From Yahoo to LinkedIn: The Evolution of Email Deliverability

In this episode, we talk with email deliverability expert, Udeme. Udeme, who has worked with major players like Yahoo and LinkedIn, shares his experience in the email industry, offering valuable advice for anyone looking to improve their email sending practices. We discuss the evolution of email, tackling challenges like spam and AI-generated content, and best practices for ensuring your messages reach the inbox.

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[00:00:00] Udeme: Know the domains that do not send mail because you could park them. So there’s domains that don’t send mail. So I’d like to have a repository of all the domains under mail, channels, control. Um, let’s say I wanna buy one strictly for summer 2025 holiday party sweaters. Example, right? Get a domain, website, shop, whatever, put your size in and all that.

[00:00:24] Udeme: But if it’s only gonna send mail, um, when orders are live. Pack the domain until June 1st, then turn up. 

[00:00:31] Ken: See, those are things that I, most people would not know to 

[00:00:34] Udeme: do that 

[00:00:35] Ken: at all. Yeah, they would not know that. 

[00:00:37] Udeme: Yep.

[00:00:44] Ken: All right. Yeah, so we’re, we’re on with Emme, it, it’s Emme ku, right? Is that the right pronunciation? Yes, sir. All right. Cool. And, and you and I have known each other for a really long time, uh, because we’ve been going to mog, uh, I think since, you know, uh, since the dinosaur era. Uh, what, when was the first time you went to a M3AAWG event?

[00:01:10] Udeme: I think that was October, 2010 in Baltimore. I think. The 

[00:01:16] Ken: Baltimore M3AAWG? Yeah. Okay. 

[00:01:18] Udeme: Yes. Wow. That was my first, um, where IW worked at Seneco back then. It’s a local Wow, um, provider here in the Buffalo area. They are the kind of skeletal piece for mail for a couple of Midwestern ISPs, like Huawei wide open west, right?

[00:01:36] Udeme: The huawei.com domain, um, central link, I think, I can’t remember. They’re still part of that invisible backdoor skeleton. So I remember attending my first mock and my boss ignored me most of the week, which threw me out the few days, and I never understood, but he said, you’re the postmaster. I don’t know.

[00:01:56] Udeme: You see you in a week. So nice. Now I look back, but I, I learned a lot. I still learn up till today. Mug is a unique, great community part of 

[00:02:06] Ken: Yeah, no kidding. Yeah. 

[00:02:07] Udeme: Yeah. 

[00:02:08] Ken: But your, your history with the email industry goes back farther than Cycore, right? You, you’ve been, you’ve been working in this area, uh, really since the dawn of time.

[00:02:16] Ken: I mean since the dawn of anything that matters in email. Yeah. Um, so, so walk us through what’s, you know, how did you get to work in the email space? What was your first email related gig? 

[00:02:26] Udeme: It was with Yahoo, the wonderful company years ago. Some of us remember the purple funds, this clinician mark and all that fun stuff.

[00:02:36] Udeme: Um, roots. So back then, I think in 2006, if I remember right, um, I applied to work at Yahoo. It took forever. Um, and then one day I was asked, Hey, we forgot to look at your resume and application. Are you still interested? I. I said, this is interesting. So you never know things happen. Right? Um, so long story short, I joined Yahoo as an anti-abuse specialist back then where, um, my responsibility with others was to.

[00:03:09] Udeme: Think reverse of how to protect the platform from anomalous activity, whether, think about any product you could think of. So, um, and then I kind of got roped into mail because, I don’t know, I think I love numbers or something, and things just took me that path where I never knew about deliverability and learned about it.

[00:03:30] Udeme: And here we are, what, 18 years later? So that, that was an eye opener. 

[00:03:36] Ken: So 18 years and, you know, starting your, starting your journey at Yahoo. I mean, I remember a time when. Everybody had a Yahoo email address. Everybody had at least one Yahoo email address. You might have had a Hotmail address as well. But these were the days before, uh, before Gmail got started, and Yahoo was a really popular platform, and Yahoo was a massive magnet for abuse.

[00:03:55] Ken: And uh, you must have seen some incredible, uh. You know, incredible patterns of abuse at Yahoo that you had to fend off. Um, you know, can you tell me about any of those early experiences where, where you were facing off against, uh, these, uh, spam or adversaries? 

[00:04:13] Udeme: Um, back then? Uh, I think pretty much up to this day, any inbound mail provider, what they focus on is protecting the user base, um, ensuring that

[00:04:24] Udeme: Just like a parent will protect their kids, they will do the best they can. Look out for maybe the crazy neighbor walking down the road that likes to give kids candy. Probably not the best example for this, but Yahoo wants to protect their kids, their users, and they will use appropriate measures, industry best practices just to protects, um, their users’ mailboxes from spam and phish and abuse and the like.

[00:04:49] Udeme: So that can be all categorized under abuse. 

[00:04:53] Ken: So, uh, you know, since, uh, since those early days at, at Yahoo, uh, I can’t believe it’s been 18 years, that that is an incredibly long time. Um, how has the email landscape evolved? Because you’ve had roles that many companies, uh, over, over the last 18 years, you’ve really seen inside of, uh, receiving organizations like Yahoo, but also sending organizations.

[00:05:17] Ken: Um, how ha how has the landscape changed broadly speaking over your career? 

[00:05:22] Udeme: A lot and there’s still some evolution going on. I don’t think it’ll stop till God knows when. Um, back then, I remember when, uh, most mail programs, when there’s an outbound delivery issue, most questions would be asked by whether it’s Yahoo or Comcast or any other, um, ISP or receiver is, what’s your ips, what’s your business model?

[00:05:46] Udeme: Stuff like that. Now I think that’s grown to, how do you authenticate mail? What do you authenticate or Probably an acronym that we would know about the Yahoo Fund. About just over a year ago where they’ve, they added a [00:06:00] lot of emphasis on one click, on subscribe, um, not just authenticating a domain but authenticating it properly.

[00:06:08] Udeme: Um, lots of big mabo jumbo words, but it’s just tell the internet who you are. Kind of like, we’re both in North America. I think we have social insurance number in Canada. Social security number in the us So that’s one identifier tied to UNI. Um, vehicles have, um, license plates, we have driver’s licenses, so flip that over to email as a whole.

[00:06:32] Udeme: And those are identifiers where as long as it’s right, it adds. X percent more value to our identities respectively. So, um, that I think we both can agree that it’s grown over the years where it’s not just, Hey, this is my app on IP address, but I. Does it have appropriate D Ns records? Not just 1 2 3 monkey head.com, but is it maybe mail?

[00:06:57] Udeme: Do mail channels.com or outbound one? Do dot com. You know, a reasonably responsible looking DNS record. All those count towards reputation and deliverability. 

[00:07:10] Ken: Yeah, I mean, standing in 2025, uh, as, as you’ve worked in these large organizations who have thousands or millions of customers, uh, each of whom are various sized businesses and or individuals who are trying to send email, how do you, you know, how do you work inside of an organization like that to help the end user do the right thing?

[00:07:31] Ken: It’s my belief that most people are well-meaning they’re just not really well educated in this specific niche area of email. So how do you, you know, how do you work inside of a large organization that’s trying to make as much money as possible in order to steer the ship in the correct direction? How do you manage that tension inside the organization?

[00:07:49] Udeme: We could look at it from a couple of different angles. So one example is when I was at LinkedIn, um, the core blue background looking platform where we connect. Um, one analogy could be the Facebook of. The career world or something like that. But, um, there were times where I would have to look at, um, different business entities or departments or business units at LinkedIn and explain to them, um, the in and outs of mail, reputation, deliverability, branding, just like your typical ESP customer at one of the larger digital marketing automation places like MailChimp.

[00:08:30] Udeme: Twilio, et cetera. Um, the, there’s a fuzziness between what the rules are on the internet, like Yahoo provides Google around best practices. But there’s also the understanding piece that what if someone is not technical? where it’s, we try our best to, um, break down the technical confusion per se, if we may call it, and simplify it with analogies, jokes, funny stuff, whatever.

[00:08:58] Udeme: But to get the meeting across, at the end of the day, I, and in your case, you as well, want to get the end user or the entity in question to understand that. Durability is not rocket science, but it’s adding a zillion identifying pieces of trusts to your outbound mail that will add, you know, value to a recipient, whether it’s, you know, bi, DA, whatever you name it.

[00:09:24] Udeme: So, and then don’t be, don’t be scared to or don’t be in a hurry to implement proper authentication. Just if it’s gonna take you a month, it takes a month, it’s gonna take a year. You have something in your mind. It’s not about rushing to do it in five seconds and blowing up everything. So some lessons I’ve learned along the way as well.

[00:09:42] Udeme: So, 

[00:09:43] Ken: okay. I mean, uh, I’m sure you’ve encountered many, many challenging, uh, email delivery issues over the years in your various roles across the industry. But can you maybe pull out one, uh, that stands out in particular, a particularly challenging situation? Anonymizing the guilty parties is totally fine [00:10:00] for this, uh, interview.

[00:10:02] Ken: Yeah. But you know, a situation where . Man, that was, that was a tough thing to resolve. 

[00:10:06] Udeme: There’s one too many, not one, not too, uh, one I could think of probably going down memory lane coming forward was, I think the day after I got married where Oh, lovely. Yep. This is interesting. So my wife is gonna laugh her head off when she sees this later.

[00:10:24] Udeme: But as geeks, whether we’re on vacation sometimes, so like we probably shut down for the holidays, maybe checked our phones every now and then that, that type of thing. So vacation, but we always have this nag to bring that computer back along just in case, just in case wedding included. I did that. Fun mistake.

[00:10:45] Udeme: So Uhhuh, the next, the next morning I get a call from my boss, the CEO, then. Saying, Hey, congratulations, and I’m here. Go, Ooh, my boss called. Pretty cool. Okay. But he said, by the way, I said, uhoh. No, no Uhoh. Yep. It wasn’t Uhoh. So, uh oh. There was a significant block listing due to a typo in the domain name or something.

[00:11:12] Udeme: I can’t remember where the misclassification happened, but there was a block no matter what affecting the corporate domain and to the domains used for one of the larger customers that were very, very sensitive. Transactional mail. You put two and two together, it was not fun. So, um, yeah, my wife looked at me and the smile went too.

[00:11:39] Udeme: Long story, but I 

[00:11:40] Ken: presume you got the problem fixed, right? Like you, you, you know, you figured it out and yes, the customer was happy, 

[00:11:46] Udeme: customer was happy, C was happy, but that was still back then when the demand authentication didn’t carry as much weight as it does Now, how I got through that was pretty interesting.

[00:11:58] Udeme: Um, figuring the problem, finding the problem, which is great, but. Someone is still blocking mail at their gateway. That part, there was a two-way, and this was on a Sunday. Right. So it was, it was fun, but we got through it and yeah. So that’s one of many stories I could tell you, but it was not fun. So 

[00:12:21] Ken: let, let’s talk about a hypothetical scenario for a sec.

[00:12:24] Ken: What if you were, uh, you know, you were advising, um, some . You know, young, enthusiastic person who has made the decision to go into the email sending industry and despite warnings that along the way they decided to do it. They’ve rolled their sleeves up and they’re, they wanna send email. They wanna send email for customers.

[00:12:47] Ken: What, what would be some pieces of advice that you would give them, uh, from your 18 years of, uh, built up scar tissue, uh, sending, uh, and, and receiving in some cases email. What would you advise them to do in order to be successful in this, in this world? Uh, you know, realizing that we’re in 2025 and, and so many things have changed.

[00:13:07] Udeme: One tip. I remember someone telling me, one of the mentors I had, and I have too many including you, but I never told you. Now, you know, um, but firstly, I look at mentors as some people that’ll give direct advice. Some you quietly look up to. Take a few hinting tips, even though they don’t say anything. But I go, Hmm, that makes sense.

[00:13:28] Udeme: Let me try it, and it works. So, um, so now, you know, he took a podcast for me to tell you, . Um, but one thing that stands out I can remember is treat an email program like a car. So, um, in New York State, for example, when you buy a vehicle brand new with five miles on the odometer. It has to go through its New York State inspection.

[00:13:53] Udeme: It blows my mind until today where it’s a brand new car off the production line. So I used to live in Oregon. You just go to dealership, get a car gone here. You have to do that even though you can’t even leave the dealership. Well, they will do it as part of the contractor, whether you lease or purchase a car.

[00:14:11] Udeme: It’s part of it. They’ll do that annual. 10, $20, um, inspection, you know, tire threads, oil levels, brand new vehicle. Flip that over to an email program. Make sure that the basics are, you know, good like a new car, tires, gas tank. Some dealerships will give you a full tank of gas as a, Hey, thank you for buying a car.

[00:14:32] Udeme: But email is the same way we talked about, you know, RDNS ips, but just know where everything is, whether it’s a scratchy, . Not too pretty looking whiteboard, just something. And then document of course. But know the ips you have, know what domains I used to send mail talking about dedication today. Know the domains that do not send mail because you could park them.

[00:14:57] Udeme: So, yep. It’s an interesting one that I figured out if few years ago, I think, um, right before when I joined LinkedIn, but. There’s domains that don’t send mail. So I’d like to have a repository of all the domains under mail, channels, control. Um, let’s say I wanna buy one strictly for summer 2025 holiday party sweaters.

[00:15:20] Udeme: Example, right? Get a domain, website, shop, whatever. Put your size in and all that. But if it’s only gonna send mail, um, when orders are live, pack the domain until June 1st, then turn on. Little, little, little things like that for obviously interesting. 

[00:15:35] Ken: See, those are things that I, most people would not know to do that like at all.

[00:15:40] Ken: They would not know that. 

[00:15:42] Udeme: Yep. So you and I can relate that, um, from a DMA enforcement perspective, you don’t flip on the switch and go to reject policy. From day one, you go through a process of starting with, you know, some sort of policy with an ROA of none, and then quarantine reject. But for me, if I know that I’m gonna set up a domain and just, you know, sit on it for a month and not use it.

[00:16:06] Udeme: The minute I buy that domain, I’m turning on adding that domain to my, um, DMA, um, ui, whatever thing flipping on that reject switch right away, five seconds done. It’s part of the domain process set up. And then when I’m ready to start using it, I’ll go in and then make sure, oh, I’m sending through a workspace, so I’ll adjust the DNS records.

[00:16:26] Udeme: Little, little. So to your point about the questions, I apologize. I ramble, but . Treat an email program like a car that’s brand new or used. Right. Know what things are, what are the 

[00:16:37] Ken: certifications you need, you know, like even if it sounds silly, what do you have to do? 

[00:16:41] Udeme: Yep. If it’s electric car, um, I should know that in Western New York where it’s crazy cold, the battery’s on a degrade a little more.

[00:16:52] Udeme: Not to be opinionated, but in the wintertime, gas vehicles do burn more gas as well. So just, oh, I have to be more alert in the wintertime, summertime email program, same thing. So it’s not perfect. I’ve made mistakes too, but treat it like a vehicle, for example, or, yeah, and I think it helps just that it cuts down some of the scaredy cat feeling of, oh my God, something’s gonna blow up.

[00:17:18] Udeme: And just, I know where to go. I know where to go. I. . It helps. It helps too. So. 

[00:17:24] Ken: In your, uh, career journey, you, you’ve not only worked for companies, but you’ve, like, you’ve, you’ve been one of those rare people who really get involved with the industry community, uh, to work on standards and best practices. I.

[00:17:39] Ken: Whether it’s within mog, which is a bit of a secret of organization, we can’t talk about it very much, uh, but if you’re in email, you gotta be a part of that. Um, or if it’s within, uh, more open standards organizations. Uh, one of the initiatives that you worked on is brand indicators for message identification or bim e uh, as it’s more colloquially known.

[00:17:59] Ken: Uh, can you tell me what, uh, maybe just for the audience, like what is BIM e what is this? Um, uh, what is this thing? Why was it created? 

[00:18:10] Udeme: Um, I think a couple years ago, um, the intent of that is to add an additional level of trust to my mother-in-law’s email or my neighbor tied to a brand and then add some sort of trust to that brand.

[00:18:26] Udeme: So examples could be Delta Airlines, um, what’s it called? West in Canada, leftanza. So we all purchase flights, we all go on vacation once in a while, but what if there is a pretty looking logo that matches the logo? We know from Delta, United Luan, we all recognize the logos every now and then. But what if that is tied to a messaging?

[00:18:53] Udeme: Quote unquote highway for the non-technical, um, scenario. So the reasoning behind that is tying some sort of trust to a brand. And I say messaging because years ago I remember there was some chatter about, it’s not just an email thing, it could be an app, which is messaging platform one-to-one. So I could tie a BME record to LinkedIn’s email, for example.

[00:19:20] Udeme: Because I used to work there. But also what about from the app perspective of, I don’t know how that would work when it gets to that phase of an app, but, um, it’s all tied to messaging. So for example, um, but to your question about BIM e um, the non-technical way to explain it is that it’s a . Dangler in front of her face, like, um, bug bunny cartoon to tease a bunny to get the carrot out.

[00:19:45] Udeme: But it’s a nice teaser to implement DAC, which is basically cut down the chances of someone abusing a brand. Using spoof or Phish. So use it, right? 

[00:19:58] Ken: Because in order to, so like bi Bii allows me to es essentially at a very simplified level. Bii allows me to associate my logo with my domain name, right? Yes.

[00:20:09] Ken: So the, when I send out emails, uh, an email client like Gmail could put my logo in the inbox right next to the message and, uh, it would be hard for somebody else to . You know, put a very similar looking logo into their bii record and spoof my domain, because Google can do stuff behind the scenes, right?

[00:20:30] Ken: Yep. So it allows me to say, this is my logo associated with my domain take. You know, if you want mail platform, go ahead and show it, but you can use your own filtering to figure out whether you actually wanna do that, you know, based on volume and stuff like that. But bottom line, it allows big brands. And small brands potentially, but you know, brands to associate, uh, their domain with a logo, which of course increases trust because now when you get an email in your inbox, if you see, you know, like your bank logo next to the message, you can be pretty sure that that actually came from your bank.

[00:21:04] Ken: It’s not from some imposter. Yeah. Yeah. But you’re saying the carrot is that it’s, you have to use DAC. In order to get a Bii logo to show up. Right. So it’s like a way of encouraging people to use DA. 

[00:21:21] Udeme: Yes. Yes. And one thing I could add to that is, Hmm most, um, for a Bii logo to reflect in a receiver’s, um, user interface.

[00:21:32] Udeme: It has to be a DMR policy of at least a quarantine or reject, uh, level. Right? Um, because the other DMR policy, which is um, non basically means, hey, maybe I’m trying to figure out where all the sources that send out from exists. It’s kind of like a cash just to make sure I don’t implement BME MD Mark the wrong way.

[00:21:56] Udeme: So I can have a peak was non record and then maybe . Give some aggregate data to a destination or something, and then I take a look at that. Um, in the case of Gmail that you said, um, they are pretty swanky as well, where they’ll put an nice, cute blue, little verified check mark, little nice and tiny and blue tie and nice.

[00:22:18] Udeme: A message that has implemented a strong DMI policy if I correct. Right. And has it been a record? I think if the domain has neither or both, then they will not reflect that blue check mark. 

[00:22:32] Ken: So if you were, if you were building a, the, if you, if you had like just gotten a hundred million dollars of venture funding to build a new email, sending service, you know, and you wanted to do everything right, you would probably make sure that there’s a Bii feature built in so that every new customer is just like, you gotta do Bii.

[00:22:51] Ken: You wanna be on our platform here, we’re gonna make it easy for you. ’cause there’s so many advantages to having that. Authentication, that blue check mark, you know, in terms of getting your mail delivered and getting it interacted with by receivers. Right. 

[00:23:04] Udeme: Uh, I never thought about that, but good question. I probably would, and I’ll give the option as a optional, not requirement, but I would probably, I.

[00:23:13] Udeme: It because every brand has different wallet sizes, and there’s a bunch of things that make the whole BB work. So it’s not just a pretty logo. It’s not just a Bim EDNS record, but there’s also, um, notarizing a trademark tying that to company brand, which if it’s a small coffee shop, like here in the city where I live.

[00:23:36] Udeme: They probably can cough out easily. Yeah. 1800 bucks a year. Um, so it, I would love to do that for sure, but, so I’ll let you know when I win the lottery then. Sure. . 

[00:23:48] Ken: Yeah. Yeah. So it’s maybe not for the Tidiest customers, but you know, anybody of significant size bivy is important. 

[00:23:54] Udeme: I would say BIM e is important, but without DMAR, BM E can’t work.

[00:23:59] Udeme: So right bi mi is great, but if we can tease, tease bug bunny with a carrot, then I can also tease someone with Bii to implement DM A and then it will be happy. So. 

[00:24:11] Ken: So you’ve been both an email deliverability consultant and a postmaster. Now that’s, those are two quite different roles, right? The postmaster is essentially, uh, the gatekeeper responsible for, uh, setting policies for in incoming mail in a platform.

[00:24:28] Ken: Uh.The, uh, deliverability consultant is the person trying to help the organization get its mail delivered reliably. And you’ve been a deliverability person for some pretty large organizations, whether directly working for the organization, helping internal teams, uh, which is, uh, my understanding of what you did at LinkedIn, uh, or end users, uh, which you did elsewhere.

[00:24:50] Ken: Um, and on the postmaster side. You’ve had some pretty significant postmaster roles as well along the way. How do those roles, how are they similar and different? You know, can a postmaster and a deliverability person have a beer together and not get into a fight? , ? Um, they 

[00:25:07] Udeme: could, um, because at the end of the day, I would like to get the quote unquote customer happy.

[00:25:16] Udeme: Like you probably a lot in customer service. The customer’s always right, but in the . perspective. A postmaster wants his stakeholders to be happy. So does a consultant. Postmasters probably two-sided where one is protect. The users with inbound mail flow, but postmas, the companies that have, um, received mail also send mail as well.

[00:25:41] Udeme: So I should also have to make sure that I’m not sending spam out to the internet because I could get mail blocked as well. Um, and the consulting piece, um, it’s pretty similar, but I only have to worry about the outbound piece, where I think a good chunk of it is . Breaking down the big skeleton of deliverability and mail policy and convincing someone that is just probably lost or need help, needs help or support to say it’s not as scary as it looks.

[00:26:14] Udeme: It’s a car, the car will drive, but let’s try to make sure it drives better and properly. Right? So let’s say the car’s been driving on one flat tire for a hundred miles. They tie and blow up. Oh, you’re lucky you’re still alive, but. It’s never too late to improve what works. And that’s helped me over the years in whatever email related role, to not do the blame game, but more of a, this is where we are.

[00:26:41] Udeme: How can we make what works better? And it’s made the conversation less dramatic, blood pressure, more stable. But think about it, any role you can think about on the planet, you know, even a call center, phone call. Most of the time or part of the time, they’re gonna have angry people yelling, you know, but they wanna keep the customer’s blood pressure down, help them out, you know, emails the same way, just a little crazier.

[00:27:08] Udeme: So. 

[00:27:09] Ken: Okay. Yeah. What, what makes it crazy? What, what makes it just a little bit crazier? Because I don’t, we, we tend to take it for granted, you know, uh, in the echo chamber, uh, of, of the email community, or we, we kind of know how things work. Like, you know, we’ve been going to mog, uh, since 2010. I’ve been going to MOG since even before that, which is crazy.

[00:27:29] Ken: Uh, and, uh. We’ve, we’ve seen, you know, the same presentations effectively over and over again. Here’s a new kind of attack that’s happening. Here’s how we fought it. You know, that, that, that sort of thing re recurs many, many times over. But for the general public, they really have no idea of the constant battle that’s going on and evolving behind the scenes.

[00:27:50] Ken: So, can you sketch out like, what does it actually look like? Uh, uh, maybe what is a day in the life of, uh, somebody who’s working in deliverability actually look like?

[00:28:00] Udeme: It’s like being a parent to a child or being a college sports coach. Um, where, and I use those two examples because I’m a parent, but also I played tennis.

[00:28:14] Udeme: I started to play tennis as a kid and then evolved to playing adult league tennis. I captain teams with adults playing local, regional, national tennis events. And I remember my first year being a tennis captain. I’m not [00:28:30] derailing, I’m just trying to get perspective. Yeah. So where some teams were just guys, some teams were guys and girls, Mr.

[00:28:37] Udeme: Captain, do whatever you want. I go, no, it takes a team. But I didn’t, I was learning a skill on how to manage different people and the word manage is more of a. Being a captain. So you manage, you tell people, you play in this court, you play with that person. And sometimes people don’t get along with each other or don’t wanna play with certain people.

[00:28:58] Udeme: But I’ve always tried to not be perfect and just, we’re a team. It takes a village to get somewhere. Um, I think, um, the anti-abuse community or mog, like you said, or even to the general public, it’s pretty similar where we have this consistent, um, day-to-day in and out of. Thinking outside the box of what we see, and then trying to be a step ahead of doing things right and make sure they’re right.

[00:29:24] Udeme: So put all the checks and balances and monitors in place, but there’s still a chance that that could, you know, fail or break or server go down and these things happen. And there’s always gonna be that constant managing cat herding, figuring out what’s going on, how to be a step ahead of preventing a problem scenario.

[00:29:45] Udeme: So. 

[00:29:47] Ken: So when you’re, you’re working at a, you know, uh, you’re working at a major internet company, uh, something like LinkedIn, let’s say, where there’s many different departments and obviously, uh, people working in a particular department need to send email for one reason or another, but they’re not email experts.

[00:30:07] Ken: Uh, and, uh, and so they come to you as the deliverability person and, uh, and . It’s kind of like your job to be their coach and to say, okay, well you wanna send email reliably? What do you wanna, what are you trying to send? Oh, uh, well, we’ve got this list that we bought. Of e you know, of a million email addresses and we’re gonna send out to this list to try and encourage them to join LinkedIn.

[00:30:32] Ken: And, and you know, like what? As their coach, you kind of have to gently pat them on the shoulder and say, okay, I mean, great initiative, but let me deliver some hard news to you about buying li you know, using bought lists. This probably isn’t gonna work out for you the way that you would’ve hoped. Is that the kind of work that you ended up doing in, in some of your roles when you’re doing deliverability?

[00:30:54] Ken: Uh, across 

[00:30:56] Udeme: since I started in mail, it’s happened everywhere. Yeah. And it’s always a challenge to tell people No, but it’s a challenge because saying no doesn’t mean you have to be right or wrong. It’s just putting feelings aside and opinion aside, and using the facts and saying, factually, it doesn’t work.

[00:31:17] Udeme: Factually, I can stick a cigarette into a gas tank and drive the. Even though 

[00:31:24] Ken: I might want to, you know, I might want 

[00:31:25] Udeme: to, might wanna try that. So to, to your point, buying list, whether it was at LinkedIn, wish Mail Jet, anywhere I’ve worked, that question has come up at least once at every single company and there’s always that, hey, actually I could point it to a zillion best practices from starting with, um, the large block list providers to the ISPs and receivers.

[00:31:50] Udeme: Not just Yahoo and Google, one-on-one in Europe or um, right. You know, I can’t remember who else. The rest in the APAC region, but it’s all the same. Why would I want to send mail to a purchase list? Because the email is, what do they call it? Spam cold uhhuh . Nope, there’s, there’s no relationship. Don’t do it.

[00:32:10] Ken: Okay. 

[00:32:11] Udeme: So 

[00:32:12] Ken: how do you deal with the tension when. The people who wanna send are customers and it’s, and so you have to, you have to go to your sales team and you have to say, you have to cut off this customer who is paying $30,000 a month. Yep. And the sales guy’s like, I’m gonna lose my commission. I, I, I won’t be able to afford my boat.

[00:32:32] Ken: I. Like, how do you, how do you play that tension within an organ, a sending organization to, uh, to tell them, no, you can’t have that revenue. It’s gonna ruin us. 

[00:32:42] Udeme: Um, I politely say no, and most times I have not done it alone. Mm-hmm . I try to save my neck and pull in my manager and their manager and say, it’s not trying to be rude or a jerk.

[00:32:57] Udeme: It’s just, it’s wrong. The facts tell us that you can’t do it. Well, we’ve done it before. And I said, well, you got lucky you didn’t get blocked. But now that we know no right, and you know, there’s gonna be a tug of war for sure, but I’ll be like, eh, it’s up to you. But I did my part. I said no. Um, and it’s, I’ve learned over the years not to do the blame game, to get the meaning across.

[00:33:23] Udeme: It’s just I told you no. Simple. I. Um, and then as I, using the tennis scenario or experience being a college referee, so maybe life story that we didn’t talk about earlier, or you probably remember, but, um, not a lot of people know that. I’m also a division one, um, tennis official as well. Um, I did not know that once in a while.

[00:33:49] Udeme: I also work professional events, so I’ve never officiated Serena or Feder or Djokovich, but. Officials, you won’t CEOs jump on CNN and jump, but Yep. I’m, I’m also a, um, tennis official. So, and you know, like Super Bowl in the US with NFL, it’s a yes or no. The whistle blows, GameStops flag goes in football, tennis, same wave.

[00:34:11] Udeme: So durability. Hmm. The facts. So like, like in Sports Match be, the fact is we saw a follow out. The fact is durability. It’s tough news to tell the sales guy No, but it’s not appro. It’s not the right money that you’re getting. Yeah. So I could say I am your biggest fan with Big Pompoms, bigger than my little kids Pompoms for anything that is not.

[00:34:37] Udeme: You know, a code list, a purchase list. I will, but this one, mm-hmm. 

[00:34:43] Ken: Cap me out these days. I feel like more and more of the email that’s being sent is being generated by large language models and it seems like it’s gonna be really tough to put that genie. Well, we can’t put that genie back in the bottle.

[00:34:58] Ken: It’s just a thing now. Um. There are so many, uh, cold outreach startups that are, are looking for email sending accounts all over the place to do their cold outreach campaigns. And if you’ve ever had a corporate email address for, uh, any length of time, you’re getting hit multiple times a day by these cold outreach campaigns.

[00:35:21] Ken: Which are a huge pain in the butt. And they’re difficult for receivers to filter out apparently, because of the novelty of every message. Right. Uh, you know, how, how are we gonna deal with, uh. These AI based sending approaches, uh, that, uh, more and more marketers are engaging in, uh, it’s, you know, the marketer says, well, it’s not spam.

[00:35:44] Ken: It’s like, we’re just getting an AI to do the research that a human would’ve done previously, and we’re sending a high value message that’s got all this rich information about the person we’re targeting. What’s wrong with that? And plus, they signed up to a double opt-in list. What could possibly go wrong?

[00:36:00] Ken: Right? That’s 

[00:36:00] Udeme: a chunky question. Um, , because it can go a gazillion ways, like an octopus, what is it? Eight arms. So like we both know in durability, um, someone can tell us the list is triple, quadruple, optin. Tell me everything. Sure. Now I heard it. Now let me see what you’re telling me. And then mm-hmm . So the a I piece to your question, I’m sure the receivers and mailbox providers are aware of that and figuring out something magical on their end.

[00:36:34] Udeme: Um, yeah. I mean, Gmail is a large mailbox provider under the alphabet umbrella, you know? Um, so I’m sure they’ve thought about this because they’ve got Gemini, for example, and stuff like that. Sure. But to your point. That’s a tricky one where cold mail, yes, it’s here and there. You see it. We see it a lot more, but I think it’s just on a case by case basis.

[00:37:00] Udeme: We’ll see what happens and the providers know how to handle stuff like that. Um, every now and then, I want, I’ll be honest, I do get requests for code email and I will just say, well, let’s talk, you know, the exploratory code? Yeah. And the minute I see anything that is unconsented related without consent, I’m here going, eh?

[00:37:21] Udeme: Mm-hmm. Because I, I, I don’t mind taking the opportunity, but there, there’s not gonna be a success, so what’s the point? It’s versus, versus, I run away from cold email and I’m rude to the guy or the lady and tell them, no, you can’t go jump off a cliff. Yeah. I handle it differently like a referee probably.

[00:37:43] Udeme: Right, right, right. Yeah, it’s 

[00:37:44] Ken: just like, that’s, that’s offside. The ball went outside the line. I’m sorry. It’s just, it’s what? It’s . Yeah, 

[00:37:50] Udeme: yeah, yeah. Um, 

[00:37:52] Ken: yeah, there was a discussion on Hacker News if, uh, sometime in the fall, uh, it was a, uh, you know, hacker News is, is the Y Combinator, uh, you know, blog style or Reddit style news service.

[00:38:06] Ken: Uh, and. Entrepreneurs can post their, their, you know, it’s called a show hn, where they can talk about their business, what they’re up to. And someone was, uh, was talking about, um, their, uh. How they do cold outreach emails, like how they do it, how they use ai, how they build the lists, and like what they were literally describing was a criminal conspiracy to defraud email platforms like Gmail.

[00:38:35] Ken: They literally, on their blog were describing, I. Uh, a criminal conspiracy to, you know, maintain batches of fake Gmail accounts that they would rotate through very carefully to avoid limits in order to send out cold outreach emails. And I thought, wow. It is fascinating that somebody is willing to.

[00:38:55] Ken: Publicly talk about how they are committing crimes, actual crimes, uh, that they not only could get sued for in, in a civil manner by one of female providers, but it could literally land them in jail. And they were just openly talking about it. It, it really leads me to believe that there’s a lot of naivety out there about not just the norms of the email industry, uh, but the legal landscape around.

[00:39:23] Ken: Uh, the basic rules that we all have to play by in any country, in any civilized country. 

[00:39:29] Udeme: That’s, that’s very interesting and very scary that they’re, I mean, if it’s snowing outside, I’d love to take the kids and push ’em down the hill and let them scream without let, letting ’em get hurt. But that, that’s, that’s, that’s above my head.

[00:39:45] Udeme: Um, but I’m also sure that . They are that naive to be that blunt. But there’s also the piece where they forget that every message that is fed into any inbound mailbox provider, um, in, um, mailbox provider or receiver is being caught seen, stamped. I’m sure there, I’m sure the, the big players and the small ones are not dumb.

[00:40:11] Udeme: I’m sure they’re aware. Yeah. So, but to your point, it’s, it’s just sad. But yeah. 

[00:40:17] Ken: Yeah. Yeah, I think these guys are getting away with it for now. Uh, you know, it’s a ton of manual labor, like creating all these Gmail accounts, rotating through them using proxies. They have to do a lot of stuff in order to keep the game going, but they seem the money they’re making from it was astronomical.

[00:40:36] Ken: They scaled to like 2 million, uh, in the first year. And it’s like three people, you know. So the money is extraordinary and that’s what keeps them going, 

[00:40:46] Udeme: and that’s. That’s the problem that makes it harder for the not bad senders, but I think we discussed a little earlier that where there’s people that will make honest mistakes or just don’t Google every single day.

[00:41:00] Udeme: And doom scroll. Mm-hmm . And I have seen a few folks where they just dunno about one click up subscribe, for example. There’s folks that legitimately do not know about it. Right. Where I think there’s even a brand I unsubscribed from last week. I understand. We understand the 10 day can spam, blah, blah, blah.

[00:41:20] Udeme: I get it. But most opt out features these days can do it right away, eh? Okay. I’ll give it a few days that it’s been about two weeks. I’m still getting . Yeah, then I’ve opted out. I’ve moved into the folder. But that’s a legitimate business that, you know, household that you and I use every now and then for like, you know, day-to-day stuff.

[00:41:42] Udeme: Yeah. So it’s, yeah, it’s, it, it’s crazy how they can still sell, but hats to them, it, it won’t, it, uh. Nothing, nothing, nothing like that will last forever. But it’s just sad. So, yeah. Yeah. I think at 

[00:41:59] Ken: MOG , I often come home from mog feeling a bit sad because I’ve seen all these presentations about how bad things are and how, uh, and how difficult it is to just get brands to do the right thing.

[00:42:12] Ken: And, and, uh, uh, you know, the extent of the criminality going on in the email space all the time is just mind blowing. Uh. Yeah, that Baltimore conference was one of the more interesting ones. And if I recall correctly, because, um, I, I won’t speak specifics, uh, because of confidentiality rules, but there, you know, Baltimore is, is a national security nexus, right?

[00:42:35] Ken: And, and so it, it attracted a lot of, uh, of really interesting, uh, presentations. Yeah. Yeah. I, I, so hopefully, hopefully the organization has another conference in that part of the world again. I found that very interesting. Okay. So, uh, you know, just to kind of wrap things up, I, I wonder if you could pass on one thing, just pick one thing that you wish, do you wish everyone, uh. 

[00:43:00] Ken: Could know about, um, email marketing or deliverability, uh, one bit of wisdom. I can kind of imagine what it might be, but I, you know, in your words, what is one thing that you wish everybody knew who watches this podcast? 

[00:43:14] Udeme: I sometimes give the example that deliverability is a planet in the solar system. And you see, you can feel the hairs on people’s head go off or they, Hmm.

[00:43:26] Udeme: Oh. And I said, well, think about it. The solar system, [00:43:30] couple planets, you know, each are different. Um, humans want to try and go to all 10 or whatever and all that. Um, forget movies and Hollywood and Neil Armstrong and all that. That’s one piece. But still, beauty is a planet of its own. It’s different from email marketing per se.

[00:43:49] Udeme: They do interject and intertwine. Um, but I think over the years what I’ve learned and . Also from people I’ve learned from like you is that experience is super awesome, but it’s also humbling that we’re also open to hear something new, learn something new, and not to freak out about, you know, if things get go wrong or bumpy and stuff like that.

[00:44:13] Udeme: So, but the reason why I say that is I. Analogies sometimes don’t even work when I pass ’em along where I’m trying to, you know, a little, um, self-employed company that runs maybe financial, um, consulting in the Bronx or Manhattan, for example, and I have to beg to implement simple authentication. I go, Hey, so back to like what we were saying, three domains.

[00:44:42] Udeme: Two, don’t send mail. One send me. I’m like, practice two. We can do it over six weeks and hop on Zoom every couple of weeks and I’ll show you how to do it or I can do it if you gave me access to your, um, registrar provider. Nope. And I’m here going, obviously, you know, other analogies, the car or in the US we have the Trusted Traveler program where you go to the airport security machine.

[00:45:06] Udeme: Sometimes you don’t take your belt out, belt off, shoes off. That doesn’t mean that every now and then I still don’t get stopped. That. Airport security. Funny enough, it’s always when we’re with the kids, go on vacation and my wife gets mad of, and I say, yeah, but the system is doing its job. Random selection, eh, fine.

[00:45:27] Udeme: Go through the machine. Do it like this. My manual, don’t laugh or head off. So deliverability, it doesn’t mean that it’s perfect, but make sure the car drives right. The tires are gonna go low. Once in a while you are gonna need an oil change. We’ve had flat tires before. Deliverability has flat tires sometimes.

[00:45:47] Udeme: So, you know, we stay abreast with, um, industry updates and get together and keep our brains fresh and I think that’s what keeps our blood blood pumping every day when we wake up and loves email. So, nice. A little bit, but yeah, that’s what I got. Awesome. 

[00:46:04] Ken: Well, it’s been a real pleasure talking with you, deme, and, um, I hope to see you at an upcoming UHM conference.

[00:46:11] Ken: Uh, I think you’ve got at least another 18 years left in you for this industry, , uh, and, uh, and email. I I, it’ll still be here in 18 years. It’ll absolutely still be here, you know, despite what people might want. Uh, there’s nothing new and better around the corner. Yep. We’re stuck with it. 

[00:46:31] Udeme: Thank you, and it was a pleasure meeting with you as well.

[00:46:34] Udeme: It’s been a while. Um, but also to your point, um, I remember when the millennium bug hit and we all thought email would go away, but pretend that you and are not technical people. My mother-in-law probably can’t get her flight ticket receipt to go on vacation or mm-hmm . Um, yeah, I don’t know. Think about anywhere that uses email as a receipt.

[00:46:56] Udeme: So what if email goes away, then what? 

[00:46:58] Ken: What are you gonna replace it with? Exactly. What, what’s the thing you’re gonna give someone so they can get in touch with you on the internet? I mean, it’s, what are you gonna log in with? 

[00:47:06] Udeme: It’s, we’ll, we’ll continue to live the email, I don’t know, evangelism, um, planet fun and keep going from there.

[00:47:14] Udeme: But it was a huge pleasure being on your podcast. I’m humbled and thank you for that.