Nathan Thompson: All right. Welcome back to Barely Shipping. My guest today wrote one of the best lines I've read so far this year, which is, " "Generic messaging fails without telling you it's failing, and that's probably one of the reasons it remains popular. It's a problem of silent failure where your marketing can be dying and every dashboard still stays green."
Meet Tyler Jacobson. He spent 25 years learning to detect that silent failure, growing a subscription business 3,400%, taking a retail chain from 70 to 100 million, building brand platforms for everyone from Housing Works in Manhattan to government contractors, and running an award-winning Denver club, uh, club night, not nightclub, club night for 17 years, where the feedback loop is a dance floor and it doesn't lie.
Today, he leads marketing at 4B Marketing. He's a fractional CRO sharp for technology, energy, and government clients. And if you're on a lean team wondering whether your messaging actually works or just exists, [00:01:00] Tyler has spent his whole career on exactly that question. Now, Tyler, welcome. Thank you again for taking the time.
First things first, what did I get wrong and/or miss about that introduction?
Tyler Jacobson: and/or miss about that introduction? Uh, it was p- it was pretty, uh, it was pretty thorough. One thing, uh, which I know you, uh, you were interested in is I've actually done two club nights that are award-winning, and, um, those-- One, one of-- Both of them are still running.
I, I quit one of them in 2009, but, um, that's been going since 2001, so that's on its, uh, what? 25th year. And then, uh, Mile High Soul Club is the other one, which, uh, celebrates 18 years this month
Nathan Thompson: Okay. And one of the reasons I wanted to talk to you, it's not often that you find someone with experience in traditional, you know, B2B marketing, uh, and also, uh, cannabis retail, if I could say that, or a dispensary, and then, uh, is also a DJ. Those are three very different things. Uh, very first before we [00:02:00] get started, what drew you to all of those different areas?
Just a curious person, just open to opportunities?
Tyler Jacobson: to opportunities Um, yeah, I mean, open to opportunities is definitely one of them. But I-- There's a great "This American Life" episode that's all about how plan B ends up being your life, and plan A really doesn't typically work out. And, uh, so this is the beginning, uh, and the origin of my marketing career, which is going back to high school and, you know, um, creating, you know, bands that I hadn't actually assembled yet and, uh, creating logos and names and, you know, stickers and all that s- kind of stuff, and seeing them on lockers, uh, throughout the school, um, 'cause people were adopting it.
And then get into my 20s and, um, I'm not in a band anymore and, uh, DJing sounds like a lot of fun. And so, um, yeah, came up with logos and names and flyers and did all, [00:03:00] you know, distribution and did all of the things that, uh, were necessary to make sure that the, the world knew about those nights. So jump forward to 2001, Lipgloss.
Um, I did PR on that. I s- you know, I reached out to the press, uh, locally here in Denver. I made sure that they were coming down to the night. I was, you know, created a logo for the night, which isn't very often that you find that, and I think it's a big miss in the, in the club night world. So if anybody here is a nightlife promoter, like logos are, logos for your, for your nights are, are a good one.
But I gave it a, a, you know, an identity and, um, me and my partners went out there and spread the word and, um, the venues kept getting bigger.
Nathan Thompson: I love that you were making logos for bands that weren't even put together yet. I think that that's where the school counselor says you should get into marketing, like immediately.
Tyler Jacobson: Yeah. No, they were like, "Can you please stop handing out stickers?"
Nathan Thompson: Yeah, for this thing that doesn't
Tyler Jacobson: even exist?
Nathan Thompson: All right. Well, I'm gonna jump into some [00:04:00] questions, and we will focus on the marketing.
Uh, though feel, feel free to s- to sprinkle in some DJ knowledge in there as well.
Tyler Jacobson: Okay
Nathan Thompson: but your LinkedIn summary opens with, "Most marketing sounds like marketing. It's the same language, same frameworks, same forgettable results." Now, you've spent 25 years on this problem, and I was curious what led you to this realization, and whether it was a specific campaign or a brief, something internal, or was it just looking around LinkedIn and doing what other brands are doing and being like, "This is just all falling flat in the same vacuum"?
Tyler Jacobson: A lot of it actually was just informed by working with, um, you know, being in agency life and, and working with brands. And, and I think it's a problem with marketers, um, as m- as much as it is the, the brands themselves. I think it can be a problem with agency marketers where they don't have the elasticity to put themselves on the other end, on the c- on the customer end of the marketing transaction, right?
Um, [00:05:00] and they're, they're just looking at it from their own needs and then making assumptions that the, that the world needs them. And so when they're making that assumption and they're not actually doing a whole lot of research and they're not, you know, um, talking to anybody, they get to live in this nice little made-up word where-- world where, you know, what they're saying is right and it's going to connect and there must be other problems, and that's the reason things aren't moving in the direction they want them to.
Nathan Thompson: It happens a lot where it f- it feels like, and I could be wrong, but it feels like a lot of, especially copywriters, but marketers in general tend to think, "If it makes me happy, it must be good," 'cause it's a personal preference thing, without thinking, "Is my customer gonna find this happy?" They may be they're different than me.
Maybe we send out something I don't like, but it works for that audience. Have you ever run into that where it's like you send something out where you're like, "It's not my personal favorite, but it'll work"?
Tyler Jacobson: customer gonna find this happy. They, maybe they're different than me. Maybe we send out something I don't like, but it works for that audience. Have you ever run into that where it's like you send something out where you're like, "It's not my personal favorite, but it'll work"? Oh, absolutely. And I love, uh, I love it when that happens.
You know, I wanna A- B, A/B testing things. I wanna go with the thing that I like, um, [00:06:00] against the thing that I don't like, because it's not about, you know, at the end of the day, and this is kind of a harsh way of saying it, but I've said this to clients before, it doesn't matter what I like and it doesn't matter what you like.
All of that is inconsequential. It matters what your customer likes, and then we wanna go hard on there. Um, even with that thinking and even with that, you know, process of, of saying you are not the persona that you're going after, right? And you need to understand them a little bit better, and you need to test for, for what will move them further through any journey.
Um, brands are still very protective and they say, "No, I, we, we don't wanna do that. We're not gonna go, we're not gonna go in that direction."
Nathan Thompson: Yeah. Have you found, I, 'cause I, I'd be curious, uh, when you're talking to especially C-suite or VPs or directors, is it hard to say you are not your customer? And it-- do they typically take that well, or is there a little bit of like a, "Mm, I don't like that," like, "Make me happy"?
Tyler Jacobson: Yeah, it's, it's-- I [00:07:00] don't, I wouldn't say that it's so much that, um, make me happy, um, as much as it is, is no, I know my customer. Okay. And, and I, and it just comes from assumption. And you know what? If you know your customer, that's great. Let's go validate that. Let's go make sure that you actually do know your customer and, and, um, then you as a leader have a, have more confidence to go out there and say, "This is what they need.
This is what they want." Um, is that hard to say? Yeah, absolutely. It's hard to say to, you know, um, it's hard to say to a VP of a, of a publicly traded company to- Yeah ... you know, step back and let the data do some work. Um-
Nathan Thompson: so much nicer than I am. I w- I just wanna say like, "Well, if you got nothing to be afraid of, then what are you afraid of?" But I-- That's obviously the wrong... That's wh- yeah, that's why
Tyler Jacobson: No, I think,
Nathan Thompson: than I am.
Tyler Jacobson: that's-- You know what? I go back and forth, to be fair. I go back and forth with some of this, um, because, you know, do you wanna go in and be the blunt object? Which, which is sometimes really [00:08:00] needed. It's necessary, uh, to go in there and say, "I am confident that we need to investigate this.
I am confident that what we're doing right now isn't working, and we need to get on a path where things are working." And I think that being able to, um, being able to do that and not try and nuance it, I mean, that is, that, that has its own power. So
Nathan Thompson: Yeah, and I imagine too in the agency they're, they're hoping to draw on some of your confidence and expertise as well. So I imagine it's the way-- the delivery and the confidence you have when you say it. Um, but I, I wanna talk less about the wins now, and I wanna talk a little bit about, uh, this subscription business that you grew 3,400% over 15 years.
Because everybody hears that final number, but not many people take the time to think about the middle. And, uh, whenever you're growing a business, there are, you know, peaks and valleys. I wanna walk through a valley, and I want you to walk me through what stalled in some of the lower points. What did you kill?
Or what did recovery look like when you were in one of those valleys?
Tyler Jacobson: [00:09:00] Yeah. Um, so it never Luckily, we were in a space and we were niched down and, you know, rich-- the riches are in the niches, right? So, um, so we were in a really good space because, uh, we were a web hosting company that was focused on supporting Macs.
And this is at the time when Steve Jobs had just come back on as the interim CEO of Apple, and that company was almost dead. And, uh, my boss, the president of the company, had already done some stuff with, like, Guy Kawasaki's Mac Evangelist and, you know, gotten the word out that way, which was good. Um, and then Apple started to rise, and it started to become the Apple that we know today, um, from almost being extinct.
And we were, we were, you know, we had our, our wagon hitched to that, to that increase, which was really nice. Now, um, [00:10:00] you're asking about valleys. There's one that there was a threat that was not inconsequential, and this is when Apple decided that they were gonna go into web hosting, and they were gonna launch with .mac.
And, uh, we were up against-- we, we, you know, a, a multimillion-dollar business but a small one, you know, are up against a multi-billion dollar company, um, where we can't talk to anybody, and we know they're gonna be able to out-market us, and they're gonna be able to do all of the things. They're, they're gonna have the resources that we're simply not.
We were worried that we were gonna be, um, wiped off the face of the Earth. So I started digging into what does .mac do and what doesn't it do. And two really important things came out of that exercise, which, one, they did not allow for custom domains. So it was going to be, you know, tyler.mac.com or something like that.
You know, these, you know, almost GeoCities-like URLs. And with that [00:11:00] also, that meant that your email was gonna be, you know, [email protected], right? And you weren't gonna have an email at your fully qualified domain name. So I was like, "Let's set up a little service here, and your domain name will redirect over to your Mac one."
So you can still go out there and you can still say, you know, tylerdjacobsen.com, and people could type that in, but then they'd end up going to the Mac address. And then also you could have email with us that was going to be at your fully qualified domain name too. So we called it, um... Boy, what did I call it?
I can't remember, I can't remember what I called it. But, uh, it was, it was a service that we put out there and, um, we, you know, s- it was like accounted for 30% of our sales that year, So, so that got us, that got us past this situation of, um, you know, Goliath and we're David, right? That got us, that got us, um, actually helped the company rather than hurt it because we looked at it [00:12:00] as an opportunity rather than just threw up our arms and went, "Well, we're screwed," you know?
Um, and then, oh, it was called MacName. That's what, that's what the project was called. Uh, and, uh, then Apple stopped doing hosting. They were like, "This isn't profitable. It's not..." You know, for whatever reason, they stopped doing it. And what we ended up having was a whole group of people who had web hosting previously through, uh, Apple, who were now, you know, who were already our customers in a, in a respect, and we were able just to upsell them and move them right into a hosting, uh, situation.
So we were able to capture them.
Nathan Thompson: That's great. That is-- I mean, what an opportunity. And I, I, y- I am a bit of a one-track mind sometimes, but I see such parallel with AI right now of human marketers worried, "Oh, we're gonna be wiped off the face of the earth," without doing the investigative research of, "Well, hold on. What can we bring that it can't?
And what gaps can we fill that it [00:13:00] can't?" And then getting creative with the solutions around that, and it sounds like you've lived through and battle tested that process already where I, I, I just think that's great ingenuity on your end, and 30% re- that's... Like I said, I hope you got a good bonus on that one.
That's
Tyler Jacobson: 30% rip. That's, like I said, I hope you got a good bonus on that part. It's awesome. I, I mean, I, I'm, I'm pretty proud of it. It's the reason I'm still talking about it all these years later, you know? Uh, you know, uh, it's, it's cool to go up a co- uh, against a company like Apple and, and not lose your ass.
Nathan Thompson: So what I'm hearing is you single-handedly took down a department of Apple. That's what I'm gonna say.
Tyler Jacobson: Abs- absolutely. Absolutely.
Nathan Thompson: All right, back to the, uh, introduction. I really liked when you said generic messaging fails without telling you it's failing, and that's probably one of the reasons it remains popular. My question is, how should teams go about detecting that silent failure?
Because it's very hard. W- is there a measurable signal or something that lets you know messaging is generic before learning from the pipeline numbers six months later when you're chasing the eight ball?
Tyler Jacobson: Uh, I think it depends on what [00:14:00] your sales cycle looks like. You know, you may n- you may not even be able to surface it for six months. But I think the biggest, uh, you know, something that can really indicate whether you are s- have a messaging problem or not that, that is giving you kind of false information is, are you moving people in-- Are you getting them into the funnel, but then they're not completing, uh, through conversion?
Are they just, you know, it sounds good, and then they take one step and that's it? Um, and it comes back to the conversation earlier about, you know, you have to understand the needs of the person that you're selling to, and you have to raise the stakes on those needs. You have to y- y- have... Okay, so there's this, it, it...
This is gonna be, uh, a little, uh, long here, but, uh, the quarter-inch drill bit. You're never selling a quarter-inch drill bit. What you're selling is a quarter-inch hole, but you're not selling a quarter-inch hole. You're selling, um, you know, the ability for somebody to put up a shelf, but [00:15:00] you're not even selling that.
What you're selling is the pride that, you know, this dude will feel when his spouse walks into the room and, and is like, "Thank you for putting that up," and feels like that person's capable, right? So the stakes around a quarter-inch drill bit are actually, um, adoration, love from your spouse.
Nathan Thompson: Love that
Tyler Jacobson: and if you can walk through that, and, and, and in B2B for frankly, it's pretty easy.
Uh, people want to make more money. They w- and they are afraid of getting fired. So your messaging has to weave into that. And if you're just staying at like, "Well, you know, we, we sell cool computers," right? It's like, that's great, but what does this mean for the person buying?
Nathan Thompson: Yeah. Will they still have a job in six months if they use it sort of a thing, or confidence that they'll have a job? I really like that drill, 'cause I've heard that drill bit example, but I've never heard it extended so far into the final [00:16:00] feeling that they have when they show their significant other, like, "Look what I built."
I've also never personally felt that because everything I build falls to pieces. But, but I imagine
Tyler Jacobson: see shelves behind you
Nathan Thompson: That my wife helped me with those, I'm not gonna lie. She, we did a revamp. I, I'm not great at that stuff. That's okay. Um, all right. So one of the things, uh, when you're marketing and you're selling, I mean, we, we've talked about this and you said earlier that mar- a lot of marketers don't have the elasticity to put themselves in the customer's shoes, and they, they start to build this little vacuum around them.
Um, and you've told founders that their first marketing hire brief is written around one deliverable, uh, usually more leads, but the actual job is different. What would a more accurate be- accurate brief look like in 2026 where they're trying to find a modern marketer? What types of things should they be looking for?
Tyler Jacobson: [00:17:00] six where they're trying to find a modern marketer, what types of things should they be looking for? Um, somebody who is willing to and knows how to do the front-end work and understand before you ever get in into a brief, you gotta understand that persona. There's-- I mean, there's a couple key things.
Persona is, is absolutely where it all starts. Who are we talking to? Who's our target audience? And then getting into, um, an empathy map. And so that goes beyond persona and it's, you know, what does this person think? What do they feel? What do they see? What do they hear? Um, and it's actually a, um, it's a, it's a construct that is already out there.
So if you type in empathy map into, into Google, you're gonna see that. But you want to really, you know, understand as much as you can. You wanna look for quotes out there, you wanna interview people, and if you can't get any of that done, you can rely on inference because at least that's an exercise where you're going through and you're understanding the persona and you're saying, "Okay, what does this person, you know, what are they seeing in the marketplace?
Um, how are they responding to it? What are they doing? What are they fearful of?" Um, and I, and I think that it starts [00:18:00] there, and then, then you can move into what is your unique value in this space? And why would somebody-- why would this person that we've, you know, created, um, that is based on, on our real customers, like, why would they care about what we do and why would they say, "Yes, this is the place that I'm gonna go"?
So I think that, um, I think that it all has to start from somebody-- from that upfront research, and then I think it has to just, uh, you know... The, the, the, the campaign is the end result of that, but you don't start necessarily with the campaign. And I, and I don't think that frankly executives quite understand that.
Nathan Thompson: Yeah. And, and you said something that I am really curious about because I love using AI for research. It's great. What you had said, though, about the empathy map makes me wonder the limitations around AI and understanding a customer to that depth, [00:19:00] because obviously it doesn't have empathy yet. Um, it has, you know, faux empathy.
And so how would you do this before AI, and what would you use AI for now?
Tyler Jacobson: Right. And so I do use AI, um, to help do some research and help, uh, assemble personas and create those empathy maps based on all of this, and we can talk about that in a second. Um, but prior to that, it was customer interviews, surveys, um, and then research out there. Has anybody published papers about, you know, um, the category that my client is in or, um, the kinds of people who are buying?
Like, let's just get as much information as we can. And there's a surprising amount of, um, of data out there just publicly available. Uh, Pew was one that I really started with, is Pew Research, because they, they have this great chart that they update every year, which is what social media, um, channels is [00:20:00] everybody on based on gender, based on age, you know, things like that.
And so even understanding where these people are likely to hang out is gonna get you, get you steps further. Um, but I gave, you know, my persona and my empathy map to an AI. I've, um, I've told it exactly what I want the output to be. I say, you know, I create a persona and an empathy map that, that revolves around, and then there's the blank.
You know, my client's category, my client's, you know, what, what they need from my client. 'Cause if you just do it in general, it's gonna be like, you know, what to make for dinner. And it's like, well, that doesn't, that's not really helpful here. Um, and surprisingly, it gets, it, it comes out with some really great stuff.
You tell it to do citations, of course, and then you go review those citations and make sure it's there, and then say, "Feel free to infer, but, you know, write down where you're, where you're putting those inferences." And, uh, and yeah, I mean, honestly, it's, it's remarkably [00:21:00] good.
Nathan Thompson: And, and especially if you're adding customer interviews, uh, and your own manual research too into the prompts and into the context, and then it's restructuring those and finding patterns much faster than, than many of us can, can do, frankly. Seems like it would be a great leverage. Um, I do like though that you said, and I, I don't wanna gloss over this, um, where you ask it to say, " "Let me know where you infer."
And I think a lot of people miss that little step because then as the human in the loop, they're just constantly reading the five, 10-page output and s- you know, start to get a little glossy-eyed and like, "Okay, is it..." But when you see those highlighted notes of this is an inference or this is the citation, I think that's so valuable to add in there.
So I just wanted to click on that. Um, when you're looking at demographics, is there ever a point where timing is more important than the audience itself or, or not more important, but meaning like either the time of the year or the time that you're delivering the message, uh, seasonal campaigns, things like that, where the persona [00:22:00] actually can take a backseat to the time that you're, you're doing it if you're doing a big launch around a certain time of the year or something like that.
Does timing ever impact how you market to a demographic?
Tyler Jacobson: Absolutely. And I, it does it on a micro and macro scale here.
So, um, when we're talking about a calendar year, every single business is going to have, um, seasonality. It's going-- They're gonna have their low points, they're gonna have their high points, and it's-- and theoretically, it's consistent. Now, the last few years have been absolute chaos and, uh, it's hard to set baselines, but, uh, you do have, you know...
Like when we, we present, uh, data to clients, we typically wanna show them year-over-year results because comparing a traditionally slow month against a traditionally, um, fast month, you know, high y- high volume month is not really fair. Um, so you do have those, you do have those. But now, uh, on the macro level, you have, um, really big, important [00:23:00] things that can impact markets, and I've seen it time and time again.
I've seen it with the club nights. I've seen it with Mac Highway, um, which was the web hosting company. Um, and I've seen it with clients. So I'll give you a couple examples there. Um, with Mac Highway, our two best years were 2002 and 2009. And the reason those were good-- Or no, I'm sorry, 2001 and two th- 2009.
No. God. Okay. No, it was 2001. So 2002 and 2009. We can edit that. Uh, so our best years were 2001, 2009, and the reason for that was because of September 11th and then also the crash of 2008. And what ended up happening as a result of that is that people, when they lost their jobs, the first thing that they say is, "I, I have to, you know, create my own entity.
I have to start creating, putting, you know, hang up my own [00:24:00] shingle. I have to start working for myself." And so being in the web hosting business while those things happened was a really good place to be because that is something that they'd be willing to invest in. Um, and then I had a v- a, a pretty successful client who was in the, um, appliance repair business, and they had a few different locations, and they'd been doing all right.
But the one event that nobody could have predicted or controlled was COVID. And what happened during COVID? Everybody's staying at home. They maybe hadn't used their oven ever, you know. And now they, now they go to turn it on and they're like, "Well, that doesn't work. I need..." You know. Um, and so appliance repair, just as a category, went through the roof.
Again, you can't control that. So that timing, um, you know, that timing was really good. On the other hand, if you were in, um, experiential marketing at that time Yeah. Your audience just [00:25:00] didn't exist. And y- and, you know, the question is, is can, can you survive, you know, this, this low point? Um, and again, nothing that you can really control.
I worked with some companies that were trying to. They were trying to get really innovative around it, but at the end of the day, it's, you know, we were all kind of in our own, in our own little bubbles at that point, and it was really hard f- to, to convince people to pay for things that they didn't really need.
Nathan Thompson: It makes me think of a, a modified version of a saying where like inspiration can find you, it just better find you ready. Meaning you have to have the work and the foundation under it when it does to keep going. It almost sounds like good and bad luck will find you. Uh, hopefully it finds you ready for either.
And if you don't have things in place to scale when the time is good or you don't have the things in place to really buckle down when times are bad, then that ti- your business can be dictated more by timing than by good strategy at some point-- to some extent
Tyler Jacobson: extent. Yeah, [00:26:00] absolutely. And so that's where that market shift occurs and, you know, are you, you know, suddenly you have a bunch of people in market who may not have looked like your people who are in market before whatever event happened.
So
Nathan Thompson: And now you have to redo your empathy maps to figure out the new customers that you're selling to. That's really interesting. I like that a lot. Um, okay, now I-- and again, we'll, we'll leave the client blank on this, but you did post about a client where, that you're technically not supposed to be able to run ads t- for on Google and Meta and figured out how to do it compliantly. Again, without saying their name, what's the playbook for when platforms say no? And what did marketing under prohibition teach you that marketers with unlimited access don't tend to learn?
Tyler Jacobson: Okay, so I'm going to say that it's for dispensaries. Yeah.
Nathan Thompson: All right. That's what we
Tyler Jacobson: That's what we got ... we'll, we'll just put that out there.
Um, and we were really struggling with this because we tried to run advertisements previously, and [00:27:00] they were compliant. We weren't getting any pushback, but they also weren't delivering. And, uh, so there was definitely some sort of gate, uh, on these platforms that we couldn't get beyond. And so as a team, we were really struggling with how do we do this?
How do we-- how are we able to do this, um, for our, for our clients? And there were a couple, and I think there still are, um, a couple of really great businesses out there doing this, but their minimums were like, you have to be spending $10,000 a month on Meta. Well, most dispensaries cannot have an ad budget that big in total, much less for a single platform.
And so it was to our benefit to figure out how we do this for companies that had much lower, um, advertising budgets. And what we found, and we, and we went out there and we, you know what I mean? We were getting some advertisements as well, you know, in d- different cities, uh, around, um, around dispensaries.
So we were l- and, and CBD, there was a [00:28:00] lot of, lot of CBD and things like that out there. And so we looked and we said, "Okay, what, what are these guys doing and what are they not doing?" And what they were doing was they were implying what they do. Um, they were showing their brand names, but they were not saying explicitly what they do.
Uh, and that was the key. So didn't, ca- not using the word dispensary, not using the word cannabis, not talking about, not talking about it. Um, and the same had to be true for the landing page. I went very conservative on this because you can lose your whole ad account, and I don't wanna do that. So I made sure that your, any, the entry point was two clicks away from actually getting to the, um, dispensary site.
I made sure that we were advertising to people who were, you know, of legal age to consume. And, um, you know, we would just, we would come up with taglines and, uh, that, that were like, you know, [00:29:00] "Hey, stop, stop on your way to the beach," you know? Um, a, a different kind, a different kind of wellness, you know? Um, and it, it, you know, actually on some of these, we got above average click-through rates, so it was kind of cool to see.
And, and we got really good distribution and able to operate in, um, in paid search and in social.
Nathan Thompson: Looking back, are you a little frustrated you had to be so conservative? 'Cause I imagine it would've been more fun to come up with all the things you wanted to say. Was it hard for you to be like, "Okay, but we-- I've gotta make sure we don't burn this account"?
Tyler Jacobson: No. I, I, I, in fact, I operate, you know, on the opposite. I love those boundaries. I love boxes. I think that's what forces creativity, and that's the opportunity to get in there and just be like, "All right, how do we achieve this wi- with all of these constraints?" Because if we have these constraints, everybody has these constraints, right?
Our competitors have these constraints. So how do we do better? How do we do better than them? How do we, how do we... [00:30:00] And, and that's just true for, for any campaign that I do. I want to know what those boundaries are so that we can, uh, operate within them, but also,
Nathan Thompson: What a great mental shift of thinking as
Tyler Jacobson: a great mental shift to thinking
Nathan Thompson: and constraints as a fuel for creativity rather than a hindrance. I really like that. I, uh, I'm gonna have to chew on that for a bit. I love that
Tyler Jacobson: Well, it, you know, I mean, it's, it's a guerrilla marketing ethos, and it comes from having strained budgets or no budgets, you know, when y- you know, I'm marketing a club, a club night or, um, you know, doing a business that hasn't defined a, a marketing budget, you know? What can we do to make a big impact without having to just spend?
Nathan Thompson: And I, I like that the, the DJ influence, the club night influence. That's wonderful. Um, okay, let's talk about, uh, we'll go a little higher level here. And you, you drove a retail chain from 70 million to 100 million with SEO segmentation and life cycle [00:31:00] marketing, which, uh, I could be wrong here, but I, I view as like systems work, uh, where you can build something once, run it continuously, obviously with people doing what they need to do along the way.
Now, 4B calls itself an AI-enabled agency, so content data analysis, personalization, and automation. And you personally post about customer psychology without mentioning AI, but I would love to know where AI actually lives in your delivery today, if you're allowed to share that, obviously.
Tyler Jacobson: obviously.
Nathan Thompson: fine.
Um, and one thing, um, on that AI-enabled page that's more aspiration than operation
Tyler Jacobson: Okay. So we are-- the tools that we are using, um, in-- that I intentionally have, uh, that are intentionally AI-driven, um, are gonna be Claude and ChatGPT. There is every startup in America and possibly the world is trying to, you know, use AI to sell you something, and most of those companies [00:32:00] are not gonna be around in six months.
And it's just, I, I... You can't, you can't be, you know, running from one tool to another and expecting efficiency. So, uh, right now we're keeping it simple with the, uh, with the tools that are gonna be around and are getting the investment that are, that, you know, um, are gonna continually, continually make them better.
Um, so what, what we could do, which I don't really do, but, um, it is a practice out there, is, uh, building your persona, building a model of your id- of your, of your consumer, and asking it questions about the business, um, how, you know, asking it to roast taglines, asking it, you know, what the expectation is once you say something.
Uh, and again, I haven't personally done that, but I have heard of other market- marketers, um, really relying on it. Um, what I do, [00:33:00] uh, I, I think AI is a great brainstorm, um, base. I think that it's, um, really strong for, like, if you're, if you've got writer's block and you're just like, "I don't know. I'm, I'm, I don't know where I'm gonna go with this," it can produce a pretty decent first draft that you go in there and you say, "You got all this wrong."
Nathan Thompson: Yeah. Yeah.
Tyler Jacobson: using the word 'actually' too much." Um-
Nathan Thompson: That happened this morning. Sorry.
Tyler Jacobson: That happened this morning. Sorry. Yeah. I mean, it's, it's, it's AI slop. I said, I said this, uh, I think, um, we have our own-- where we had our own podcast. I was like, "AI slop is gonna look so different in six months," because, you know, it was-- That I, I said that, you know, when it was, like, the Will Smith eating spaghetti, and you could obviously tell it was crap.
And I was like, "As that gets better, you're gonna see what A- AI slop is just probably gonna be something that you
Nathan Thompson: Yeah,
Tyler Jacobson: I think we're at that point now. We can define what that feel looks like now, but it's just gonna keep going where you're just like, "Uncanny Valley, there's something [00:34:00] that's not right here," and so it feels AI.
Can I
Nathan Thompson: Can I ask you a question? This is my-- This is the, the hill that I die on, and I'd be curious about your take. I, I still think that AI slop is a human problem, not an AI problem. By that I mean it, it does not publish itself, and anyone who hits publish and pushes it out there was a human who said, "Good enough for me.
Good enough for my brand. That's fine." And then they say, "Well, it's AI's fault. It didn't do it good enough." And it's like, well, yeah, but you're in charge of that. That's kind of your role. And I, I just wanna stick up for the-- I wanna, you know, especially if the Terminators take over, I wanna get recorded sticking up for them.
I do feel like it gets a bad rap sometimes, and it does really good, but it's not a magic box, and it still needs a human to take away that empty feeling and inject some of that personality in there. I'm happy for pushback, though, and to be corrected on that. I was just wondering your take on that.
Tyler Jacobson: on that. Uh, so my take on it is a lot of the things that you're referencing [00:35:00] from my LinkedIn profile were generated with AI, and I absolutely hate them. Um, I am not, I am not pleased with them. We, uh, you know, we were working with a consultant who was like, "You gotta be on it, on LinkedIn.
You gotta be publishing. Here's, here's kind of the method that, that I use." And I'm like, "I'm willing to try it." I hate LinkedIn as a platform. Um, I mean, I could go off about that, but I gave it a, I gave it a shot. And these are coming from, you know, previous writing that I've done and concepts and theories that, that, that I have.
And so it's directionally accurate, but it reads like... It, it just reads like AI crap. And I am, and I'm a writer and, but I just... Yeah. So I tried it. I don't love it. Um, and you're absolutely right. Somebody at the end of the day is hitting, you know, publish on that. And this is the f- th- this is one of the fears that I have as we progress with [00:36:00] AI, is that we are going to lose institutional knowledge, people who know what things should look like and can detect when there's a problem.
And right now it's not an issue, but we have an AI-native generation that's, that's growing right now. And by the time all of us, you know, uh, Gen Xers are, and millennials are out of, out of the picture, you know, like, what happens? Are they-- Is that institutional knowledge gonna be passed down? Is it gonna be ingrained into the AI, or is it gonna be a situation like it is now where it's like you have to know?
You just have to know from, from, you know, having this discipline for how, you know, a decade plus.
Nathan Thompson: I do think that younger Gen Zs and all of Generation Alpha is at a major disadvantage because if I started copywriting in 2014, 2015 and doing all the SEO stuff, I had 10 [00:37:00] years of doing it all by hand that just got-- became second nature and, and you've been doing it for 25. It's like, it's really easy to spot where something went off the rails and go back.
And there is a concern that in 20 years it's... What is that movie? "Idiocracy," where just the level goes down so much, but everyone's levels ha- went down so much, and that I, I do think that's a valid concern.
Tyler Jacobson: Where just the level goes down so much, but everyone's level, it went down so much. And that, I, I do think that's a valid concern. Th- that movie used to be funny. I can't- Right ... I can't watch it
Nathan Thompson: It's too scary? Hitting, hitting too close to home?
Tyler Jacobson: Yeah. Oh my goodness. Um, but yeah, I mean, I think that that's, that's ultimately the fear, right? Is that peop- is that there's just not gonna be people who know how to do the things, and we've just offloaded it to the robots, and we trust that, that they are doing it correctly, and there's nobody there to really be able to be like, "No, that's, that's wrong."
Nathan Thompson: Well, time will tell. In the meantime, on more optimistic notes before I get depressed and change this coffee for something else to [00:38:00] deal with my sadness, uh, you taught digital marketing at General Assembly for four years, including a 10-week boot camp, and I would love to know what you taught in 2019 that you now think needs to be changed, and is there anything from that curriculum you think that survives everything, including AI?
Tyler Jacobson: Um, you'll be surprised to hear that persona and empathy maps and talking to your customer, that, that survives. Um, it-- Yeah. Yeah. Go
Nathan Thompson: Yeah, the foundations
Tyler Jacobson: marketing is, marketing is so, uh... It, it has to be, it has to be centered around that end person or it's just not gonna work.
It's just not. Um, things that, that I couldn't teach now, um, Google Analytics has changed dramatically. It is such a different beast now. Um, and, uh, there's some other, you know, there's some other technologies in there that, that we've just moved past. Um, or they still [00:39:00] exist, but they exist in a different form.
So, um, it just wouldn't look the same. Like A/B testing. I-- A/B testing used to be free through Google, um, with Google Optimize, and now y- you know, it's gonna cost a business at least a few hundred dollars to do, you know, functional, uh, multivariate testing. So can't-- It's hard to get, you know, it would be hard to get a classroom of, um, marketing newbies to be able to use those tools because, yeah.
Nathan Thompson: Plus money. Pay to play. Yeah. And that is frustrating on your own website that it would have to be pay to play. And everything, I guess the more the value of something goes up, the mo- the more dollar amounts you realize it generates, the more it is gonna come with a price tag. But back to that institutional knowledge, how do you teach a new generation of structured A/B testing how big the audience needs to be, how to read things, you know, not changing too much on a page without letting them play?
Tyler Jacobson: Yeah.
Nathan Thompson: Uh
Tyler Jacobson: thing, another [00:40:00] thing that, um, would probably be very different there too is, uh, organic social, um, and how you structure that and your expectations around that. Yeah.
Nathan Thompson: Yeah, I, um, one thing that I've liked about talking about you and, and looking through your professional history, and even now the fact that you hold three roles at once, and like you brought up organic social, Google Analytics, we talked a little about SEO. It's so varied in terms of the fields where a lot of people are only good at one, and then they just can't even think of the others.
And I was wondering if you thought that the shape of, uh, a senior marketing career is gonna more-- look more like a portfolio rather than a chair, especially someone who's now currently at three roles, right? It's VP of marketing at 4B, marketing directory at the Cannabis Agency, and then a board advisor at Splinge.
Um, you have all these different backgrounds. Do you think that the future of marketers-- Should marketers start thinking about this in terms of, "I need to build a portfolio of experience in different areas," or, "I [00:41:00] need to just stick with this one thing and move forward"?
Tyler Jacobson: move forward?" "I think specialists will always beat generalists, and I say that as a generalist."
Um, so i-i, I think, i-i, you know, the numbers, the numbers out there prove it, that you, you know, you have to know what you're doing, and you have to know what you're, who you're doing it for.
And the more f- the more laser-focused you are on that, the, the more likely it is that you're going to remain in that industry and in that role. Um, so I, uh, I mean, B2C, I can definitely see portfolio as being a really important piece there. Um, B2B, it's gonna be more around case studies, I think, and, and just showing, you know, industry expertise.
Nathan Thompson: Yeah. Getting all those logos, it's always frustrating when I see all I, I, uh, wow. I, I digress. Sorry. Okay. Last question here, and again, I, I've taken you for longer than we agreed to, so I really do appreciate it. [00:42:00] Um, but 25 years across startups, billion-dollar brands, retail subscription, and a nightclub, is there, uh, any type of marketing problem that you've watched each one of those environments fail at in the same way?
Or do they all have their different failure models that you had to figure out?
Tyler Jacobson: Um, it's not-- There's not gonna be an-- There's not gonna be a universal one because some of these companies have more resources than another. But one problem that I see pretty consistently is companies who are using marketing as a Hail Mary. They never invested in it ear- you know, when they should've been investing in it.
Now the company is on decline and they're like: "Well, we gotta do something," and they're looking for marketing to save their ass. And it's-- I, I, I, I run my own agency. I have-- I feel for people in that situation. Being a, being a business owner is stressful, extremely stressful. Um, so I feel for them, but that's not the time [00:43:00] to turn on marketing, and so many businesses do it, and it's just, it, it, it's, it, it, it's just bad news 'cause there's-- We're not gonna be able-- Uh, uh, there's not a magic bullet here that is going to change that traject- trajectory.
In marketing, there's not a mag- magic bullet. It comes from, you know, grains of sand that make the mountain, and you're gonna have some big wins in there if, you know, the more you have in, the more y- I mean, the more you have in the mix, the more opportunity you have for luck to favor you, um, and for an audience to know you and trust you.
But yeah, you're not gonna be able to say: "Let's, let's do, uh, let's do SEO," and then your company's going to suddenly rebound and everybody's gonna be millionaires.
Nathan Thompson: I always love that, the idea of like, "Let's do SEO," and then 10 days in, "Why are we not, uh, ranking over all these competitors that have been doing it for 10 years? How is this-- Is it a bad writer? Is it-- What, is our strategy wrong?" It's, it's a slow-played game, [00:44:00] unfortunately. And you're right, the time to switch on that switch is not w- when it's, uh, when it's going under
Tyler Jacobson: Well, I mean, uh, and, and to that point, I think that you can deliver good news when it's an SEO campaign, which is this is a marathon and we're taking steps, right? We're moving towards that. Where I find it to be e-e-extremely, um... I, I w- I wish this mentality would just die, frankly, is we need to win on social media.
And the truth of it is you don't need to win on social media. I mean, social media is not, uh, is not typically a driver for business unless you're selling, you know, inexpensive B2C things. Um, but no, you don't need to blow up on social media. It's-- it-- that's not, that's not the path to making a lot of money
Nathan Thompson: I should cancel my TikTok account. My dances have done nothing for me. I, uh, just realizing that now. I'm kidding. I don't have a TikTok. Um, okay.. And where can people, uh, reach you if they would like to get in touch with you?
Tyler Jacobson: Yeah. [00:45:00] So, uh, my website is tylerdjacobson.com. Um, and then also you can find me at 4bmarketing.com. And then on LinkedIn, where I'm gonna post a bunch of AI slop
Nathan Thompson: favorite platform, I was gonna say. I was like, "Oh, is he gonna bring up LinkedIn?" 'Cause he loves it so much
Tyler Jacobson: Well, it's, it's got, it's got its, it's got its positives, but at the end of the day, like, I, it-- let's bring work to social fun. No, that's Let's make a s- let's make a social platform where people can check out and think about work. I, I'm still convinced- Oh, love that. I'm still convinced that LinkedIn is a s- is the place-- It's, it's just inhabited by salespeople and people looking for jobs.
Yes. Like, if you got rid of those, like, if you got rid of those people, you'd have, like, 10% of the audience there left.
Nathan Thompson: Build a platform where I can go to check out and think about work. That is ex- that should be LinkedIn's new tagline because that is spot on what it is. Oh [00:46:00] my
Tyler Jacobson: come on Microsoft.
Nathan Thompson: Oh, I'm crying here. Uh, all right, Tyler, thank you so much for joining me. Really, I really appreciate it.
Tyler Jacobson: Thank you, Nathan. This has been great.
Nathan Thompson: Thanks. All right. Bye.
Tyler Jacobson: Bye. Bye.