TCC Podcast #41.5: The "Mentee Mindset" with Kevin Rogers - The Copywriter Club
TCC Podcast #41.5: The “Mentee Mindset” with Kevin Rogers

Copy Chief Kevin Rogers is in the club for a special inbetween-isode. This is a rare, second episode this week and it’s a good one. Kevin shares his journey from high school drop out with ambitions of stocking shelves at the grocery store to highly paid copywriter, then chief of his own community for copywriters and other business owners. Here’s a sample of what we covered:
•  How Kevin landed his first job (and had to create writing samples first)
•  His “go with your gut” principle for writing good copy
•  How relationships propelled his career forward and the “mentee mindset”
•  His four-part joke formula for creating stellar sales hooks
•  The three rules Kevin follows when he gives a speech (and the results)
•  What it takes to be an expert in something (and why most writers should have a “bat signal” talent)
•  John Carlton’s Pro Code, and
•  What really makes Kevin angry

Plus we got the details on Kevin’s upcoming event in St. Petersburg called Copy Chief Live. It sounds like an amazing event that anyone who writes copy that gets conversions might want to check out. One more thing: it looks like Kevin may have set a new record for links on his show notes page. And it’s easily the funniest list we’ve ever published (at least until we get to Carrot Top. That guy’s not funny). Check them all out. And don’t forget to click the play button below, or scroll down for a full transcript.

Most of the people and stuff we mentioned on the show:

Sponsor: AirStory George Carlin
Rodney Dangerfield
Jerry Seinfeld
Sam Kinison
Bill Hicks
Jim Breuer
Billy Gardell
Star Search
Ed McMahon
Carrot Top
John Carlton
Gary Halbert
Gary Bencivenga
CA Magazine
Nothing in Common
Vin Montelo
Copy Chief
Clayton Makepeace
Daniel Levis
Carline Anglade Cole
Rachel Rofé
Ryan Lee
Dean Jackson
Nicole Piper
Todd Brown
Ryan Levesque
James Schramko
Ben Johnson
Ross O’Lochlainn
Jody Raynsford
Wardee Harmon
Parris Lampropolous
Joe Schriefer
Marcella Allison
Henry Bingaman
Copy Chief Live
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
Intro: Content (for now)
Outro: Gravity

Full Transcript:

The Copywriter Club Podcast is sponsored by Airstory, the writing platform for professional writers who want to get more done in half the time. Learn more at

Kira: What if you could hang out with seriously talented copywriters and other experts, ask them about their successes and failures, their work processes, and their habits, then steal an idea or two to inspire your own work? That’s what Rob and I do every week at The Copywriter Club Podcast.

Rob: You’re invited to join the club for this special in-between-i-sode as we chat with copywriter and copy chief, Kevin Rogers, about his journey from standup comedian to highly sought after copywriter. The joke formula that became his secret for writing great hooks, mentoring other copywriters, and a special event he is putting together this Fall.

Kira: Hey Kevin. Hey Rob. How’s it going?

Rob: Hey guys.

Kevin: Hey.

Rob: Kevin, it’s great to have you here.

Kevin: Man, it’s great to be here with you guys. Appreciate you having me. This will be a lot of fun.

Rob: Yeah, we’ve actually had you on our list for a while, Kevin. Wanted to talk to you. You’ve got a lot of stuff going on, but let’s jump in maybe and start with your story, where you came from and how you got into copywriting?

Kevin: It felt like a miracle when I found copywriting. It was like lightning striking twice in the best way in your life because I spent 10 years as a standup comedian and that was such a miracle thing to experience. A high school dropout, just had no direction. I was restless and I really hated, at one point, showing up to school every day. It just felt stupid. I don’t know what … This isn’t for me. I wasn’t going to pursue college, and I just thought it was so much cooler to work at my job stocking shelves at grocery stores like, “If I could do this all day, I’d have it made.”

Rob: Aim high.

Kevin: Yeah, that’s right. Quickly came to the reality that it’d be good to have something going on in life. “I don’t know what I’ll do.” Was funny enough, I was really good, I understood comedy and I loved getting laughs. My mother inspired that when I was a kid. She was my biggest … As mom’s are supposed to do, they love when you’re funny. I always had some kind of bit working, and she would, when friends would come over to the house, she would have me do my latest bit, be like an impression or I’d be wearing my little cowboy outfit and I’d do a Western accent.

They were all stoned because it was the 70s and so they were a great audience, and I was killing. It really embedded in me at a young age that, “Wow, this feels good. I like this whole laughing stuff.” It was perfect timing because in the 80s, all the HBO comedy specials started coming out. They always had Carlin and some people like that doing their yearly specials, but I don’t know if you remember Rob. Kira, you may be a little younger for this, but I’m 47. I don’t know your age, Rob, but in the 80s these great specials were coming out, these Dangerfield, Rodney Dangerfield specials, and it was the first time anybody had seen Jerry Seinfeld and Sam Kinison, and Bill Hicks, all these amazing comics.

We just soaked those things up and recorded them with our VCRs, and wore those tapes out. I could do everybody’s act from those specials, so we’d go to parties and everybody would have me request all these different bits. What was interesting was, obviously I loved getting the laughs but I found two things. One was I started to really dissect why people were laughing and more importantly why they weren’t laughing sometimes. I’d realized, “Oh, you know what? I tried to follow that Seinfeld thing with that Kinison thing and that’s not going to work.” I was always dissecting, reverse engineering the science behind getting laughs.

The other thing I learned was, it was much more exciting when something spontaneous would happen in the moment, rather than just sort of repeating other people’s material so that got me excited about potentially writing my own stuff and really just being in the moment with comedy. That’s how that started and basically on a dare, did an open mic and was hooked. That was it. It was three minutes that changed my life. It was supposed to be five, and I told the owner, “Five minutes? I need like 20.” My first time up there, they’re like, “You’re an idiot.”

I get up there and I’m like, “Goodnight.” It was like three minutes, but I came off stage a changed man and that was it. Fortunate to get the house emcee gig in that club. Didn’t realize at the time how valuable stage time was and so I was doing eight shows a night after four months of starting and did that for like a year, which was incredible. Made lifelong friendships there with guys like Jim Brewer who you might know from Saturday Night Live.

Rob: Yeah.

Kira: Oh wow.

Kevin: Yeah. That was his own club. Billy Gardell used to come there and he’s still one of my best friends. It was just an amazing run and I did about 10 years professionally, about 7 years straight on the road, and started wanting to do other stuff. Went in the gym, I had to make the really tough choice to stop because frankly I didn’t know anything about business or marketing and I was of the mindset that success just happened to people. I didn’t realize that you could engineer such a thing. I didn’t see it happening for me in stand up because I just never clicked with the important people.

I felt like they were part of this other culture that I wasn’t welcome in. Some of it was self-destructive, like I threw a star search addition in front of Ed McMahon because I hated what he said in the beginning, which is, “Tonight we might find the next Carrot Top.” I was like, “Yeah. Like hell we will. Not during my five minutes we won’t.” Broke every rule and went up and swore, and did my set but I wanted to kill the room. All these comics were going up and not being themselves and it was really annoying me. I was like, “Screw that. I do this for the moment and I want to kill the room. These people came here and look at them. They’re showered. I want to kill this room,” and so that was always my role, just kill the room, so that was it.

I got out when I wasn’t getting any signals that somebody was going to come with their magic wand and give me this amazing career. Glad I did because it forced me to go legit, doing air quotes, and did a lot of oddball jobs. I was a bellman, I was a bartender and that led me to copywriting in a strange way. Ultimately that’s when I discovered it, but I’m sure you guys and everybody listening, you just feel like, “What is this?” I used to tingle. I still get chills thinking about when I first discovered copywriting and started to understand it, and started reading Carlton and Halbert and Bencivenga and just going, “This is magic. I can’t believe this has existed all along and I never knew about it,” and just became obsessed.

Rob: I totally relate to that. I remember seeing ads in a CA magazine, targeted advertising agencies, but they were by Wall Street Journal and they profiled all of these great writers and designers. I remember reading these ads and thinking, “Wait a minute. You can do this?” Like the light bulb moment. I’m like, “This is… Yeah, I want to do this. This is for me.”

Kevin: I remember the first time I ever thought it would be an amazing thing to do creative work like that. I was already doing standup but standup is a very individual art. Standups are terrible improvers, in actual improve, like part of a team because we’re just looking … We all want the punch lines and so there’s no…

Rob: Not a team player.

Kevin: Yeah. No reciprocity, no yes/and. It’s just, “Look at me!” It’s just like everybody is trying to get there faster, but I remember, Rob, seeing the movie with Tom Hanks and Jackie Gleason called Nothing In Common. In that movie. Tom Hanks’s character was a creative director at an ad agency. Just seeing him and his team create ads and sit around and throw pencils into the ceiling and and do all this creative brainstorming, I thought, “Wow, that would be the greatest way to spend a day, even better than stocking shelves.”

Rob: Barely, just barely.

Kevin:Yeah, it would be even better and now it’s essentially what I get to do with hundreds of people every day so it’s fantasy personified.

Kira: Kevin, once he found out about copywriting and you found a magical one to jump into it, what did those early days look like for you? How did you land those first few jobs and what did those look like?

Kevin:  It was a lot of fits and starts. It was like, “All right, discover it, get excited,” and the only real course out there at the time was the Masterson course, which is still a great course, so devoured that. Sent in my restaurant letter, already was starting to feel a little too formal to me that the whole getting notes from… I don’t know. It’s like, I just felt like whatever this is it’s going to come from within and I have to somehow be in a position to do it in order to understand who am I as a copywriter? Then the tricky part is, well, who’s going to pay you to do it or who’s going to even let you do it?

I got real lucky when I found out another friend of mine who I knew from comedy, who’s also a great television writer named Vin Montello, was taking the same course. Just though a fluke, I learned that he was doing it and so we immediately connected on it. Vin was a little ahead of me, even though I had been studying it a little longer. He wasted no time getting people to pay him to do it because he’s a smart business guy so Vin showed me the ropes on how to get clients. He introduced me to a thing called the copywriting board, which was an amazing place, which I basically modeled Copy Chief after as far as the forum goes.

I’ll tell you exactly how my first gig went down. Vin told me, “Hey. There’s a guy in the copywriting board looking for an autoresponder series. Tell him your normal price is this, but you’ll write all five emails at this price as a bulk discount or something.” I’m like, “All right. Perfect. I’ll go do it.” I said, “Only one thing. Well, what’s an autoresponder?” Literally, I kind of heard of it but I didn’t even know and he explained it to me and so the guy says, “That sounds like a good offer. Let me see some samples.” I literally, that night, sat there at my kitchen table and wrote out a made up autoresponder series for a golf product and I don’t even golf. I’ve literally golfed once in my life, but it just seemed like I can write about golf. I don’t know why, but chose golf.

I did it and it was really fun to write, and I turned it into the guy and he hired me. He said, “I want you to know that your price was a little higher than some of the other offers but I can tell that you really get it.” It was really eye-opening. It showed me a couple things. Number one, other people charge less than you might expect. Number two, not overthinking stuff is sometimes the best method. Go with your gut and a lot of times it’ll be right. If you’ve been studying copy and you really are passionate about it, you’ve probably got enough knowledge to get going. We all freak out and think it’s this big formal thing to actually get a gig. I’m not saying lie or fake it to make it, or any of that, but I think we’re all very guilty of way overthinking what it takes to become a professional in this industry.

Rob: Kevin, I’ve heard you somewhere talk about how the thing that rocketed you into the limelight was what you did around hooks and it was a joke formula, or something like that that you turned into an e-book. Tell us a little bit about that process and where the idea from that came and what you’ve done with it.

Kevin: Well, the first thing that really helped me was John Carlton, like getting into John’s world is the thing that fast tracked me to a higher level.

Rob: How did you do that? How did you connect with John?

Kevin: Well, I obsessed on John. I got to this point. I think your listeners will relate to this. So now I’m working as a copywriter. I had that first gig, that autoresponder series, and basically never not had a client after that. There would be gaps, but it’s amazing how fast it happens. I’ll tell you this. When a copywriter should be a copywriter, two things happen. They get good. Really good, really fast. Within two or three years, are shockingly well off in their career. It does not take a long, long time to be in the flow and working and getting paid well to do this, if it’s for you. I’ll avoid the sidebar, but John was my obsession, so I was working as a freelancer, but I’m reading, and it must be even worse now because there weren’t that many resources then.

There was the copywriting board. That alone had reams of like mind blowing stuff, but then Clayton Makepeace had his blog at the time, which was just crazy how good the content was. He had Daniel Levis and Carline Anglade Cole writing articles. I’d be halfway through a client’s sales letter, and I’d read something on one of those places, and it would be so mind blowing to me. Suddenly I’d be like, “Oh. Yeah, I get it,” and I’d feel like if I don’t incorporate that tactic, I’m not doing my best work. I would kick over the anthill and start the sales letter all over again just so I could implement that tactic. It was really messing me up because it was taking twice as long to do jobs, so trying to implement what I was learning in real time was actually hazardous, although necessary.

What I decided was, “All right. Here’s what I’m going to do. I’ve got to get rid of the overwhelm, and I’m going to choose one great copywriter, and I’m going to study only them,” because my theory was if I can get half as good somehow as one of these great copywriters, I’ll be really good. I’ll be better than 90% of the people out there if I can just get half as good as one of these legends. I pretty easily made the choice of studying only John and turning off everything else just because John’s writing really resonated with me. I found it very exciting. His kick ass marketing copywriting secrets of the marketing rubble I’d listen to over and over and over in my car.

John was my guy, but there was not a lot of Carlton out there at the time. There was no simple writing system. He had no course. It was just like bits and pieces of stuff that was on YouTube. I would go to marketing events or copywriting events and all I wanted to talk about was Carlton. I would ask people, “Hey, do you have any Carlton stuff that I …” I remember Rachel Rofé had his collective letters. It was like the equivalent of being a deadhead and bootlegging. I’d get something like that, and they were like, “Oh my God.” It was like a gold mine. You wouldn’t see me for three days.

When I finally got into John’s world, was earning enough money to buy into his forum, I wasted no time trying to shine and get his attention, and offer a lot of value in there through a few little favors I did for John. He was going out of town, and he said, “Who wants to take over the critiques this week,” and I jumped on that. When I had his audience, I just wanted one thing from him. I said, “John, all I want is if you could look over a couple of my pieces and just tell me, do I even know what I’m doing?” I was at that imposter syndrome stage of my career where it was like, “People are paying me and they’re getting results, but what if I don’t even know what I’m… What if I’ve just been lucky?”

John read my stuff, and he said, “You know, there’s a few things I would maybe do differently but overall I can see that you’ve got the goods and you know what you’re doing.” That was all it took for me. When I had John’s stamp of approval, I was like, “All right. Lights out. No more hesitation.” Things really took off after that. That’s short story of how the Carlton thing went down. Mentors are everything. To really get the best value out of a mentor relationship, you have to have what I call the mentee mindset. What it does is it forces you to reassess where you are and how dedicated you’ve been and what kind of moves you’ve been making.

Just like signing up with a mentor makes you better instantly because you’re sending a signal to yourself that you’re worth the investment, and that alone is really life-changing. That was a huge first step so then I was at the point in my career where five, six, seven years in and things are great, progressing. The client work keeps getting better. The money keeps getting better, but I keep finding myself every December as I look back on my year saying the same thing, which is, “This is all great, but I really need to get my own thing going at some point. I can probably only do this client work thing for so long because it’s unscalable,” but I didn’t know what that was.

I was starting to experiment with some products, did like warrior special offers and really rinky-dink stuff that at least got me in the groove of creating products and seeing how they resonated back in the day. I have no idea what it’s like there now, but it was a cool platform to just test out your ability to deliver a product. I needed a bonus for one of the products. I can’t remember what it was. I just had this idea. John had taught me, he’s like, “Why aren’t you talking about the standup stuff? That would be a great way for people to remember you. You have to understand that so many people would find that fascinating and want to hear about it.”

I was like, “Oh yeah. Wow. That makes sense,” but I learned to not talk about standup because it would always cost me real jobs so I wasn’t even talking about it. John was the one who said, “Why don’t you write an article about it and I’ll put you as a guest poster on the guest author on the blog,” his legendary blog. I was the first ever guest post on his blog. It was an amazing honor. People really loved hearing about the stand up. I was like, “Okay. Wow. There’s something going here.” When I needed a bonus for one of these small offers, I thought, “Well, that’d be cool. I’ll take a joke formula and I’ll change it to be a sales hook formula.”

Honestly, to be totally transparent, and again, this is that not overthinking thing, I didn’t actually have the joke formula. I just knew what a good salesman formula was, and I knew there must be a joke formula similar to it. I was going on my experience and all the things I had sort of instinctively learned as a standup to guide this thing, but I didn’t even have an actual joke formula when I first released it. I just skipped straight to the salesman formula part, said it was based on a joke formula. It was identity struggle discovery results. It was good. People resonated with it. I got a lot of good feedback on it, but I’d sort of tucked it away. It was just a little made up bonus.

Then, life-changing moment number whatever, Brian Lee invites me to speak at his event called SAM, Sales Advertising and Marketing, based on, it was a Ted style event in Park City Utah. This is back in probably 2012. It was very exciting. I hadn’t thought about even speaking at a conference, and I thought, “What will I teach?” I had three rules for myself once I accepted. I said, “All right. I got three rules for this 18 minutes. Number one, I’m going to do my time.”

Rob: No, “Give me 20 minutes,” and then only fill three.

Kevin: I was actually more afraid of going over. I didn’t want to be that guy. Nothing worse than comics who don’t respect the time. They’re disrespecting the other comics and everything so I was like, “I’m not going to get up there and go over.” Ironically Rob, I did end up going a little short, hilariously. Rule number two was I’m going to get three laughs, and rule number three was I’m going to teach the most actionable thing they hear over this two-day conference. That was my criteria, and I think I did it but I was the last speaker of the event. I didn’t know how to take that-

Rob: A lot of pressure, yeah.

Kevin: I was like, “Is this an honor or is this…” Well, at this point, everybody would be so tired, Kevin can blow it and nobody will mind, right?” I didn’t know how to take it. It was a lot of speakers because it was 18 minutes each. It was in the theater. The stage was beautiful, and they did a really cool thing. They would have a marketing talk and then they would have a musician go up and play a song or two. It was this really cool mix and variety of different stuff so it never felt tedious for the crowd. Although, at the end of two long days, everybody’s brain is just fried. It did really well, and I taught…

I don’t remember. I think I called it then like the KLT formula. It was all about how to generate know, like and trust with your audience. I probably should’ve just stuck with that because it really resonated. I’ll tell you something interesting, a little side lesson. People started referring to me after that as “The thing Kevin teaches: know, like and trust.” I’m like, “I didn’t invent that.” That’s been around for years, but because I owned it, and I gave it a title, and I taught it my way, people instantly started calling me the “know, like and trust” guy. I was like, “Oh. That’s eye-opening.” Another great lesson here. Don’t think that because something’s been taught before that you can’t teach it a new way and sort of own it. It’s really powerful.

Rob: Yeah.

Kevin: After that happened, a lot of things changed. One more great lesson was totally overthinking the book, planning it out for six months, bought some coaching from Dean Jackson, went to his Mastermind and he was just exploring his 90 minute book thing, and said, “I want everybody in here to do one.” I realized mine was done, just needed to put the thing out, and so instead of writing the book, like going to lock myself in a cabin and smoke a pipe for six months to write the stupid thing, I just transcribed a talk I’d given on the 60 second sales. I gave it that name, put the cover on the book and life changed dramatically after that.

Kira: Kevin, it sounds like this hook really changed your business dramatically, like you said. Do you think new copywriters, or maybe even all copywriters, need to figure out what their thing is whether it’s their formula or their method, in order to really become this … We all want to become authority figures and stand out. Is that what we all need?

Kevin: 100%, 100%. I’ll tell you this, I will put a caveat on it. You do not have to become an authority to succeed in this business. However, if you want to really own it and call the shots and get top dollar from top level clients, you have to do it. There are a lot of shy writers, very introverted. I’m an introvert. I’ve learned the art of extraversion but I’m at heart an introvert. I get very drained after long stretches surrounded by a lot of people. I need to power down, but if you’re just not going to do the authority stuff, you don’t want to be in the spotlight, you can still have a great career.

However, doing some authority stuff will teach you a lot about yourself. You’ll be sending signals to yourself that you’re worth it, you’re special, you deserve to be paid attention to, you have something valuable to teach. It’s exciting to take all this knowledge that we procure along the way to becoming good copywriters and being able to share it and teach it and light up somebody’s brain who’s a couple of steps behind you on this journey. To be an expert in something, you only need about 10% more knowledge than the person you’re teaching. You’re their expert, so again, I’m not saying this to cheapen the gravitas it takes to do it well, but again, I think people wait around too long for some signal from the heavens or something that it’s time for them to go out and teach.

You should be teaching all the time. It’s the easiest and most powerful way to create content. Yes, Kira, to answer your question, every copywriter needs to do it. You may not stumble on it immediately like I did. I got a little lucky, but the truth is I’d been blogging for years before I had a reason to blog. I just had this innate sense that it would be really valuable for me and hopefully a few readers if I shared what I was learning along the way so I started a blog because I felt like you’re supposed to have a blog. I would basically write endlessly about John Carlton about how amazing he was.

Rob: A fan boy blog.

Kevin: Yeah. That’s basically what it was, but people really resonated with it. I had 300 subscribers for the longest time to my blog and I’d get between five and ten comments on a post, but it really taught me what resonated. It gives you a through line when you start to look back and go, “All right. Nobody cared at all when I talked about that, even though I thought it sounded genius when it wrote it. Nobody cared at all,” and something sort of unrelated to copy got a huge response and maybe there’s more there or more meat on that bone. 100% need to be creating dialogue with your audience no matter how new you are to this.

Rob: Kevin, you’ve done a lot of coaching with writers who were building a platform for themselves. How would they get started in your opinion? Is it starting a blog? Is it writing a book? Is it something else now? Is it a combination of all the above? What’s the best way to do that?

Kevin: I think the best way to do it is to just go where the need is. The hardest part is what’s going to be my thing? I call it a bat signal talent. Here’s how I describe it. It’s not the only thing you do, but it’s one thing that you do particularly well and really enjoy. That’s key. You have to have fun doing it. You have to like it. You should also combine with your other experience. We can’t all just be copywriters and all we talk about is copywriting principles, because that has been talked about to death. What’s that other thing you bring into it? For me it was standup. Well, that’s an easy choice. Well, yeah, but I went out and did it for 10 years, so it’s nice that it paid off well and it was a really colorful combination but I’ve trained people who did seemingly boring stuff like WordPress or other things. It had allowed them to really stand out as a copywriter and specialize.

I call it a bat signal talent because when people know you for it, it comes up, hey, who knows about, say, branding? Nicole Piper is someone, she had 22 years in the trenches of high-level branding for like the Nickelodeon and she was doing what I did with standup going, “Oh. Well, that was my other life and not I’m just a beginning writer.” No. It’s all you. All of you needs to show up for everything. When that happened, her career just exploded and she gets bat signal now, so in Copy Chief somebody will say, “Hey, I’ve got a branding question,” and people are immediately tagging Nicole. That’s what we call bat signaling. It’s one of the most powerful things you could do for your career when you become known and get bat signaled for something, so that’s why specializing is so powerful.

Kira: Yeah, and I love that idea of showing up as the full you. Everything you’ve done in the past, not forgetting about those last five jobs and just showing up as a copywriter, that it all counts. I think that’s really important. I want to pivot a bit. You host three podcasts, which is quite impressive. You’re managing this group. You’re doing a lot. You’re planning an event, which we’ll talk about soon. How do you do all of it? How do you manage it? How do you make it all happen?

Kevin: It’s pretty insane.

Rob: It’s crazy insane.

Kevin: Yeah.

Kira: I want to do it.

Kevin: I don’t notice until I look at, “Wow, that was…” I literally had four promos going last week. Here’s the thing. I don’t want to be called a machine, “That guy’s a machine.” I care a lot about making it all really personal. I only want to talk about things that I’m excited about so I only promote three other people’s products in the world: John Carlton, Todd Brown, and Ryan Levesque because they’re incredible products. They’re really life-changing stuff, especially for copywriters, but how do I do it? Now the answer is, I have a team and that is one of the most tricky things I’ve ever had to pull off is assembling a team and leading a team. It’s a whole different skill set.

I used to hate when people said that, “Oh, you’ve got to outsource and you’ve got to …” because I’m going, “What does that even mean?” I’m just trying to get any attention right now. Looking back to when I first started Copy Chief, I don’t say it almost killed me, but man, it was supposed to be … Here was the irony. I told you that I had this ongoing dialogue with myself, got to get my own thing going. When I discovered that a form could be it through one of my brilliant coaches, James Schramko, it was easy to do because I was just following his model. It was also incredibly daunting.

I still had a full client load and we were doing serious work. I had a writing partner, thank God. There’s no way I could’ve ever done it. Ben Johnson who’s a brilliant copywriter, we were partnered for five years, but we were doing $50,000 launch packages, one every couple months, like really, really intense work. That took up all of my brain. Now I have this side job, and once I launched Copy Chief we quickly became a second full-time job. To be honest with you when I look back at that first six months of Copy Chief, I was like, “Why did people stay with me?” Seriously, there was no onboarding, but these hundred people, most of whom I’d never met, came rushing in the minute I opened the doors to Copy Chief.

They were brilliant. They were amazing. Ross O’Lochlynn and Jody Raynsford and Wardee Harmon and these people who are a little more known now, I’d never met. A lot of them still in other jobs. I don’t know what to equate it to, just some small team of ne’er-do-wells but all really passionate and then you look back. It was like the beginning of Apple or something, not to ever be silly and compare the two things, but you hear those stories of like, “They didn’t know what they were doing. They were just in a garage trying to build a cool computer.” It was that sort of thing, but now I had to try to split my brain and this constant stress of, “Oh man. I’m not answering this post or that post, and people are going to get frustrated.”

Copy Chief was supposed to be the answer to my overwhelm with client work and it only doubled it in the beginning, so that was a huge problem. It’s just one of those things you have to go through if you want to find out what else is out there. I did it all myself for a while, then the beginning of last year I made the decision to just fire all my clients and say, “I’m going all in on Copy Chief. I’m going to reinvent how I get paid.” I literally had told people, “Stop sending those checks.” A lot of it, I’ve got to tell you, it was easy money. Look, if you want to have integrity in this business and build a reputation, you have to listen to that instinct that says you’re not serving this client, like you’re not giving this your all.

So I severed everything. I need to go see if I can make Copy Chief into what I think it can be. I’ll tell you, man, it was a tough year. I had to reinvent how I make money. The membership fees for Copy Chief were nowhere near my revenue from freelance work. It wasn’t like I got to step off the ship, the sinking ship, onto land like Jack sparrow in Pirates of the Caribbean. It was like, “Go swim, man.” So yeah, there were definitely some lonely nights and some minor freak outs, but I was having fun and I got to discover what is it people really want from me?

Then, Kira, to answer your question, you’ll notice I’m not very direct in my answers. I’m sorry. At that point I started to say, “Well, one of the things I have to invest in here is help,” and so I started to recruit from within Copy Chief and put people on whatever payroll I could make sense of. A lot of it was in trade for coaching so then there was the irony of like, “I need this person’s help, but in exchange for their help, I’m teaching them how to be busy with freelance work so they don’t have time to help me anymore.” You know what I mean? It was just a lot of figuring it out as I went and then happy to say this year, it really feels like a company. I have staff that are with me and have been with me. They’re amazing. Now, it actually is easier than it ever was, but getting here was daunting.

Rob: It’s impressive what you’ve built. I’m curious, Kevin, in your relationships with the writers that you coach, what are some of the big mistakes that copywriters are making? What are some of the big opportunities that are out there, but maybe people aren’t seeing?

Kevin: The mistakes I think I’ve touched on a little. Tactically, you’re going to make mistakes and you’re going to learn from them. One inexcusable mistake is not raising your fees. Let me say this. The foundation to my answer to any of this is, you’ve got to be good. You’ve got to follow what John Carlton calls the Pro Code, which is showing up on time, having done what you said you would do. Pretty simple. Don’t be the kind of person who breaks that code. Don’t miss deadlines. I hate this BS about, “Oh, deadlines are a suggestion.” No, be the kind of person who is known for hitting that. You have no idea how frustrating it is for clients to find out that you were very on time in collecting their money but gave no credence to their deadline.

If you’re missing deadlines, it’s your fault because you didn’t set the tone and the criteria for how this is going to go down with your client. They’re looking for you to be a leader and say, “This is how this is going to work. This is what I need from you.” Your client needs to have as many deadlines as you do in getting you the stuff you need to do good work. So when you establish with them that they have deadlines and that if they miss those deadlines, it does not mean that the project gets pushed back a week because they forgot to tell you they were spending a weekend in the Maldives, and couldn’t get you those files or couldn’t give you an interview. Screw that. That means they lost their deposit.

I’ll tell you the most uncomfortable conversation I’ve ever had in my life professionally was telling a client, a good client, a repeat client, that his $20,000 deposit was now mine unrefundable because despite my repeated request for the information I needed, he didn’t give it to me. Believe me, that was very counterintuitive to a former hippie comic, but the truth is, we’re freelancers and we live and die by our calendar and it’s imperative that your client understands that. You’ve got to show up big and not be timid. They’re looking for you to run the game here. That’s why they’ll hire you. That’s was Carlton calls being the adult in the room.

I’ll tell you the outcome of that. That client said to me, to his credit, he said, “I don’t like it, but I respect it and let’s look at your calendar. When can I get back on?” Then he paid me another $20,000 to get back on my calendar. That was incredibly eye-opening, and he remained a great client. We did like two or three other projects together after that. That’s the level of respect that you should have for what you do and what you should demand from the people who hire you. Otherwise, what’s it all about? What’s the point? Why would you be stressing over $1000 and feeling pressure from some fly-by-night wing nut who wants to tell you, “This better convert man. Your reputation is on the line. I’ll tell everybody if this sucks.”

I’ll tell everybody right now that you suck. How about that? It just gets me angry. I hate the way I see some people talking to freelancers in this business. You’ve got to buy in to your value first and then set a standard. It’s not about being cocky or arrogant. It’s about knowing that you’re going to pour your heart and soul into the gig, and if you’re willing to die for it, then they should be willing to meet you halfway there. What was the question?

Kira: Oh wow. I need to share this with every single copywriter. We need to wrap up and I want to ask you about your event. You have an upcoming event. We’ve seen the video, it’s hilarious. Rob and I are both going to be there and we’re really excited to be there, and we’ll figure out some type of event for the copywriter club to accompany that.

Kevin: Oh great.

Kira: Can you just share more about what we can expect, why we should be there?

Kevin: I’m going to get even more excited. I discovered something about myself, and this will be valuable to copywriter, but some people have different motivations. Like I said, I get that some writers are very shy. I discovered that I am performance driven and for me, having a live gig on the books is the greatest gift in the world because I fantasize about it for like every day leading up to it. I just can’t wait to get onstage and feel the audience and affect the audience. It’s where I live. To be able to host my own live event is an amazing gift. It’s me at my best for three days, two days officially, and then an extra day for my members.

I’ve been very blessed. I’ve cashed in all the relationship capital I’ve built up over my career. I’ve got John Carlton speaking. That was my big get, obviously. How many times have I mentioned his name? He’s everything to me. Whatever you think about him, he’s twice as brilliant and twice as bighearted as you could ever imagine. He’s also an amazing musician. The fact that John and I, as part of this event, are going to perform together, our own passion crafts on the same night, I’m going to do stand up and then John’s going to play with the band, that is such a fantasy to me that it’s just going to be amazing, but the event itself, it’s kind of closed-door content.

The things that the speakers are sharing are things they’ve all promised me they’ve never shared anywhere else. Some of these speakers are people who do not share very openly. For instance, Parris Lampropolous, who is one of the greatest living copywriters on the planet is very secretive. He’ll speak at a Clayton Makepeace event occasionally but they’re usually like $5000+ events. Parris and I are very close. He’s willing to do this for me, but this is a man who doesn’t even, he won’t even give me a picture.

Kira: What?

Kevin: Yeah. He won’t even… Look on my podcast. I have a hundred and whatever, 20 episodes. One guest doesn’t have a photo and he’s the guy with an amazing two-parter and it’s Parris. I’ve called in all my capital man, and so Parris, John Carlton, Joe Schrieber from Agora, Marcella Allison, Henry Bingaman. I look at it … There’s like three … Todd Brown, like crazy. As far as the content goes, there’s three categories. There’s the legends, which is John and Parris teaching us something they’ve never talk before. There is what I’m calling the Chiefs, which is real working copy chiefs at the highest levels, which is Henry Bingaman who’s the new copy chief and creative director at Natural Health Sherpa.

Then there’s Joe Scrieber, who is the copy chief at Agora Financial, which is on track to make $170 million in sales this year, and here’s what’s amazing about those two speakers. Guess why they’re extra willing to come present at this thing? Because they need copywriters. They want to meet copywriters, so how cool is that? Not only are they-

Kira: That’s why I’m going.

Kevin: Yeah. I want everybody going, “Who’s going to kill this room the hardest?” You better show up ready to kill this room because everybody’s bringing their best stuff, and so they’re trying to impress you because they want to hire you. How cool is that? The networking is going to be totally through… Oh, and the third category is the A-listers. Marcella is the only copywriter I know who’s ever been chiefed by Clayton Makepeace, Parris Lampropolous, David Deutch, Mike Ward and Mark Ford. Crazy, forget about it. She’s amazing. She’s brilliant. She’s so cool. Then Todd Brown representing the marketers.

If you’re a marketer, you’re going, “All right. Great, but I don’t want to be a copywriter. I’m not even really looking to hire a copywriter.” Well, Todd’s the guy who takes the highest level copy stuff and puts it into marketing funnels and he’s amazing at teaching it, so I’ve get everybody covered. It’s going to be a lot of fun because I’m going to be making relationships. I’m getting on the phone with every single person who buys a ticket to this event because I don’t want the networking to be about dating. I don’t want dates to happen. I want honeymoons happening all around us. People that I’ve already connected and are already working on-

Kira: Babies, you want babies.

Kevin: Yeah, I want babies, Copy Chief babies nine months from now. The other element is I want to show people that, like we talked about before Kira, what is that other thing you bring to it? All of you all the time and I want to put that on display and that’s why I’m doing standup so you can see that the way I write copy is because I think like a standup comic. The way John Carlton writes copy is because he plays lead guitar and sings with a band. That’s the intangible. That’s the thing that you’ll bring to a copy project that no other writer could and I want everybody to leave there inspired to go, “Wow, I’ve been ignoring my passion. I need to light that fire again because that’s the thing that’s going to make me a really great copywriter.”

Rob: We’re excited to be there. Kira and I are both going. We’re looking forward to connecting down there with everybody, but stuff to learn as well, it’s just going to be a great experience.

Kira: Yeah. Selfishly, I’m excited to hang out with the club members and with you Kevin, but selfishly I’m going because I want those connections with people I would not meet otherwise.

Kevin: Yeah, that’s what I’m all about. That’s the thing. I’ll be talking to you guys about, “All right, in your own careers, what’s up? What do you want? What are you passionate about? What’s your specialty? What have you written?” I want to deliver, especially the people who I know are there looking for copywriters, in their gift bag I’m going to put an envelope with a welcome letter and a list of names of people they need to make sure they talk to during the event. I am not leaving the networking to chance at this thing.

Rob: So tell us dates and at least initial price.

Kevin: October 9 and 10th. That is Columbus Day right here in St. Pete. Get there on the 8th, which is a Sunday night. For my members, there is a special day, Wednesday, where we’ll do some really cool stuff, a lot of freelancer focus stuff. When tickets go on sale to the public, they’ll be $1299. Prices go up every two weeks so you’ve got to have that urgency. There’s only a hundred seats by the way, and 30+ are sold already just in the first couple weeks here in Copy Chief. I want this thing sold out as quick as possible so that I can really focus on making it even more spectacular than I’m imagining now. I don’t want to be worrying about filling seats as this thing is approaching. I think the price is a screaming bargain for what you’re getting. Again, my goal is to have you look back on this as the event that changed everything for you.

Rob: I’ll add, we don’t have an affiliate relationship here Kevin. We’re sharing it with our group because we think this is going to be an awesome opportunity, and so we hope that people take the opportunity to hook up with Kira and I and everybody else that’s going to be down there. It’s going to be a lot of fun and maybe more importantly a lot of learning and connecting.

Kevin: I appreciate that. I’ll do whatever I can to make it extra cool for your club to be there and to hang with you guys, maybe even sneak them in side doors to different stuff.

Rob: That’d be awesome.

Kira: Awesome.

Rob: Okay Kevin, aside from the event, if people are looking to connect with you online, obviously you’re everywhere. Podcasts, Copy Chief, but what’s the best place to find you?

Kevin: Good luck not hearing my voice.

Rob: All Kevin all the time.

Kevin: is where you can find everything, the podcasts. There’s only one podcast that’s not there. That’s the one I do with John. That’s called Psych Insights for Modern Marketers. That’s the worst URL ever It’s a great podcast. It only happens occasionally, but it’s always magic. Yeah,, if you go there and only see the wait list page, when you come back, you’ll be able to see the blog and everything else. Lots of great content there. Yeah, that’s about it. Also, an app, a free app if you search in wherever you get apps for Copy Chief, you can get all the content on your mobile phone. Really cool app for members and nonmembers so check that out as well.

Rob: If people want to join Copy Chief, we’ve set up sort of a referral. We might be able to sneak people in outside of the wait list or whatever, but they need to reach out to us individually to find out more about that. Cool. Thanks Kevin. This has been awesome.

Kira: Thank you, Kevin. Yeah. Seriously. I’m pumped up. This has been incredible. Lots of great advice. Thank you. I’m excited to see you in October.

Kevin: Likewise. Thank you. It was a lot of fun. Let’s do it again.

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