Secrets of a Billion-Email Sensei to Dominate the Inbox and Keep You Out of the Spam Penalty Box
In a world where email marketing rules are rapidly changing, understanding how to keep your emails deliverable and your customers engaged is more crucial than ever. From redefining engagement metrics to tackling the Google Yahoo Armageddon, Big Jason Henderson reveals indispensable strategies in our exclusive interview.
Meet the Expert: Big Jason Henderson
Jason Henderson, also known as Big Jason, brings a unique blend of professional sports and digital marketing expertise. Having sent over a billion emails, his insights are invaluable for understanding the evolving landscape of email marketing. In our interview, Jason delves into the challenges and strategies essential for success in today’s email marketing world.
Key Insights from the Interview:
- Understanding the Google Email Update: Learn what this significant change means for your email strategy.
- The Importance of Engagement Metrics: Discover why old metrics won’t cut it anymore.
- The Myth of 30-Day Openers: Jason busts common misconceptions that could be harming your email strategy.
- Effective Strategies for Cold Emails: Get expert advice on navigating the tricky world of cold emailing.
- Adapting to Audience Behavior: Understand the importance of evolving with your audience’s needs and preferences.
Navigating the New World of Email Marketing:
As Google reshapes the email marketing landscape, staying informed and adaptable is key. The insights shared by Big Jason are not just theories but battle-tested strategies from the front lines of digital marketing. Whether you’re a seasoned marketer or just starting, these tips are crucial for keeping your emails deliverable and your customers engaged.
Conclusion: Staying Ahead in the Game
Embracing these strategies will help you navigate the challenges of the Google Email Update. It’s about evolving with the times, focusing on user engagement, and understanding the nuances of email deliverability.
Google Email Compliance Strategy Video Transcript
Steve Rosenbaum 0:00
Hey, Steve Rosenbaum from flawless follow up. I’m here with a longtime friend. It’s been Jason Henderson. Big Jason, how are you?
Big Jason Henderson 0:08
I’m doing good. Thanks for having me, Steve.
Steve Rosenbaum 0:10
Absolutely, absolutely. You know, I saw you online talking about the Google Yahoo. Armageddon, I think you call and that’s what I want to talk about today. But you know, a little bit of a backstory, because you’ve been in email marketing a long, long time. When did you start? You
Big Jason Henderson 0:26
know, just after Al Gore invented it invented the internet. You know, I remember that day. Yeah. 1996 and playing professional basketball in Australia.
Steve Rosenbaum 0:37
You know, that’s it was the first time I met you at the, by the way, he said, and you can’t tell why he calls himself big Jason. But first time I met him at the big seminars. It was a Armand Morin Big Seminar. Yep. And yes, big Jason is correct. Is correct. I didn’t I don’t think I knew that you were playing professional basketball in Australia.
Big Jason Henderson 0:59
Yeah, yep. Australia, Germany. Oh, Salvador, China. Very
Steve Rosenbaum 1:03
cool. Very cool. And from there into email marketing, and it’s, it’s fair to say you’ve sent out a couple emails in your day. Is that right?
Big Jason Henderson 1:10
Yeah, probably sent over a billion, a billion. billion.
Steve Rosenbaum 1:16
So Jason is an email deliverability expert. I mean, he and I were talking about the roster of people. He does this for some of the biggest names, you know, and they’re the guy Jason calls to fix your deliverability. Currently, he’s working over 40 different domains. Something crazy, right. But I mean, that
Big Jason Henderson 1:34
was a recent gig I did for an ESP where I was managing 40 Plus domains at the same time for like months.
Steve Rosenbaum 1:41
Big Jason Henderson 1:44
Yeah, the biggest one I’m currently doing deliverability for is digital marketer with Ryan Deiss. Ryan
Steve Rosenbaum 1:51
Deiss. Absolutely, absolutely. So you know, there’s so much talk right now about the Google Yahoo, Armageddon. And so I logged in the other day into Facebook, in Germany in the morning, you’re an early guy, too, huh? Yep. You were live at 330 in the morning?
Big Jason Henderson 2:09
Yes, I was.
Steve Rosenbaum 2:12
Was that for your us? Audience?
Big Jason Henderson 2:15
No, it was, I was just, I was just up working away. And I said, Hey, you know, I came up with, it dawned on me that this is something important, I need to say and went live. Yeah, you
Steve Rosenbaum 2:27
know, I think that we should, we should give people a link to that video, maybe in the down below or whatnot, because you were talking about in that video, it was DMARC. Yeah, you know, and this was one of the factors. And I know, and it’s a great video, we don’t need to go into the technical aspects of it here. But, you know, you broke it down. And most folks don’t understand what DMARC is all about. In fact, I thought I knew DMARC and I learned something from that short video you did. And I even posted a question. I posted a question about SPF that you answered there as well. So I mean, there’s just lots of questions, and who better to answer it than somebody who sent out over a billion emails. So let’s talk about it for people in the email marketing game. And you know, my audience are both online marketers, but also businesses that use email businesses that love to send cold email for prospecting. How is the Google Yahoo, Armageddon going to affect all of this?
Big Jason Henderson 3:27
Sure, it’s one of the biggest things that not a lot of people are talking about is engagement. And the big thing that I’ve been finding with all my latest clients, even the big ones, even the ones with really smart people that, you know, they know, you know, quite a bit about deliverability themselves, is you got to do away with the old 30 Day openers, you will not believe especially with some of the bigger lists that I’m doing segments on 30 day openers who haven’t clicked. And it’s literally sometimes in the six figures. So they’re constantly hammering these people thinking they’re engaged, you know, you know, iOS 15. Right? You got the fake opens. problem now. Well, that’s that lends to this, this issue where you’re emailing all these people, you think they’re engaged, they vote in the last 30 days. And you surprise lens to what you do is lead generation and follow up is, you know, you’re generating new leads, and you’re hammering them for 30 days thinking that, hey, they open they’re interested, when it could really just have been a fake open. So you really got to tighten up your engagement set up different criteria. You know, clicks if you have a system that measures replies, I think GHL can measure replies to right Yeah, absolutely. So you need to set up different engagement factors. It doesn’t mean you can’t exclude opens whatsoever. But you can’t just, by default, make that your main criteria, you know,
Steve Rosenbaum 5:05
interesting. You can’t rely on them exclusively, I think is what you’re saying. Yeah,
Big Jason Henderson 5:09
what? Exclusively or as your primary like I always tell my clients, no primary is seven day clickers 30 Day clickers and then possibly, sometimes the seven day opens, sometimes it’s 14, but mostly seven day opens.
Steve Rosenbaum 5:29
So what happens if people? Okay, so what should we do as email marketers? If somebody doesn’t take action in 30 days? Do we just throw them out? And never talk to them again? Or approach them a different way? What what what are you advising?
Big Jason Henderson 5:47
So it kind of depends on what you’re offering them, why they opted in is they’re trying to download something, are you just starting the video, like, I start a lot of clients that, you know, they get them to opt in to watch the video, and they just hammer home 30 days to go back and watch the video, well, there’s a good chance that they’ve watched the video already. And you need to follow up with something that’s I always encouraged them to, even if they have a really good video to offer some sort of lead magnet, which gives them a reason to get them to click and engage. And then it’s another medium and it could possibly convert more sales. But if they haven’t clicked replied, or any true engagement, within sometimes seven days, then you have someone that might be just be a looky loo, so what you want to do is possibly tag them, and put them in a different automation maybe approached from a different angle, you know, maybe, you know, they were kind of intrigued with your lead magnet or the video or whatever, got them to go in the Facebook ad. And they just decided now this is not really for me, but maybe they’re still in your target demographic, and then maybe you approach them in a different way. But you just don’t want to keep emailing and hammering them. When, you know, you’re, you know, go high level saying they’re, they’re not clicking.
Steve Rosenbaum 7:17
Yeah. Interesting. Now, so this is for optics, you know, in the business world, people love cold emails, they love their scraping their buying lists, whatever. And then they’re just sending out cold emails. What’s going to happen now?
Big Jason Henderson 7:37
Yeah, they really gotta, you know, tighten up their their leads, where they’re getting their leads. The targeting, like I recently worked with a bunch of lawyers who are trying to become, you know, the number one conglomerate of one sector, you know, going out and buying businesses. And, you know, I wrote their emails for them. And I talked to the person, or the company that is generating the leads, and it is like, laser targeted, they’re not messing around, they’re not going broad, they’re going narrow. So obviously, the amount of leads is not going to be as much, but they’re way more targeted. And they’ve hardly get any spam complaints. They get really good response. And even if they’re like, totally not interested whatsoever, they’re all friendly replies like, no, that’s really not a good fit for me, you know, but no, thanks for reaching out. So that’s, that’s a lot different than a lot of people are sure, just going broad, and generating spam complaints, or people just ignoring or deleting, which is all negative single, negative deliverability, signals, deleting unsubscribing spam or just simply ignoring, and that’s all going to lead and be compounding negative effect on your deliverability specially coming February.
Steve Rosenbaum 9:01
Excellent, excellent. So I’m hearing you say there’s a we’ve been talking mostly about a behavioral component. There’s also technical things that you got to make sure you’ve got in place. And that’s what your video was about the other day, right? Yes.
Big Jason Henderson 9:16
And I think if this doesn’t directly address what you’re coming to, then we can still continue on. But I think the biggest issue is this 5000, emailing 5000 contacts per day, a lot of that’s in their recommendations or their their guidelines. But I see a lot of marketers saying, Oh, if you don’t email 5000 contacts a day, you don’t have to worry about it. And I’m just like, What are you talking about? Basically, everything you’re saying is stuff that you should have been doing? Long time ago, like take DMARC it’s been available for over 10 years. I literally set up DMARC for the first time over 10 years ago. And now a lot of people are saying, Oh, don’t worry, you don’t need To set up DMARC, it’s like, yeah, you do. And
Steve Rosenbaum 10:03
to your point, there’s a lot of bad advice about that, again, that was your video, hey, even what they’re telling you to do with DMARC, they’re telling you wrong, they’re, they’re telling you some wrong settings. And, you know, you explain the difference between, you know, doing nothing a quarantine or reject, and that we most people probably don’t know what those differences are. And you explain what it is. And that’s important. Yeah,
Big Jason Henderson 10:25
so they’re either saying, Don’t worry about it, or just do the minimum requirements, which, like I said in the video, like, why wouldn’t you take it? Like literally 30 seconds more to do it? Right.
Steve Rosenbaum 10:40
Tell me something. Have you noticed? And I started seeing this in my Gmail account, that there is now an unfollow link at the top of the email next to the next to the address. I mean, that’s Google is putting it out there, right? Yes,
Big Jason Henderson 10:56
it’s been since probably July. And it’s become even more prominent. They want to, you know, you shouldn’t be afraid of that. If you’re doing good stuff. If you’re targeting the right people. It shouldn’t be an issue, is it going to impact you? Possibly, but I don’t see how it could be that much of an impact if you’re doing good Legion? Yeah.
Steve Rosenbaum 11:20
And if you’re not, then it could, because it’s just, it’s just much more visible. You know, a lot of those people that aren’t doing it, they’re burying the unsubscribe link down below. And you know, like funk, you know, white on white, that kind of stuff.
Big Jason Henderson 11:32
Yeah, there’s two, there’s two aspects of the unsubscribe, there’s the unsubscribe header. And that’s what you’re talking about next to the from email and all that that’s what Gmail is putting, for most people, if you’re using go high level Mailgun, Active Campaign, stuff like that, that’s already taken care of for you, they do that for you. So you don’t have to worry about it. But especially with cold email, I won’t throw the company under the bus. But I was speaking about, you know, the lawyers and the cold email and the company that was generating the leads while that company was using a cold email service that I had the lawyers stopped using, because they didn’t include an unsubscribe header. They were pretty much clueless. So if you’re doing cold email, and you’re using these, you know, email services that are not like well known, they’re probably done like they’re doing anything shady, but they’re just under the radar. They’re not like Active Campaign. They’re specific for cold email, you want to check to say, hey, like Steam all those reports? Say, Hey, are you ready for the February 2020 for Gmail and Yahoo standards? You got you got to make sure that they are doing that. And then like you said, the unsubscribe link. Yeah. You just don’t want to hide it. If they don’t want your email, let them get off versus hit the spam. Yep.
Steve Rosenbaum 12:52
And but the the unfollow in the header that’s, that’s put there by Google, right? That’s not I
Big Jason Henderson 13:00
mean, Google displays it. But now it’s your email service provider, whoever’s dry, sending your emails, whether it’s Mailgun, you know, go high level uses, you know, you could use their lead connector, or you could use Mailgun. Right, whatever that service. That is. That’s who’s putting that in there. And then Google displays it.
Steve Rosenbaum 13:20
Got it? Got it. Got it. Got it. All right. Well, is there anything else that you think people watching now should know? About? You know, about the apocalypse? So three tips that you might give them? We talked about engagement, but go ahead and sum it up for us? Yeah,
Big Jason Henderson 13:36
related to engagement is, and we talked about the spam complaints, you want to keep those low point 1% or less is ideal. Gmail and Yahoo have said, you know, don’t go over point 3%. And I see even a lot of good mailers, you know, they get a little greedy, sometimes they, they tighten up their engagement, and they’re like, Oh, I’ve got a promotion. You know, these people haven’t engaged with me in six months, but you know, I think they’ll be interested. And all sudden, there’s spam complaints spike, depending on the number of emails in the promotional campaign, if you do it too long. Gmail is going to be like, and Yahoo is gonna know. And it’s gonna hurt deliverability for everybody, even your engaged people. So you want to take notice of that. Which leads me to Google postmaster tools. You know, the postmaster tools? Right?
Steve Rosenbaum 14:24
Tell us more, please. Yeah, so
Big Jason Henderson 14:26
a lot of us still today. A lot of people don’t know this, that when you have your ESP whether it’s go high level or Mailgun. And they tell you your spam complaint numbers or your spam complaint percentages. There’s one email provider email address provider that doesn’t report to go high level Active Campaign. They don’t tell them anything about that is Gmail. So you may think, Oh, I have like point 000 1% In actual emails, yeah, if like 70% of your list is Gmail, that you need to have Google postmaster tool set up, you literally just google google postmaster tools, it’ll say, log into your Gmail account or your Google workspace account. And, you know, it’ll authorize that you’re the owner of it. And boom, depending on if you have enough volume, which is typically anywhere from 1500 to 2000 emails per day, you start seeing some data. And you gotta monitor your Gmail spam complaint rate, and Google postmaster tools, not in your email service provider. That’s
Steve Rosenbaum 15:43
a good tip. And that’s one I know about the postmaster tool, but I did not know you needed to do that. But it’s simply just going there and doing a D, a DNS settings, so they can verify you and then they can, then they can report those stats, correct?
Big Jason Henderson 16:00
Correct. All right. It also reports on how successful you’ve implemented SPF D 10, DMARC. And I’ll give you percentages as well. And that’ll help you because that’s the next big thing is they want stricter authentication. So basically, it’s like, you’re sending a postcard, and you have an address there. Okay. You’re sending it, you’re authorizing it to be sent via the post office. But you don’t want to post the somebody intercepting it before it gets to the post office and sending them Sodra. Wait a second. I didn’t authorize that. So basically, the DKM and SPF all work together. And the DMARC record to say, yes, the Postmaster General, he’s authorized to send it to the my contacts, this person is not, you know, Active Campaign go high level Mailgun. Yes, they’re authorized. And anybody else? No. So that’s what you were talking about before, there’s the report only, there’s the quarantine, the reject. You don’t want to stay at the minimum requirement, or these new standards from Gmail and Yahoo at report only. Because most people, even if they do this correctly, they’re probably not going to spend the time monitoring it like they should. So basically, you’ve, you’ve got all these email services reporting back, hey, this person is trying to spoof you this person is trying to email, you know, penis pills as your your domain, it could be ruining your reputation. But you’ve told it, just report this report back to me. But if you’re not paying attention, you’re not seeing that. And you do not believe the number of clients anywhere from one to five trusted email sources. They’ve literally just forgotten. You’ve got so let’s just say take you, for instance. So you have your go high level account is connected with Mailgun.
Steve Rosenbaum 18:12
No, it’s with LC now. Okay.
Big Jason Henderson 18:14
So let’s just say, if you’re one of my client clients that I’m talking about, I would come to you, I’d be so I’d authenticate or the lead connector. And then I would turn DMARC on report. And it would say, Well, wait a second. Here’s the email from SendGrid. Oh, I forgot to authorize SendGrid. So you set up the DNS, the D, Kim and SPF for SendGrid. And then your DMARC says, okay, SendGrid is good. Alright, we’re authorizing them. Oh, you got your membership site or use go high level? Maybe that is
Steve Rosenbaum 18:54
help desk you gave an example the help desk? Yeah, you
Big Jason Henderson 18:58
get your help desk. You don’t want your customer service emails to go to spam or anything you want that authenticated and authorized, like yes, my Help Desk is good. You got your shopping cart, like go high level we already talked about other people might be using, you know, thrive cart or whatever. And so yeah, that basically reports it and then eventually, you want to get a quarantine. So that basically says, I’ve authorized go high level Mailgun Thrive cart. Say postmark Zendesk, no one else is authorized to send on my behalf. So the quarantine says sent everything is spam. That’s good. That’s much better than going to inbox but it’s still going to people’s inboxes but still not the best. So then eventually, when you know you’re sure everything’s good. All your trusted email sources are authorized and authenticated. Then you switch it to reject and then that That way someone tries to email as you. You reaches Gmail. Gmail says no. And it doesn’t deliver it.
Steve Rosenbaum 20:07
Excellent. You know, I’ve got one more technical question for you, because this is your brought up something that you touched on. So let’s talk about setting up a sending domain. For your like, for me, I’m a high level agency. All right, and so my, my domain is flawless follow up.com Should I send? What should my sending domain be flawless? Follow up.com? Should it be a subdomain? Should it be something else?
Big Jason Henderson 20:34
Whatever is easiest or contacts to remember to get them to add to their contact list, if you’re going to be, you know, saying in video, so like, just say, for Mailgun, typically, you’ll see you know, mg.yourdomain.com, or send.yourdomain.com. That’s called basically the return path. You can set that up, but still use your domain, you know, [email protected].
Steve Rosenbaum 21:05
So I’ve heard his reply, okay. Yeah, yeah.
Big Jason Henderson 21:08
But you can, you can do that. In most cases, when people do that, they like to silo different channels. Because when you do a subdomain, it’s not a 100%. But it kind of alleviates possibilities. So let’s just say, for your lead gen, you’re using Stephen at flawless follow up.com. And you’re like, Okay, you know, I’ve got a good lead gen, but the engagement is probably 20% Less than, say, my customer service emails that are going out. And I kind of don’t want that to negatively affect my customer emails. So you might set up instead of Steven, at all a follow up.com, you might say, Steven at support dot while a follow up.com. So the Gmail and Yahoo, they see that, and the support dot follows. Flawless follow up.com kind of has a separate reputation. Now, if you just go nuts, Hank, and get like 10% Spam rate, and a really bad reputation on [email protected]. It can carry over, but generally speaking, it should differentiate it and not negatively affect one or the other.
Steve Rosenbaum 22:34
So that was that was my very you answer my follow up question. If if you trash a subdomain, is that going to trash? Your regular domain?
Big Jason Henderson 22:44
Yeah, not 100% of time, but most likely, yeah.
Steve Rosenbaum 22:48
Okay. So would I be advised to use but if I use, like flawless follow up dot code, even though that looks familiar, that’s a completely different domain. And that’s going to trigger a domain mismatch? Correct.
Big Jason Henderson 23:03
You can, technically, you could set it up that way. But it’s as far as separating it, they’ll know. Right? Jack? Come on, really? You won’t know. We’ll
Steve Rosenbaum 23:17
know in the header when you do that. There’s a fail, isn’t there? Because it’s a domain mismatch? Yep. Yeah. Okay. All right, big Jason, this is awesome, great stuff. I appreciate all that you do. And, you know, with your experience, this is just great information for everybody that we just keep hearing all the rumors and reading all the scare tactics. So stuff. How can people reach you? And who can you help? Sure.
Big Jason Henderson 23:43
email inbox warrior.com email inbox warrior.com. I have a course that’s live right now, I have a done for you. Service if you want to want that instead, usually book 30 days. Because sometimes it takes a while depending on how many email sources you have. And taking DMARC from, you know, reporting only to quarantine to reject and monitoring all that. And then you can decide at the end of the 30 days, like alright, I think I’m good to go. I think my team can cover this or, you know, we want you to stay on, you know, indefinitely or for a certain period of time to make sure things you know, stay running smoothly and someone’s on top of everything. So who do I serve? Like, essentially anybody with a decent amount of leads? If you’re like really just starting I think you could probably get away with you know, reading the articles and everything. But if you have a significant significant size a list I would say. I mean, I have to tell you, like some of my recent clients are only have lists of 3000. But typically, I would say my ideal client is typically 15,000 or more leads. Yep, All
Steve Rosenbaum 25:00
right. And I know you’ve been doing this a long time you said something funny, which was true, you know about, hey, this isn’t new. Right? And, and people that are truly male marketers and truly care about deliverability and doing it the right way. This really isn’t a big deal, because this is just the way it should have been doing it correct?
Big Jason Henderson 25:19
Well, yes, and no, that is a very true statement. But the other thing I see is like, well, the only people that have to worry about it are bad mailer, bad spam spammers, well, is digital marketer, a bad mailer spammer? No, they’re like a really trusted source of spam complaint is like, nearly zero. But that doesn’t mean they know everything about, you know, engagement, you know how to properly segment so they’re targeting the right people. And because, again, even if an agenda of spam complaints, if people if that’s part of the coming, Armageddon is if you’re emailing too many people that are just not truly engaged, that’s going to negatively affect you. So yes, it’s something that everybody should have been done. But even really good, smart marketers have not known everything that should have been done doing all along. Well,
Steve Rosenbaum 26:13
I’m glad you said that. Because one of the reasons that I brought it up and I brought it up, the way that I did is I know, you’ve had a course out there for a long time about email marketing, and deliverability. What’s the name of the course? email
Big Jason Henderson 26:28
inbox warrior? Yeah, that was that was a while ago, and I literally just started the new version, the live version, like a month ago. So it’s all current.
Steve Rosenbaum 26:39
Exactly. And that’s, that was one of the points I wanted to make. Was, Jason’s been talking about, we talked about behavioral about the engagement about getting people you know, these are not new concepts. Jason’s been talking about the for a long time, and just go back, you could you could Google big JSON, you could find out you’re redoing the course now is is the old one. Is it still out there? It’s just still relevant, or that’s why you’re renewing your readme.
Big Jason Henderson 27:04
A lot of it’s still relevant, but I think it’s more valuable, that you’re seeing more current strategies. Yeah, I have actually, like, at least three current clients that are saying, you know, what, if you want to go live, you know, in the members area, and the private Facebook group, you know, optimizing my deliverability you know, feel free, I don’t mind. So people are seeing, you know, actual live deliverability in action on real lists and seeing the difference that makes.
Steve Rosenbaum 27:40
Alright, Jason, thank you very much. I’ll let you have the last word.
Big Jason Henderson 27:45
Yeah, you know, don’t be scared, just, you know, get it done. And don’t do it. Just meet the minimum requirements, do it to get as many emails in the inbox versus the spam folder. You’re just gonna, you know, get more response and make more revenue.
Steve Rosenbaum 28:04
Absolutely. Absolutely. All right. Thanks so much for Jason. Appreciate it. Thanks
Big Jason Henderson 28:07
for having us, Steve. Appreciate it.