TCC Podcast #388: Becoming a Copywriter with Eddie Shleyner - The Copywriter Club
TCC Podcast #388: Becoming a Copywriter with Eddie Shleyner

What does it take to become a copywriter? How do you learn the skills you need? What are the best ways to “get in the game’ so to speak? In the 388th episode of The Copywriter Club Podcast, Kira and Rob talk with copywriter Eddie Shleyner about the process of becoming a copywriter—and how he made the jump from literature student to booked-out-copywriter and author of a book about copy. Click the play button below, or scroll down for a full transcript.

Stuff to check out:

The Adweek Copywriting Handbook by Joe Sugarman
4000 Weeks by Oliver Burkeman
The Copywriter Club Facebook Group
The Copywriter Underground
Eddie’s website

Full Transcript:

Most weeks on the podcast we take some time to dive into a different copywriter’s origin story. Why they became a copywriter. How they made the switch from whatever they were before to what they do now. It’s a process we all go through, and yet, we tend to skip over a lot of the details. We jump from one client to the next, or from this service to that product. We cover a lot of what and don’t go very deep into the how.

Hi, I’m Rob Marsh, one of the founders of The Copywriter Club. And on today’s episode of The Copywriter Club Podcast, my co-founder, Kira Hug, and I interviewed copywriter and soon to be book author, Eddie Shleyner. Eddie shared the details of how he learned to write copy, the feedback he got along the way, and the books he found most helpful. And that’s just the beginning. We also talked about sabaticals, burnout and book writing. This is a good one, stay tuned. 

But before we get to that, if you’ve been listening to this podcast for long, you’ve no doubt noticed a recurring theme… how do copywriters and content writers find clients TODAY. We recently updated our guide to finding clients… it now includes more than 21 different ideas for finding clients… things you can do today to attract a client—maybe even in the next 24 hours. Some of the other ideas will take a bit longer to bring in clients. But they all work. We’ve either used them ourselves, or know other successful copywriters who have used each one of these ideas. And we want to give you this report for free. 

But don’t just download this document and let it die on your hard drive. If that’s your approach, don’t bother. This isn’t a one page pdf that’s easy to ignore. It’s a comprehensive… 36 page mini book… that includes the 4 mistakes you can’t afford to make when looking for clients—if you make them, clients will run away from you—the exact opposite of what you want. I already mentioned it includes more than 21 ways to find clients, as well as several templates or scripts you can use to reach out to clients, and finally it reveals the five things you need to do to improve your odds of landing a client. If you want a copy of this report, visit — find a client is all one word and we’ll send you a copy for free.

And with that, let’s go to our interview with Eddie.

Kira Hug: All right, Eddie, we want to start with your story. How did you end up as a copywriter?

Eddie Shleyner: Oh, well, I guess it was a pretty organic thing for me because I majored in English. I was an English major. I studied literature at U of I, and that’s what I wanted to do, I think. I wanted to graduate and write novels and short story anthologies, and obviously that’s It’s really hard to do right out of college, so I had to get a day job. I got a job in sales, and I was selling software. I was selling computers. It was basically inside sales, but it was trying work for me. I didn’t really enjoy it. I think I really wanted to write, and so after about a year in that role, my buddy came home. My roommate came home and he said that his work was looking for a copywriter. And I didn’t know what a copywriter was. Actually, I had to look it up. I knew somebody was out there writing these ads, but I didn’t know they were called copywriters. So this goes to show how little I knew about this discipline in this profession before getting into it. 

But I looked it up and I was like, yeah, sure, I’ll try that. And I went in and I think I got the job just on the back of my English degree, because It was a brand new department. They were writing job ads. It was a contract role. I wasn’t getting any health insurance. I was making $15 an hour. So it was one of those. And I took the job just because I was like, hey, I can make a living writing. And quickly learned that my worth in that role was based on how many times I can get people to click and how many times I can get people to take an action. And so independently, just kind of doing my research, realized that I was doing something called direct response copywriting. And then I kind of went down the rabbit hole. I got really interested in that profession and that discipline and started consuming as much as I could about it. I started just reading books and watching seminars, listening to podcasts, reading articles. Yeah, whenever I would come into an insight, whenever I would hear a principle or a technique that was really compelling to me, I would try to write about it. And that turned into a very good copy eventually, my blog and my newsletter. And then, you know, it just kind of progressed from there. So I think that that’s how I got into copywriting was kind of a slow burn.

Rob Marsh: Do you have a novel in your desk drawer that you’ve been working on in the background, Eddie?

Eddie Shleyner: Thanks for asking, man. It’s not a novel. It’s an anthology of my work, but yeah, there is something that I’ve been working on, if that’s what you’re getting at.

Rob Marsh: Yeah, we’ll wait for that to hit the bestseller list so we can talk about it then. In the meantime, you know, as you were studying, as you’re learning, obviously podcast books, whatever, what were like the main sources that you used or that you were there were your go tos that you were pulling this stuff from? I’m asking mostly because I know there are beginners who are listening to the podcast and may want to replicate that, learn and write about these insights and learning ideas. Where’d you go?

Eddie Shleyner: Well, the first book I picked up was by Joe Sugarman. It’s called The Adweek Copywriting Handbook. And I really wore it out. I mean, it was so overwhelming in its completeness. I just felt like it covered so much. And what was really interesting about that book was when I picked it up and I started reading it, being a literature major and studying English all those years and reading the classics. And I started reading and I was like, man, this sounds like it’s like reading air. You know, it was like it was so simple and so plain. I was almost unimpressed at first. I was like, well, you know, is this really the resource that I should be reading? Is this really where I should be gathering information? Because it seems so trite at first, because it was so simple. But I think that was just the first couple pages, and then I realized that this was really just a treasure trove of information about direct response copywriting. And not just that, but it was something to emulate. 

It was a writing style that I needed to emulate, and I referred back to it time and time again and copyworked it time and time again so that I can get that so I could get it into me, you know, the type of writing, the tone that he was using and the word choice and just the sentence structure and the simplicity in general. I really wanted to write that way and not the way that I was writing in college. You know, I had an editor that was like, “you write like a fire hose, I need you to write like a nail gun.” And that was Joe Sugarman. Joe Sugarman was so intentional about every word that he used. He was even intentional down to the punctuation marks. He wouldn’t use unnecessary commas. He was always trying to save space on the page, make it as simple as possible. And so, yeah, I took a lot away from that, both in the principles and techniques of direct response, but also just in the style and how those guys wrote.

Kira Hug: So you shared your lessons. It sounds like you were learning and writing and sharing. Yeah. What was the reason for that initially? I mean, we can look back now and say, that was really smart, because now you’ve developed this entire resource and website, and you’ve grown since then. But what was your initial thinking with that?

Eddie Shleyner: Well, my initial thinking, I think, was that, you know, I missed writing. This was coming off of an entire writing and literature education, so I missed just the act of sitting down and composing vignettes and these little stories, which is something that I did pretty regularly, I think, in college. And so I think I missed it a lot, and I wanted to have an outlet for that. I wanted to exercise that a little bit. Also, I just thought, hey, if I can write about this clearly and concisely, if I can make it engaging, if I had control of this concept on the page, then that meant that I was ready to use it in my own promotions and my own ads. I think that was probably the driving force. They say millennials want to document everything in their lives. Maybe I just wanted to have some way of documenting all of this effort that I was putting in. I don’t know. It’s a good question. It’s hard to pinpoint exactly why I chose to do that, but somewhere in the intersection of those three things is the answer, I think.

Rob Marsh: When you weren’t only documenting what you were learning, you know, as part of your blog, you started interviews with other copywriters. Yeah. And there’s some really good copywriters that you interviewed for that. Yes. I’m not necessarily putting myself in that category, even though I was part of that, that series. But I am curious, were there lessons that you learned from them as you did those interviews and post those on your website that you look back and think, oh, yeah, that was brilliant. Anything that you can call out from what was shared there?

Eddie Shleyner: Yeah, definitely. You were actually, Rob, I think you were the third person I interviewed. I was very gracious of you because, you know, you didn’t have to do that.

Rob Marsh: Well, things really got good after the first three or four people, I think.

Eddie Shleyner: I don’t know. You were great. But to answer your question, themes that emerged were probably more than anything that just the fact that we are so similar. We are also so alike as copywriters and you know as people doing creative work for a living. I was really surprised by a lot of things that people wrote in that? It’s the same six questions over and over again, and the first question is: do you have a routine you have a way of working and this wasn’t like across the board, but so many people talked about how focus was really the key to doing good work and their production in general. Just being able to have blocks of time where they sat down and they were uninterrupted and they could focus on the problem at hand. I took that to heart back then. I think it’s a lot harder after you have kids. You have to be a lot more regimented with your time and just plan everything out to a T. But I think thematically, that was one of the things that really stood out across the board.

Kira Hug: Going back to your storyline, can you share a little bit more about once you realize you’re a copywriter, you have this job, and then you go deep into learning mode, what happens after that? What are the next few steps?

Eddie Shleyner: Oh, you mean like in my career progression? Yes, yeah. Oh, yeah. Yeah, so I actually worked at CareerBuilder which is where I was writing those job ads for about a year and a half. And so those are like three month contracts. So they just, you know, they extended those contracts probably five or six times. So I worked there for a year and a half and then afterwards I got a job at an agency. And it was, it was an SEO agency. We created SEO websites, but a lot of that work was very much rooted in direct response as well. You know, we needed to capture people’s attention when they got onto the site and convert them as well. So everything on that site was just pointing towards the fill in lead form. And a lot of our clients were, you know, kind of, you know, hand to mouth with their leads. So, you know, dentists, trucking companies, moving companies, that sort of thing. So I worked there for a little while and I continued to build out the blog and build out—I don’t even know if it was a newsletter at that point. 

For a while, it was just like a running list of like 50 or 60 of these little essays that I wrote in a Google Doc. I was never going to show them to anybody. They were just there just for me. I just thought, hey, I’m making this repository for myself. So I worked there for a little while. I think I worked there for about three years. And then after that, I got a job in-house at a software company. And that’s where I got a lot of SaaS experience, or at least my first SaaS experience. And then after that, I went and worked really briefly at a content marketing agency. It was called Animals. And then after that, I went to, which is kind of like Yelp, but for B2B businesses. And I was the copy chief there until November 2020, something like that. And that’s when I went out on my own with their copy. So that was the progression.

Rob Marsh: You mentioned you started out in that sales job that you didn’t necessarily love all that much, and yet you basically became a salesperson for all of these roles that you did. Did you learn anything in that first job that you carry through all of these things? Obviously, there’s a theme here anyway of you learning and picking insights and growing as you move from place to place, anything stand out specifically about sales?

Eddie Shleyner: Oh yeah, of course. I was in sales before this job after college. I did door-to-door sales for a little bit. I think at the end of the day, whether you’re selling one-on-one to somebody or whether you’re selling one-to-many as a copywriter, the point is that you have to gear everything towards the person that you’re speaking to, towards that prospect, towards the person that you want to sell. If you can make it as much about that person as possible, then you’re giving yourself a good shot at engaging them and compelling them in the long run. I think a lot of that transfers over from one-to-one sales to copywriting, is to know your audience, know who you’re talking to, know what they really want and need, and then try to channel that into your copy.

Kira Hug: So I’m going back to the storyline, because I have to complete it in my head. This is how my brain works. I’m like, OK. So then you went out on your own. And how did you get that going? Did you have enough colleagues, former colleagues, that you could just get business going pretty easily at that point?

Eddie Shleyner: I think when I started at G2, that was a really fortuitous thing for me, because everybody there was so supportive of this side thing, this very good copy thing that I was doing. And everybody from the CEO to the CMO to the marketing directors, all my bosses, everybody loved the fact that I had this blog on the side, this newsletter on the side. And I think a lot of that came down to hey, you know, you’re teaching yourself and others how to be better copywriters. That’s only going to benefit the business in the long run. So keep doing what you’re doing. Um, I think, you know, I was performing well in the role anyway, so there wasn’t like a, Hey, you’re distracted, uh, kind of narrative there. 

So it was just very lucky that I started at G2 and I was surrounded by people, um, that were supportive and genuinely wanted to help me. The first break I got there was just being around like a bunch of growth marketers, really talented growth marketers, people that taught me not necessarily how to write or what to write, but how to spread my stuff around the Internet really efficiently. And that’s when LinkedIn kind of came into the picture, when I started posting on LinkedIn and when I started creating growth loops from my website to my newsletter to LinkedIn, that just kind of amplified each post. And yeah, I really, I started growing a following on LinkedIn while I was still at G2. 

I couldn’t ask for more support than those people showed me. I mean, it was really great. And I think, you know, I was really lucky to have it. So by the time I left G2, I had left because there was already so much incoming so many incoming leads, so much incoming business that I felt safe, you know, walking away, even amid, you know, we were in the middle of the pandemic and everything, which was, I think a lot of people, they just looked at it sideways. They were like, I can’t believe you’re leaving now, but I just felt like it was the right time to go and kind of take advantage of this network that I’d built. So, yeah.

Kira Hug: I like the idea of, who said spread stuff, spread your stuff around the internet and growth loops. Yeah, efficiently. I mean, I want to do that. So how, how do you approach that? How are you doing that today? What’s working?

Eddie Shleyner: Well, certainly in the very beginning, I started creating growth loops from my newsletter to LinkedIn. So every single time I wrote a new micro-essay just as a branding exercise—they’re basically little essays that teach one principle or technique at a time. And so I would post it on LinkedIn, and then I would send out the exact same essay in my newsletter. And then at the end of the newsletter, I would just ask for support and be like, hey, if you like this, go reshare or go leave a comment or like it on LinkedIn. And by posting and sending out that newsletter in such close proximity and transferring my audience from the newsletter to LinkedIn, it would just amplify the post to all those folks. So now there’s the commenting or the pod trend, the commenting trend, where you kind of get together with a bunch of people and everybody comments on one another’s stuff. You know, it’s the same concept, only I was doing it with people that were in my newsletter and just asking for their support organically that way. And, you know, that, I think that helped me grow quickly. Just, just the fact that, you know, there was this audience transfer and this amplification on, on LinkedIn. on the platform itself. And then inside that post, there would be a CTA, a call to action to go to if they wanted to read more. And, if you look at it, I mean, it’s basically designed to get you into the newsletter. Like, you know, I don’t know how many thousands of CTAs there are across that site, but I would say 90% of them are designed to get you to subscribe. So it would just be a virtuous circle. People would see the post, they would go to the CTA, see that there’s more on, they’d go to VeryGoodCopy, get into the newsletter, and the next time I sent out a newsletter, there would just be more people there to amplify the post. So I think there have been You know, over time, there’s diminishing returns like everything else. But in the very beginning, that was definitely an effective way to grow.

Rob Marsh: So I want to ask some follow ups on this. You started doing this when? Is this 2020 or before that? 2020 is when I left.

Eddie Shleyner: I think I started doing this about 2019. Okay.

Rob Marsh: And you were sending out how often? Once a week or less? More?

Eddie Shleyner: I think I was sending out once. I wasn’t that regimented. I mean, I think I was sending out once a week. That was my goal. I didn’t have any sponsors at that point or anything like that, so I wasn’t that obsessed with the frequency. But yeah, I think once a week is a pretty good estimate.

Rob Marsh: Yeah, the reason I ask, obviously, there are people teaching these things on LinkedIn, you know, post three times a week or whatever, and yet you were able to do it at least a few years ago, without that kind of frequency. How often do you post or share newsletters now?

Eddie Shleyner: Well, the newsletters still go out once a week, ideally. I take pretty frequent breaks, kind of like hiatuses. At least once a year, I’ll go three months and I’ll just kind of go a little dark. I won’t go on LinkedIn. I won’t send a newsletter out. Sometimes I’ll even kind of leave an away message on my email and I just won’t really check that or it won’t be that frequent. And usually that coincides with a big project that I’m doing, like this year was the book. So I took a couple months off and just kind of focused on doing the book. Last year was the course that I made and I just took like three months and literally just heads down, didn’t do anything else besides the course. And then sometimes it’s really just to kind of get back to, you know, like craft and just get back to what got me into this in the first place. You know, as a solopreneur, as somebody that’s doing this on their own, I think it’s really hard to balance craft and growth. 

And for so long, you know, like in the very beginning, Kira, when we were talking about like, you know, how this all started and I was kind of walking through like, uh, you know, the, the, the, the impetus behind Very Good Copy, that was very much like a craft phase. I was trying to go from like zero to 80% and trying to learn the fundamentals of this discipline. And then after I got that down a little bit and I started writing these essays and sharing them, and I realized that there was an audience for it and there was some potential for a business there, then I became really interested in growth mode. And perhaps that was like, you know, a consequence of the people that I was around. I was around a lot of growth marketers, around people that were good at it and wanted to see me succeed. 

So I just went into this kind of growth mode for a little while there, probably a couple of years where I was still writing and still trying to do my best work. But there was this kind of like, I don’t know, there was this tension between like, hey, how much time can I put into writing? And how much time do I need to put into all of the administrative work that goes into growing this thing? And I found over time that that was like, like a perfect way to burn out and a perfect way to really hate your life. You know, it’s just impossible to do all of that at once. 

And so now I kind of oscillate between growth and doing all the things that I need to do to spread my work around the Internet and do it efficiently and do it in a way that’s going to be effective. And then every now and then I’ll be like, OK, a lot on that. I got to take a break and I got to really focus on going from you know, really focus on growth going like going from zero to 80% is easy. I think compared to going from 81% to 90%, you know, that’s super hard, you know, comparatively. And then going from like 91% to 95%, you know, is exponentially harder than the last phase, you know, and then going from like 96 to 99, you know, that’s exponentially harder. And then like going to getting to a hundred is probably a fool’s errand. Like that’s probably never going to happen. So it’s just like growth. or I’m sorry, like craft is just this ever increasingly difficult thing to do and to develop. And I think it just, it deserves time, like dedicated focused time. And so that’s what I try to, I try to do that whenever I can.

Rob Marsh: And last question about this entire process, at least for me, as you’re putting this out and talking about giving back to the craft and learning, sharing your insights, does customer acquisition come into it at all as you’re sharing? Are you posting on LinkedIn in order to attract clients? Or is it really about sharing what you’re learning?

Eddie Shleyner: Well, sometimes, yeah, if I’m heads down, I’m probably not posting. I’m probably just dark. My account just kind of sits there. Every now and then, I guess I will. But yeah, the client acquisition piece, I think it’s more like a subscriber acquisition. I think that’s what I’m focused on. I’m not focused on getting direct leads from LinkedIn. I’m focused on getting those folks in front of my brand, in front of Very Good Copy, into the newsletter. And then from the newsletter, that’s usually where people decide to work with me or decide to buy a sponsorship or decide to buy a consultation or my course or something like that. So once they’re in the newsletter, that’s when I think I have much more control over the message. And so that’s always my goal is to get people into the newsletter. whether they become clients or sponsors or consultees or what have you. It all happens in the newsletter, I guess is what I’m saying.

Kira Hug: What does it look like today? How are you getting paid the different ways… sponsorships, consulting. But what are you primarily focused on? Is it all spread out and you kind of have revenue coming in multiple ways at this point?

Eddie Shleyner: Yeah, definitely. So a few revenue streams, client work. I made a course and I’ve been selling it for about a year. So that’s a revenue stream. Sponsorships for the newsletter and then consultations. So people buy a couple hours of my time and then we’ll sit and talk about their problems. And it’s definitely shifted from the majority of my income coming from client work to the majority coming from just these products. So the course, hopefully the book, sells a few copies. I’m interested in productizing the brand as much as I can and creating things that scale. And I don’t think I’ll ever stop doing client work. I think as a copywriter, it keeps you fresh. Solving real world problems is a great way to stay on top of your craft and on top of your discipline. So I don’t think I’ll ever stop doing it. It’s just there’s obviously an opportunity cost there. If I’m doing client work, then I can’t take the time to create a course or write a book. And so there’s that give and take, and I just have to pick a lane. And so I’m trying to live in that lane, the productized lane.

Rob Marsh: the newsletter and sponsorships, the economics of that, if you’re willing to share. We had a few months ago, maybe a little more than a few months ago, John Bijakovic was on our podcast and talked a little bit about this newsletter he’s building outside of the copywriting space. I think there are a lot of people who are listening who would love to build a newsletter, whether that’s on Beehive or Substack or ConvertKit or wherever, and look at that as possibly its own business or a significant part of their income. I wish it was that easy, you know, put up a newsletter and suddenly you’re making lots of money, but we just kind of talk through the economics of how you do it. If you’re willing to share the numbers, awesome. If not, you can be a little bit generic, but just curious about what that looks like.

Eddie Shleyner: Yeah. So yeah, the numbers fluctuate depending on how many subscribers there are and, and the time of year. And, and so, um, you know, the carrot that I kind of dangle over, over, over folks on the website is like, Hey, email me for, for rates. And so, you know, I can’t, I probably can’t share exactly what I’m charging. Um, you know, I’d like people to, I’d like to have those conversations one-on-one I think. But, uh, yeah, the economics are, um, yeah, they’re pretty simple. It’s a matrix, you know, and, and, uh, the more you buy, the more you save. And, um, you know, it’s, uh, It also depends on what your goal is. If your goal is conversion, then newsletters could be a good medium for you to advertise in. They could not be. Usually I like to go after folks that are interested in raising awareness and getting their brand in front of people, maybe associating their brand with very good copy. Yeah, so I certainly wouldn’t turn away anybody that wants to convert my subscribers into customers, but that would take a very specific offer, a very specific campaign, and we’d probably have to work together on that to make sure that it’s successful. But if it was an awareness campaign and they just wanted to get their logo out in front of 15, 20,000 people every time I send a newsletter, that’s a much easier conversation. And that does happen pretty often, actually.

Kira Hug: So if you’re, if I hire you and you’re my consultant and I also want to sell sponsorships to my newsletter, what advice would you give me as far as what’s realistic? Like how many people do I really need on my newsletter to even have a sponsorship conversation and be attractive to sponsors as a baseline? And then secondly, How do you create that win for your sponsor clients when it’s around awareness, which is sometimes harder to measure? It can be measurable, but it’s a little tricky at times as far as brand awareness and creating a win for them so they continue sponsoring in your newsletter.

Eddie Shleyner: Right. Well, I’ll answer the second one first. I think when it comes to awareness channels, it’s really about, hey, how many people saw this? you know, how many eyeballs from a very specific nature, a very specific discipline saw this. So if I could say, Hey, you know, every time I send out a newsletter, 20,000 marketers and copywriters are going to see your logo and your message above the fold. So it’s the first thing, you know, in my newsletter, it’s the ads are the first thing people see. UThat’s enough for them to say, Hey, that’s, that’s a win. And then if I could just show them the open rates, show them how many unique people opened it and saw the message. For a lot of people, that’s enough. Obviously, if you click through and you take an action on the other side of that click, then that’s obviously another KPI that they take into consideration. But from an awareness standpoint, yeah, sometimes it’s just enough to show people that logo. And a use case for that is like, hey, if you’re raising capital, maybe you’re raising your series A or B, and you just want to be a more known entity in the SaaS space or in the marketing space. That’s a big reason why people pick up ads in my newsletter, just to get that awareness level up. Your first question, I think that was about how many people in a newsletter?

Kira Hug: Yeah, I mean, we have a, our audience wants, I mean, I’m sure many of them would like to do something similar, get sponsors, but maybe they have 2000 people on their list and they’re really excited about that. Is it realistic? You know, Hey, you probably need to get up to 10,000 before you have any conversations with sponsors or like a rough number.

Eddie Shleyner: Yeah, I, I wouldn’t, I wouldn’t discourage anybody. Um, from pursuing sponsors at really any size newsletter. Because I think what’s more important than the size is just the quality of those people and how alike they are, if that makes sense. If they’re all marketers, or they’re all copywriters, or they all have this one very specific interest, then it’s very valuable for people that are going after that group, that segment, to advertise with you, even if you have 100 people or 200 people? I think that’s my answer is, yeah, obviously, the bigger your newsletter, the bigger your audience, the more you can probably charge. But yeah, at the same rate, if you have 200 or 300 people that are fanatical about a certain subject and somebody with a product that’s aligned with that subject, once they get in front of those people, that’s still very valuable. And that could still turn into sales.

Rob Marsh: While we’re talking about audiences and all of that, I’m curious about the audience for your book. Actually, I’m curious about all things around your book, the decision to write it, your approach, methodology, what it’s about. Tell us a bit about that.

Eddie Shleyner: Sure. Yeah, I appreciate you, Rob. I mean, you know, the book is like very good, I think in print. You know, I, it’s a lot of people have asked me for some kind of like physical, tangible thing, you know, and I’ve never, I don’t know, maybe one day I’ll make hats or something or stickers, but that just never felt like the right thing to do, and I’ve always wanted to put my best work together into a book, and this is just that opportunity to do it, I think. It’s just, you know, it’s 10 years into Very Good Copy, and I would love to, you know, present all of these essays that I’ve written in a new kind of fresh way. And so I’ve been taking some time to go back and edit like my, all of my, all of the articles that would make it into the book, which is actually, it’s kind of a horrifying thing because it’s like, I can’t believe I, I published this at one point. It’s just incredible, like how much you, I guess, develop when you do something every single day and, you know, just reading some of my work back, it’s just, it’s just unbelievable to me. So I think if there’s anything that I’ve learned in the process, it’s that, you know, That craft bar is constantly moving, or it should be. And as it does, you are going to be extremely unsatisfied with a lot of the stuff that you’ve done in the past, a lot of the work that you’ve done, or at least I have been. So yeah, it’s been kind of an interesting process going back and editing and arranging everything. But that’s what the book is. It’s very good in print. you know, organized and arranged in a way that I think makes a little bit more sense than the website. And it has the benefit of being like me today, as opposed to me four or five or six or 10 years ago.

Kira Hug: And how does it fit in? I mean, other than you’re excited about it and it’s important to you, how do you see it fitting into the business? Is it like, OK, this is another great way to get people on my list and get them into my world or another purpose?

Eddie Shleyner: Yeah, I think it’s just another product under the umbrella. And it’s a much more accessible product, I guess. hundreds of dollars and being purchased by folks that have a very specific goal or need in mind, a very specific problem that they’re trying to solve for. The book is probably a much more reasonable price point, a book price point, and it’s much more accessible to people and I feel like it could do a lot of the marketing for a very good copy as well. If people buy the book first and then they can make it into my ecosystem that way instead of seeing me on LinkedIn or Twitter or something first. So yeah, I think it’s a product. It’s a marketing channel. And then it’s also just something that would feed my soul, I think, and make me happy. And a lot of times that’s very much overlooked. by creators. It’s like, what can I do to get bigger, faster? And, you know, a lot of the joy is sucked out of this profession when you do that. You know, a lot of the reason why we started doing this in the first place becomes kind of null and void when it’s all about growth and it’s all about how fast can we grow. And, you know, you start looking at it as a competition between creators. It becomes really unhealthy. So it’s one of those things where, like I said, it’s something that’s gonna feed my soul and give me energy at the end of the day so that I can hopefully go out and put on part two and part three and part four.

Rob Marsh: And when can we expect the book? When’s it hitting store shelves by us?

Eddie Shleyner: Yeah, so it should be this spring, so spring 2024. Yeah, probably like May, probably like May. I’m gonna send you guys copies. because I really appreciate you.

Rob Marsh: It’s amazing. Okay, so you mentioned earlier, especially with these big projects that burnout can become a thing. We’ve talked a little bit about your experience with that and how you push through it or overcome it or deal with it. I know there’s a lot of different approaches to burnout and making sure that stuff gets done. Just how do you look at those kinds of challenges?

Eddie Shleyner: Well, for a while I just kind of white knuckled it, you know, like I was just like, man, I’m tired. You know, you wake up when you’re burnt out, you wake up and you’re like, man, I, I really just don’t want to do this. I think it’s a hard thing to describe. It’s not like the most tangible sensation. It’s just like this feeling that, Hey, this thing that I once loved or that once gave me energy is now sucking it out of me. And, um, you know, for a while I, I, uh, I just kind of white knuckled it because I was balancing G2 and I was balancing this newsletter and I was balancing the ebbs and flows of that. Not everything I put out was successful. I just kind of forced it and that would usually make the problem worse. I would usually become more unhappy. I’m more anxious. And so that’s when I would start taking these kinds of breaks, these two, three month kind of hiatuses. And I realized that that’s kind of a luxury and not everybody can do that. But at that point in my career, I felt like I was so deep into it that that’s what I had to do, was just step away. So that’s how I dealt with it. 

Now having kids and living kind of a more family life, I’m forced to not be in my work constantly. Not forced, that’s the wrong word. My priorities have shifted. I want to be with my family. I want to be with my kids. That’s the most important thing in my life now. And so I’m not constantly around work and I’m not constantly in work. And that’s really kind of healed the problem for me. It’s just like knowing that, hey, I have a certain amount of time, you know, that I can allocate to work every single day. And I just got to come in and I got five hours and I start the clock and I just see what happens. I just see what I can put out, you know. And then after that time’s up, go pick up the kids, go do that thing, you know. And it’s forced these boundaries. Whereas before, I didn’t really have those boundaries. Before, I was just so dedicated to making this thing successful that I might work 80 or 90 hours a week in a silo, not really having a lot of people around me to tell me, hey, you need to back off of this right now. So yeah, I think that’s what That’s the way I see it now is I have these boundaries that I have to respect. And that keeps the burnout at bay, I think, because I’m just not in it. I’m just not doing the work. And so I’m not doing as much work, I guess.

Kira Hug: Yeah. Kids make really good boundaries. Yeah. They help. They help, definitely.

Rob Marsh: They also step all over your boundaries.

Kira Hug: They create burnout in other ways, but we don’t have to get into that.

Eddie Shleyner: Did that make sense, Rob? I mean, I’m not sure if I’m answering it right, but I don’t know how else to put it. Burnout is such a strange thing. You just have to-

Kira Hug: I mean, you addressed it with this sabbatical that you’re taking. It’s like, I want to hear more about that. I mean, OK, I’m listening. I’m like, that sounds great. You’ve talked about it maybe a couple times with Sage Polaris, right? And maybe it’s come up in a couple other conversations. But a lot of people aren’t taking these sabbaticals, even though they’re focused. It’s not like you’re just going to the beach. You’re working on projects. So what advice would you give us? so that maybe we could do it? I mean, is it like, hey, you gotta go really hard in September and October, bring in a lot of client work, and then the best time is to take it over the holidays, take a couple months, come back in February, and get this going? Like, what works, practically speaking, to make this work for you?

Eddie Shleyner: Yeah, I mean, the timing is a very personal thing, right? It’s like, you know, I usually take them in November, December, January, because that’s a slow time anyway. And I think the opportunity cost of taking it in that quarter or towards the end of the year in general is just lower. And it probably just aligns with when I’m most tired. I don’t know. It’s the end of the year, and I’ve been going for a while. And you just want to take some time to relax and be with your people. But it depends. I remember Brian Clark saying that Copyblogger would go on this really low maintenance schedule in the summer because you only have so many summers and you want to get out there and do things in the summer. And so that was when the Copyblogger team would go out and be with their people and be with their family and do their thing and kind of take these little mini sabbaticals where they didn’t work as much. So the timing is completely up to you. And from an economic standpoint, that’s also pretty personal. It’s like, how much are you willing to take on in order to be comfortable for the next four, eight, or 12 weeks without work? So there is a fair bit of planning that has to go into it. It’s just a matter of how prepared are you to plan and how well can you stick to that game plan in order to enable it. And then I think the third piece is just like, do you have something really important that you want to do in that time? For me, there was the goal of creating the course or getting this book off the ground. Sometimes it’s like, hey, my daughter’s zero days old. I just want to be there for the first three months and just make sure that I’m experiencing this part of her life, you know? Everybody has their own kind of motivations, I think. But it’s just like, yeah, it’s just kind of at the intersection of like, is the timing right for you? Can you get the planning right? And then there’s something really compelling that is worth kind of taking your attention away from more

Rob Marsh: So you may have just answered this question because I was thinking through like, what does the sabbatical look like on a day to day basis? Obviously, you know, if you’re spending time with your kids, you’re working on a project like a book, that’s a big part of it. I imagine that if I were to set aside time for myself to take a sabbatical, day one would start with a lot of Netflix catching up and time wasting. It’s not really wasting if you’re getting something out of it, but a lot of vegetation as opposed to letting me rejuvenate my creative juices in some way, right? So I’m curious if there are things that you’re doing specifically during that time period that you’ve set aside or is it just letting life come as it is and you just know at the end of the three months or two months, whatever that timeline is, you’re going to kick back in and start working just like you always did.

Eddie Shleyner: Yeah. Well, for a while, I did have that kind of feeling of like, Hey, if you know, even if I’m taking a break, I still need to be doing something semi-productive. And I think I read a book called, uh, 4,000 weeks by Oliver Burkeman

Rob Marsh: Yeah. Oliver Berkman. 

Eddie Shleyner: That’s right. You’ve read it. I think it’s safe to say we could recommend that book to anybody because it’s, it, it speaks to this. compulsion that people have to constantly be doing something, even when they’re supposed to be taking a break. Just constantly be doing something productive, useful, and maybe that’s not always necessary. Maybe it is just necessary to just totally turn off and feel bored or feel like you’re not getting anything done. And maybe that’s what you need in order to incubate properly and rest properly. 

And so I read that book. I read it a couple times because it was just so fascinating to me. I was like, man, I’ve been living my life kind of the wrong way for a long time. And like on one hand, I was kind of, you know, like this like workaholism kind of enabled Very Good Copy and enabled my career. And so it’s hard to condemn it completely, but maybe I just read the book at the right time in my life where this is the ethos that I need in order to sustain the longevity that, you know, a creative career demands, you know. This type of work is really hard and it’s really taxing. And so maybe it only makes sense that, you know, it’s easy in the same way when you’re taking a break. And it’s mindless in the same way when you’re taking a break. 

So to answer your question, what does it look like? I kind of work. Like Austin Kleon once said, he was like, I come to work and I put in my hours like a banker. Just four hours, five hours, I see what gets done. I do that. But then also, when I’m away, I’m away. And I binge on Netflix. put the kids down and just kind of try to do nothing. And it’s a stark contrast from the way that it used to be because it’s like I’ve been living a pretty domesticated kind of existence for a while now since my kids were born. So it’s not like, you know, I would put them down and be going out or be doing anything too crazy. I’ll go on the couch, but I would go on the couch and write, you know, I’ll go on the couch and I’d watch something. And I couldn’t get through the show because I would be like, oh, that’s a great idea. And I would pull out my phone and start writing something. Yeah, again, it’s like it’s a double edged sword because those habits enabled a lot of the work that I’ve done. But at the same time, they also burned me out in ways that made me really unhappy. 

And so I think coming out on the other side of it, I think the latter is more important. You know, your long term happiness and your long term mental health are going to enable your long term creativity and this career that we’re all trying to kind of make it in. So I prioritize, I guess, those habits now. So, you know, during a sabbatical, that’s what I do. I put in my hours like a banker and then I shut off and I don’t put undue pressure on myself because whatever, you know, we’re all dust in the end anyway. So it’s like, why am I doing it?

Kira Hug: How old are your kids now?

Eddie Shleyner: Bo is two and a half and Sophia is almost six months.

Kira Hug: Oh my goodness. Wow. Okay. So what does the future look like for you? I mean you are someone who seems you’re a planner in some ways enough to plan sabbaticals and so you’re thinking about longevity. It’s important to you. What do you see as your future also considering dramatic changes we’ve seen in the creative space over the last few years with AI and other shifts? How does that change what you’re thinking about if it does change anything?

Eddie Shleyner: well, I’d like to just I’d like to keep doing what I’m when I’m doing, you know, I think you know, I like thinking deeply about what brings me the most satisfaction is is writing these these micro essays and and putting together resources that help folks. And so I’m really interested in continuing along that path and being consistent with my output as far as the essays go. And, you guys ever seen that Giru Dreams of Sushi documentary? I love that documentary. It’s so good. It’s excellent, Kira. If you get a chance, I don’t know where it’s streaming, but it’s streaming somewhere, probably Hulu. But it’s an excellent documentary about this. I mean, during the filming, he was probably 85 years old. He was a sushi chef. And he was just obsessed with creating the same 30 or 40 pieces of sushi and doing it as best as he could. And I drew a lot of inspiration from that. And I would love to just get as good as I can at writing these essays. you know, putting out the best product I can and hopefully just putting out more and more volumes of these anthologies. That would be like a dream come true for me. And I guess the way AI plays into that is, you know, I guess time will tell. We’ll see where AI goes. But right now, I don’t think that AI is capable of really emulating, you know, like the human condition. expressing humanity and these really human moments that we all go through in a really accurate and authentic way. And I think a lot of my work is rooted in my life, my experiences, my people, the things that I’ve done, the anecdotes that I’ve come into. That’s the formula for these essays. I’ll take some kind of story, some kind of narrative about my life. And then I’ll take a lesson about copywriting or creativity, and I’ll see if I could put those together in a kind of flush way in a certain number of words. Those are the three, I guess, prongs or pieces to each one of those essays. And so I think that AI can probably teach the lessons, but it can’t really replicate those really specific human moments that I’m referencing. And so I don’t see it playing a huge part in the future, a very good copy at least.

Rob Marsh: Eddie, thanks for sharing so much about your business and what you’ve been working on, how you grew. I think it’s fascinating and a lot of good lessons to take from that. If somebody wants to get on your list, Join the other 15 to 20,000 people who are there getting your essays, notified about your book. Where should they go?

Eddie Shleyner: Yeah, just go to That’s home base. And that’s where they can get access to the full library. They can subscribe to the newsletter there. They can get on the waitlist for the book there. They can get the course there. That’s home base. So is the place to go for sure.

Kira Hug: Awesome. Thank you, Eddie. Appreciate it.

Eddie Shleyner: Yeah, I appreciate you guys. Thank you.

Rob Marsh: That’s the end of our interview with Eddie Schleiner. I want to add just a couple of thoughts to our conversation, give you a little bit more to think about. Eddie mentioned the book that he loved. It’s called the Adweek Copywriting Handbook. That book is also known as Advertising Secrets of the Written Word. It’s actually the same book. There’s two different titles. One was printed by Adweek magazine, and the other I think was printed by Joe. It really is one of the better books about response-driven copy, how you get people to engage emotionally, how to write headlines, how to find ideas. It’s worth picking up your own copy of that book and we’ll link to it in the show notes in case you want an easy link to do that. 

When Eddie mentioned being told by a mentor that he writes like a fire hose and needs to write more like a nail gun, I thought that was a brilliant illustration of the rule of one. As a writer, you can’t write to everyone. You have to write to your prospect, the buyer. Seeing them as a unique person rather than a large group of buyers or people with a particular challenge or problem, it changes the way that we write as copywriters and as content writers. And by the way, the same thing applies to going out there and finding clients. Take the nail gun approach rather than a fire hose approach. You will connect with your prospects better than if you try to talk to everybody in every niche about every kind of project. 

Let’s also talk about this idea of sabbatical. So Kira mentioned that this first came up on the podcast a long time ago when we were talking to Sage Polaris way back on episode 32 when she talked about taking four months off every year. It might be worth a listen if you like that idea. It also came up on episode 68 with Ashlyn Carter and again on episode 285 with Tyler McCall. So check out Those other episodes, 32, 68, 285, if you want to dive more into this idea of taking a sabbatical. The idea of taking time off or away from your business is a powerful one. Whether you do what Eddie did and you focus on a project like writing a book, or you’re just getting away from everything to recharge your batteries and refill the creative tank, it’s worth considering doing. Now, you may not be able to take a month off each quarter or even more than a few days in a quarter or in a year. I still think that it’s helpful to think about taking time away, away from clients, away from your desk, away from projects, away from the laptop, away from pitching and marketing, or even thinking about pitching and marketing. It helps light the fire again if you’re burned out, or it helps you avoid the burnout in the first place. Taking time away for weekends, for evenings, putting the work aside is critically important. Sometimes it’s not even taking away time from your business as much as it is just changing the scenery. So go work somewhere else for a day or two or for a week or two if you can. Go to the library instead of working in your basement or the kitchen table or in your office. Get a hotel room and work there. Go sit in the park if you’ve got a laptop. Just change your environment if you can’t stop working right now. And even if that’s not possible, start planning for a future sabbatical or a week off where you can leave everything behind other than maybe a notebook and a pen and just be off. If you make it happen, I’d really like to hear about it, the impact that it has on your thinking and what you bring back to your business. 

Okay, thanks to Eddie Schleiner for joining us to chat about his business and becoming a copywriter, that process that we all go through. Be sure to check out Eddie. He’s on LinkedIn. He’s also at where you can subscribe to his newsletter and watch for his book coming out in the next couple of weeks.


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