Modern Marketing with Jim MacLeod! ⭐

Like so many sectors, the rise of AI, social media, and personalization has changed what it means to have effective marketing. It's also changed what it means to be a marketer, a practitioner of the art of marketing. To unpack these heavy topics, I talked to one of the best in the industry, Jim MacLeod. It's going to be a hoot, so let's get started. Jim, it is great to chat with you. Before we go too far into our conversation, can you please introduce yourself?

Yeah, thanks for having me. My name is Jim MacLeod. I have been professionally working in some sort of marketing capacity in one way or another for about 23 years now. I started as a graphic designer working for a book publisher, but then quickly began working within the marketing department to develop new products, and from there I kind of kept focused on graphic design. Then I got into what was at the time called web design, which we now call UI or UX, and then that led to web development, and then that led to digital marketing, and then that led to social media and it just kind of keeps growing and growing.

So now it's all kind of digital experience and design and brand all kind of mixed together.

So you mentioned that you started out as a graphic designer, and at some point you were like, ‘I really enjoy graphic design.’ When did that happen? What got you thinking about graphic design as a potential career path?

It's actually kind of an interesting almost mistake. So I originally wanted to be a comic book illustrator, That was my original goal was to be a comic-book illustrator and one of my favorite artists at the time was a guy named Todd McFarlane and I knew he had studied graphic design in college and I liked how he and a couple other artists really had some graphic elements in their illustrations. So I thought, okay, I'll study graphic design and originally I just studied it as a fallback in case illustration didn't work out. And two things happened, which was- this was the mid to late 90s, so the comic book industry fell apart.

Marvel was in bankruptcy- if you can even imagine that now, considering what Marvel is- but at the time they were failing and I really fell in love with graphic design because it really appealed to the meticulous nature of how I like to do my work. It's so much easier to hit undo on something than to have to like erase and redraw something. So it kind of worked out in both ways, where I really got interested in graphic design at the same time that the industry I wanted to go into was falling apart.

You mentioned that you were using digital tools essentially from the very beginning. What was the first tool that you used?

The first design tool I used was Photoshop, and it might have been Photoshop 3. I know we were excited when they introduced layers. This was 1995 or '96, when I started using that and then I learned QuarkXPress and I kind of cheated my way through Illustrator. I didn't really cheat, but I didn't do all the work I was supposed to do, which is funny because at the second company I worked for, I used Adobe Illustrator for everything and ever since then it has still been my favorite program to work in.

Did you ever doodle or sketch before you got into Photoshop, or was Photoshop mostly the inspiration, in terms of how easy it was to create content, that really sparked it for you?

Well, one thing I used to say in my early interviews was: I'm looking for a way to design, to kind of mix my ability to draw- like I can do some rough sketches- with computer technology. That was my line when I was starting out because I had a really weak portfolio. But, now, even still, I do a bunch of sketching.

I mostly use the iPad now and that was something that I was doing a lot of at my most recent company and I've just started doing more illustration on my LinkedIn posts because I realized that, okay, like I'm posting on LinkedIn a lot more and I'd find some sort of image and stuff and I'm like: wait, people have paid me for years to do sketches for them. Whether it's a book cover, whether it's a diagram to raise money, whether it's a newsletter header, people tend to like my sketches.

I'm like, why am I trying to find stock photography that everyone else is drawing from, when I can actually just create my own illustrations in a style that people tend to like?

Yeah, I noticed in one of your latest newsletter posts that you talked about switching the visuals from stock photography to your own. How much does that add to the time it takes to create your content? It's one thing to go to Unsplash or a stock-photography site, find something, add it, modify it, and tweak it, versus coming up with your own sketches. Do you have a portfolio of sketches in the background that you pull from, or do you create something custom for each piece of content?

I create them custom. I've only done that twice. I have a third diagram, so I'll get to that in a second, but I've got a third one also that I haven't put in. Yesterday's was based on the show Succession, because the most recent episode tied into a story that I had lived through, when I was working for a company that was going through layoffs, and so all I did was I found a photo and I kind of drew on top of the photo and added some effects to it, but that was six or seven minutes to create that illustration, because it's something that I do for fun already.

So just drawing on the iPad is fun for me.

Yeah, I think that's the part I was curious about. You generally enjoy sketching, so this is a way of combining something you already enjoy with another thing you enjoy, which is creating content. Combining those two things makes a lot of sense.

Yeah, it's one of those things where I'm like I can't believe it took me this long to realize. I'm like: wait, this is what people like. Why am I not providing that? And it's something that I like to do. I would much rather draw than sift through stock photography. It sucks. Looking through stock photography is painful, especially if you have something specific in your mind. Now, one of the things that I've tried dabbling with a little bit, but I haven't gotten too deep into, is using some of these AI programs for, generating images.

And so, like I keep asking, like, okay, I want two people standing back to back, shoulder to shoulder, and so on. I have the picture in my head and I'm trying to tell whatever system I'm using to generate that image. But one of the things I've started thinking about about, and actually what led me to this realization, was what if I did a sketch first, uploaded the sketch and said: do it based on this general layout? Then that's when I was like, well, wait, why am I doing this?

Why am I using Midjourney or something else, when I can just take my original sketch and use that as my image, because nobody else can create that.

Yeah, I was about to ask about AI tools, because that's a big area these days. You can either have AI generate approximately the content you're looking for, or, if you already have the skills to create a basic sketch, use that as the basis for what you end up creating. We should touch on that a little later, because there's a lot to unpack in that whole world of AI tools. Getting back to how you got started: you were working in graphic design. What was the transition from graphic design to marketing like? At least today, they are two different career tracks at any company you go to.

They definitely are. And one of the things, last year I co-wrote an article for ZDNet with my old boss, a guy named Bala Afshar, and it was about the road to CMO. What we did was we found: okay, here are 10 or 20 of the top marketers, I think it was 20 that are out there, and where did they get their start? Most of them didn't just take the traditional route, like, okay, I went to school for marketing and I started as marketing specialist and worked up to CMO. A lot of them had, really unique career paths, including the CMO for Salesforce.

I think she started as a chemical engineer, which is a pretty long journey. But to get back to your question, my journey was I realized that a lot of companies don't really value graphic design. It's something that's kind of a nice to have. It's often added on after the fact. So what I did is I started to extrapolate out my career and think: okay, where am I going to be when I'm 50? When I'm 60, what's my salary range going to be? And then the scary part was okay.

If I'm 55 years old, making X number of dollars, why wouldn't the company hire somebody that's 25 years old, that makes half as much but can provide 80 percent of what I provide? And when companies are going to do that, every day of the week. So I realized, okay, my career, on the trajectory that it was on, is going to end before I'm ready for it to end, because- and we're seeing that now with AI- like a lot of careers are coming to an end pretty soon.

So, okay, I wanted to kind of almost future proof my career and start to move to the side and take another avenue and- and I was fortunate because at the time I was working with all these great, amazing marketers and I was like, okay, I need to learn as much as possible from them. I just started consuming everything- books and courses and everything. I went back, I got my master's degree in marketing, and to this day that's really where I find a lot of interest.

Somebody recently described me as a marketer who happens to be good at design, which is great, and I'd much rather be that than a designer who also kind of knows marketing, because, like I said, there's a ceiling to a designer, which is usually creative director, and that's about it. How many companies have a chief creative officer or VP of design? It's very few.

Yeah, and even in companies where they have that official role, at least from my observation, the influence they have is often not very large. Every company has a primary driving force. It could be the engineering team, the sales team, and so on, and there's always a stack ranking of where each discipline falls. It's often difficult to find design and marketing being a core part of the decision-making structure, so that's spot on.

Yeah, and it's tricky. Anybody in marketing knows that everybody else outside of marketing is the best marketer in the world and their ideas are better. Because marketing is one of those things that everyone thinks that they understand it and can do it. We'll multiply that by 10 when it comes to design, because everyone's got an opinion on design and the problem is, if you're paid enough at a certain level, your opinion then becomes fact. No matter how much somebody might have expertise, their opinion matters more than somebody's expertise if they have a better title and get paid more at the end of the day.

So that's where it can be frustrating. As a designer, like most designers you meet have at least a little bit of a chip on their shoulder because they've spent their whole career being told what to do by people that don't have their level of expertise.

Exactly. Another example I often run into is that you might have a great idea or a talented in-house team, but then you hire a name-brand agency from elsewhere. By default, what they say becomes, ‘Oh, they said it, so it must be good,’ even though it might be exactly the same as what your own team came up with a short while ago. The optics are always tricky. How do we rationalize that? It doesn't scale, because budgets for external companies are very high, but you also spend money hiring talented people. How do you reconcile this rift? In other disciplines, like engineering, it's often very clear-cut, yes versus no.

When it comes to emotion, there's a wide range, and it's hard to pinpoint the right answer. So much of it is in the presentation and how you prepare the messaging, as opposed to the message itself. It's like art.

Yeah, and this was something that I really tried to drive home with the last group of designers that I managed. I managed three different teams of designers at my last company. You need to be able to show the value to why you made the decisions that you made, because it's really easy to be like: oh well, I think this works better in a blue button with rounded corners works better with this design. That doesn't matter. Like personal opinions don't matter when you're talking to people that have a higher level of authority than you.

But if you can say: okay, studies show that if we use a magenta button here, our click-through rate is going to go up 12 percent, then that's what helps. Because I found that once you start talking about the science behind design, then people will listen more often, and I've gotten into battles with people about this. They're like, I don't like this, there's too much white space and so on. Then what I do is I explain the science behind why a particular paragraph can only be so wide on a page. I had this discussion one time where somebody they didn't like all the white space on the page.

It was basically like less than a third of the page was white and then the text took up the other two thirds and they said no, the text should go the full length. And the question I asked was: when was the last time you read a book that was eight and a half by eleven? You don't, because books are smaller, and I talked about the science behind it: your eyes, get tired if they have to carriage return further over. It's harder to find where it is.

You're not supposed to have more than 12 words across in the line like kind of all the science behind why that design was made the way it was. It's not just because I liked it, there's knowledge that I was given to make those decisions.

Yep. One of the things you often talk about is how important it is for people in marketing and design to understand mathematics and science and to be able to rationalize some of these things. I think it's partly to provide an extra layer of validation. Yes, this is the right design because it looks good and it's aesthetically pleasing, but in a business the goal is often more tangible metrics. Will it lead to greater conversions? Will it cause more sales? Will people spend more time on my content because of these changes? Being able to tie those decisions to those kinds of metrics is often critical.

What do you do in situations where the data isn't there or is incomplete?

And that's when it can become a tug of war a little bit. But you can refer back to other campaigns that might have worked well in the past and be able to draw certain lines to say, okay, we saw this thing in the past that worked or didn't work, and we can infer from that- because we don't necessarily know, okay, this new campaign that we don't know how it's performing, it has these attributes. Like we, usually you put certain attributes into a campaign that's based on stuff that's worked in the past to say that like, okay, there should be some success.

Even if there isn't a clear-cut result, even if there isn't a clear-cut result: 30 people downloaded this white paper. 15 Of them became customers. Because there's always, it's a lot more. Marketing is a lot more complex than just that. It'd be easy if it were, though.

Do you conduct A/B testing sometimes, or is it too complicated to use at scale?

When possible, I try to do A/B testing. More often than not, it's something I haven't had enough time to do in my career, but one of the things I try to do because I like digging into the analytics of things, like there are times where I'll spend, six hours in Excel spreadsheets, just pulling data in and sorting and cutting data to try to see, okay, what's performing, what patterns am I seeing across all these different campaigns or posts or whatever it is, so that we can see what's working and what's not working. Sorry, I fell off track.

To get back to your question about testing and how frequently we test, what I try to do is: okay, like I look at the data, like three days later after a campaign launches, for example, and say, okay, is this working, yes or no, if we don't have time to do full A/B testing, because it's a lot of work to come up with two completely different campaigns- look at the data and see, okay, is this working, is this not working, and then try to assume, like I said, based on previous campaigns. Are there assumptions we can make to try to optimize this so that it might work a little bit better.

And then, just keep measuring and adjusting, but you have to give it some time, in order to have a big enough sample size, in order to be able to see what's working and what's not.

Do you think it's valuable for marketing and design teams to have data scientists and UX researchers on staff, especially these days? In digital marketing, you're going to a large audience, and the variations can be very large.

Absolutely. When I was leaving EBSCO Information Services back in the fall, we were just starting to hire a data scientist because there was all this work being done. But the problem is, you've got marketing managers, product marketing people, campaign managers, whoever they might be, doing all this work. Generating the content, generating the campaigns. It's better if an actual expert who really knows what they're talking about can go in and analyze what's going on, because if you have a product marketer that needs to go in and spend a day cutting through data, well that's a day that they're not thinking of the next campaign.

We're thinking of ways to shift the current campaign. So I'm a big fan of specializing your team once you get to a certain size. Specializing your team so that you can have the right people working on the right things and you don't have just a whole bunch of jacks of all trades, masters of none working for you or it's kind of like, well, I do a little of this and a little of this and a little of this and a little of this and I'm barely above average on all those things. It would be great to have a whole bunch of great people doing what they should be doing.

No, that makes a lot of sense. But what I often see in trade journals and business papers is that when the economy is doing great, everything is fine. When things get tough, marketing and typical outreach efforts are often among the first places companies try to trim. Those efforts are critical to reaching customers but often aren't seen as core enough. How do you counter that trend?

Well, it depends. One of the things that's important to know when that happens is: what is your sales cycle like? Because most of those cuts are short-term thinking, right, like they just need to make the next quarter's numbers. But the problem is, if you cut back on marketing now and you have an 18-month sales cycle, you're not going to feel that pain for a while, so it's okay. Things slowly start to go down. It's not as if you stop marketing and everything stops immediately. It's always a slow burn going down if you're in B2B and you have a long sales cycle, or even like a medium like sales cycle.

So what you try to do is show: okay, This is where metrics really come in handy. It's like: all right, what's our pipeline influence? What's our closed-won influence? If you have those numbers that can help, Stave off the cutting machine. And it also helps you determine what you should do more of and what you should do less of. I worked with somebody a few years ago who knew marketing technology perfectly and she knew which dials to turn when you wanted to raise certain things or lower certain things, A skill like that is really important to have.

So, instead of like, okay, let's cut people or, cutting headcount or program dollars, okay, what if we reallocated from here to here and did this instead? And let's not do like this trade show next month, because that's only going to get us, 40 leads and 20 of them are going to be junk. But what if we actually, change that over to, some sort of ad spend or some other type of outreach?

I think that's where it's important when people come to start cutting budgets, they're like, all right, let's reallocate to something we know is going to work, if we really need the bump right now, and then we can try to revert to normal afterwards.

Yeah, that sounds very reasonable. I want to take a few steps back. We talked earlier about data-driven decision making and so on. The tension I often see is that the conventional wisdom is that when you do data-driven decision making for marketing or creative ideas, you don't get the next big thing. You just get iterative, minor improvements over something.

But if you have something really big that you want to do, the data will never be able to back that up, which often results in either designers being frustrated or the marketing agencies being frustrated and then leaving to do their own thing where they get to try their ideas out and experiment with it and then those ideas becoming the norm. My view always is like what if we took a bet on them early, before they had to leave and do all these things? What is your thought process on that?

Yeah, I think it needs to be a healthy balance of those things. You need to be able to take chances to try to get ahead of the crowd, because as soon as one thing works, it's a follower world- everyone starts heading in that direction. Like we saw it a couple years ago with podcasts, where everyone's like we need to do a podcast, and everyone put out four episodes and then a month would go by, they put out a fifth episode and then, four months would go by, they put out a sixth episode and that's it.

So they were taking chances because they're like, oh, this is the next big thing, but they didn't really have, kind of the wood behind the arrow, if you will. Because they're willing to take a chance, but, it wasn't the right move to take at the time. Yeah, so, but being data driven- sorry, I'll get back to a point in a second- being data-driven, I think is important because that will help, make sure that you're still at least doing something that works.

But you need to be able to take chances also, because otherwise, yeah, it's just going to be exactly what you did last quarter with like doing the same work and getting the same results every quarter. To me that sounds really boring. Like yeah, it might be safe, but you need to challenge people, like people want to do exciting stuff and challenging things, but obviously we still need to keep the lights on and we need to do what works on top of it.

So one of the things that I've often tried to do is like: okay, if you want to take on something new or if we want to try something different, that becomes like a plus one project. Where it's like: okay, in addition to all your regular work, you're also going to try this thing, and then: if it works, great, we'll figure out how to reallocate your workload. But if it doesn't work, it's not like we stopped doing something that is working.

I was about to ask exactly this: how do you balance someone's personal career ambitions within the confines of the organization they're ultimately in? You answered that nicely in terms of experimentation. We'll do an experiment and see if it works. I see that in engineering quite frequently. Do you see it often in your industry as well, where the plus-one stretch idea you give to someone sees the light of day in a small, targeted approach to find out whether it gains traction?

Yes, and sometimes it works, sometimes it doesn't, and sometimes you'll see somebody bite off more than they can chew, like the podcast example I just gave. Or we've seen it many times where people will try to be like, oh, I want to do this thing, but I need to drop all these other things. Well, you still need to do your job, your regular job too, because we've got numbers. We need to hit this quarter, right? So it's trying to find the balance of: okay, how do you grow in your own career? And still do the work that's required of you.

And I know like when I was learning web development, it was like, okay, I'm going to spend my nights and weekends learning this stuff so that I can go to work or get my next job where I can do these things. Like, I first picked up WordPress on Fourth of July weekend, 2007. And it was just basically like, okay, like I said, this weekend, I'm going to teach myself WordPress. I didn't teach myself all WordPress, but I taught myself the basics of it- and it was like, okay, now that's a skill that I can bring to work.

I was working for an agency at the time and this is now something else that we can offer in addition to the other things that we have. I was willing to take that time because I didn't have the time to spend. I couldn't spend three or four full days of a work week learning this one thing, because it was a small agency but, in larger businesses, hopefully, they do have education budgets and, more importantly than that, time to actually do that education, because you need to let people grow.

There's that old saying that was going around a few years ago, which is: what if we train these people and they leave? And then the counter is, what if we don't train them and they stay? Too often, people are just kind of complacent in their jobs, they're not growing, they're not challenging themselves, they're just punching a clock, which is great, and some people do that and they're great at that. But you want those people that are willing to take chances and try new things and constantly be learning, so that you can let them thrive and bring something new to the table that you didn't even think was possible.

That brings me to the next point. A lot of things have changed in marketing, just as they have in technology. WordPress is still extremely popular today. If you group all the technologies out there, I think WordPress probably accounts for 25 or 30 percent of the entire web's traffic, so it's still a dominant player. What are some of the biggest changes you've seen in marketing during your career?

You know what? I was having this conversation yesterday in one of the groups I'm a part of, which is okay. How has social media changed, for example? Because when I really started to focus on this stuff, social media wasn't really a thing. I remember sitting in client meetings pitching a blog and having to explain to them that it's not some 12-year-old girl's online diary, like it's something that'll actually help, and that Google SEO loves WordPress and telling this to companies because they're like, what blog? No, we're not going to do anything like that. Or being in a meeting and having social media categorized under new or alternative marketing.

I think it was called at one point and I'm like, well, I'm like, no, what's alternative marketing? It's like putting ads in the newspaper. That's alternative marketing because nobody does that anymore. Like This is where we're going. So social media obviously has changed but now we're seeing a whole new generation of it, which is kind of the bifurcation of all these social media networks and we're getting more into the community aspect of things, because communities are really where you can get real value out of these things, because people will listen to people more than they'll listen to any company.

It's like word of mouth is the best marketing that there is. It's way better than any marketing you could ever create. And so a community is a great place for this, and I'm a part of a few communities that are. They are sponsored by companies, but there's nothing about the company in the community, and I think those are great because I'm meeting lots of other marketers and leaders in these different industries.

But what's also happening in the background is it's creating brand affinity, for when I do need a product that this company offers, they're going to be top of the list because, well, I already know a bunch of people that work for the company and a lot of other people in the group will vouch for them, because a lot of them were customers beforehand.

Yeah, which often echoes the common saying that communities are about people and not about brand logos, and we see that in a developer space with developer relations. Oftentimes I look at them as an extension of effective marketing, because these are people who resonate with the target customer in a very nice way and they happen to also work for a company, so they have, like this nice connection between- I'm going to speak in a language that I understand, I'm going to talk about things that they're familiar with and care about, but it's also going to be done with the background of knowing that this is something that my company also provides.

If you ever need to use a solution, it works really well and I think every industry has that. I was reading a document recently around this. I love reading earnings reports from various companies, one of the things that I always enjoy- I was actually reading about how aviation companies have now started going into the more the personalized route where, yes, they can always sell to the big organizations and the big buyers, like all the larger airlines around the world.

But it's also about how do you sell to individuals who might be interested in it, or like communities of people, like universities, might want to have like something to make travel between, like their, sports teams more efficient and so on on, how they have people who are both aviation fans but also have a strong connection with either athletics or with some business or with some group that they are also actively a part in, and tying those worlds together has been a very effective way for them to increase their business.

I remember thinking that is actually very interesting because it's not traditional marketing anymore, it's not as someone who just comes in, has a nice dinner with you and then you like have a conversation. These are people who are in the weeds with you at the games and at the sales conferences that you're also participating in, and they also happen to also sell airplanes on the side, and the connection has been really nicely tied together.

I worked for an IT networking company, like a Wi-Fi company, and originally the target audience was CIOs, but then what we found was, well, it's not the CIOs that are doing research on products like ours, it's the lower-level people. So we need to speak to them and get them enthusiastic and, most importantly, help them sell it up the chain, and so it's basically okay. How can we empower them? How do we make them the heroes in their company? And potentially, something that works well in any industry or any type of marketing is how do we make them a hero outside of their company.

Raise their profile across the industry and that helps. That helps get the vendor in and it builds brand affinity even before they're a customer.

Yep. You've touched on this in several pieces of content over the years, especially the differences between dealing with B2B and B2C companies. In the case you mentioned, the person making the decision is very different from the ultimate user of the product, whereas in the B2C space you're marketing to the person who will actually use it. Can you talk more about some of the big things you've learned from the distance between those two worlds?

Yeah, it's interesting being in B2B because in some ways you almost have to market to the end user to have them ask. Like you see this with any average like drug advertisement that you see on TV. It's always like here are all these benefits and then they talk about the million ways you can die. But it always ends with, ask your doctor about whatever it is, because the average person can't buy this. They have to get it from the doctor. But in a way it's kind of an end around around. You go to your customer's customer, which is a difficult way to do it.

Especially in B2B, in some situations your end users don't actually know what your product is because a lot of times it's white-labeled. So, for example, when I was working for EBSCO, it's amazing how many people have used EBSCO products and didn't know who EBSCO is or what they offer or anything like that, because it's always white-labeled and repackaged as a university's online library system. Same with you, know, working for a Wi-Fi company, same deal. Nobody cares who's providing the Wi-Fi, they just want good Wi-Fi. And so you almost have to think about, whether there is a way to figure out what the customer satisfaction is?

Sorry, not the customer, the user's satisfaction is and somehow find a way to present it to the prospect to say, Hey, if you have this particular Wi-Fi, it can help you in these ways, because people will want to stay at a hotel that has this type of Wi-Fi and that might be something that you can promote. Same with online schools. It would be great to say: oh well, people who subscribe to these databases have a higher graduation rate than people or institutions that don't have that. Like that's an easy way to sell a product by saying your end users want this.

You have another case, especially with enterprise software, where the end user just doesn't want the product. Why are so many data-entry products that people use, whether it's a point-of-sale terminal in a cashier area or something people use to enter inventory data, so horrible or poorly done? It's almost as if the marketing is designed for the decision-makers, the CIOs or CTOs, rather than the users. For example, you have compliance. It works well in Europe because GDPR is now implemented. You and I probably don't care that it's implemented. We have a cookie banner now, and we hit dismiss every now and then.

On the flip side, I often see cases where getting in the door for the B2B stories you mentioned is extremely difficult in the first place. I apologize, he's decided to go for a visit right now despite the door being closed. You also have to figure out how to balance appealing to, in the earlier example, a doctor, who in this case would be the CTO or CMO, while having the end user realize the benefits. In many cases, the end users have no say in what ultimately happens. How do you justify marketing something when the end user is disconnected from the person who ultimately makes the call?

Yeah, that's a tricky one, because if you manage to sell a product to somebody that's not using it and then their end users or their customers don't like it, you're not going to get the renewal. That just leads to a bad taste in everybody's mouth. So I think a good way to handle something like that is to make sure that the people you're selling to know what their end users are looking for. Have they surveyed their end users to see, okay, we want A, B, and C from a product like this. And then figure out: okay, do we offer that?

And of course, any salesperson's gonna say yes, whether they do or not, but how do you make sure that what you're selling is actually what you're selling? That's where, like customer success stories or case studies, really come in helpful, because it's like: okay, well, they saw this sort of uptick when they purchasedd this product.

Yeah. One of the other big changes I've seen over the years is personalization. Google was a big part of that with AdWords and making ads contextual. If you're interested in A, B, and C, you'll see ads related to A, B, and C. That was often limited to text-based ads. Over the years, I started seeing sports stadiums with different types of screens. You wonder why there's a giant green screen all the way across the stadium. It's not for the people in the audience. When the event is streamed, they replace the green screen with contextual ads based on the data your TV or connected media player has collected about you.

How much has that influenced how you think about marketing these days?

It influences it a bit, but the reality is, whatever we're doing today is going to be totally different than what happens six months from now. And I know, Google and all these other ad networks have been using AI to really hone in on these things, but it's gonna go through the roof pretty soon. I'm really fascinated to see where advertising goes and how personalized it can get with AI and how hyper targeted it can get. Eventually, it's going to be completely tailored towards me.

If I'm watching a baseball game, for example, the ad that's on the TV is whatever ad Fox, ESPN or MLB or whoever, that's the ad that everyone's seeing.

But as time goes on, I think it will get more customized, more personalized in that way and it's going to be amazing to do that, and I've heard some people joke like we're eventually going to see content that is produced that is just made for individuals, because they're going to be able to swap story pieces in and out, so that it just becomes completely tailored to this person, like this is the greatest show I've ever seen because it's got all my favorite actors, all my favorite music and it's got the type of humor that I like or the type of story that I like, and it's there.

We're definitely a ways off on that sort of thing, but I can imagine it's coming at some point.

This goes into the AI world that we touched on briefly earlier, where, with just a few prompts in English words, I can get visuals that are tailored to whatever needs to be done for what I entered. We're also seeing a lot of text-to-video outputs now, where you can type in some text and you get videos out of it. You get audio as well. A lot of audio programs are doing all these various things. A few years ago- I don't know if you remember this, but Salesforce previewed something called Einstein Designer, where you enter some ideas on, like here's some layouts for a website.

It'll generate many versions of it and you can pick and choose, like these are the five versions I want to A/B test, essentially- and then deploy it and have people give feedback on what was done. And that was seen as like a completely new way of doing things, because we talked about earlier, it simplified the technical complexity of both generating the multiple variations- because it requires dedicated teams traditionally to create each variation and give it the right level of polish and expectation of it being the final output- and then also how the technology to make it all work.

And now it was, one click away from being able to have like very customized shopping pages and things. They're very sensitive to minute changes in layout and colors and things. That's like an experiment in real time on this with AI. One of the things I can totally foresee is that every time I go to like Instagram Reels or TikTok and I see a video, for example, and half the time like this video is very on point- you see a little sponsor text at the bottom, like this is very relevant. Based on my interest, this video is very relevant and it's clearly sponsored because the sponsored label is there.

At least I, of course, I can tell it was done by a real human being, a real creative team and so on. Do you ever foresee a world where all these things- just like how AdWords is able to give you text and links programmatically based on your interests- actual, rich, interactive content will also come out purely from this AI, where you can't tell between reality and what is really just a virtual version of something trying to sell you things.

Yeah, it's absolutely coming. There were a couple years where I wasn't really dealing with AdWords at all. Then when I picked it back up all of a sudden I was like, oh well, I just have to upload pieces of the ad. I don't even need finished ads anymore, I just upload the elements and then Google puts it together and optimizes it so that it's going to work in whatever way works best, so it gets the most clicks and downloads or whatever else. I was like, oh, okay.

That was not the beginning, but that was early days of yeah, you just upload a couple ingredients and then it makes the cake for you and you sit back and watch the results.

Yep. I think it's like the Content-Aware Fill feature in Photoshop, or one of those things. I always forget the name. It might be Smart Erase or Smart Fill. If you had a power line in your photo, you could tell it to get rid of it. It would intelligently interpolate between the surroundings and put the right visuals there. That was mind-blowing five or six years ago. Now we're seeing it go to a completely different level, where you don't actually have to be in a location. It can make it look like you positioned yourself in that area and make it look really nice.

Yeah, what's been going on over the last six months is absolutely incredible with AI. We all know AI was baked into a lot of products beforehand, but now it's basically like: come to the people and it's come down the mountain to the people and, yeah, seeing what we've seen in the last six months is insane. I have no idea where we're going to be six months from now. If you just think about the rate of change over the last six months, six months from now, we're not even going to recognize the world.

Exactly. The example I like to use is like you're trying to fill up a dam with water and so right now, the water is flowing really quickly. Most of the time, by the time we realize the water is flowing very quickly, the water hits the end of the wall and it's just totally just like rising very slowly. We're like six months in and we still haven't found the wall. Yet the water is still going as fast as it can and so no one really knows where the actual wall even is.

At this point it's like, while there may be a wall somewhere, that doesn't really matter, because the end result of it is so compelling. In all these areas. You create content, I create content, and for me, the thing about AI that often comes up is that in some ways, it's almost an existential threat, at least for me, specifically because I create technical content, I create long-form articles and videos and that might find its way into books. I've been using, like all both Bard and ChatGPT for the past few months, and the quality of what it can create.

When I tell it, ‘Write me a detailed article on topic A, B, and C,’ it's very good. Sometimes I ask it to write in my style and put in my name- there's enough content indexed under my name. I mean, I'm like this is exactly how I would have written it, with the random jokes and stuff thrown in there. It's missing the visuals, missing the images. That's a moment in time thing, because before it didn't do the code snippets, now it's doing code snippets. I'm like, okay, it's only a matter of time before it realizes I'm going to combine Stable Diffusion or Midjourney, and create visuals as a part of it.

And then I see externally all this data from, like other marketing orgs that talks about a team that trained ChatGPT. This team over here trained ChatGPT to build 700 pages a day programmatically and publish it using the top SEO data that they've analyzed from all these areas, and so over a period of six months they went from zero page views to almost a billion page views purely from this programmatically generated content where no human being was involved, a pure pipeline of the top keywords that we want to target, create the content, publish it and then just let us know what their metrics are.

And there's often talk about like: will search engines end up, like banning auto generated content or not? My thing is that? How will you tell at some point? Once it gets really good, it's gonna be hard to tell the difference between what is auto-generated and not generated, where I feel like this world might make a lot of what I'm doing very much, irrelevant- which goes into the topics you've been talking about recently: how do you manage your own personal brand, your own identity, in a world where AI is commoditizing so much of what you might have thought were very unique capabilities that were not easily replicable?

Right, yeah. The last month or two I've realized I'm like, man, I am glad that I made the switch from design to marketing because design is being commoditized and it's so easy to just create your own designs. When I first heard about this I kind of fought it. I'm like I'm not going to use that, like I'm not going to empower this thing. Then I realize I'm like that's fighting gravity, you're like you will not win. So I started using it and I had a shift in perspective: this is this is, in a lot of ways, no different than when Photoshop came out.

When I first started studying graphic design, we were still setting type and letters by hand, like we weren't allowed to use, like the computers were like tiny little things, like nine-inch screens or something in some other side room. So we were doing graphic design by hand to start, which worked for me because I came from an illustration background. I bet a lot of graphic designers up until the mid 90s fought against the computers, the machines taking over. But now you wouldn't even think of laying out a magazine or a newspaper or something like that, without using InDesign, right?

So like it's just the way that it is and I think with AI it's the exact same thing. It's just another tool, but the good thing is skilled people will be able to use it better than non-skilled people. Like I'm going to be able to figure out what that prompt is to get that exact image faster than you might because I know exactly. I have the picture in my head that I'm looking for on a screen and somebody else might have. Well, I kind of want to be like this and like that, and it's.

I can better describe in theory, I can better describe what my prompt is than somebody that hasn't spent decades working in design and creating that image that looks up at a certain angle with the light hitting, and front light and backlight and all those sort of things. So in that way I think AI is just going to happen. We can't fight it.

Yeah, this is often called creative destruction. You did something before the world has gotten to the point where that skill is no longer needed because it became simpler or became unnecessary anymore?

Think of traditional things like being very good at like fixing, mechanical things around in the house, which is now like all electrical and automatic and so on, The question is, what is the next level of higher-order activities that we can now focus on, that we can now focus on after spending all this time doing those things The great promise of industrialization from like the, 1800s onwards, was that, because of machines, we'd now have more free time to do things that humans are very good at.

What we found is that the free time that we've had, was filled up with more things to do to make us more productive, and that smartphones have only made it more challenging, because now, every moment of your day, you have an extremely powerful computer in the palm of your hand, Anything you do is basically a zero-sum game. If you're spending time on, say, Twitter, that means you're not spending time on Facebook or Instagram or LinkedIn and so on. All these companies are trying to figure out how do we squeeze every ounce of usage from you, from all these devices.

And I always worry that personalization and AI and some of these activities would make it that much more appealing, because imagine, my phone knows far more about me than anything else that I do, so it has all the data about what I'm doing. Imagine it turns all the data into something convincing, a convincing narrative that I am now excited about. I'm like, oh yeah, that sounds exactly like what I would do. The reality is it's actually based exactly on what I do. I change my behavior completely. I'm looking forward to seeing. What what this world looks like.

Part of it is also a little terrifying, like how will it change how we often behave? Because we often read about people spending less time in libraries. Children don't go to parks anymore a whole lot, right, because they're always on their phones. So I'm like, yeah, this is a big change and, I think we can make a case that maybe it's good for you to be able to go to the park or go to the library. How many more things will be changed as a result of it, for the good or the bad?

Yeah. As somebody that used to like to draw a lot, I stopped for a long time and then I found like I just filled my time with other things and you can definitely feel your creativity levels go down. When you're not using it's like a muscle that you have to use. I've heard some people talk about how creativity is the result of boredom in some cases, and the problem is we're never bored anymore because we have the entire history of the world in our pocket that we can access at any time, like there's always something you can be consuming.

In the early social media days, I wrote it off as learning. I'm like, well, I'm learning all these things. Like that's how I kind of justified spending all my time on social media. Then I was like, okay, this, I need to slow down, and so what I would do from time to time is do a detox, like I would just, delete Facebook for a while or delete Twitter for a while and force myself to not do those things so that I would be more creative, because I think the big thing is for me, I would rather be a creator than a consumer.

As much as I like to learn, I like creating things, so, I learned for a bit and then I take that learning and create things from it The problem is, like you said, these devices and everything around us are trying to turn us into consumers, and we don't want to end up like the tubby people in WALL-E that are in those kind of like weird tub type things that it's just kind of like they just sit there and consume all day long. In theory, we turn into the batteries in The Matrix, it's a bad thing to just be a consumer.

So I think we need people to create these things and create human experiences, like you touched on earlier. I think that's going to be the key differentiator with everything being automated and changing into this, almost disposable content, because there's going to be so much low-effort content being created thanks to AI that the humanity is what needs to shine through, and that is something that. It AI's going to get there sooner or later, probably sooner, but for now it's still the differentiator. I see the Iron Man in your background.

Anybody can wear the Iron Man armor, but Tony Stark is the only Tony Stark and he can do things in the Iron Man armor that Jim Rhodes can't do. There needs to be that human element driving the technology and not the other way around.

Yep, that's really well put. As we start wrapping this up, I have one question for you: what's a misconception about marketing that you wish people would reconsider?

The misconception is that it's all fun and games. I think a lot of people are like, oh, that looks like so much fun. And I've actually heard my mother talk about this and she was always on the product and engineering side of the house in her career. She'd say, ‘Marketing is just the team that spends money.’ I would say, but we're doing things like yes, we're one of the few departments that's actually spending money externally. Trade shows, events, mailers, whatever. But there is a science behind it, there's a reason behind what we do, and if it didn't work, companies wouldn't invest in it.

We're not there just having fun blowing money. Yes, people do have a lot of fun, when they're on marketing trips or whatever. But have you ever been to a sales conference? You think those folks are sober for three days in Las Vegas? I don't think so. Everyone's having fun in what they're doing. But some people see it as kind of like, almost like the important stuff and the not important stuff, because you need a great product and you need somebody to sell that product. A lot of engineering-driven companies think those two things, but without marketing creating that triangle, nobody knows about that great product or who that salesperson is.

I came up with the thing a while ago that said that the SiriusDecisions stat from 10 or 15 years ago, which is 70 percent of the buyer's process, is done before somebody raises their hand and reaches out to sales, or 70 or 80 percent, whatever that number is. It's been a long time. It almost made me think of a baseball game.

So marketing is basically your starting pitcher and it's going to go five or six innings and then hand it over to middle relief, which is probably your SDR And then your salesperson comes in as your closer, but you can't win the game in just the eighth and ninth inning, You have to, have a good beginning of your game in order for the whole operation to work. Your salespeople going in cold is usually not a great thing.

Yeah, that's true of so many disciplines as well. Engineering talks about design, design talks about engineering, marketing talks about engineering, sales, support, and all these various disciplines. Every discipline has its own idea of the most important value it provides in the organization and how it's better than everyone else. It's fun to see how that ultimately plays out. Okay, I thought that was going to be the last question. I actually have one more. I'm a huge fan of Mad Men. That's one of the shows I've always been fascinated by. I'm guessing you've seen it as well, correct?

Yeah, there's a character on the show named after me.

Really?

In the sixth season there's a character named Jim MacLeod who's in like one episode and he's in one episode. You've watched it all the way through.

Yes, always.

Okay. So it's when Joan and Lou are out. No, they're not in California, but they're in some other office. They're not in the main office, but it's like, hey, what time is Jim MacLeod coming in today? And they're talking about this person. It's when Joan meets the guy that she dates through most of the last season, like that guy that kind of walks in and pretends to be somebody else. He pretends to be a character named Jim MacLeod. Wow, wait, what's the TL; DR on that? How did that happen? Years ago, I created a poster for Mad Men, just like a bootleg silk screen poster.

I designed it because I loved the show. I sold it on my website. I sold like 50 copies. It was silk screened, limited edition, signed and numbered. A director from the show reached out to me because he wanted to buy one. I'm like: sorry it sold out. He's like: can I commission you to make another one? And I was like: yeah, absolutely. We wanted to update it and then he was going to do another one and then he went quiet for a while and he came back.

He's like: you're a bootlegger and I'm associated with the show, so because I sold Mad Men materials without Lionsgate approval, he couldn't work with me. It's one of those like because I sold illegal stuff so and I was like, okay, well, that's too bad. And then a year later I'm watching the show and Joan walks into a room and says: is Jim MacLeod here yet? I'm like wait what? And so I'm guessing, because I also heard Matthew Weiner was someone involved with that discussion about the poster. That it was almost.

I don't know why, but it might have been a coincidence that the only TV show that I've had direct access with somebody also had a character named after me, but I think it's unlikely.

Yeah, I think it's unlikely too. How accurate is Mad Men in general in terms of how marketing, design, and sales work, especially the marketing and creative side of the house?

I haven't seen it to be all that accurate. I've worked with some great creative directors. I've never seen creative directors that can boss around everyone else in the agency. It's usually the account people telling the creatives what to do, not the other way around. As much as I'd like that, there's a great line in there. They can't do what we do, and they hate us for it, or something along those lines. The idea is that the account people hate the creatives because they can't be creative, I don't buy that. Anybody can be creative.

Creativity is unique, I wish it was like that, and definitely without the drinking and the sexism and all those things. I don't know where that exists, if at all, anywhere in the world, thankfully. But, I never worked for an agency like that, but I also didn't work for a big agency, so I'm not entirely sure what that's like. I've seen some online. I've seen some all-star creative directors, but my favorite part about that show was seeing that spark of creativity, seeing when that light went off in his head and then seeing his process of how he got to that creative inspiration.

That was my favorite part of the entire show because I love learning about process, I love creativity, and just seeing both of that in an all-time great show was a perfect thing for me.

Jim, thank you so much. That was a perfect conclusion to a very entertaining and informative story. Keep creating content. I've always been a big fan of it, and hopefully more people will find it and be as entertained and educated about these topics as I have been for many years.

Fantastic. Thanks for having me.