It’s like Yahoo! Answers for smart people, and there’s some great stuff on there where it’s about, “Does God exist?” Or the most interesting things you’ll learn from splits tests and some really intelligent responses.

Anyway, that was how I found Brenda. He posted on someone’s- I think there was a thread on Quora about how to get your emails read, “What’s the latest stuff that’s going on that’s really helping people at in getting their emails read?” Then Brendan jumped in there and had a great response so I thought I’d send him an email and get him on the show. That’s what we’re doing today. Brendan, how are you going today?

Brendan: Doing great, John. Thanks for having me.

John: Good to have you on the show, mate. Before we get into the deliverability stuff- I’ve given the listeners a bit of a background on who you are and what you do, but fill in a few of the gaps and tell people who you were.

Brendan: Yeah, so I’ve been working with Office Auto Pilot and Ontraport as Postmaster now for about five years. I’ve worked with a ton of the top internet marketers in the world. Having sent so many emails for so many marketers, I’ve really come to see a lot and gained a lot of information that a lot of people just don’t have access to, especially considering that we send for everything from the hardcore internet marketers to mom and pop working on the shops. Just giving me some really unique insight and I’m able to share it.

John: Okay, cool. You said postmaster. That’s your title at Ontraport?

Brendan: That’s my title at Ontraport, yeah.

John: That sounds pretty cool.

Brendan: It’s pretty all-encompassing so not everyone’s happy to hear from me. We do try to get our customer’s email in the inbox but unfortunately sometimes, we have to have to be strict with our customers as well and make sure they’re not getting complaints and bounces.

John: What specifically are you doing? You’re the guy who’s in charge of making sure that emails get to the inbox and get opened, right?

Brendan: Exactly. Another term that some people use is compliance or abuse at other companies. We’re trying to move away from that simply  because we think your email service provider should be your partner and not sort of a big brother, as it were.

John: Okay. I’m curious, do you have to reprimand many customers because they’re getting too aggressive and getting too many complaints?

Brendan: I would say that we probably warn about two customers a week, so really not that many in the grand schemes of things. Most of the time, it’s a really case of people just not knowing. You don’t know what you don’t know. With a quick message and some follow up education, we generally never see repeat issues, which is pretty awesome.

John: Obviously, the emails go through a few of your demands so your job, as I suppose, is to maintain the reputation of Ontraport’s demands with the various ESP’s so that you don’t get blacklisted so then all your customers … This is getting pretty technical. I just want to be technical. I want to try to fully understand  this stuff. The idea is if someone sends too much spam or too many emails that get complaints from your domain or through your service, that can ruin it for your other people so your job is to make sure that doesn’t happen, that the domain stay in good standing, right?

Brendan: Exactly. That way, anyone who’s sending mail can be A, that not only is their mail going to reach their servers but for example, a friend of theirs signs up, that their behavior isn’t going to affect their buddy who signs up as well. It’s definitely a full-time job and I’m really lucky to have a fellow associate who does deliver here. His name is Brad. Things are good.

John: Okay. How do we do this? That’s what I wanted to get you on for, is to talk about how you- because it’s really in your best interest and it’s in the best interest of your customers, of the clients who are sending the actual messages that you need to get the emails to your inbox, you need to get them read, opened. I know you need to get them engaged with so click on Reply to, that kind of thing. This is all going to drive that send score or the scorer and say, “the domain’s up or Ontraport’s demands so that Ontraport looks better and everyone’s happy.” That’s how it works, right? Am I …?

Brendan: Yeah, that’s pretty accurate and it’s been a really interesting trend over the past, I would say three years or so, as engagement is becoming more and more important and peer reputation is becoming less and less important. We can clearly see this because all of our IP’s with Ontraport are in the mid-90’s range, so that’s pretty solid. Higher than most ESP’s, in fact.

John: Okay.

Brendan: What’s strange is that we’ve got all of these people using the same IP’s, yet some people will only get 50 to 60% inbox rate, while we have others regularly pegging 100%. We’re saying that engagement and less hygiene by the individual marketers really was becoming king and IP reputation is becoming less important.

John: You just said something very interesting. You’re saying some people, because their engagement score is low, they only get 5 or 6 out of every 10 emails into an inbox?

Brendan: Yeah, and to be honest, that’s not even worst case scenario. I’ve had people who have gotten down to 15 or 20% simply because they just send so much cold mail. They get so used to an open rate that’s slowly declining that they think nothing is wrong and it’s just business as usual.

For me at least, one of my favorite things about my job is to be able to contact them and work with them and say, “Hey,  you’re messing up. Let’s fix this,” and seeing them light up when their inbox rates go back up to in between 80 and 100% and over the rates double or they triple. It’s a really, really cool thing.

John: I’m curious, when you’re getting 50, 60% off of an inbox rate, what sort of open rates it may sound like?

Brendan: To be honest, it really, really depends with what business you’re in, how frequently you mail and how well you set your expectations. I would say someone who gets 50 to 60% inbox rates on average probably be getting about a 5% open rate granted, like I said, that is a gross generalization simply because it varies so much by your target audience and your frequency of mailing.

John: Let’s talk about engagement then because this sounds really key. It’s not IP’s or just to clear something out. I’m speaking to a friend recently. We had lunch here in Thailand and he said it started around a podcast, he listened to a few episodes. Then he asked me, he gave me this idea to go and get some more interesting people on the show. I’ve been doing lots of copyrighting guys marketing guys but it would be good to hear from someone like you on the deliverability side.

He mentioned stuff that I have just no idea what’s going on and how it works, which is not just the IP address but the email header. I think he’s got the SPF records or the technical details. Do they affect the deliverability?

Brendan: They definitely, definitely do. The nice thing though is if you’re with a professional email service provider like Ontraport or any of our competitors, that’s going to be handled for you. The truth of the matter is, is you don’t have that infrastructure in place, your mail just simply isn’t going to get delivered at a rate that makes sense.

There’s a ton of great resources out there for how you can create an SPF record, which stands for Sender Policy Framework, or a DKIM record as well, which is also equally important if you’re looking to do some self-hosted email. The one other thing I would suggest if you are looking to go the self-hosted route, DMARC is also very, very important. It’s one of the newest authentication methods they’ve created.

The short version basically, it makes it so that you know if someone is trying to impersonate you via email. If you have high brand value and you think someone may benefit from impersonating you via email, DMARC is key, D-M-A-R-C.

John: Interesting. Are you doing DMARC with the offshore part of stuff on Ontraport?

Brendan: Yeah, we are. We have DMARC authenticated on all of our outgoing mail simply because we don’t want anyone trying to trick our customers.

John: This is very interesting though. IP address, that technical stuff, sounds like it’s gradually becoming less important and you talked about engagement. What is engagement specifically?

Brendan: Engagement is just the monitoring of the touch points that your customers have with your emails. If you think back to how emails evolved over the years, when it started, it was completely unregulated. As time progressed, people started using it for marketing, which isn’t it’s original intention. Originally, it’s, “Holy crap, we can send information from here to Washington in three seconds.” That blew people’s mind. It was one to one communication.

Then marketers came along and they’re like, “Wow, we could make a killing with this stuff.” Then, email marketing was born. It made sense. It was much less expensive to communicate with our prospects and our customers.

However, some people went down the route of spamming and ruined it for everyone. Then, ESP has noticed that the people who receive spam frequently would just shut down their accounts and move to another provider, which was a major bummer. They realized they had to start regulating what was going on.

IP reputation worked for a while but it became very apparent that a spammer could get an IP, do a broadcast to five million spammed addressed and then just buy a new IP and then mail from there. IP reputation didn’t cover it all. It wasn’t an end-all deal.

Now, they measure, “All right, well, how long do your readers have their email opened for?” In other words, how long are they reading it for or how often do they click it? Do they delete it right when they get it or do they file it away and read it later? How many times do they open it? Google actually has a very, very advanced algorithm for this and they published it in a white paper, if you check out their blog.

To be honest, it’s a little too complicated for me but it’s a very, very interesting read. The bottom line is, if your people are engaging with their email, you’re going to see lower and lower open rate and you’re going to start to see that 50 to 60% inbox rate we are talking about earlier.

John: The big picture in here for people to understand is that when they’re sending an email, they need to … We’ll talk about the specific stuff that they can do in a second but they basically need to- I’ve been doing this, you need people to get to reply, you need to get people to click stuff if you’ve got resources and emails that you said. I don’t even know some of the stuff.

DMARC tracks how long the email is open for as well as how many times its clicked, how many times it actually gets opened. What you’re saying is a whole bunch of different metrics that Gmail uses to figure out like to rank sites, or the Facebook gallery with page rank, whatever it’s called. They figure out what email is important and what’s not. If you’re not important, if you’re not sending valuable stuff that’s helping people, it’s just not going to work.

Brendan: Exactly,  yeah. They even keep track of how far down you scroll down below default. They literally track everything you can imagine.

John: In that sense, I’m getting so many different ideas. Let’s go through the stuff. How about we just go through all the different metrics that they track and then what you can do to get a good metric?

Brendan: Definitely. My first and favorite is just simply asking people to add you to their address book. It’s really, really simple. Basically, if you’re in someone’s address book, you’re white listed with them. This engagement stuff and the spam filter kind of takes a backseat. You get to skip that and you just get front row seats right into the inbox. Even better if it’s priority inbox and you’re in their address book. You’re going to place even higher in their folders.

John: Some people are going to hear that and I think there’s no point asking my subscriber to put me in their address book. There’s no way they’re going to do that. You’re saying you can say this and people are actually putting them in their address book?

Brendan: Yeah, I would say generally about 5% of readers take action on it. Another way that you can be added to someone’s address book, and this one is kind of sneaky, but it also works. If you get someone to reply to your email twice, most email providers, that will add you to their contact book through Gmail and also through a Hotmail. That’s something that you should definitely take into a consideration. As for a reply, golden.

John: Once you get two replies, they’re in your address book?

Brendan: Exactly, and then you’re golden.

John: Damn, that’s some interesting stuff. Okay, what’s next?

Brendan: Next stuff is going to be just overall opens. I’ve seen a lot of people in the past do anything to get that open. Obviously, subject line is key when you’re hunting for opens. The problem is if you’re using that sort of, “Anything goes,” in the subject line method, you’re going to lose credibility and sure, you’ll get that first open but guess what? Next time, they’re going to see your name in the front line and they’ll be like, “Oh, what a bullshitter,” and then you’re going to end up in their trash can or their spam box.

It’s really just being clear and interesting with your subject lines. I know that’s kind of obvious but far too often, people will anything on the subject line to get the first open. You just want to make sure you summarize your email to get the click.

John: That’s what I find too. With email, especially with a subject line, you don’t have to be clever or anything like that. Often, it’s just simple as finding a really concise way to say whatever is in the email because then, what will happen is this sort of person that would respond to whatever is in the email will be attracted to the subject line and will open the email. There’s no point.

Everyone else who the email contact is not relevant to, there’s no need for them to open an email if it’s not going to help them. There’s no need to make them or try and trick them into opening an email. That’s a waste of your time, that’s a waste of their time.

Brendan: Totally, totally agree with you, yeah.

John: After I add you to my address book, overall opens. It sounds like you’re saying don’t focus on the single open, right? Focus on how can you cultivate an ongoing, long-term open rate.

Brendan: Agree, and this is another one that is semi-nebulous but have that conversational tone. At least in my experience, people don’t like being spoken to in emails; they like being spoken with. Be it as simple as asking them what they want to hear about via survey or asking them how often they want to hear from you.

One of the best engagement tricks I’ve ever seen is companies set up a survey specifically and ask how often their subscribers wanted to hear from them. It seems so simple and so obvious but it made a huge, huge difference. You interact with people how they wanted to be interacted with, not how you want to interact with them.

John: Just actually one of the features of Ontraport, right? If you hit Unsubscribe, it will actually get them to change the mailing to once a week, right?

Brendan: Yeah, through various tagging methods. It’s definitely easy to set up with OAP.

John: Interesting. Those things that we open and we write in conversations. What’s the next thing?

Brendan: The next thing is with Gmail. I’m sure many people have seen primary social promotions tab. Marketers were all up in arms saying that their business is going to explode and their professional lives were over with this one change that Gmail made. If you’re smart,  you can actually use this to your advantage. I really suggest putting a call to action in, if you advanced auto-responder service that can fire off rules.

You can set up rules so that any time someone gets added to your database who has an @gmail.com in their email address, automatically fire them email that says, “Hey, we want to make sure that you get all of our stuff so to make sure, just drag this email over into Primary.”

John: That’s very cool.

Brendan: From then on, you’ll automatically hit the Primary box and that dragging into the Primary tab is one of the biggest compliments to Google’s Engagement metrics there is. I’m getting a little bit tongue-tied today. That’s something else to take into consideration.

John: You can tell them to drag it or you can send them an email like that?

Brendan: Yeah.

John: What are some other ways like if they’re interacting with email- I’ve often wondered about this. If you send them an email and ends up in their Promotions tab and they go through it, if they reply to it a certain amount of times or click on it a certain amount of time, is that going to move you to the main inbox?

Brendan: Yeah, it is so that’s also something else to consider. Based on engagement, you can generally tell whether you’re running up in the Promotions box or the Primary box. You’re going to get less opened up if you’re hitting the Promotions box in Gmail. It’s a little bit different with every business but I highly suggest going and checking out just your Gmail section of your list and seeing where you’re coming through consistently in getting opens and where you’re not, and then sending less mail to the people that you’re not getting open from.

This makes sense when you think about the grand scheme of things. If email delivery is a lot about engagement and it’s also a lot about percentages. If you think about complaints and bounces, it’s a percentages game. If you’re sending more engaged email than un-engaged email, that percentage is going to stir you in the right direction towards the Primary box.

I highly suggest mailing your active engaged users who have opened or clicked an email from you, say in the past six months. Mail them twice as much as you mail your inactive people and you’re going to start to see a big shift in the way that your new subscribers interact with you.

John: This would be an interesting business idea. I don’t know if you guys are doing this yet, but like a smart email orders on the service, that what happens is it basically changes the right at which it sends and not depend on how people interact with it. Let’s say if someone enters your sequence and they reply to your first email and then they click a link in the second email, they’re going to be in daily email or something like that.

Then, if they stop replying or if they stop opening, they gradually get less down to say- or maybe you could set the settings to a minimum of once a week and a maximum of once a day. Depending on how much they interact with it, basically you could have an algorithm that then caters or structures or sends the auto responder based on their engagement level. That would be very interesting?

Brendan: Yeah, it’s actually completely possible with Ontraport or Office Auto Pilot. It is a very, very amazing tool and that’s one of my favorite things about the platform is that it’s very, very flexible. If you can think it, chances are we’ll be able to do it.

John: One thing, I’ve asked this question and then this next question. Sounds like some people find that they read a lot of data … I’m always interested in asking something like this, but here it is. What’s the most interesting or some of the most counterintuitive things you’ve learned doing the marketing for all these big name marketers with lots of data?

Brendan: One of the funny things I’ve ever seen is that a marketer actually took our Unsubscribe link and he attached it to one of his emails. Then he put a red banner and it said, “Complain, or This is Spam,” or something of that sort. Whenever anyone would open one of his emails, there’s this big honkin’ red button that says, “This is Spam,” at the top of his emails.

His messages have gotten some of the lowest complaints I have ever seen because instead of clicking the in-app, this spam button and a complaint being sent to Hotmail or to Yahoo! and penalizing his sending, they would  click what they thought was a spam button, which is really an Unsubscribe button, so they would just be unsubscribed. I thought that was pretty tricky and pretty awesome.

John: Did his unsubscribe go up or down with that?

Brendan: The unsubscribe rate went up slightly but I would take an unsubscribe versus a complaint any day. An unsubscribe is completely unconsequential. It’s one of those things that people don’t unsubscribe because they want to buy from you. Just like happy people usually don’t get divorced. It’s kind of the same setting there. They’re unsubscribing for a reason and that’s okay. They don’t complain and you’re better for it.  Your list is cleaner, your list is more engaged and you’re better off without them.

John: Because like the spam, the spam complaint will hurt you. It hurts the domain, it hurts the center score, it hurts Google’s algorithm engagement score but if they just unsubscribe, they’re just saying, “Yeah, it’s not for me. It’s all good.”

Brendan: Exactly. The ISP’s out there, they understand that too. That’s why they have feedback loops. When someone complains with one of the major providers, it sends out a notification assuming your provider’s hooked up with them about them complaining so they can be unsubscribed. The idea is that they want unsubscribes, too.

John: I’m curious, with some of these guys, do you have an engagement algorithm so you can track the engagement for your customers?

Brendan: Right now, what we do is we just have a last activity field that updates based on whether someone has clicked an email or opened an email. That’s been sufficient so far. Looking forward, we are looking into more advanced methods. Maybe having an automated scoring method. I know Mail Chimp, who’s another great ESP out on the market if you’re only looking for email. They’ve got a five star rating system so when you look at your list, they’ll just break it down and tell you who’s engaged and who’s not, who you probably shouldn’t mail. With us, we have the data available but it’s really more of a judgment call than something we force on you.

John: Right, okay. I’m just curious, we’ve talked about some ways to increase engagement. I’m curious what are the best customers doing? What are the guys and girls with the highest engagement scores doing for engagement?

Like in my email in my sequence, I ask people to reply than in email, I usually get them to click a link. At various emails throughout the rest of the sequence, I’m asking them to click something or reply to the email with feedback on something?

Brendan: I would say that all of these tricks definitely help, but at the end of the day, the guys are doing the best or really the guys that are just out there to help and to make a difference in the lives of their prospects and their customers. That true voice and that true intention, it can’t be replicated. Your customers can tell if you’re trying to BS them into a sale.

If you’re really just out there and providing value, your customers are going to engage, whether you’ve got this spam button at the top or not. That certainly helps but at the end of the day, content is key. I would say another really good thing is if you’re really good at writing hooks in a paragraph or two, write a hook and then put a Read More link to your blog.

I know that’s standard operating procedure for a ton of people but that will get you a click very easy. If someone is reading and all of sudden, to finish it, they have to click to the next page.

John: Just to have a really engaged list, instead of giving them a content in the mail, just give them that Read More link.

Brendan: Yeah, exactly.

John: Okay, interesting. That sounds a great note but there’s more about why you can go and figure out all these tricks and these ways to hack I guess the engagement. At the end of the day, what really counts is are you solving a real problem in the marketplace? Are you creating value?

Brendan: Exactly.

John: Tell you what, before we go then, let’s wrap it up here. Tell people where they can go to learn more about Ontraport, Office AutoPilot, what’s the difference, all that sort of stuff.

Brendan: Yes. Office AutoPilot is the current version of our software. Ontraport is a new version, 3.0. We’re currently in beta and we’re getting less and less bugs by the day, which is awesome. We’re looking to go live soon. If you want to sign up, I highly suggest to check out officeautopilot.com. Don’t worry, when the new brand and the revamped version comes out, we will be doing an account transfer so no need to worry about.

If you listen to this podcast, I’m also offering a free 30 minute, one on one deliverability consultation. Shoot an email to [email protected] and we’ll be able to get something set up for you.

John: That was cool. Thanks for coming on the show. This has been really helpful.

Brendan: Of course, great. Thanks for having me, John. It’s been awesome.

4 thoughts on “Episode #50 – Brendan Dubbels on Ninja Tricks to Skip the Waiting List and Get Your Emails Prioritized”

  1. My notes for that show (excellent show btw John, helped me a ton):

    How to improve deliverability

    – Add to address book

    – Reply twice

    – Consistently high open rate with relevant subject line/content

    – Survey (get people to click)

    – Let people choose their email frequency

    – Email “active” subscribers more often (auto-send on click would do that)


    – Two emails on subscribe; one asking people to just reply and say if they’ve got the other one (“Did you get my email?”)


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