The 8 Hidden Infrastructure Issues Tanking Your Deliverability Right Now - with LB

Foreign.

Welcome back to another episode of Audience Bridge Insights. Today we got a whammy. We got LB here. An industry veteran, a deliverability expert, she is known as a full stack email solutions architect. She knows everything from the bottom up and I'm excited for this chat lp how are you doing?

I'm doing great. I'm doing great and hopefully this will be big money.

No whammies because email whammies.

Yeah, email, when it's done right, if you're really making it a profit center, I mean honestly, you're trying to press your luck.

Yes you are. So that being said, why don't you kind of describe what you do as far as like being a full stack email solutions architect for those newsletter operators, email publishers that are listening so they get an idea of what you do.

Yeah, I mean honestly I help senders everything from individual brands and newsletters, commerce platforms, all of the above and all the way down to the email sending platforms and even sub processors. I help them, you know any with problems anywhere in the chain of email and even somewhat adjacent because there are ways in which your website and your site security can, can also impact your ability to land emails in the inbox. So anywhere there's a problem caught anywhere along the chain from the C, you know, from the sending server all the way out to your website, I help identify those issues and remove the blockages that are preventing you from reaching your audience.

Perfect. So some based on that, what are some of the most common problems you get or issues that your clients come to you with that fit that?

Yeah, yeah. So I gotta be honest, it depends on who I'm talking to for sure. Cause I, I these days I work with a number of agenc and help them with their internal teams and also I help several email sending platforms. So definitely the advice I'm giving platforms is going to be very different than what I'm telling someone running a newsletter. But I would say if you're folks running newsletters, the biggest trend I'm seeing right now, at least at Google and honestly Microsoft as well is filtering due to content, filtering due to content and less the words that you're putting in it because while there are a few exceptions, there are a few spammy keywords that'll still cause you problems. For example, don't put the word free in all caps in your subject line. That will cause you mass problems at Hotmail and all of Microsoft's free infrastructure. But more talking about kind of the technical construction are all of the links in the email HTTP secure. Do all of the links at least align with the sending domain. It doesn't have to be the exact sending domain, but you know, are you putting your links on link.sending domain. Com? Right. And also is your HTML bloated? Is your code bloated? And don't trust these drag and drop editors because those things will produce bloated code in a lot of cases as well as the images you're putting in it. Like a lot of people think they can just take an image off their website and put it in an email. Absolutely not. Email is a different viewport, it's a different display, you know, and the majority, we all know the majority of email. I used to work for validity and I worked with a lot of top brands there, auto manufacturers, you know, just newspapers with mass circulation. And you have, we would see things like 60 plus percent of the, the audience opening on mobile devices.

Right. I actually just saw, I think it was yesterday or maybe today, possibly today, one of your chats where you're talking about the lossless, lossless image optimization on pressing images before you kind of upload them to your, to your esp. Kind of want to touch on that Because a lot of, a lot of I would go with traditional email publishers and stuff. You know, they're publishing their content on a CMS, whether it be WordPress or something else and they're, you know, usually uploading a freaking real large image. You know, physically there's different plugins and stuff to help compress. Some may be doing it, some are not. And then off of that there a lot of them are using some sort of automation cron to just schedule their emails to whatever system they're doing it automatically gets sent out. So understanding that yes, a lot of people will build emails in their email platform and upload an image there and that's where the server and you're talking about this lesson in this image compression, we'll shrink it for them. But I guess it's talked about that just a little bit so people understand because for people that don't know, like when you send images in your email, you're not sending the actual image. You're, you know, you're sending the URL to the image so they can render for them. If not it would be an attachment which would not deliver bulk Sunday anyways.

Could be waking alerts, not a good idea.

Right. So they understand like how that impacts the sending based on the size, even though you're not really sending that image. And then how, you know, maybe the best practice for people that are necessarily uploading to the ESP or I think we're talking about Send Post, I think is the one you're talking about.

Yeah. So one of, one of my clients that I can disclose is sendex. Send Post. So honestly, we noticed so many people were struggling with this that we just implemented it on our server. If you send an email through us, we're just going to compress the image before it ever sends out the door. Anyway, we're going to compress it. When you, if you build a template in our system and upload it and we're working, we're going to compress it. If you even just pass it through our system, like your API integrated or something like that. Because so here, here's why it's a concern. Because even though, yes, you're just sending, when you send an email, really you're sending, you know, the HTML packet and it has references to the images. However, when people open the email, you have to download the images, which this causes a few concerns Google worries about. First of all, server storage, server space ain't cheap, it ain't free. And like, if you think about how much computing, how much pressure AI has put on computing resources, I think this is part of why we've started to see this squeeze in the last like 18 to 12 months release and say, lock down that authentication, you know, all those authentication requirements. I think we're now seeing more focus on content and because that's also where spam still lives. Like, people can get new IPs, they can get new domains, but ultimately they're sending the same offer and they leave little breadcrumbs. But yeah, Google doesn't want to store all these fat images when somebody opens the email for like half a second. And the other thing you got to realize, I like to talk about attention spans in the age of TikTok. Think about this. You have a big, beautiful hero image. It looks great on your website, right? But then somebody goes, you know, some I'm out on my mobile phone, I get your email, I want to open it. And if that thing takes like more than half a second to load, I'm probably out of there. Like, nobody has the attention span anymore if your image doesn't load. So that's really it. It's pressures on Google and their computing resources and all of the service providers. I've seen Microsoft, they've honestly been strict about this for much longer because one thing a lot of people don't know, mailbox providers, like when you deliver your mail, they look very closely at the first, like you know, several, probably thousands of folks that open that email, they, they can move it to spam post facto after delivery. Like, they, they will do this more generally when there's like any kind of cyber security concern, if there's a broken link, if there's, you know, malware or something found on the website, because it's a really common hacker technique, send it, send a link through that's clean when you send it, but then put the dirt up, like after it's already delivered. So spam filters have had to adapt. You know, people open the email, you get a lot of complaints or you get a lot of people just bouncing right out of that sucker. Kind of in the term of not an email bounce, but what like Google Analytics on your website would call a bounce. Like somebody just spending, I think, less than half a second.

Right.

But it's really those concerns.

Are there, are there any tools or plugins out there that can kind of help publishers do this?

Yeah. Yeah. I will say if your ESP doesn't love you and they're not compressing their images, well, what I'll say is you can use. Honestly, I have a simple. It's tiny T I N Y P N G P. You. Oh, gosh, what is that? I don't remember the, the military numbers for that or, you know, call signs for that. But tinypng.com is a free tool. You just upload, you just put your image in there and it will compress it. And I use this tool all the time to check and see if people have those kind of issues. And I literally, in a lot of cases, and it's lossless compressions, you don't lose any image quality. And I can often save people up to like 80%. So you make that file nice and lightweight. It's going to load fast for the user, so you don't have user experience issues. And it's going to make Google less, less concerned. Because the other concern is too. A lot of people don't realize hackers will, like, hide malware and images. I recently had to escalate a case to my mentor. This was happening on a website. Hackers will hide malicious executable code in image files. So if that file's big and heavy and bloated, Google's just going to look at it and go, I don't want to store it. I don't think it's going to be a great user experience because it's not going to load fast on mobile and maybe there's some yucky stuff in there. I'M just not. I'm just going to throw it in spam and not worry about it.

Right, perfect. I'll put that link to Tiny.

Yeah, yeah, I'll put it in the chat for you. So you. So you have it.

Yeah, that's great.

And I get nothing for plugging these guys. Like, I mean, they provide a great free service. So if you're just doing your campaigns and here's the thing, test a few of the images you're using. If you're only shaving 10, 20% off, you're probably already doing great. But if you're saving a ton of space, then it's a sign you should keep doing that.

Well, we'll have to reach out to Tyler to see if they're integrating that in Beehive.

Yeah, yeah, I should, I should ping him. I haven't chatted with him in a bit, but there do Beehives doing amazing things with how they manage newsletters for people and also help them monetize them.

Yeah, I send, I send my audience bridge newsletter through there, but I'll always compress the images before I upload them. But I don't know if they do it themselves. I haven't heard that they have, but maybe they do and don't really tell anyone.

Most ESPs, I think they're backended by SendGrid and SendGrid does not. Most ESPs do not.

Got it. Cool. Talking about the inbox we're talking about, you already brought up some things. Images, subject lines, you know, there's list hygienes. Can you kind of explain your thoughts on what's under the hood when it comes to getting your email sent to.

The spam or getting, getting them in inbox instead of spam, for sure. I mean, I'm going to be really honest. It is a complex and ever shifting algorithm that involves a variety of factors and frankly that's because that's how Google's spam filtering algorithm works. They're frankly always testing several variants of the algorithm at the same time, I would assume, because that's also what I've heard they do for SEO. So they're always constantly testing, which I will give a plug for that. You know, the best way to know anything in email is to test and find out. But I would say this hygiene absolutely important and frankly I even use it. I even use email hygiene integrated into web forms to help stop fraud. Because one thing a lot of folks aren't, aren't aware aware of as much is what's called list bombing. And that's where malicious actors will find an open web form that has like an autoresponder, like a welcome email confirmation email. Thanks for signing up. Right? And then they will start throwing email addresses in that are tied to financial accounts they're trying to compromise. This is what I always tell people. This is a personal cybersecurity. Tip, everyone, if you start getting a bunch of welcome emails you did not sign up for, that is a sure sign you were about to experience an attempt at a financial account compromise. I had this happen to somebody in like real time. They came in the Email Geeks channel, which is where Chris and I met. They, they came in the Deliver channel and said, hey, I'm on the design side of the house, but I just started. You guys know anything about this? We're like, oh, honey, lock down your cards. And she's like, I haven't, I haven't seen anything. You know, I haven't seen anything. I haven't got any alerts. Comes back to the thread 30 minutes later. Oh, my gosh, you guys, you're not going to believe this. I just got a text from a credit union that said that they declined a $900 transaction.

So.

Honestly. Yeah, so it's, it's nuts. It happens a lot. And if you basically don't have your web form protected, you are letting your domain, your email infrastructure become a vector for attack. And what I've seen is people, they won't spam, complain right away. A lot of times they'll, they won't even realize there's so much chaos because that's what the hacker is trying to do. So. Because at the same time they're hitting, you know, if they're trying to hack me, at the same time they're putting my website through your web form, they're also putting it through Chris's and everybody else's that they can find. So, yeah, that's. You have to. And honestly, it's pretty simple. You just put Captcha, or even simpler than that, have a hidden form on your field that just looks innocuous. And if you see the robot put any value in that field, don't, don't like just suppress it.

Yep. We, on all of our stuff and we recommend to our client to stuff that. To have Captcha on the website.

Yes.

And Google has the version. Was it three now?

Yeah. Three. Yeah. You don't want to use the other two. They've been compromised too much.

Right.

So there's also H Captcha as well. There are a variety of options and they're Frictionless.

So we do that, then we have the hidden fields. On top of that, we tell everybody to get on cloudflare and set up bot protection there. And then we're also on every email that gets submitted before we even post it to the esp. We're doing a third party email validation through any of the number of providers out there just to confirm that it's a deliverable, it's not a known malicious actor, spam, any of that stuff. So that's kind of how we're protecting all the data on the front end.

You're a cybersecurity expert. That's what I call, that's defense in depth. That's defense in depth. You don't just have belt and suspenders, you've got defense in depth, you've got the captcha, you've got the hidden fields, you've got validation. And honestly, I hate to say it, that's what it takes. And the insidious thing these days that I've seen is because all of the, you know, large corporations have really hardened their cybersecurity after seeing, you know, big corporations getting hacked left, right and center. It's been pushed down to smaller and smaller businesses. So I mean, and that's that, you know, small businesses just don't have the resources to have a massive cyber.

That's a scary part because the ones that compromise but then they're giving you the information to the big, their big accounts. So they're obviously we, we, you touched on it, we went through the big update with the bulk sender requirements, Gmail and Yahoo a couple years now back and now Microsoft adopted it. Can you explain briefly, you know, just in layman's term for the newsletter operators, email publishers, kind of the requirements, spf, dkim, dmarc, so they understand for those who don't really understand this stuff, a lot of this is going to be taken care of. When you're configuring your esp, your ESP usually walks through the process to make sure that, you know, your sender requirements are in place. I've seen some that have not, but that's, you know, neither here nor there. But if you can get into that. And then I have a follow up question off of that.

Yeah, for sure, for sure. The big change, honestly the big change that Google made was requiring DMARC authentication, which DMARC is an anti spoofing policy. That's a, you know, you put the record in your DNS, but it really sits there as like an authentication protocol and policy that helps Protect your brand against anyone out in the wild trying to use it. Because this, this is the thing often tell people it blows their mind. Like if I want to send from your domain I can, I could spin up, I could spin up a, a email server on my computer in like 10 minutes and be sending from your domain. Authentication and the anti spoofing policies are what prevent that from being counted against you. So DMARC's kind of like this umbrella. So you put it on your parent domain and it protects it against anybody who doesn't. It's really saying how think SPF and DKIM need to authenticate in order to for a mailbox provider to consider the message valid. It's basically DMARC is an instruction you the sender, you the domain owner get to put in, you know, out there in the wild to tell the mailbox providers like Google, Yahoo and Hotmail how you want them to handle your mail, what it should look like from an authentication standpoint. And it also gets you some really great reporting back because I even work on the back end of that. I operate an easy DMARC msp. If anybody needs help with dmarc I have super affordable options. But what I because it's really for me it's just people need this and what I can say there a lot of ESPs will help you with the SPF and the, the DKIM. They do not as much help you with the DMARC and they usually don't give you reporting. And frankly some of them out there have been giving people very bad advice that that cuts you off from the reporting info which I find very vexing. But I won't name any names right now.

Right?

Yeah, it really just kind of locks everything down so that you're the only one that can use that access. Because here's the thing I will tell people I worked I came up a lot in the upwork like freelance space helping folks out. What I'll say there is I had a lot of people would do what I would call flashing me. They would just hand me the login credentials to their domains, DNS, leer text. And what I'll say is please don't do that because that is the keys to your digital castle and you need to keep those very close to the vest. And that's how Google and everyone treats it. If you're able to put. So like if you're setting up Google Analytics or your Google Postmaster tools, they tell you put that text record or that cname is because they're asking you to Prove you own the domain and should have access to the data feed by putting a record they can see in the public DNS.

Yeah. As far as the DMARC goes, can, can you touch on your recommendations when it comes to the policy from P equals none to quarantine to reject, as well as percentages like best practices of when you're, when you're moving it over. It's one thing to have it set up, but then to be secured on it and making sure no issues are happening.

Yeah, absolutely. Typically I recommend most folks start their initial deployment at P equals none. And I generally, unless you're a massive institutional sender with like just a huge complexity of mail streams, if most of your bulk volumes going out of a, a single platform, you know you've only got a limited number, go ahead, I would just put it at a hundred percent. If you're sending less than a million a month, just go ahead and put it at a hundred percent. And honestly, you don't even have to enumerate it. The assumed default is 100%. And, and I set it to P equals done. But you got to get that reporting. You want to look at that reporting. I tell most people at least 45 days because I had an incident once. I had a client that found me on upwork. They're like, oh gosh, it deployed DMARC with a policy of P equals reject, which the policies, what those are is that's the instruction you're giving the mailbox providers. Your P equals none says hey, even if it fails, don't do anything. Now that doesn't mean that's what they're actually going to do. They might put you in spam anyway. Quarantine means put it in the quarantine folder, which for most consumer recipients is also just the spam folder. But for corporate mailboxes, like if they're using like a proofpoint SP spam filter, there's like a zone before the individual mailboxes that only the IT admins have and reject is super simple. It's saying, hey Google, if this message doesn't pass my DMARC policy, I want you to reject it. Because that makes you a really unattractive target hackers. But yeah, I had this poor client, they come to me and they're like, oh no, it flipped DMARC to reject. Now none of our HubSpot emails can, you know, they're all getting balanced. Help, please help. So I help them. No problem. We set up custom dkim. That's the most common way because some platform Providers out there will not allow you to customize what's known as the return path, which is what SPF gets authenticated off of. So, like, mailchimp is a big example. They just don't allow for it. And that's fine. It's not really essential. But you can always pass on, you know, setting up custom dkim signing and then that makes you pass your DMARC and et cetera. But they came, you know, they came to me. I got them all fixed up, thought the job was done. I was happy. Then they hit me up like two weeks later and I'm like, hey guys, what's up? I thought I fixed you. They're like, yeah, yeah, we're fine. Accounting had a problem. We didn't realize netsuite was using the domain. And half of people didn't pay their bills this month because when the emails went out, half of them bounced. And that was super painful for this business and their cash flows. So this is, this is why you start with none, start with none, collect at least 45 days worth of reporting so you catch any monthly billing cycles or anything going out and then look at all that traffic. And if it's all compliant or majority compliant, you know, go ahead. For smaller senders, like I said, under a million a month, I typically recommend just go straight to reject because I don't love quarantine mode because when mail, if mail is getting rejected, at least, you know, if there's a problem with your systems, you start getting the bounce backs. And it also makes you a really unattractive target for hackers because. And spoofers because they don't want to deal with all that crap bouncing back at their server. So, yeah, that, that's the main thing. There are some uses for quarantine that I found. Like I had somebody that was being cyber attacked. They were, they were trying to do. This is super technical. They were trying to backscatter emails in off of the DMARC reject policy. So we had to move them to quarantine because they, they were trying to compromise an employee or something. And so there are some limited cases for quarantine, but in general, I like none. Watch it for 45 days. Move that sucker to reject to make yourself unattractive and open up the opportunity for Bimmy, which I was hearing some buzz at the most one of the recent conferences. They think it produces like a 10 to 15% lift in open rate in some cases. So I can't say in every case. Newsletters, y' all are typically hitting the primary tab Already but it helps a lot with visual identification. It's just really quick.

Just had my follow up question about Bimmy.

Sorry. Well yeah, yeah that's good.

I was going to ask you if you've seen any lift from it as well as do you know if they're. So those of you that know what BIMI is it's another you know, basically identification policy that's out there to prove who you are. You go through a process, get a certificate. All this stuff, the verified mark certificate you need a trademark for. They came out with a common mark certificate version so you don't need the trademark. But it doesn't seem like it in my experience. Doesn't seem like that validates through right now completely. It could be wrong. You could probably explain that to me. It validates but not like the, the, the, the logos and stuff still aren't showing up on Gmail and stuff like that and I don't know if it's because it's common mark and not verified mark. I don't know if you have any names.

Gmail had announced they were going. I, I thought the big move to cm, CMC Common Mark certificate was that Gmail and announced they would support it. I will say this, one of my mentors is on the BIMI working group. I would be happy to troubleshoot, we'd be happy to troubleshoot any like incidents where it's where CMC is not working. There are some additional hurdles you have to go through if your volume isn't sufficient. I would say, you know, if you're not, if you're not probably sending at least like 10,000 per campaign you may not be a high enough volume bulk system sender. I don't know where the exact threshold is and I don't know they haven't really.

This one should be, should be enough. I mean it's sending.

Yeah, we might have to take a look at that one because Google had announced they would support cmcs. However there's been some drama in the whole certificate biz anyway because Entrust got D trusted by Google like not just their Bimmy certificates like everything and then now that business unit's being sold so yeah it's there, there, there's some drama.

Going on but the, so what's funny is you know a lot of these policies, spf, dmarc, they've been around forever, they just weren't enforced. I don't know what took them so long to enforce it in my opinion. But now you have Bimmy as well which to me seems like the next evolution of proving your identity that they would kind of make that a standard at some point, a requirement. I don't know how long that would take to get through the process. Probably a while. Just because of stuff you're saying right now is like well the certificate providers are kind of having issues and stuff like that. What are your thoughts on Bimmy as a more of a large scale policy?

I'll be honest, I don't think they'll ever require BIMI because to be really honest, it was created as the carrot to drive DMARC adoption and it didn't really work in part because I've worked with brands on BIMI implementations and yes, back when it was only verified mark certificate, the biggest hold up is the US Patent Trade Office. It was like a 13 month plus backup to get that trademark on that specific logo you want. So I don't know that they'll ever require BIMI because it's more of. It was more created as an open standard due to the fact like when I was at, you know, I got my start in email tech at IBM working on their marketing cloud and support and frankly how do I control my contact icon? Was one of the most common questions we got asked and the answer used to be well you go to Yahoo Business and create it. You go to Yahoo and create a Yahoo business page and put your contact icon up. You go to Google and you create a Google page at the time and put, you know or you create a Google business page and you put the icon there and there's. I have heard for anybody, I've heard this works for other people trying. If you were on Google Workspace and you were sending, you know, from your root domain or even if you're sending from a subdomain just makes it more complicated. Set up a Google account for that mailbox and put the contact icon you want as that account's picture. And I've heard that will in many cases display at at least Gmail that.

A hundred percent works. We do that in all of ours. Icons do show up on Gmail but then they don't show up on Yahoo.

Yeah, it won't show up on Yahoo and you can still do the Yahoo Business page and stuff like that. But it's really. Yeah, BIMI was designed to be like an open standard to just make that function. And also you know, the requirement for that is you have to be at dmarc, quarantine or reject in order to be. You have to be at what they call enforcement. You know, you're not Just at a none policy. Hey, don't do anything about it. Right?

Yeah, let's, let's switch gears here and kind of infrastructure shared IPs versus dedicated IPs. A lot of people don't really, you know, at least news droppers don't really understand the difference, especially in the beginning. What are your recommendations as far as the shared versus ip? When to switch to dedicated. I'm sorry, shared versus dedicated. When to switch a dedicated. What are the options? You know, are certain we'll call them mass ESPs. You know like you're saying mailchimp for example, constant contact. Some of the bigger, more commercial ones. When, when is their service maybe not a use case for you? Do you outgrow it? Like what are your thoughts on that space?

Yeah, for sure. I think there are a couple different questions there Jared. Versus dedicated IPs I think is there. There are a couple. There's a really simple kind of matrix to evaluate that which is a. What is your scale? Below a certain scale, dedicated IPs are not going to work for you. You're just not going to send enough volume for it to work. And the other thing is inconsistent sending volume. Like if you only need to send like if you only send once a month and you send like less than 50,000, you know, right. If you only send once a month, dedicate dedicated APs aren't going to work great for you because they're going to sit dormant the whole time. And I think Google looks, I think Google, a lot of providers look at what is your historic like your average 30 day volume. So they take your one day send volume. You know, you send all your volume on one day, they divide it out. You're always going to be spiking way above your 30 day average and triggering anomaly. This is how I kind of advise my senders toward the path of least resistance. Because I worked on the other side of the house like in corporate internal support support and security and I, you know, I, I dabble a bit in cyber security as well and my background's in computer forensics and IT audit. Which means, you know, really IT audit is looking for variances. That's what spam filters do. They're risk management systems and risk management systems hate variances. So if you're gonna have really inconsistent send volume, shared IPs are a good choice. However, most platforms will not let you use their shared IPs above a certain volume. So SendGrid, which backends a ton, they're probably the single largest institutional sender In North America at least, and possibly the world. Because they back in platforms like Klaviyo, I think Beehive, I think, gosh, I can't even list it. Like just tons of them, tons and tons of platforms that sit on top of them. What it they they cut you off at? If you send more than a hundred thousand a month, they force you to dedicated IPs in most cases. Now if you're on a platform that is using them, they may have their own custom pools and their own rules and that's fine. But in general, if you have really inconsistent volume or really low volume, like I would say low volume, I even know some setting platforms will let you. When I worked at Click Dimensions we were a B2B platform. We didn't let anybody have dedicated IPs under 50,000. And frankly that was kind of what we would. I guess in medical terminology they call the LD50 lethal dose in 50% of the population. In that 50% of people be okay at that. About 50% would struggle. So it depends a bit on your, your volume and send cadence. What I would say is if you have weekly pretty consistent volume or even daily consistent volume, dedicated IPs are generally a better way to go. Because you have to ask do I think my send practices are better or worse than the average? And the other thing a lot of people don't know is most ESPs have more than one pool. And generally they will have like a default pool that everybody kind of starts in. They'll have a yuck pool for the kids that like to pee in the pool and cause problems, the pee pee pool. And then they'll have like a high rep pool for people who maybe had an issue. Because I will tell you this, when I manage shared IPs it is like a constant game of Whack a Mole to like keep them off of block lists. I'm just, I was just constantly every day delisting shared IPs and we didn't even have that many. Like we didn't even operate that massive of a pool. So. So yeah, there's, that's, that's kind of the concern. I can give an example. Back 2020 during the pandemic, I helped launch the hottest streaming service to launch that year, the big mouse eared one. And we had to use shared IPs to start because it simply was not going to be possible for dedicated IPs to do like a vertical takeoff. So we, we had to rely on shared IPs and I literally, my job was every several hours I would just delist all of Amazon SES's shared IPs, every last one of them.

Well that's a nightmare.

Sometimes Microsoft would even accept it.

Cool. Talking about some of the requirements, the One click unsubscribe is one of the newer ones that came out during that stuff. It seems like they kind of maybe are enforcing it or not enforcing it yet fully. I'm not, I'm not sure there. I have seen people who have the honor unsubscribe, you know, showing that there's an issue which means that they believe that well someone clicked the one click unsubscribe but you're still sending them emails where they're still receiving emails from you in some manner and try and navigate how that's done. Like no, they're unsubscribed here. Yeah. But if you have 10 list you're sending to and they think it's a global unsubscribe or something. I don't know. But you think that's affecting deliverability right now?

Yeah. So Google actually so I work with a lot of e comms as well and Google just announced this month like that they put at the top of the Google sender guidelines which I will also drop that link. But they actually just announced that they're going to start enforcing. They're going to, they're absolutely going to start enforcing.

Yeah, I saw this month they were going to start.

Yeah. The requirements. Yeah. So they're going to start and I'll see this. I had. So actually I found an issue in the go high level platform where their One click unsubscribe was not always unsubscribing people. I found out I eventually the best I could get out of them as an RCA was that there was a problem with the HTTP post process. But my client, my client and my buddy who had an agency with a lot of go high level clients, all their people. The only thing wrong in the V2 dashboard for Postmaster Tools was that honors unsubscribe and they were on low reputations and stuff and that was the only thing being flagged wrong. So I think there are. They're already enforcing that one. If you're not honoring unsubscribes. I mean that's a legal compliance issue too. Like can spam is the most permissive law of the land.

That is, that is the, the bulk of the.

Yeah is honor when people say unsubscribe. I mean so that's the other thing is, you know, sometimes you shouldn't have to test your, you should not have to quality test your platform that you're sending from. They should be doing that. But yeah, there's, that's an issue. I think not having it is also a big issue though. I had an interesting example. I had somebody, um, basically and it's, it's based on the domain. What'll happen is if Google sees you continue to email from the exact same domain that they know someone unsubscribed from. Because you gotta think when they use that one click unsubscribe in the header that powers the in app unsubscribe at Google, Yahoo icloud, et cetera. Right. They can track that. They know that person unsubscribed. So if they see email keep coming from your domain as problems and they look at the fingerprints too. I think if they see it, oh, it's just a transactional receipt, that's probably fine. But I actually heard somebody who said, well this I've got marked on my parent domain that I'm non compliant with one click unsubscribe but I don't send any bulk mail. I heard they put a ticket into Google. Didn't get a response because you never do. But actually the flag cleared up. So that would be my advice. If you have a domain and you know you're straight and you know you're maybe only other things, sending from that domain is like your, you know, your correspondence mail, your outlook, your Google workspace, whatever you may use. I put a ticket into Google because it could just be a false positive, you know, and they'll, they'll reevaluate it for you.

That's, that's not the first time I've heard go high level having issues with their email. It's, you know, I don't know, it's, I was working with someone and they're having issues with it and they basically had to build a middleware to just send those requests to and then they were sending from their middleware so they could provide the, the proper headers to pass through to verify that. But then it messed up all the tracking and this and the opens don't make sense. And it's like you can't even like optimize their process or the deliverability because you don't really know what's true.

Which the crazy thing is they're back at their bulk mail at least is back ended by mail gun that has that stuff all figured out. It's like y' all did something extra to do it wrong and break it, it would have been less work to just rely on mail guns tech because they got it straight.

That's, that's, that's, that's when you get a platform that tries to do everything instead of just focusing on their core thing.

Yeah, yeah, no, like ypo, honestly, yo, they share.

The mess they got everybody into and all these people had to move to new ESPs and all this stuff.

Yeah, they could have timed out a little better because I'm like, oh my gosh. This is because I had, I didn't have any clients on the email there. I had people using the like review user generated content, you know, thing. But they were piping it through their klaviyo. But yeah, it is like y' all should have maybe put that off till March because it's like crap. I've either got a migrate now so I'm ready by Black Friday Cyber Monday or I've got to migrate as soon as that's over. And that's usually like all the marketers get a little bit of a break. Definitely, definitely caused a few email ops headaches for people for sure.

What else we got here? So this is a good one. And a lot of people don't really know how to diagnose those, especially if they're not. They don't have the technical chops or you know, not really necessarily. Email deliverability specialists, when a sender has their inbox placement, just totally cropped the bed overnight, they were fine and the next day they're just nothing. Maybe their open rates went from 40% down to 10%. So obviously a lot of stuff's going to spam or maybe they're, you know, stops bouncing. Whatever they're getting, they're getting deferrals. What's your first move when you're diagnosing the issue?

That is a great question. So very first move. Honestly, if it just bottoms out overnight, I'm checking for a block listing and to be honest, spam is about the only one that matters these days. That's going to cause you to just get mass blocked or mass spam filtered at Google. But I would, yeah, check your esp. First of all, check and see if you need to look at the metrics by mailbox provider. So check first. Is it just one provider that got gutted or is it like across the board? If it's across the board, I'm definitely going to look for a block listing on like the domain or if I have a dedicated IP level, I'm going to throw another link in the chat in that spam house actually just low key released, you know, a tool that allows you to check your domain reputation with them and it's actually got several dimensions in it and you can check and see if your SMTP I E Email reputation is positive or negative. Your infrastructure reputation is positive or negative. The other thing I would check is Google's safe browsing report. Make sure they're not reporting there's malware on your site because that could cause your inbox placement. So if it's just literally very precipitously overnight, I'm going to check asset reputation and I'm going to check the content. Maybe you just put a super fat image in there or a broken link or something that Google just doesn't want to inbox or you know, none of the mailbox providers do. Maybe you put an HTTP link instead of HTTPs. So the first thing I would check is sending asset reputation, you know, or check my ESP stats. Is it one mailbox provider? Is it all of them? And then if it's all of them, do I have you know a block listing somewhere on my domain or IPs and if not that I'm going to check the content next and see if there's just something egregious in the content. But those are for, if it just craters overnight. Those are my suspicions. It's usually an event has occurred, something's happened or something in content by just missed qa.

Perfect, that's great, great, great recommendations there. And we'll have that also in the descriptions links to that. Let's talk a little bit about your infrastructure and helping, you know, business over time, you know, more on the business ROI side as far as cutting costs or saving money on their infrastructure sending. You know, you said that you, you've helped people's, you know, companies save millions on their sending costs, you know, over time. What are, what are examples or what are you doing to help them kind of lean up as their, as their volume or you know, stack increases in their outgoing sends frequency, whatever it is, like what are you doing there to help these people?

Yeah, so for sure, definitely. One thing I will say is super important. If you know your volume is going to go up or if you know, if something happens and it goes up Precipitously, contact your ESPs, make sure you're in the right plan. So really just auditing, I just audit. Okay, what are you sending? What plan are you on? Sometimes it's a simple, is you're on like a month to month sending because you just started your business, you're like I don't want yearly costs but in a lot of cases you can save yourself a lot of money if, if you've been in it for a minute and you're, you're really scaling up and things, you save yourself a lot of money by locking into like a contract and get a much lower. CPM is typically what emails quoted in cost per mil. Cost per thousand effectively. So definitely yeah. Check what your CPM is sometimes changing platforms. Some platforms just have a floor, they don't go below. Like honestly I think mailchimp is a great platform for a lot of starting senders because they have a lot of rails on there that prevent people from shooting themselves in the foot, which they need. Absolutely. However, it can get a little cost prohibitive if you scale up. And I think also I've seen it run into platform performance issues when list size creeps over like 100,000. Granted that was many years back now I haven't worked on a super large mailchimp center in a while but that's what I is really, you know, make sure you're in the right plan for the amount you're sending. Because if you're, you know, let's say you're sending three, let's say you sign up for send grid or something and you're sending 100,000amonth. But let's say you creep up to where you're really sending 300,000amonth, you are probably paying way more per thousand email than you need to than if you upgraded your plan. So first of all I check to see okay within the existing platform is there a way we can bring that cost down by just making sure we're right sized. And honestly if you're a good sender, if you're getting great results, you're putting up great open rates and things like that, you know, get in a plan, contact, you know, contact sales and be like hey, I'm the type of sender you want on your platform. I'm boosting the rep for everyone. Like what can you do for me? I want to get in a plan, I want to control my costs. But you know, do you have a great sender discount? So get an account manager and work with them generally is going to help a lot. Thing I did, you know, when I was managing email infrastructure for an E comm conglomerate, I really, you know, kept a log of all the platform issues we ran into and how much they cost us. And you know, I, because it was E commerce, everything was very trackable revenue wise. I would, you know, Document how much projected revenue. I was like, oh, you guys failed to drop our Black Friday email. And we generally make $50,000 per email. This was Black Friday. We think we would have made more. But, you know, you just failing to send that cost us at a minimum 50 grand.

Right.

And, and so things like that, document issues actually put some financial numbers to what any platform, because no platform is infallible, but a good platform will remunerate you or compensate you, at least in credit or something on your bill if they make a legitimate mistake and if.

They'Re not willing to have a big AWS outage, that. Yeah, yeah, that's some serious issues across the board for all types of platforms, not just email, but some email platforms were obviously affected. Tracking things, not going out, not getting sent, didn't it?

I was working at click dimensions in 2017 when, when that happened before, and it was worse. It was worse. EC2 was down for like a while. And I honestly was the easiest day in support ever because there's just nothing we could do, right. Because of the esp. We work the esp, we were backended by Message Gears. They were hosted in aws, so it was just cooked. And it's just like, guys, take a break, go touch some grass. Like, I don't know what else to tell you.

Just look at the news, watch the news, you'll know.

I literally just sent them c. I had a CNN link that I sent to the team. I'm like, look, just send people this.

Oh, that's fine.

Like, Netflix is down. Like Amazon, half of Amazon's. Like, if that stuff's down, I don't know why you're worrying about email sending.

When you're talking, when you're talking about the contracts and stuff. I just want people to be aware as well. Like, talk to an expert or someone who's working at your business. Make sure they, they understand the complexity of everything. Because, yes, scaling up and getting into annual, annual contracts can save tons of money on anything. Server costs, if you're, you know, if you're a SaaS, all these other things, especially ESPs as well. But unfortunately you have to commit to a certain amount of volume and if you don't get to that bottom, you're still paying. So actually your cost could go up when you're trying to save them. And I've seen that plenty of times where, you know, people, you know, they might be at a few hundred thousand, they think they're going to get to like 500, 600,000 and they increase their, you know, Their plan and they can never get there. Yeah, they can't get enough lead volume to start growing there. They can't, you know, whatever the issues are that come up, ability issue, there could be a data acquisition, degen issue, whatever it is and then it could kind of backfire. So make sure you have an expert giving you the right information before you make that commitment.

Yeah, yeah, absolutely. And if, if you know, you don't have the money to splash on an expert or what I would say is even do this, just take whatever your existing ESP whatever quote they give you. Here's the easiest way. Go Google their platform name, see who else is buying on their keyword. Because I swear the last time I last time I googled sendgrid I was trying to find the login URL. Like six or eight platforms came up before that. So look at those guys. Reach out, get a quote, ship over like the requirements of what all you were going to get from your platform on that plan, quote or whatever. Or even just ship what you're paying. Like hey, I'm currently getting this much and paying this much. Can you beat it?

And a lot of times you can, you know, just increase an annual contract a bit because they'll always let you go back and rework the contract to increase it and they'll just start a new start date for another year out. But at least you're, you're slowly incrementing your, your, your rate versus going all in which I've gone all in before to my detriment. So that's why I know that yeah.

You should always try to undershoot your volume. Don't get too optimistic about volume you don't have yet. Like you want a future. This is honestly just true in all of tech. You want to future proof enough so that you don't get stuck in a bad state full of like tech debt and an unwinnable solution. But you also don't want to fall prey to what I was told what I've heard called Yagni. You ain't going to need it. So definitely don't want to pay for Yagni for sure. So yeah, always try to like undershoot. Don't get too optimistic and frankly a lot of contracts will also let you increase the contract mid cycle for more email volume without having to resign a new contract. At least in email. That's pretty, pretty common. I don't know about web hosting or other things, but email is pretty common. I think Klaviyo, they even have a I have a client on there now they have like an automated. They'll just step your bill up to the next tier instead of charging you like ridiculous overages. But that's what you really want to avoid if you're hitting crazy like overages, just ridiculous.

We're getting to the back end of this. There's one other question I do want to kind of touch on before we wrap things up on the business side and especially for media businesses, newsletter operators that are looking to sell possibly or exit their thing or acquire other assets to, to increase their, their size. What recommendations do you have or have you made in the past to. To different people? I think I believe you touched that you helped Milk Road when they were, when they were scaling originally. What things do you help with or make sure they have in place for auditing purposes or whatever? When someone's coming on, that's a big thing. Businesses, when they're doing their, their audits, financial and all that stuff. Email is very different because it's the list size, it's this. But really what are you sending to? What's the engagement happening on that list? So there's a lot there. How do you help people? What do you recommend people to think about when they're thinking about that type of scenario down the road?

Yeah, absolutely. So one of the things that I would recommend tracking is the unique number of people you're reaching each month. So track some numbers in terms of. Because honestly, I'll say this, deliverability is really just a fancy word for reach. It's just what is your reach into the email channel? How far can you reach people since last engagement? How many new subscribers can you reach at one time and things like that. And really I will say, you know, for Milk Road, I was brought in to help, you know, audit, you know, audit deliverability, make sure it was good so that like, you know, they would have a professional statement saying, hey, this is where things are and this is my qualifications to say that like, kind of like, you know, almost like, you know, really that's the only thing a CPA can do that just a random Joe off the street can't do is they can give an opinion as to the fairness.

Yes.

Of your, your tax documents and preparation. But yeah, your financial documents. So, you know, yes. If you're looking to sell, certainly I would tap in an expert to validate that, you know, a. Make sure there's no problems so that you know about them before they do and fix them. Because generally I. There's almost no email problem out there that isn't fixable. So I would say though, you know, really the biggest thing that I think a lot of platforms don't do a great job at is showing what is your reach into your main like your top five mailbox providers, right? Like generally for most folks in the consumer market this is going to be you know, Google, Yahoo, Microsoft, Icloud and then generally like the ISPs like Comcast, MT. But I typically group all those folks into just like one one other everything else category bucket. But basically what is your reach into the different mailbox providers? Inbox placement testing I do find very, very helpful. Especially though it would appear that once again reports of Google domain and IP reputations demise have been greatly exaggerated. I heard there was a bit of a fuss among some folks and it is remaining for the time being.

Well, it's still there, still getting updated.

Yeah, yeah, it's still. I have, I have data point yesterday when I checked I had Data points through November 3rd. So what I'll say is it was supposed to go away. They had a banner, it said end of, you know, December 31st it was gone. But yeah, I would say make sure that your acquisition is healthy. I had a client that was doing like giveaways and they weren't, they were very loosely related. She was like a skincare newsletter but she was doing giveaways for like Birkin bags and trips to Tahiti and those people were just unsubscribing on mass. So if you're gonna do giveaways for list growth, make sure it's super relevant. Like whatever it is is going to be super relevant to what your newsletter talks about. Right? I would honestly say even do your own giveaway, don't do some like platform or something, but really, you know, and also rigorously assess your lead sources. That's one thing I think too many senders don't do is assess where their leads are coming in and tag the leads in their mailbox, you know, their email platform and see where am I most of my openers coming from. Like okay, I know where most of my leads are coming in through. But how good, how well does that lead sources cohort of people actually perform when I send to them and cut the ones that are what I call high risk, low reward. That's an easy kill. It saves you money and it makes your deliverability better. It's just win, win, win. Like if it's high bounce rate, high complaint rate, low open rate, you know, that's a high, high risk, low reward, kill it and reinvest that money with your best Three lead sources or try a new one. But continuously rigorously keep testing your lead acquisition sources if that's my best advice. If you're trying, trying to grow your list that's applicable to just about everybody, don't trust, trust these people to give you good stuff. Verify, trust. Or if you want to trust, also verify.

Right. Trust my verify. Awesome. Well, thanks for all that insights and advice you gave to wrap it up. Where can people find you online?

I gotta say, to control my ADHD, everything's on LinkedIn. So I, I, I just stay on LinkedIn, I think, I wonder if my little macro's working. There we go.

You do need to find her by, by Beth, unfortunately. LB. Yeah, if you want to find her on LinkedIn, it's probably the easiest way to find her. Lori Beth Blair. We'll have her link in the descriptions below here. And then if you want to plug your business website. Anything else?

Yeah, honestly. So my consultancy is called Send Edge. Edge is a concept that I stole from Magic the Gathering because I'm a horrendous nerd. World of Warcraft, Magic Gathering, Euro games, all that good stuff. And Edge is really this idea that there's not that much difference between a good card and like the best possible card. But that's where the champions live. That little sliver of difference, that 1% edge, that's where the champions live. And that's what we try to bring is just maximum intelligence to email sending, forensic diagnostics if necessary to determine what's causing your mail to go to spam and then generally you know how, how to fix it. I would say also I've got a lot popping off over at Send Edge or SendX email sending platform. You can always find me talking about stuff there as well. I think we're building something honestly truly cool in that we're really trying to make the system the email setting platform where you don't have to worry about your deliverability. We'll handle that for you. Because I think ESPs have gotten off way too easy for way too long. Most people, y' all don't need to be worrying about this stuff because I'm going to be real with the drop of dmarc, that's for nerds. That's a cybersecurity data feed, forensic data feed. Like most marketers don't want to deal with that. And that's really what we, you know, at my consultancy, that's what I really try to help is bridge that gap between the marketing and the technical teams so that marketers can do what they do that I'm not good at. Don't ask me to design an email. I'm garbage at it. It's going to be black and white. What else do you need? You know. You know, so that's not. I stay in my lane, but my lane is making the tech work so the creative people and strategic, you know, marketing strategists can do what they do the best.

Well said. Appreciate the talk. I think we had some good stuff there. I enjoyed it a lot. I'm looking forward to digging in some more stuff down the future.

Absolutely. Chris, thank you so much for the opportunity and the great questions. And I'm super excited to, you know, really just be a help to people. I think we can all make email a better, more functional place and a lot less stress for everyone.

Awesome. Till next time. I'll be Hey, I hope you enjoyed that episode of Audience Bridge Insights. If you did, go ahead and do me a solid, click the subscribe button right around here. You can also subscribe to the newsletter. I have a link down in the description below. Now we have a lot of amazing guests lined up, but until then, keep sending smart.