Michael Hartmann: 0:24

Hello, everyone. Welcome to another episode of Opscast, brought to you by marketingops.com and powered by all the MoPros out there. I'm your host, Michael Hartman, flying solo today. And today I'll be talking about email deliverability and trust, specifically where modern marketing outreach has crossed the line from helpful to harmful. And joining me to do that is my guest. Today is Jacqueline Friedman, CEO and founder of Monarch Advisory Partners, also a fellow Dallasite, and global head of advisory at the Martech Weekly. Jacqueline works across both B2B and B2C organizations and has been increasingly outspoken about spam, cold outreach, thought leadership, and the real consequences of how marketing teams show up in buyers' inboxes. This episode is about why cold email is often just spam with better branding, how sales volume impacts availability, more than marketers once admit, and what B2B teams can do, could learn from B2C when it comes to earning attention and trust. So well, welcome, Jacqueline.

Jacqueline Friedman: 1:18

Thank you. Thank you for having me. I'm excited to be here.

Michael Hartmann: 1:21

I'm about to tell you that my dog is in a bark. It's all good. Um someone dared to come to the door. Um all right, well, let's get going here. Um it's funny, we were we were just talking a little bit before this about uh an example email that I got. But um before we get into all that, let's like walk us through your background a little bit. You were because we said you work across B2B, B2C, um, which I do think is a little bit of a unique vantage point. Uh not many people I have. I started in B2C, moved to B2B. But um how'd your career evolve into that space and how'd you end up, you know, how do you think about marketing today from that background?

Jacqueline Friedman: 2:01

Yeah, for sure. So by no means did I plan out to work across all these different business models. I just I kept ending up in these environments where those lines either didn't really exist or it didn't matter. And so I've been fortunate and that I've worked with a lot of different startups of all shapes and sizes, um, both, you know, as an employee, but also as a consultant, of which include WeWork and Grammarly. We're dealing with lots of hyperscale.

Michael Hartmann: 2:28

And um, so I've been very fortunate that all of these have Grammarly of very different kinds of very different, but you'd be surprised how similar at the same time.

Jacqueline Friedman: 2:39

Yes, I believe it's the the nuts and bolts are not that different. Um, just what your what the actual product is is very different. Um, you know, software versus virtual and physical. Um but yeah, having worked in all these different kinds of capacities, um, I was really able to realize that there's always a through line. It's always serving the customer, and that is not just through revenue and product, but of course marketing. And so um the beauty of it is B2C was able to train me how to respect folks' attention and really notice just how quickly people just engage. And it's only getting more and more the case as we get more bombarded, as our attention spans have been slowly declining. Yeah. Uh yes. And then also with B2B, it's really trained me to understand the incentive structures, governance systems that shape our behavior, but also just it's a different way of thinking. And at the same time, all these are not the ways that's not a way to say it. Uh, sorry. Um, all that to say, like I don't think in channels. I think they're all one, and I think more in systems between intent and friction, and honestly bringing humanity back. And that is something I think B2B can learn from B2C more often than not.

Michael Hartmann: 4:01

Yeah, I mean, I'm a probably would describe myself and others probably would be as a serious person, but like I still like will poke fun at myself. And oh yeah, I think there's a lot to be enjoyed, even when you can be serious. And so I think maybe what you're hinting at is like maybe there could be a little more humanity brought into B2B communications in general, right?

Jacqueline Friedman: 4:22

For sure. I think something we mastered really well at WeWork in particular was like the approachable professional, and that was the tone we set. And I think that is something every company should make sure that's the bare minimum. Unless I understand if you're a governmental agency, very different strokes. But across the board, everyone wants to talk to a person, especially in this world of AI and AI-generated slop where it's just you can tell there's no tone and all these different aspects of reading comprehension that we didn't care about in school really are are showing their muscle now. And so it's just bring back humanity into everyday conversations and it's really noticeable.

Michael Hartmann: 5:08

Yeah, it's funny because you I talked about grammarly. I I avoided it, thought I never needed it, and about oh, maybe 18 months ago, I started using it, and now I'm like, I love it. And I like the complications too, because they it there's a little bit of a gamification, right? For those who like to compare where they are and all that, but it's it's fun and but and you know, insightful, right? It goes like, oh, I'm actually making a little improvement here and there.

Jacqueline Friedman: 5:35

So yes, without a doubt. I always kind of chuckle at folks who are naysayers of a tool like Grammarly.

Michael Hartmann: 5:41

Yeah.

Jacqueline Friedman: 5:42

Not because anyone is perfect at grammar or anything like that, because it's so much more than that. But I have always used it as my second set of eyes. The second the Freemia model came out in 2015, yeah. I immediately started using it because I was a team of one. And I needed another set of eyes because we didn't have a formal approval process in place for emails. And so I just needed help to make sure I didn't send something out to thousands upon hundreds of thousands of people in the wrong tone, in the wrong this, you name it. And so and also make sure it was grammatically correct.

Michael Hartmann: 6:18

Well, or or intentionally not like sometimes I ignore the corrections too.

Jacqueline Friedman: 6:22

Right. Oh yeah. I don't accept it at a face value because it's not always right. And also I have a writing style. I don't want to uh make mine sound anything less than myself.

Michael Hartmann: 6:35

So you're not a English professor.

Jacqueline Friedman: 6:39

Uh no, I'm much too probably my own chagrin. I would probably enjoy it, but not that much.

Michael Hartmann: 6:46

Well, I mean, uh every once in a while I especially when I get corrected a bunch from my writing with Grammarly, I will think, I really wish I had paid more attention to that diagramming sentences when I was in seventh grade. Yes. That I nearly failed.

Jacqueline Friedman: 7:00

Um I never got grammar taught to me ever. I missed I switched schools a few times, and so I just happen to always miss the lesson, and so yeah, I have to do it all phonetically in my head or talk in order to actually understand it.

Michael Hartmann: 7:16

Yeah.

Jacqueline Friedman: 7:16

Learned more actually learning another language.

Michael Hartmann: 7:19

And that's still funny, right? That's crazy. Well, English is it's a special place. That's for sure. There's so many things that don't make sense. There's so many things.

Jacqueline Friedman: 7:30

There's far too many exceptions to every rule.

Michael Hartmann: 7:32

Yeah. Um all right. Well, we could I could spend it all like a whole episode talking about grammar and the crazy things about English language, but um we were gonna talk about email, uh, cold email and that, but you know, I and I I think I've noticed this too. Like you're very direct on LinkedIn or wherever talking about email and that cold email is still spam. So yeah, I know that a lot of us in marketing ops get pushed, especially, I think especially from sales teams who want to push the boundaries on this stuff. So yeah, how do you how do you think about framing that with for marketing ops folks and maybe with other teams if when you're working with them?

Jacqueline Friedman: 8:12

Yeah, it's always gonna be a struggle between what your legal team allows, what your legal team is willing to risk, because there's an implied business risk in every decision you make. And so really navigating how to mitigate and minimize, but also not impact business objectives is really hard. So it doesn't matter where you're at, what set of variables you're dealing with, that is what you're up against. So there are ways to think through it and set the guardrails and parameters. Well, one, you need to find out what countries are we working with, what regulations do we actually have to abide by, and what are the consequences if we don't? And so that's all part of that risk process that really your legal team should be um focusing on. However, sometimes they can use a little extra help if that's not their maybe specialty. Yeah. Um which is not a lot of a lot of places. They do contracts. Yeah, they're great. Um, yeah, little privacy lawyers or dime a dozen, they're incredible. And um that's where sometimes you can educate that lawyer on like, hey, here's some resources that might be helpful and it'll understand. Um, so yeah, I am a huge fan of legal first. My father's a lawyer. That's like the my way my brain works uh in the best way possible. But that's first and foremost, but also figure out what you are and aren't willing to risk. And so, like paid lists, there's never a time or place. It's just not worth it. You're gonna get put on on spam traps, and that's gonna impact your entire brand's reputation. And if you can't send an email to someone who consented to it, how are you going to have conduct a business?

Michael Hartmann: 10:02

Right.

Jacqueline Friedman: 10:02

So you have to really think the big picture in that regard. Um, but as you mentioned, I am very direct as a person, whether you like it or not, sorry. Um, I I swear on a friendly face. Yeah, well, like I I mean it in a friendly way. It's never I just don't like wasting time on nonsense when I know we have the answer. Why why sugarcoat it? And so I think the concept of outbound and cold, those are just really fancy ways of saying spam. And it's just soft language when actually accountability is required. And um and the same thing goes for sales teams of like that are outbound, we're doing this, we're building out our you know, feature pipeline. It's like it's the same thing. Same thing goes for like the rebrand of go to market. It's the exact same thing, nothing has changed. So let's let's stop imposing on others and actually help them. And also there are ways to do the concept of paid lists, but in less I don't want to say intrusive, but less gross, honestly, frankly, ways. Like you can retorge it with ads. Yes, it's it's more respectful. You can do softer touches of like looking at someone's LinkedIn profile. And all these differ, of course. If you're in B2B, that makes more sense. B2C, it's not really gonna be the same. Instagram, Pinterest, you name it, or TikTok are gonna be much more of the avenues to go about this, but there are ways to create intent signals that don't create and perpetuate the general fatigue of how many emails do I need Marcus spam today? Um, and also I don't really want that to be associated with your brand. Right. Sorry, go ahead.

Michael Hartmann: 11:55

No, no, I I think I think your framing of this at the beginning about risk tolerance is a really important one. I mean, and that's that's kind of a way I've done that before too. Like I have a scenario, I probably talked about it here before, where I was new to a job, CMO caved me, said the CEO wants to do right by uh a partner publication that had just highlighted the company and wanted to share our our database basically with them to try to get and I was like I was like first thing I did was went and looked at our privacy policy and was like we really trying to we basically say we're not gonna do this, right? Um, and I was like, so I was like, I had to get called. I was I was only a few months in this job and I was I was scared.

Jacqueline Friedman: 12:40

But I was Yeah, you don't want to give up all your political capital on something that you weren't planning on even dealing with.

Michael Hartmann: 12:45

So I'm at I'm gonna call with the CEO and CMO and me, and I'm going, I don't think we should do this. That said, like if you really want to do this, this is the only way I think we should do it. And I gave him a kind of an outline of what I thought would work, which um just kind of shielded us and and the other place, made it more made it more difficult and required a third party to be involved. Ultimately that became too much and we never did it. So I was glad, but like I I had I had to go through this process. Like I couldn't just say no because right, like I I realized that there was a little bit more to it. Um and honestly, it wasn't my decision, right? Exactly.

Jacqueline Friedman: 13:25

That's where that risk and business objective balance, you're not in charge of that. And that it that is above most people's pay grade on determining it. But thankfully there are some glimmers of light. So, like for example, Gmail has finally, after years and years, is really listening to the consumer and the customers of we're getting too many emails, we're getting this. Of course, they've had, you know, inboxing with different tabs and promotions, things like that. But now they're doing, you know, almost a global unsubscribe management option. And so all of these things from an email marketer or a spammers perspective makes it harder.

Michael Hartmann: 14:05

Yeah.

Jacqueline Friedman: 14:05

But at the same time, from a human to human perspective, it makes your life better. So I'm actually a huge advocate for it because we need to get with the times. And if the technology and the systems we're using don't match the practices and what we're seeing day to day, like how are we going to move forward? And so I'm grateful some of these changes are finally coming into play.

Michael Hartmann: 14:28

Yeah, I think it's um my experience, I've seen some places where I've worked, I've been working lately, have had struggles with, even though they had an existing brand and reputation changing email platforms and starting up a new IP, have really struggled because of some of that stuff.

Jacqueline Friedman: 16:02

Oh, yeah. Yeah, it's not a magic fix. There are very few magic fixes besides just consistent daily doing things the right way, which sounds really boring, but it's true.

Michael Hartmann: 16:16

So I mean, I've been I don't think I'm the only one who's seen and heard of like deliverability or inbox placement kinds of issues recently, especially with like things like IP warming or what is that? Yeah, what what's your kind of what's your take on like what are the things that are commonly causing people's deliverability to go down or inbox placement to go down, um, that they could try to avoid?

Jacqueline Friedman: 16:41

Yeah, I think the the most straightforward response is deliver what the customer is expecting. And if they aren't expecting your email, that doesn't sound like a good starting place. So really think about it as a relationship. Like, ah, you go out on a date, you both consented to be on this date. One of you decides I don't want to be here anymore, but you keep being like, we're going on a date, right? And it's the same thing. And so this is where I I struggle where B2B and B2C get like treated these separate instances when in reality, no, it's still a relationship. And you treat the other person how they want to be treated. Do they want to receive your newsletters? Great, because they want to be in the know. Do they want to receive every promo? Great. They're looking for a deal. That's awesome.

Michael Hartmann: 17:29

Right.

Jacqueline Friedman: 17:30

Do they want to be in touch with your sales team? Great. They want to speak to you, but you have to follow what they want. And so those short-term like decisions actually impact the long run. Because also, and this is gonna be kind of a hot take, but inbox placement providers, as much as I love them, they're not actually real. And that if you think about it, no one can replicate what an individual user does in their inbox, which sometimes they're looking at an email 30 times over the course of three years because it has information of something they really need from a brand. Like I have, for example, it's not a marketing email, but I have an email with my accountant I look at to get my EIN number. I should just write it down somewhere else. And I do probably have it there. I just know it's there. And I've probably looked at that email 45 times in two years. But that is not a regular behavior that an inbox placement provider could identify.

Michael Hartmann: 18:25

Sure.

Jacqueline Friedman: 18:25

And yes, that's a specific use case. However, a lot of people use their inboxes as search functions. They're like, oh, can I find a deal? That earlier. Yeah. Exactly. And so there is no inbox placement provider that can replicate human creativity to not have rules. And so um, all that to say there is a place for tools like that, mainly to identify the signals of things aren't working and help you figure out how to navigate it, but it is typically much more complex than it seems.

Michael Hartmann: 18:58

Yeah. I mean, that's this is the hard part. And even why I stopped saying deliverability, uh, we had um we had somebody on a couple years ago and or and I saw them speak to is talked about deliverability versus inbox placement. It was my first like uh-huh, like those are not the same, right? Correct, correct.

Jacqueline Friedman: 19:16

So they seem they they're very related. You know, there's a Venn diagram, but it's they are different.

Michael Hartmann: 19:21

They're not as they're not as the overlap on that Venn diagram, Venn diagram is not as big as I thought it was, for sure.

Jacqueline Friedman: 19:28

And that's also very fair, especially if you're not a deliverability expert, which I definitely know I'm not. Yeah, it's a fair assumption.

Michael Hartmann: 19:36

Yeah. I I'm in that stage of knowledge where I can't I remember somebody's talked about, but there's this one where you kind of go from like, you know a little so that you think you know more than you actually know, and then you get to a point where you know enough, they're like, oh, there's a whole lot more I don't know. The Kruger effect.

Jacqueline Friedman: 19:49

Yes. Yep. Yeah it's it's definitely, I think um those who are at this level recognize you know nothing. Like you know enough to be dangerous, but you at the same time know absolutely nothing. Yeah. And you know when to seek that expertise from someone who does know a whole lot more. It's like who has the equivalent in our field of a PhD in this? Let me confer with the professional. Yeah, because I know I'm not.

Michael Hartmann: 20:16

Yeah. Um what so one of the things I'm struggling with and you when you were describing this is I I I agree with it in general sense, but one of those is, and I'm thinking about my own personal experience because in general, I try to, because I want to see what other companies do, I rarely, this is not an invitation for people who start adding me to their list, by the way. I rarely unsubscribe to stuff or mark things as spam. I just I just don't do it, don't do it very much because I'm curious. I want to see what happens. And I find, I find um it's interesting every once in a while I have to go to my spam folder and I Google account and I see stuff they're like, oh, that's not really spam. I don't, I don't change it generally speaking, unless it's just something I would know I was looking for. But what I struggle with is like if these they're so for example, my kids are now older. Uh there were uh online retailers that we bought stuff from when they were really young, and I continue to get stuff from them, even though I probably have not opened a single email in years, years and years. So to me, on the one hand, I'm not sending signals that I'm not I'm actively saying not, like in other words, I haven't send anything explicit, stop sending me stuff. But implicitly, I've kind of like I just am not engaging at all. So how like how important is it to do like look at both implicit and explicit kinds of signals?

Jacqueline Friedman: 21:41

Yeah, it's it's tricky because also we even factor if you have pixels turned off, if you have images turned off, that pixel is not picking up if you opened it unless you clicked. And so there's even more to it. But um, I if you'd asked me this question a couple months ago, I would have probably had a different response than I would today, only because I have been, I've seen the light of another perspective that I don't fully agree with, but I appreciate the perspective. So yes, your your children have outgrown, let's say, you know, Fisher Price when you bought that 15 years ago, 10 years ago. But you could have grandkids. So from Fisher's Price. That's right. I'm not sure I like that. It's just I I understand. However, you didn't opt out, so they're respecting your subscription, and also you might become a customer again. It's a bit of a fresh perspective. It's directly from the thinking of De Laquist. Like, that's how he thinks about it. And I struggle with it because it goes like against everything I've ever learned and known in that, like, you're unengaged, we don't need to send to you when he has brought in a new perspective where actually your unengaged list and audience is some of the most interesting. And that's where the most important things can be learned. And I'm still honestly wrapping my head around it because it's just such a different way and different um just it's just thought provoking. It's almost an experiment amongst the things we've learned and really questioning the status quo. That said, if you're working on your deliverability and you're struggling, do not focus on your unengaged users. You need to focus on your engaged users, you need to focus on your transactional emails so that you can warm up those IPs. But don't forget, even if you're on a shared IP pool, you also Have to warm it up a little bit. It needs to get to know you too. And that often gets overlooked. And so I don't know if I even answered the question, but there's a lot of it's just it's so much more complex than just it is working, it isn't working.

Michael Hartmann: 23:54

Yeah.

Jacqueline Friedman: 23:54

There's I with without knowing, I would say 30 different variables you have to think about first. And then there's more of a mind mapping flow chart to go through after you know those answers.

Michael Hartmann: 24:04

Yeah. Well, it's interesting, and that's the point, like that's part of the point of this. It's funny because like you, that scenario you just gave, like actually I I'm with you. Like I'm I'm torn because on the one hand, right? It makes sense. And it reminds me of, I guess, when I was doing search optimization stuff where you had like everyone talks about the long tail, right? The long tail, there's a lot interesting stuff there that you you know you wouldn't expect. Um that's really interesting. I struggle because I struggle with that. It is. I mean, I'm like, yeah, okay.

Jacqueline Friedman: 24:35

Yeah, it's not as cut and dry as I thought it was.

Michael Hartmann: 24:38

Yeah. Well, for me, it doesn't really bother me because I it's not like I I've intentionally made the choice to just let that stuff come in. Now, if I was an inbox zero person, which I am not.

Jacqueline Friedman: 24:50

I am. I have a uh I have a separate fake account with all of those types of emails that I'd never engage with unless I'm looking for something. Um, and it's fascinating to see how many lists 10 plus years later I'm still on because I started it for competitive research and analysis years and years and years ago.

Michael Hartmann: 25:07

Yeah.

Jacqueline Friedman: 25:07

So I understand the plight. Yeah.

Michael Hartmann: 25:11

Um okay, so because this is hyper complex and like scenarios I hadn't even thought about even coming into this, right? That you just brought up. Was it called De La Quist?

Jacqueline Friedman: 25:22

De la Quist, yes. He um he was just on my podcast. Uh that's why it's top of mind because I was helping edit it. And I was reminded just how thought-provoking he brings a fresh perspective of of things from I almost consider him like a philosopher of email. And um it's it's so not what you're expecting in the best possible way.

Michael Hartmann: 25:48

That's interesting. No, I love that. I love it. All right, we'll have to see if we can point people to that when it comes out. Um we think so, okay, so it's complicated, bots of nuance. You and I are fairly deep in this, but we don't consider ourselves experts. How would someone who's listening to this know, like we're having struggles? We think we kind of don't we've worked with our IT team to get, you know, you know, all the settings right, yada yada, but we're still having problems. We contacted our email providers, yeah. How do you know when it's time to bring in someone who's truly an expert? And then how do you find him?

Jacqueline Friedman: 26:26

Yeah, great series of questions. There's a couple, it depends. How sudden has the shift been? Do you know if something happened in the past week, or is it just a slow burn? It's been happening for a long time and you've just ignored it. Because there could also be actual outages that caused it. Like just in you know, real-time Q1 2026, there's been a number of outages um across Microsoft and that's caused issues with Gmail and its own capacity and certain ESPs. So, and even Yahoo. So it's it's very specific. If it's an outage, it's rare that it happens, but guess what? Rarities become less and less rare these days as we as a population just keeps scaling everything we're doing. And so um definitely identify if it's a one-off and if it goes back to normal. If it is a consistent and slow and steady decline, and you're also not noticing unsubscribes or other important what I usually consider to be vanity metrics, I consider them to be signals more than anything else.

Michael Hartmann: 27:34

Right.

Jacqueline Friedman: 27:34

Um I think they're extremely important, just not in the way people use them. So if you're starting to see lagging in places where that the numbers just aren't adding up, um, the first line of defense is do you already have delivered platforms? Do you have Everest or Inbox Monster or um I don't even remember the rest of the tools because they all get bought out every three seconds? But do you already have existing um platforms that you're monitoring things? No, that's okay. You might not need it in the long run. But do you have any support within your ESP? Do they have deliverability services? Right. Caveat, they're not the best, but they exist and they can at least help with initial components. And if that is not changing anything, that's when you need a deliverability expert. And the easiest way, frankly, actually is just going to the community email geeks and um asking in the deliverability channel, like, hey, I need help. Um, see if they can help. There's a lot of really wonderful people who will diagnose things just on the spot for you. But also if it's a bit more complex, you might need to hire someone. Um I've always been able to find my folks through that or LinkedIn. Um, but there is a very large difference between a real deliverability expert and someone who says they are. Yeah.

Michael Hartmann: 28:54

And so someone you get off work.

Jacqueline Friedman: 28:57

Correct. Um, yeah. If anyone is just maybe the red flags are the most important things to notice of whether or not someone's an expert. So they're saying they can get you into a primary inbox, don't trust them. If they're saying everything I do automatically gets you out of spam, don't trust them. There are no guarantees. It is a special sauce of many variables. Think of it as like a recipe. Just because you replace one thing, it's going to have another chain reaction elsewhere. So it is not just cut and dry. Um, but yeah, I think if anything, actually the red flags are easier to spot than the green flags, what someone's doing and knows what they're doing.

Michael Hartmann: 29:37

Yeah. I mean, it's probably one of those ones kind of going back to the uh Kruger effect, right? Where the people who know best are gonna be less, less seem less confident.

Jacqueline Friedman: 29:49

Correct. They're gonna be much more um judicious, judicious. I can't say that right now. Judicious with their words. It's just beginning today for me, but yes, they'll be much more judicious. Ugh.

Michael Hartmann: 30:02

Judicious. I gotcha.

Jacqueline Friedman: 30:03

There we go. Uh, much more judicious with their words and always be mindful of like, hey, this might change. This might not work. We want to um be mindful of this. And so there's gonna be a lot more of education on this overall strategy, not to mention just the short-term quick fixes and double checking of things. Yeah. It reminds me mindful of quick fixes.

Michael Hartmann: 30:31

Yeah, yeah. It reminds me of um this concept of the Kinevin framework that one of our guests, oh, probably now uh I was say half a year ago, but it might have been longer. I've my sense of time is off. And it was a really um it was a really interesting idea that I didn't know about, but the short version is people can can uh confuse a situation as a complex situation. There's not necessarily an answer, which is what this we're talking about, versus complicated, which is it may be difficult to understand, but there's an answer to how you quote fix something. And if you treat a like my son, that's it's it's it's a Welsh word, so I'll have to spell it because it doesn't C-Y-N-E-F-I-N. So can I fug um anyway? It is uh I think about it all the time, and this is a great example where like the the example would be complicated, would be an F1 car, right? Highly complicated machine, uh, but someone who has the right training, experience, understands it, like can probably fix something if there's a problem, right? Whereas correct. I mean, the extreme, almost extreme example that we use was like D-Day, right? Highly complex, almost chaos, right? Which there's actually two other ends of the spectrum that this is in the middle of where you don't know what the right answer is, right? So the solution to that is try lots of things, right? Until you see what has the effect. But you also have that what call it the butterfly effect, unintended consequences, right? Like, so when you do something, there's a little bit of a risk of being overconfident in taking that action, right? Especially, especially if it's one that you can't back out of.

Jacqueline Friedman: 32:18

Without a doubt. Um, and I'm always happy anytime Ray Bradbury gets get brought up with the butterfly effect. Was that him who came up with that? Uh yeah, it was um in his short story, The Sound of Thunder, which is one of my favorite short stories.

Michael Hartmann: 32:32

Um So even though I'm an engineer, like people are always surprised I was not a science fiction reader ever.

Jacqueline Friedman: 32:41

Yeah. I'm not really either, but I just have a certain proclivity for Ray. I don't know. He just he knows what he's doing. I wish he was still around to keep writing, because we need him more than ever. But he's just an excellent writer.

Michael Hartmann: 32:56

Yeah, it's a little bit frightening when I I've been well, I need to get back to it this year of going back and reading what I would call classics or at least books that were like had lots of influence over people. And yeah. Uh there's some that are like reading them and I'm like, it's a little bit too close to home.

Jacqueline Friedman: 33:12

Mm-hmm. Yeah, Fortnite. Fahrenheit 451 is is a little too close to home at the moment. Um, so yeah, Sound of Thunder is a nice reprieve for the most part.

Michael Hartmann: 33:21

Yeah, I was thinking like Animal Farm, but you know.

Jacqueline Friedman: 33:24

Same, same.

Michael Hartmann: 33:25

Yeah. Yeah. Um, okay. Well, let's we could okay, now we don't need to get into a literature cut podcast. Let's not do that.

Jacqueline Friedman: 33:33

Well, I did say I did want to maybe have an English major in a different life, so that's right.

Michael Hartmann: 33:40

Um, okay, so maybe like you mentioned like Google has changed some of their stuff, which is playing into deliverability and inbox basement situation for some people, but how much of that, how much of what people are experiencing as email marketers is um maybe marketing versus sales versus just the the the email provide ISPs and stuff like that?

Jacqueline Friedman: 34:11

Yeah, I will always stand by if you're doing what the requirements are and what you're supposed to be doing, you're gonna be fine. So, for example, if you're an immediate adopter of what the latest legislation is going to be or is becoming, if you are following the latest rules from specific senders and they're the postmaster's guidance for Yahoo, Gmail, you name it, you're gonna be fine. That said, unless your sales team is ruining it. Um, but though those are two separate things ultimately. If you're doing the right things, you'll be able to get back on the right track. If sales is outpacing, it is far exceeding, it's the only thing your company does, you're gonna have some issues. And they're very, very hard to come back from. And also, if you talk to anyone who's gone through a horror story of something like this happening, they will tell you never again. It's never allowed to happen again. They refuse to make it something they have to fix because it is a really difficult, lengthy process. It can take years, yeah, in some cases. And so it's yeah, if you're doing the right thing, you'll be rewarded. So do the right thing. The golden rule applies.

Michael Hartmann: 35:39

Are you well? So on the sales side, are we talking? I mean, I was in sales, I would send emails, but I would do them directly, right? One-on-one kind of things. Are you talking about that kind of stuff or more about like things where they're using a platform that allows them to send essentially mass email, even though even though it might not be as big of an audience as, say, a marketer might have for a general email, but is that the real culprit here?

Jacqueline Friedman: 36:06

Um, it's definitely amplified. There's still culprits, both of them. Um they all require an unsubscribe. Um I'm just talking about the US. Like you can't, there's like very skirted potential rules with GDPR where you can be like, ah, we have you know some sort of business relationship already, but no, you don't. Um, and same goes with SL in Canada. Like there are very explicit rules of what you can and can't do. And so there is the issue of enforcement, there is a lot of lack of accountability. You can have a law and it's not followed, feels a little dystopian. I wonder why. And so there are, I don't want to say gray areas, I don't want people to think they have opportunity to take advantage, right? But you can't, it's kind of like an asymptote. Like the limit does not exist, but it gets really close. So why try to cross it? Um and so you you have to have a balance without a doubt. And I don't want to, you know, rid of people's jobs on sales. However, if you're just mass sending to large amounts of people, it's not very personalized, it is not super specific, you want them to be like, oh, this person wrote this because of my experience, my this, my that. You're gonna be much more inclined if someone reads an article you wrote and is like, hey, we know so-and-so from this one company, small world, and that is gonna immediately take the guards down or put someone less on guard and less unwilling to engage and and speak with you. And so bringing the humanity back, and you can't bring humanity back at scale easily, and that's a good thing.

Michael Hartmann: 39:19

It's a good thing. I think it's a good thing too. I say I that yet because I don't know. I don't know if it's fear or hope or some other weird feeling. I do think it's gonna happen sooner than we think. I I'm in about AI type stuff has been way off by like factors of I don't even know what.

Jacqueline Friedman: 39:42

I agree and I disagree. I think it's possible, but I have yet to see the possibility. I mean, we I think everyone can relate. Their GPT or their prompts never follow directions correctly. And so hallucinations, right? Exactly. Hallucinations happen all of the time.

Michael Hartmann: 40:03

Yeah.

Jacqueline Friedman: 40:03

And unless you are, and this goes back to really the systemization governance, like if you have really strict guardrails that your AI cannot get around and circumvent, okay, great. However, I mean, there we're living in a world now where there's complete and total platforms just for agents to talk to each other and they're creating their own religion. So I have uh a questionable um perspective on what is actually possible in terms of this. And so I think humanity will win out no matter what. And that's maybe too simplistic and overly optimistic, but people can read through it and we're only getting better, and the media literacy around it is becoming more and more, which is a good thing.

Michael Hartmann: 40:51

I'm I lean towards a little bit towards what you're saying, but also towards I think as this stuff kind of grows and becomes more ubiquitous or common, the value of true connection and human connection is gonna be high much higher value.

Jacqueline Friedman: 41:11

Oh, yeah. I mean, a great example. You and I have met in person a few times. I have a feeling this conversation is more enriched and there's more trust because we have met in person. And that makes a huge difference. And I'm fortunate that you know we're both in the same general like Metroplex and City and things like that, but that's not always true. And yes, you can make connection virtually, but nothing quite beats humans.

Michael Hartmann: 41:35

It just doesn't know. Look, I've I've worked with teams globally, and I think of there's a couple in particular where I work with with colleagues that were in Asia, and it's funny to me because so many businesses here sort of treat Asia as one big sort of common thing. And I'm like, every country is different. It's not smart, every single country is different, and every city, every yeah, everywhere. Yeah. And what I found is the relationships that I completely changed for the better after we met in person. And it didn't take very much a difference, it's just like exactly being able to like be there and talk to somebody and shake their hand or give them a hug or whatever that is, right? Um it just made remote context different.

Jacqueline Friedman: 42:26

Exactly. And zoom it out. What if they speak multiple languages but they have a preferred language and you're not emailing them in that language? Like these are just the immediate things you can easily dissect and recognize. Oh, wait, I'm not actually respecting this other person on the other end in the way they would like to be respected. I mean, even this week, Salesforce Marketing Cloud, they send a bunch of emails to folks who speak English and German and in Spanish. Wires get crossed, things happen, but it doesn't instill trust.

Michael Hartmann: 42:56

Right. Yeah, it's interesting. Well, so one of the things we talked about, I want to bring it back to one of the things we first talked about, um, where you and I both have had experience with B2B and B2C marketing worlds. And we talked a little bit about the like how B2B could learn marketers could learn from B2C. Maybe like what like can you go deal deeper? What do you think that means? Like what kinds of things would you think would be useful?

Jacqueline Friedman: 43:23

Yeah. For B2B, I think seriousness is very much confused for credibility. And an easy example on the B2C side to explain is like Wendy's social media. The reason why they're so successful is because you can tell there's not an approving committee along that versus. And that also means there's gonna be some misses and some mistakes and be a little messy. But guess what? That's human to be a little bit messy. And so when things are either too perfect, too crisp, too, everything, you can just tell. And if anything, I think psychologically it exposes the fact that everyone is scared to sound human. Yeah, and so it ultimately undermines the initial thought of credibility and authority. And so everyone is calling themselves, as an example, an agentec platform, an AI native, AI first. It means nothing now. It's just jargon, it's product marketing, and that means you mean nothing, which means you're invisible. People want to talk to people. People want to understand what you actually do and understand it from your tagline. Like it's easy to use examples like B2C, like Nike, just do it. It just makes sense. It's easy, it's straightforward, you know, and it gets lost in the sauce when you're like, oh, we're a compounding engine for AI, this, that, and the other. And it's like, are you really? What does that even mean? Ah, if that they think well, and to your point, they want to be a thought leader, but you can't lead with thoughts. You have to lead with actual principles, action, ideas, concepts that people can understand. If people don't understand you, you can't lead. And so you have to break it down in ways, it's like a really great teacher. They can make something super complex to your Welsh saying that I'm not gonna be able to say. Make something super complex, super simple. Yeah. And then once you understand the bare basics, all right, now we're gonna dive in deeper and understand more. But you have to grasp someone's attention, you have to bring them in, wheel them in with something and lure them into they can meet you where you want them to start at at the starting point. And I think a lot of people are jumping straight to all right, this is the buzzword, this is the word, this is the way we're gonna get folks to come in the door. And it's like, actually, I think it's a repellent ultimately.

Michael Hartmann: 45:52

Yeah, I think I I I haven't gone and done this in a while, but there was a point in time where every once in a while I would just sort of I'd see something about some B2B company, I'd go to their website if I didn't know much about them, and I'd go like try to read their homepage and like, I I'd take five minutes, I'm like, I don't know what you do. Like lots of words on here. Uh-huh.

Jacqueline Friedman: 46:12

But yeah, uh a good friend of mine actually, she created a a no BS detector. She was just vibe coding and wanted to make it, and it's actually pretty accurate. You just plug in, like, I've plugged in a bunch of vendors and they're like 75% BS. And you're like, ooh, okay, good to know. I love it. And uh, I'll have to send you the link because it's excellent. Um, even if it's just for yourself, to be like, do I sound like a fraud? Am I a fraud? I don't know.

Michael Hartmann: 46:40

So in the early days of like the web really blowing up, there was uh a bunch of like uh, I guess there would be like editors for like tech magazines and stuff like that, who got together and they created a website that was called Bu The Buzzsaw. And I wish it was still around because they would basically they would. Just take verbatim the pitches they would get and post it. And it was just such slugs.

Jacqueline Friedman: 47:09

Sounds like that needs to come back into place.

Michael Hartmann: 47:13

Yes.

Jacqueline Friedman: 47:16

I mean, I think you you you're equipped. I think you could make it happen.

Michael Hartmann: 47:20

Sounds like we need an AI agent to do that with no humanity. There you go. It'd be it'd be the B2B version of uh dad jokes, maybe.

Jacqueline Friedman: 47:31

You know, I'm never upset by a dad joke. I my husband rolls his eyes at me a lot for all the puns. And I don't mind. I don't care. I love it. Maybe that's just like the millennial in me. I'm not sure, but doesn't matter.

Michael Hartmann: 47:46

I love a wordplay. There we go. Wordplays are great. All right. Um how about, and I think we're probably gonna have to maybe wrap it up here, but maybe the flip side.

Jacqueline Friedman: 47:56

I do if it's helpful, I have 30 more minutes before my next meeting. Oh, but I don't, I wouldn't be mindful.

Michael Hartmann: 48:01

Yeah, I do not. I wish I could. But so we've kind of bashed B2B marketers a little bit. Are there are there any things that B2C marketers could learn from B2B marketers from what you've seen?

Jacqueline Friedman: 48:13

Oh, for sure. Um, I think B2C completely overindexes on its creativity. It is always designing the most wild out there concepts, campaigns, but there's no actual, not just durability, but thematic concept. Like there's no tent poles that stay the same. And a great example is the Super Bowl. Spend so much money. Exactly. So it's so much money on this campaign, and it's done. Why would you do it like that? It should either be the starting point of an entire campaign for the next 12 months or the ending point of like, all right, now we're gonna introduce the new thing. And that is something because of its rigidity that B2B excels at a bit more.

Michael Hartmann: 49:02

Yeah.

Jacqueline Friedman: 49:02

Uh the concepts are a bit more long-lasting. And you can be shipping a lot of software and things like that, but it's still not as new new new in the same way B2C typically is. And so that rigor just it helps stack what is complex and it just it makes it easier, honestly. Um, and so not everything's a one-off moment, it's it's more consistent and broad, which can be its own problem too. You know, you can have one good thing and it creates other problems there too. But you need to have systems, thoughts, campaigns that scale. And same goes for autonomy for your folks. If you're allowing the wendy social media person, you know what, maybe that subject line or that silly, this, that, and the other, like, is it really a big deal? If anything, it would be exciting to look for a funny CTA. And I know I intentionally try to do that because after years and years of learn more, read more, explore more, I want to have fun and I want to be unexpected in my comp in the way I speak with businesses and things like that.

Michael Hartmann: 50:08

Yeah, I I love the idea of giving people guidelines and autonomy and not punishing them if they go overline.

Jacqueline Friedman: 50:16

I mean, it's a teaching, but like you can't let it just continue until the prime example of your Whookse email typically does better than anything else. Yeah, because one, you showed your humanity, and two, you made a mistake.

Michael Hartmann: 50:31

Right.

Jacqueline Friedman: 50:31

Who doesn't want to notice it? Right. And so sometimes it's actually a good thing. I'm not suggesting ever start testing mistakes, but it's not a mistake if you learn something from it. And I know that's like a life saying, but it's also particularly an email, it's so low grade. We're not saving lives, we're sending an email. It's zeros and ones. Yeah, it's it's not much.

Michael Hartmann: 50:51

Yeah.

Jacqueline Friedman: 50:52

Not to degrade it, because I love it. Yeah.

Michael Hartmann: 50:54

Yeah. So it's funny because like I think um it's funny that you and I in my head, I was like, I wonder if she's gonna reference the Super Bowl. So for those who are listening later, we were recording this a few days before the Super Bowl in 2026. So uh that's why it's top of mind probably for both of us. But I think I think just in general, a lot of B2C commercials, advertising, whatever. Um I find myself sort of scratching my head like entertaining, you know. Um at the end of it, I'm going like, but I don't understand how this ties to what you do. And so I go, try to be generous. Is it all about building brands and like recognition and recall? Okay. Seems like an expensive way to do that.

Jacqueline Friedman: 51:39

And it's a very expensive way. And re-referencing my conversation with Dela, your inbox is the cheapest advertising platform. Use accordingly. Yeah. And those impressions cannot be beat on a cost per person.

Michael Hartmann: 51:57

Cost public, you name it. It's also if I think the way I'm going to sort of summarize today is like if you treat the people who are on the other end of whatever you're sending via email, right? You can build trust or you can tear it down.

Jacqueline Friedman: 52:12

And both are very easy.

Michael Hartmann: 52:13

Well, building trust takes time, right? It takes time, but it's not hard. Like, but losing trust is pretty easy. Like that um, it doesn't take much to do that, or at least start it takes I think it takes more effort or more times of building the trust than it does to times like it's almost a you one one, yeah. If you have two if you have a uh something that tears down trust, it's like taking two out while you're putting one in for each time you're building trust.

Jacqueline Friedman: 52:42

For sure. But I do want to push. I don't think trust is hard. Keeping it is hard. Because I think most folks, I mean, we can get philosophical. It's like, is everyone nasty, bridge, and short, or is everyone much more thoughtful? And so uh do you start assuming positive intent? You might not, and that's okay, you're not for everyone. But I think most people want you to succeed. And whether that's a company, you know, whether that's a product, they're like an example, they don't want to buy your product and then not work. Like that's not what they want. So as long as you consistently show up both in the things you're selling, the way you guys are as a company, and when it's more unified and you can tell, oh, this is the culture they bring to the table, and this is how they interact with the real world, the more trust there is. When there's a disconnect between what maybe leadership says on one way and your customer support says in a different capacity, that's where trust erodes, and that's not even marketing related.

Michael Hartmann: 53:47

Right.

Jacqueline Friedman: 53:47

And so it it's not as hard as people it's hard to maintain, without a doubt.

Michael Hartmann: 53:54

Fair enough. I will I I can agree with that.

Jacqueline Friedman: 53:58

So it doesn't make it easy, but no, it's I think it's simpler than many assume it to be.

Michael Hartmann: 54:04

Yeah. What and what what you're also describing, regardless of the interaction point with a customer, prospect, client, whatever, um it's an opportunity to either continue to build and maintain trust or to lose it. And so if it's inconsistent, it can it can it's easier to erode it faster if you're inconsistent across those different interaction points than it is if you're yeah, you can okay. Yeah, I think we're good there. We're in line.

Jacqueline Friedman: 54:33

Yeah, and I think I can say one last thing. Uh I would also say those values that you present publicly have to be felt internally, and that will inform your deliverability. That will inform your marketing structure. So it's far more important than people think. And, you know, you had to go into that room with the CEO and CMO. And ultimately it was actually a philosophical question. What do we agree to? What do we promise to our customers? And which promise are we willing to follow or take back? And so it's not trying to get that existential, but that's truly at the core of it.

Michael Hartmann: 55:15

No, I it it's interesting because since we're in Dallas, right? I don't know that it's still this way, but Southwest Airlines was the epitome of it, right? The culture internal really manifested itself in the way that they interact with their customers. Like kind of across the boards.

Jacqueline Friedman: 55:32

It's gonna be interesting how it has or hasn't changed. I haven't taken a flight in just yet since the switch.

Michael Hartmann: 55:37

Yeah.

Jacqueline Friedman: 55:38

Um, so we'll see.

Michael Hartmann: 55:39

Yeah, yeah, yeah. Well, hey, this has been a ton of fun, Jacqueline. This is great. Uh we have to get together again sometime since we're in the same cities. But um Thank you so much for having me. Yeah, we love it. And I know you've got a little bit of a slug left for the rest of the day. So I'll wish you luck on that. So if folks want to continue this conversation or pick your brain or learn more, fill follow up what you're doing. What's the best way for them to do that?

Jacqueline Friedman: 56:02

Yeah, the best way is LinkedIn. I embarrassingly am on there a lot. Don't DM me because I probably won't see it, but you can try. But um, I send her send her send her a cold email. Uh yeah, you'll immediately mark as spam, and don't think I won't remember. Uh but no, LinkedIn's definitely the best place, or you can go to my website at monarch advisorypartners.com.

Michael Hartmann: 56:28

Awesome. Well, it was it's been a ton of fun. I know we could have gone on for a while of a lot of different topics. Um, so I appreciate that. So thank you. As always. And then uh as always to our our long time and you listeners, watchers, now that we've got video, uh, we appreciate you and all the support. If you have ideas for topics or guests or want to be a guest, you can reach out to Naomi, Mike, or B. We'd be happy to get the ball rolling. Till next time. Bye, everybody. Awesome. Thanks.