TCC Podcast #223: The Ins and Outs of Cold Pitching with Chris Collins - The Copywriter Club
TCC Podcast #223: The Ins and Outs of Cold Pitching with Chris Collins

Copywriter and philosophy graduate, Chris Collins is our guest for the 223rd episode of The Copywriter Club Podcast. He’s a member of the Underground and the Copywriter Think Tank so we’ve seen first hand how cold pitching has transformed his copywriting career and helped him get the clients he wants.  We knew this is something we wanted to hear more about directly from Chris, so we asked him about…

•   how being a mommy blogger launched his career
•   how he saved himself hours of time streamlining his pitching process and scaling it
•   how he got past his fear of cold pitching
•   exactly how many emails should you send to your email list?
•   the importance of building relationships versus up leveling yourself
•   why just learning “stuff” isn’t enough
•   what to do if you don’t have money to invest in yourself or your business
•   why research is critical for a stand-out cold pitch
•   Chris’s highest converting subject line – averaging over a 90% open rate
•   how he combines automating with personalization
•   his not-so-secret shortcut for how he built his copywriting business from 0-10K per month in the same year
•   his advice on pitching if you’ve never had a client
•   what his graduate studies in philosophy taught him about strengthening his copy
•   what he did right in the beginning of his business that you should too
•   Rob and Kira’s advice on getting started and dealing with rejection

To hear more of what Chris has to say, scroll down and hit the play button. Keep scrolling for a full transcript and, of course, you can subscribe with your favorite podcast app to make sure you never miss an episode.

The people and stuff we mentioned on the show:
The Copywriter Think Tank
The Copywriter Accelerator
Chris’s LinkedIn
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
The Copywriter Underground


Full Transcript:

Kira:   There’s an old cartoon that was published in the New Yorker Magazine of a dog in front of a computer, and the caption says, “On the internet, nobody knows you’re a dog.” That might ring true for a lot of copywriters who write for clients in voices that don’t quite match their own, like our guest for the 223rd episode of The Copywriter Club Podcast, Chris Collins, whose first assignment was writing content for a mommy blogger. In real life, Chris is an academic, doesn’t have kids and gravitates to philosophy, not family planning. We asked Chris how he transitioned from mommy blogger to SAS, and in the process, he revealed a ton of tips about the ins and outs of cold pitching.

Rob:   But before we dive into Chris’s story, this episode is brought to you by The Copywriter Accelerator. That’s our program for copywriters who want to build a solid business foundation for everything that they do. Members of The Accelerator work through eight different modules together, and those modules cover topics like branding, pricing, client management, getting yourself in front of the right clients, and a lot more. If you’ve struggled to get transaction in your business, or you’re making a change in the kinds of clients that you want to work with, the kind of work that you want to do, or any other thing in your business, you simply want to get better at your processes and the services that you sell, you owe it to yourself to learn more at

Kira:   Let’s jump in with a question about how Chris got started as a copywriter/ mommy blogger.

Chris Collins:   My first gig was being a mommy blogger, and that wasn’t necessarily where I wanted to be as a writer or where I wanted to start out, but it was just honestly the first gig that I got. I had just been thinking, “Well, maybe I can try my hand at writing online. I’m a pretty good writer. Let’s see how that’ll go.” And the first client I found, she ran a sleep consultancy to help new moms. And she was looking for a blog writer and I sent her something and she really liked what I was doing. That ended up being my first gig for the first six months. And it was the first time that I really understood the power of research actually, because right off the bat, I was writing on topics that I did not know anything about.

I’m not a mom or a dad, I don’t have kids, I don’t have a ton of firsthand experience with kids, but what I could do was research these topics that she would give me. She would want to write about, why do kids wake up in the middle of the night? Or, why is my kid a reluctant pooper? And so I would dig into all these articles and research the why behind this and write I think pretty well-informed articles that… She was really happy with the content, but I also knew that I don’t speak the language of parents. I’m not in that social circle, I don’t know what parents talk about, or are interested in.

Kira:   I don’t know either. What do parents talk about? I have no idea.

Chris Collins:   I don’t know, but what I did to make my articles I guess more relevant was search for phrases like “Potty training” on Twitter, or Facebook or whatever, or things like, “My kid won’t poop.” I would just get all these posts and it was the first time I’d ever searched for VOC data. And I really didn’t know what I was doing, but I would just get all of these social posts where people were like… I was reading what parents were saying in their own words about their kids potty problems. Anyway, I think this is a lot, but it ended up being a really good first experience in doing VOC research and writing about that topic wasn’t necessarily what I wanted to do forever, but it did leave me to other kinds of content writing and copywriting that were a better fit.

Rob:   Before we jump to that stuff though, Chris, in addition to the voice of customer research that you were doing, did you have to adjust your writing in any way to match the mum blogger voice, or does that just come naturally out of the research that you were doing?

Chris Collins:

That’s a great question. It’s been a while since I did it. I definitely felt like I had to go… I looked at a bunch of other mom blogs to see what their voice looked like and sounded like, and I was trying to match that. I was definitely doing some competitor scanning as well, because the way I would naturally write, I think, is a little bit less personality-driven, a little bit better suited to the SAS world where I’ve gravitated to. But for sure, I had to do some research just on, what should the voice of this piece be? What should that look like?

Rob:   In all the research that you did, was there anything that shocked you about children or about parenting that you’re like, “Whoa, I did not know that?”

Chris Collins:   Well, it definitely reinforced my impression that parenting is really hard. As someone who is not currently a parent, I would go over to my sister… My sister has two kids, and I would go over to her house and it was right about the time my niece was potty training and she would be having exactly the kinds of issues that I was writing about. And they had tried three-day potty training without a ton of success. And they tried different things to make it go smoothly. And I would just be like, “He’s to young for that. You should try this.” Mary, my sister, she was just not having it. She was like, “I’m not interested. I don’t want to hear it.” I don’t know, nothing terribly shocking, I guess.

Rob:   But how did this first gig then launch you into gig number two and to the point where you could start your own freelance business?

Chris Collins:   Even as I was writing for this client, I wasn’t making much money doing this, to be frank. I think that by the time that contract ended, I think I was making less than $40 per post. So not a lot. But I was very aware very early on of what was possible in the world of copywriting. I had been following this very podcast that we’re on very early on. And I think I was pretty clear that I wanted to work for better clients and clients that I would be more interested in working for. I started to just try to find clients who were more of an ideal fit.

I think for most of the first year, I was still on Upwork and trying to reach clients on Upwork, and I think it took me a long time to realize that was, for me, not likely to be where I was going to find my best clients, but that whole first year was a process of gradually finding clients who were going to be more in the tech space, clients who were going to pay me better than what I was currently making. I think over the course of the year, I landed… This was over 2019. I landed a couple of four figure projects, which at the time just was a big mind blowing thing for me and just helped me to see, “Well, you can actually make some decent money doing this and you can work on projects that are really fun.”

Kira:   Can you talk about what you were doing before you got into copywriting, your background and education in philosophy and how that background and lessons in philosophy have shown up in business?

Chris Collins:   Oh my gosh. Yeah, I can talk about that. I never ever thought that I would be doing copywriting at all, although I think what’s turned out to be the case has been it’s been a really natural… coming full circle in terms of being something that really leverages the writing and research skills that I developed early in my career. But I started my career going to grad school planning to be a philosophy professor. The thing that jumps out at me the most from that experience was just that when I was in graduate school, it was just very different right off the bat from anything I had done before.

I remember my very first seminar that I was in, we were reading philosophy of language that was just at this really high level that I’d never read anything like it before, I was having a hard time with a lot of it. And we had to write a seminar paper every single week. The idea was, you’re going to come up with something original to say about what you’ve been reading. And for me that was just… I remember those first few weeks just doing the reading and just being like, “I got nothing.” I would write a paragraph and delete it, I’d write a paragraph and delete it. I would just do that over and over again.

But eventually, that first week, I remember, I knew I just had to get something down on paper, so I just wrote out my thoughts, edited it into something presentable and brought them to class. They weren’t very good, but I got through it. And then over the course of the rest of the time that I was there, I just started to learn how important it is to just get all your thoughts down first and then clean them up later. So it really taught me separating the ideation from the cleaning up and the criticism, which needs to come separately, and being satisfied with work that may not be a hundred percent perfect. You can get your work to a place where it’s to a really good point and then you can iterate and improve it from there. So it was the first time I really had to ship work consistently. It wasn’t easy. That’s for sure.

Rob:   I don’t think we’ve talked about philosophy on the podcast, at least not philosophical concepts or anything like that before, so I’m curious, in addition to the writing exercise of getting ideas down on paper, editing, shipping, that kind of thing, are there any ideas from the world of philosophy that you apply to your business or to copywriting?

Chris Collins:   I would say that there’s a mentality that I learned very early on that has stuck with me, which is just that… And I think a lot of people in academia, not just in philosophy, would have learned this, but in philosophy, when you write an article, it’s a lot law, you are building an argument and you want it to be as strong as possible. And so when you share something you’ve written with colleagues or friends in your department or whoever, you just expect that people are just going to vigorously critique what you’ve written, they’re looking for flaws in your argument, but it’s coming from a place where they’re trying to help you. They’re trying to help you make your work better. So they’re looking for issues with your writing that they can help you fix and address so that your overall argument will be as strong as possible.

And so pretty early on, I just learned when I show something to anybody, I can expect it to be subjected to pretty strict scrutiny. It’s going to come under the microscope for sure. And so I just learned to be really laser focused on quality. It just doesn’t feel good to share something that you haven’t really thought through and get it torn up. And that definitely happened a few times when I was in grad school and it taught me to just make what I was writing as strong as possible before I send it out the door.

Rob:   Then, moving from this, you mentioned that you’re on Upwork for a while struggling to find the kinds of clients that you really wanted to work with at the prices that you were happy with, what did you do that changed that in your business?

Chris Collins:   I started pitching a lot. I feel like that’s pretty much the answer. I just hit an inflection point around the end of last year where I’d gotten quite a few clients on Upwork, but I could just tell that it was going to be real hard to break through to an income level that I was going to be happy with on Upwork. I know that some people do use it to either supplement their income or that there are enterprise jobs that you can’t get through there. So, I don’t want to poo-poo it entirely, but I just got to a point where I was like, “I just need to be pitching more clients who are more aligned with the kinds of ideal clients that I want to work with.” And so that was just… That’s really honestly been a big focus for this entire year, has been building and improving my pitching system over the course of the year. And right now, I would say most of the clients who are best aligned with what I would consider my ideal targets are coming from cold pitches.

Kira:   I definitely want to talk more about pitching, but before that, just curious, what changed for you? Why did you choose not to become a philosophy professor?

Chris Collins:   That’s a good question. I wasn’t very good at it. I shouldn’t say that on this podcast. Maybe we should edit that out. Let’s-

Kira:   I think we should leave it.

Chris Collins:   …I don’t know, sure. I think what I would say is, academia is very rigorous and I don’t think it was ultimately what I was meant to be doing with my life, to be perfectly honest, I think. I got my degree and then I taught for a year after that, and I really loved the teaching side of philosophy. And even now, in my writing career, when I’ve done teaching in The Think Tank or whatever, that’s something I’ve really enjoyed, but I think there’s also a side of academia where it’s really important to continually publish at a high level to be really successful. And that is increasingly important as academia moves more and more to this sort of arrangement where there’s fewer and fewer tenured faculty and more and more adjuncts. It’s become increasingly competitive. I just knew I wasn’t going to be able to have the kind of life that I wanted, that I would probably be taking on a ton of adjunct jobs if I stayed in academia. It just wasn’t the life that I wanted to have for myself.

Kira:   Cool. I appreciate that honest answer.

Chris Collins:   Is it too honest? Sorry.

Kira:   No, it’s good. We like honesty on this show. Back to the pitching, we have talked about pitching a bit on the show, but I’d like to hear more about the mindset around pitching because we know it works. We know there are systems you can use, you’ve used systems, you continue to improve your systems, but I also know there are many copywriters that we’ve worked with too that just struggled. They just won’t pitch. They just can’t take that step to start pitching because there’s some mindset block there that they have to work through and sometimes they work through it, sometimes they don’t. Did you experience that or did you just bulldoze through and just start pitching and you didn’t really have that problem? What was that like for you?

Chris Collins:   For sure. I was that person who would not pitch. That was me for most of 2019. I made several false starts where I would make lists of clients that are potential clients that I wanted to pitch. And I would send one or two pitches, but what would always happen would be that I would spend far too much time on the pitch. I would send it, I wouldn’t get a response. I would get discouraged and then I would stop. And I think those kinds of mindset issues are the kinds of things that a lot of copywriters run into. When you send a pitch, you put a lot of effort into it. If you’re going to keep doing something, you want to get positive results. And you’re not going to keep doing something if you’re investing a ton of effort and you’re not getting anything back.

So for me, I just knew I needed to get pitches out the door consistently. And so what I ended up doing, and this was something that I learned from Diana Mayfield, was to template my pitches so that I didn’t need to spend a ton of time writing each one. So I created a templated sequence that just started with an initial pitch that reached out to people. Said, “Hey, I’ve noticed this problem with your website messaging. Here’s who I am. Here’s how I can help.” And then just really lightly customized it with their name and maybe the name of their company.

And then over time, I gradually added in more elaborate customizations. I had my VA research companies and write a custom opening line that would try to draw people into the message and get them hooked. And so that really got me much better results because I broke through that. I can’t get myself to send pitches and I just started getting pitches out the door. And I remember the first week I sent 16, I think, and I got two responses, which was more than I had ever gotten off of any cold pitches.

The other key thing, I think, that was really important with that was just putting them in an automate… running them through automation software so that follow up would happen without me having to manage it. What ended up happening was all these touches would go out for my email and I didn’t have to spend a ton of time managing the process and it just happened on its own. And that worked really well for me. I’ve brought in several clients this year from that system that have turned into really good fits. So I think automating your cold pitch system is definitely something to look into, particularly if you’re having trouble getting started, because it takes the burden off of you once you get it up and running, it doesn’t take a ton of effort to keep the system going and then you’re not in this mindset block of having to write pitches consistently and send them out consistently because the system is doing it for you.

Rob:   I’d love to dig into the numbers a little bit, but before we can talk about that, 16 pitches sent, two received, which feels really good, but that’s also 14 rejections. How do you deal with the mindset around rejection? Because just like reaching out to somebody that somebody might be attracted to and you get rejection, that feels very personal. You’re being rejected because of who you are, maybe how you look or something like that. And it feels the same way when we get rejected in business. How did you make the shift to the point where 14 rejections doesn’t feel like a loss and the two acceptances are the win?

Chris Collins:   Well, I think there’s two things about it, when you are automating your sequence, you’re really depersonalizing each pitch in a way because you haven’t sat with each pitch individually and invested your own time and effort into it, beyond maybe if you have taken a little bit of time to customize an opening line or something like that. Like I said, those are the things I’ve worked with my VA to have her help me manage. But the way it goes for me is I spend maybe an hour each week taking a set of leads and putting them into my automation software. And then they’re going to get the first touch this week. But that way, I’m not looking at any one particular lead and feeling like I’m really invested in, “I’m I going to get a response or not?”

So there’s that. And I think the other thing is having a follow-up sequence that’s already planned makes you feel… You’re not necessarily worried if you don’t get a response on the first email. I think a lot of people don’t necessarily follow up that much. I know for sure, like in a B2B sales context, 50% of sales outreach stops after the initial email. So if you can keep a sequence going with multiple touches, you’re significantly increasing the possibility that you’ll get a response and a lot of the leads that I’ve had come in have not come on the first email, they’ve come on a first or second or third follow-up. So I think it’s just shifted my mindset a little bit around what rejection means. It’s not necessarily a no, it might just be like, “Not right now.”

Rob:   Let’s talk about numbers then. In an ideal week, how many pitches would you send out, and then what does the follow-up sequence look like, and what kind of responses would you maybe get?

Chris Collins:   I think it really depends on where you are in your business.

Rob:   Let’s say I don’t have any clients and I want to get started. What should my pitch sequence, what should that look versus maybe we look at somebody who’s maybe got some clients and they’re trying to up-level a little bit?

Chris Collins:   If you don’t have any clients where you’re looking to get people in the door now, I just think it makes sense to send a lot of pitches. And that was where I was when I started this experiment. I did not have much business going on at all. And like I said, I did 16 that first week, but for several weeks I was sending 40 or 50 pitches a week. And by the end of June, I had a ridiculous number of sales calls on my calendar because what was happening was these follow-ups that were going out, and I was just starting to see what had started as a trickle turning into more of a flood of responses by the time I was a couple of months into running the sequence.

I think, though, what I have found is once you have a steady calendar of work, it makes sense to dial it down a little bit. Right now I’m probably sending 10 pitches some week and some weeks I’m not sending any pitches because right now my calendar is full for the next several weeks. So I just don’t have an urgent need to be getting more pitches out the door. So I think it really depends on where you are in terms of just needing to get leads through the door.

Rob:   So, if you send out 10, about how many would respond to, say the first email versus the second email versus the third email, and how long does your sequence actually go?

Chris Collins:   That’s a good question. I’m pulling this up. With my sequence, I’ve got a 91% open rate, which I feel pretty happy about that.

Kira:   Did you say 91%? That’s amazing.

Chris Collins:   Meaning that 91% of the prospects have opened at least one of the emails I’ve sent them. And then of all those, just under 10, like 9.7%, have gotten back to me and been like, “I’m interested, let’s start a conversation.” And so I don’t have stats on exactly how many I’ve closed at this point, but I think those numbers are very achievable for anybody who wants to try and experiment this. I use, which is I think a really good solution for something like this.

Rob:   How long is the sequence? Is it four emails, six emails?

Chris Collins:   I started with just four. I just felt like I needed to get it out the door. I think that’s another side to it I would probably emphasize, is just if you’re not pitching at all, I would say, don’t worry about getting it perfect. Obviously, you want it to be good, but it’s more important to just start getting pitches out the door. Now my sequence I think is seven emails. And so that gives me the first email and then six touches over several months, which I feel is getting pretty good results at this point.

Kira:   Which subject line is converting the best right now?

Chris Collins:   I’ll tell you what didn’t convert. I had read somewhere that using emojis as subject lines would convert really well, which I tried, and that may work for people in other verticals, maybe people who are working with personal brands or something like that, but that completely fell flat with me. Did not work. I’m trying to look at my data for you right now. Hang on. I would say I still am getting the best rates off of the first email, which is just a very simple strategies and ideas for company. There’s nothing super exciting about it, but it promises a benefit and it gets a pretty high open rate.

Kira:   Other question, can you just talk about the success… Clearly, anyone listening can tell that you’ve had success with this, it’s working, but can you talk about how much success you’ve had over the last year, how your business has changed, how even income wise it’s changed and allowed you to go from basically leaving your full-time job and going full-time in your business? Can you talk about the impact that building a system like this has had on your business and life?

Chris Collins:   I would say that, like I said, earlier this year, I knew that I needed to do something to start getting more business in the door because it was obvious that I was seeing a lot of people around me who were doing really well, and client acquisition was my big problem. For several months, I was just sending a lot of cold pitches. And just my income grew pretty steadily month over month, all through the year. I remember in March, at much of The Copywriter Club, I don’t think I had any income in March, actually. And just brought in 2K in May, 5k in June, and it just kept growing from there. And then I hit my first 10K a month in October, which was the big milestone. And then at the end of October, I left what was a full-time job and took my side hustle full time. It has been pretty impactful, I guess.

Rob:   Let’s jump in here and talk about one or two of the things that have stood out to us. We’ve waited a little longer than we normally would to get talking about this because Chris was just talking about so much stuff in pitching, and maybe that’s where we should start, with the stuff that Chris is talking about, pitching. Is there anything that really stands out to you about this, Kira, about Chris’ approach and how he’s able to do so much pitching in so little time?

Kira:   Well, I think what stood out to me is that it’s worked for Chris. He has taken his business from when he joined us in The Think Tank, he was working full time. Didn’t really have many copywriting projects, if any, and he built this pitching system and has been able to leave his full-time job, is really successful financially, has created this consistent revenue for himself and his business because of pitching. And I think pitching is one of those things that it’s really scary and it feels hard to jump into it, but once you figure out a system, you take the personal side out of it and the rejection out of it and you can just crank out 40 pitches to 50 pitches a week like he was doing, or reduce that number to 10 a week consistently. It will transform your business. So I hope that if anything is just proof that this stuff works, this is something that can work for everyone, and it’s not like Chris is a unicorn, he’s just tinkered and worked really hard to figure it out.

Rob:   And I think when we talk about pitching or when we’ve talked with other guests about pitching, there’s these two different approaches, one is you go all in on personalization. Sometimes people are talking about how they spend a couple of hours doing research and personalizing the message and making sure that it’s just right. And then there’s the other side of the spectrum where it’s almost unpersonal, it’s like the stuff that we see on LinkedIn all the time, people just pitching a service and just trying to connect with as many people as possible because you know that one out of a hundred or one out of 500 is going to hit. And Chris has walked the line between the two, and he’s able to do a lot of pitches because of the system that he’s built, but he’s also adding personalization so that it feels just a little less impersonal, a little less automated. And that seems to have really worked for him.

Kira:   And what else stood out is that he has built his pitching system so that he doesn’t just email the people on his list one time. I think now at this point he said he has seven emails in his sequence, so every dream client on that list is hearing from him seven times. And so I think just thinking through it, and again, taking the rejection out of it, not just sending one email and assuming it didn’t work… So many people are busy and not in their inboxes today. It takes probably seven or 10 emails to get their attention anyway. So, if you are going to build a system like this, build in the follow-up sequence so you don’t set yourself up for failure.

Rob:   I think it’s really important to do that because like you said with the rejection, especially when you spend a lot of time crafting the perfect pitch and you send out two or three and you keep getting rejected, that feels really personal. But when you’re able to send out more, you land the project, you get the financial reward and that dopamine hit, or the reward that you get can cover up a lot of that rejection. So if you’ve been trying pitching and it hasn’t worked, keep going, adjust your system, try different things, but just know that when people start saying yes, it makes up for all of that rejection that you’ve put yourself through. And as you get better at it, ultimately you get to the kind of business where you actually don’t have to pitch anymore because people start coming to you. You’ve just got so much success with so many clients and your business just starts to grow on its own.

Kira:   Chris talked a little bit about the rejection side of it, but also, it’s not even rejection, it’s just plain old people are busy. So I think it’s just remembering that and not taking it personally, like, “This person’s ignoring me.” It takes me hearing from someone about five to six times before I’ll take action. Not because I’m not interested, but just because I don’t like to spend time in my inbox. So I’m not in there. I avoid my inbox. So it will take me five to seven times. And, again, it’s not because there’s rejection involved or the lack of interest is there, it’s just people are so busy and saturated and overwhelmed. So again, it’s not about you, it’s about the person you’re pitching and doing them a favor by showing up consistently so that you can help them because there’s a good chance they are interested.

Rob:   You’re right. Nobody wakes up in the morning with the number one thing on their list, “I’m going to respond to cold pitches today.” It does take time to break through and to really earn the response. Chris has done a lot there. I admire what he’s built as far as his pitching system goes.

One other thing that stood out to me, in particular it goes all the way back to the beginning of the interview, and that is the fact that Chris was a mommy blogger. And that sounds maybe a little funny or whatever, but it’s not really about the thing as much as I’m impressed with the fact that Chris wanted to be a writer, and so he just got started. And the first thing that came through was a project that wasn’t necessarily a fit from the kind of stuff that he wanted to ultimately write, but as somebody who wants to be a writer, he knew he’s got to write stuff and so he might as well take this project and get started.

I can think back to my first writing project, it was for an MLM. I don’t remember what the thing is that I wrote, but it got me started. It was the thing that woke me up and said, “Yep, this is going to work. And this is a possibility.” And so for anybody who’s at that starting point thinking, “I want to be a copywriter, what is my next step?” The next step is to get started, find something to write, whether it’s for yourself, whether it’s for a potential client, whether it’s for an actual client, whatever, just get started on something and then start moving towards the thing that you want to be.

Kira:   In addition to that, what also stood out to me was just what Chris shared about allowing peers and colleagues to poke holes in his argument. And I think his background as a PhD student and the rigorous training he had with just daily writing and really synthesizing ideas and exposing himself to that type of critique has made him such a strong writer. But I think more importantly, it’s just given him the right attitude that we all need about feedback. And not even just about being open to feedback and wanting your colleagues to really poke all the holes in the argument you’re making on your sales page, but what I really is how he summed up that conversation with us and said, he knows before he sends anything out the door to a client, he wants it to be as strong as possible before people, colleagues, clients, poke holes in it.

And I think it’s really important because I know sometimes, especially when we’re a newer copywriter, we feel like we want feedback from the client early on, and we want them to look at it. We even want their praise and approval, but we know that it’s not quite final yet, it’s a draft and we treat it like a draft, but with Chris’s approach, and I think more experienced copywriters know that you really don’t share with the client until you feel like it’s 95% there and you give them really clear instructions about what’s missing or what’s needed next, but you don’t share it when it’s 50% done because it’s called a draft.

Rob:   And if you decide to share your draft with the client, you’re opening yourself up to all kinds of pain. I think we’ve all probably been through that, but clients expect final work. Even if you tell them, “Hey, this is just a draft,” or, “Hey, I just want to get your feedback on ideas.” If you’re sharing ideas, literally share the idea. Two lines that expresses the idea. Do not share full-blown copy. Clients need to be pretty sophisticated to understand the difference between a rough draft and a final draft.

Kira:   All right, let’s go back to her interview with Chris and talk about why he left his job to freelance full-time.

Rob:   Let’s talk a little bit about what the mindset and the decision process around leaving your almost full-time job were, because I know you wanted to get some things lined up, you’re a little bit risk averse, not wanting to just jump into this thing, what had to happen to make that possible?

Chris Collins:   I think that for me, I was very conscious of the opportunities that I had had for my business because I had a stable income. During my first year, over 2019, I wasn’t making a lot of money as a copywriter yet, but because I had a full-time job, I was able to invest in memberships, I was able to come to TCCR all this year, things like that. I could take advantage of opportunities to grow my business and just continue to invest in things that would help me move forward. I think my big thought process was just like, “I don’t want to do anything that’s going to put me in a position where I’m going to compromise those opportunities, where I’m going to have to… where I’ll feel like I am not going to be able to bring enough money in to support myself, much less invest in my business.” So I just wanted to get to a place where I felt really comfortable with my lead generation and customer acquisition. And so working on cold pitching really helped a lot with that.

Kira:   What advice would you give to someone listening who is in a similar place that you were, working full time, building the business on the side? What do you wish you had known or done differently that could have helped you, or maybe what… I don’t know, maybe you didn’t have to do anything differently. What would you recommend?

Chris Collins:   Something I did that I would tell people to definitely do, and something that I didn’t do that I think people should do. I think one thing I did was just very early on, I started following The Copywriter Club Podcast, for instance, I started following people like Joanna Wiebe and Joel Klettke and all of these copywriters who were at the top of the field. And I was just very aware of the possibilities for people who are ambitious and work hard and try to really set themselves apart in this field. So I was thinking of it very early on as, “This is something that I want to take seriously and do professionally.” And so that was a mindset that I had very early in my freelance career.

I think one thing that I didn’t do that people should do is, what I was saying earlier, it took me a long time to really get a pitching game off the ground. And I just think the easiest thing… I know so many people struggle to get clients, and I think the easiest way to find those first clients that you’re looking for is to send cold pitches. I think it really will grow your business. And I think a lot of people are looking for… Particularly early on. I know I was doing this. I think looking for, what’s the easy way to get clients? Or what’s the shortcut? Or how can I get clients the fastest way possible? I think pitching is the shortcut. I think that is how you can quickly connect with prospects and quickly grow your business. So I think that’s the number one thing that I would say beginning people should probably focus on doing.

Rob:   And in addition to pitching, are there other things that you have done that have helped you make leaps in your business? I know you mentioned that you had invested in a couple of courses type things, but what else have you done that’s just really helped you to-

Chris Collins:   What have I done? I think that building relationships has been really, really important and that was something I didn’t appreciate the importance of early on at all. I thought I needed to up-skill, I thought I needed to learn how to do copywriting. I felt like I didn’t know enough and I needed to improve my skills, but what actually happened was in those communities, I ended up meeting a lot of people who are still really good friends in the copywriting space. And those relationships have helped me to advance my career as much as anything else. They’ve been good friends, they’ve been good sources of referrals and they’ve just helped me to learn a lot. So I think being in communities where you can build relationships, particularly in communities where you’re surrounded by people who are maybe a little bit ahead of you and you can start to think through, “Well, what could your vision for your business look like?” I think is really, really important. That’s probably the biggest thing that jumps out to me.

Kira:   I’d love to hear more about what you’ve struggled with the most over the last year, and even how being in The Think Tank mastermind with such a smart group of copywriters, like you mentioned, has helped with those struggles, if there’s a clear connection with the struggles. And then how a support and a savvy group of copywriters and a mastermind have helped with that.

Chris Collins:   I think The Think Tank has been a complete game changer for me. Where to begin with The Think Tank?

Kira:   Well, let’s start with your struggles. What have you struggled with, and how has it helped?

Chris Collins:   Writing can be a very solitary enterprise. You can feel like… And I think that’s compounded by this social media-saturated world that we’re in where people are always online sharing their successes and how things are going so great for them all the time. And you know that’s not really true, but that’s what you’re seeing in front of you. I think it’s very easy as a writer to feel like what you’re going through is just something that you’re going through. And just being in a community like The Think Tank helps you to understand that you’re not going through the struggles of being a writer on your own, that other people are going through the same challenges.

And not just that they’re going through the same challenges, but that often being in a group of really smart copywriters, you might not have the best solution for how to deal with whatever issue you’re dealing with, like if you’re facing a thorny issue with a client or you’re just overwhelmed and you’re not sure how to prioritize or whatever it is, but someone else in the group can give you an outside perspective and chances are they’ve been there and they can help you think things through.

So I think both just being in a group with other people and also getting their perspective and advice has been really helpful. And I think just seeing what other people are doing is incredibly inspiring. We just had our retreat a couple of weeks ago, and I just came away with so many ideas for things that I want to do in my business going forward from the presentations that we heard. So it’s a really great source of inspiration for things you want to do in your business.

Kira:   What is one struggle that you’ve had over the last year? Because it sounds like, Chris, you’ve had so many wins, you’ve done really well and you’ve made this huge transition. What has one struggle been for you as you’ve had these wins?

Chris Collins:   Working on my mindset, working on limiting beliefs, working on mindset traps. You’re with yourself a lot as a copywriter, and your brain just has all kinds of sneaky ways of holding you back or telling you shouldn’t do something or make excuses for you. What I’ve found is that there’ve been just a lot of limiting beliefs that I’ve run into, and I just need to continue to work on going forward.

Rob:   Chris, I know we’re almost out of time, but I want to ask you about this because I happen to know that you just deleted all of the social media apps off of your phone. Tell us why and what you expect to happen to that.

Chris Collins:   I’ve already had a pretty rigorous social media blocking game going. I block my internet almost completely on my computer from when I go to bed to 2:00 PM the next day. And that’s been going on pretty much since I went full-time as a copywriter, so for almost a month now. And I just realized I haven’t even been on my phone to use those apps for a couple of weeks, there’s no point in having that potential distraction there anyway. So I hope that it will remove a potential temptation to get sucked into these distractions that can sometimes pop up, drain away productivity.

Kira:   That wraps up our interview with Chris. Before we sign off, let’s talk about one or two more ideas that Chris mentioned.

Rob:   Another thing that stood out to me from what Chris was talking about is just when to invest. And I know we’ve talked over and over on the podcast about the things you can invest in and how you need to invest in networks and communities, and the kinds of programs that maybe are best to invest in when. Obviously, we’re partial to our programs, but that doesn’t mean that those are the only things out there. But Chris specifically mentioned that when you’re not bringing in enough money to afford something, that that’s just not the time to invest.

And I think it’s got that bad bro marketer vibe to tell people, “Put it on your credit card,” because you’re going to get a result, you’re going to have all these results at the end. And that can happen, for sure it can happen, but you really shouldn’t be making investments in anything, including yourself, unless you can afford it. And so it’s much better to work a couple of projects or to save up the money and then invest when you can afford something. Chris doesn’t dabble, he’s following people at the top of their game and he’s doing some really smart things in this business.

And then the last thing that I liked about what Chris said was that he’s doing this experiment with blocking social media, he’s opting out entirely. And that’s maybe a little bit of a 180, because at one point he was experimenting with going live a couple times a week and being there, but I think he realized that it didn’t resonate for him and it wasn’t moving his business forward and maybe his clients weren’t there and so he’s turned it off. And that’s from a personal standpoint, a business standpoint, and maybe that’s something that we could all do just a little bit more. In fact, you know you’ve done some of that, maybe not all, but you’ve blocked out quite a bit of social media from your life recently.

Kira:   I’ve reduced it. I can’t safely say I blocked it. I couldn’t say I blocked LinkedIn just because I don’t go into LinkedIn. I could say I blocked Twitter because I don’t actively use Twitter as a tool, but I pop in there just especially in these crazy times just to see what the buzz is all about. But I definitely have reduced my time on social media. I have a hard time blocking it completely or shutting down accounts. I haven’t reached that level yet. That’s the next level that I’m focused on.

Rob:   I think I block by platform. I never go into the Facebook feed, I only go into The Copywriter Club groups, it’s the only place I even use Facebook, which means when people even use Messenger with me, I just never see those messages because I just don’t do it. I see a little bit of Twitter, but like you, I’ve really tried to cut back, especially recently but even moving forward. Just other than when I use it for business, it’s a total time suck and someplace that I don’t necessarily want to be.

We want to thank Chris Collins for joining us to talk about his business and how it’s changed over the past couple of years. If you want to connect with Chris, you can find him, or simply do a Google search for Chris Collins copywriter, and you’ll see his page at the top of the results.

Kira:   That’s the end of this episode of The Copywriter Club Podcast. Our intro music was composed by copywriter and songwriter, Addison Rice. The outro was composed by copywriter and songwriter, David Muntner. If you’ve enjoyed what you’ve heard, please, please visit iTunes to leave a review of the show, or better yet, think of one person who could benefit from what you’ve heard and email them a link to this episode. To learn more about The Copywriter Accelerator, which if you’re listening when we go live, closes to new members this week, go to Thanks for listening. And we’ll see you next week.




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