TCC Podcast 175: Laid Off to Freelance Success with Derek Hambrick - The Copywriter Club
TCC Podcast 175: Laid Off to Freelance Success with Derek Hambrick

For the 175th episode of The Copywriter Club Podcast, Kira and Rob talked with copywriter Derek Hambrick about his path to freelance copywriter… including his first failed attempt and what made him successful the second time he gave it a go. We also talked about:
•  the path he followed from communications to copywriting
•  the surprising emotions Derek felt when he was laid off… panic and excitement
•  how he relies on relationships to find clients for his business
•  what he did to step up his copywriting game as he went out on his own
•  the importance of giving and altruism to Derek’s ROI
•  the process he follows as he works with his clients
•  why he chose his niche and the impact its had on his business growth
•  the pros and cons of working in the higher education niche
•  how he moves from one client to the next and gets referrals
•  the changes he’s made to his mindset in order to think bigger
•  his experience in The Copywriter Underground and what he gets from it
•  how to get the most from a course or community you belong to
•  the mistakes he’s made as he moved from full time to freelance
•  what comes next… how Derek keeps growing

To hear what else we talked about, click the play button below, or scroll down for a full transcript. Or better yet, subscribe with your favorite podcast app and never miss an episode.


The people and stuff we mentioned on the show:

Ry Schwartz
Joel Klettke
The Copywriter Underground
Cantilever Creative
TCCIRL Copywriting Event
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
The Copywriter Underground


Full Transcript:

Kira:   This episode is brought to you by The Copywriter Club In Real Life, our live event in San Diego, March 12th through the 14th. Get your tickets now at

Rob:   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 Kira and I do every week at The Copywriter Club Podcast.

Kira:   You’re invited to join the club for episode 175 as we chat with copywriter Derek Hambrick about moving from full time work to freelance, choosing his niche and what that did for his business, what he did to find his first clients and how he finds people to work with today, his experience in The Copywriter Underground and what he’s doing differently in 2020. Welcome, Derek.

Derek:            Hey guys, thanks for having me over.

Kira:   Yeah, I feel like we have wanted to have this conversation with you for a while. We’ve been able to hang out with… Well, I was able to hang out with you in person not too long ago and chat with you then, but we really wanted to record this and find out more about you and your business and what you’ve done because it’s worked well. So, why don’t we kick it off with your story? How did you end up as a copywriter?

Derek:            Yes. So, I always knew I wanted to work with words for a living, but didn’t know exactly how. Long story really short, I found myself working at Delta Airlines, not really knowing what I wanted to do with my life, but I figured Delta was a big enough place that I’ll probably find it there and get paid as well along the way as I figured that out. I remember working on the International Concourse, writing a few articles for newsletters, that kind of thing. Nothing big.

But one evening the last flight pushed out to Santiago, Chile. That was done. Went back to the break room, working on an article, looked at the clock and an hour had gone by. And at that point I realized, ‘My God, I must really enjoy this.’ And that’s when I realized I’ve got to find some role, some place capacity for me to write for a living.

So I applied for a bunch of corp-comm jobs, marketing roles and that kind of thing. Nothing really panned out because I didn’t have a degree is what it turned out to be. So I got one. Working full time, went back to school. I got a communications and rhetoric degree from my Alma Mater. Essentially once I got that… by that time I had landed a corporate communications job, but figuring that I had my degree, I had some experience, I’ll go ahead and make my own way in the world as a writer. So, quit the job, jumped out of the eighth floor of corporate communications and into the tea cup of freelance. And to paint the picture of it, this was back in 2008. So, it was not the best time financially to start your own business.

And that turned out to be my biggest failure was trying to go out of my own way too early and really without any kind of plan. Went through our savings, racked up some debt, wasn’t good. But some good lessons. So, that’s a positive of there. So what did I do? I decided to go in-house, get a full-time job, benefits, had a family at the time, still do. But I had people depending on me as the main breadwinner. So, for security and to provide for them and also get some more experience, I got a job at a big four professional services firm as an editor. Great organization, got some more experience, but I was really feeling that that writing itch, just wanted to write versus edit and proofread and that kind of thing.

So, a few years after getting that role, I left the firm to a senior writing gig. And it was great, but it was very short-lived for a number of reasons on both sides of the conference room table. So after that point, what I did was go to a number of smaller agencies from gig to gig essentially. Some really bigger names like Home Depot and whatnot, but also some local brands and businesses, Peachtree Bikes, FORM yoga in Atlanta.

I was just piecing things together. Even had to deliver pizzas at one point to pay the bills, but decided to go back to the firm in a marketing writer capacity, which had me doing some internal external kind of stuff. Again, building a lot of experience. While at the firm though, could kick myself for doing this, but I took another role, which was decidedly less writing, more project management communications in the broader sense, which was good. And it had his own lessons but wasn’t really writing.

So, a few years later, I left the firm again and took a job as a ‘copywriter’ officially. And it was great for about a year until I got a call one day and said that they had eliminated my role. So at that point, I decided to go ahead and say, ‘You know what? I’m going to take my side hustle, I’m going to move this thing front and center.’ I had known for a long time that at one point I was going to be my own boss running my own company and writing for a living. Kind of determining the terms rather than having them dictated to me. This was my opportunity.

There is a moment where I thought, ‘Well, maybe, okay, I really should go and stay in-house with somebody, again, for that security.’ Right? But honestly, that lasted for about 15 seconds. And I said, ‘You know what universe, this is what I need to do.’ And so the business Cantilever Creative officially began and celebrated a year back in November of 2019.

Rob:   So, can we go back to that moment when you were laid off? We’ve talked with other people who have found copywriting after being laid off in a few episodes ago. Kira and I talked about how I had to lay a bunch of people off and was laid off myself from a job like that. Tell us what did that feel like and was it a moment of panic or were you ready to go? Was it a moment of excitement?

Derek:            Well, Rob I guess it was a very, very short period, minutes really of panic when I got that call. Like I said, I hadn’t expected this, right? It hit me out of the blue. The work was good. It’s just they got rid of the role and I’m a casualty of corporate America. But I was really excited after I got over the anxiety. It’s like, ‘Well, wait a second. Wait a second, wait a second. Derek, you got this man.’

You have to understand, I mean, as soon as I’d started that job and here’s the really cool thing. When I started that job, I had a commute and I wanted to use a commute to my advantage. So what turned out to be like an hour and a half every day, I listened to y’all. Honest to God, the first week I started there I was like, ‘Okay. Well, let me see what kind of podcast I can tune into.’ Did a Google search, Copywriter Club popped up. Rest is history.

So, pretty much every day to and from work, I was listening to these great copywriters, Rye and Joel and everybody else. Just learning from them. I felt like I got a masterclass in the car to and from this work, the work that I was where I was. But to me, there was an excitement because I had had basically a year of experience and education under my belt. I built this incredible network with The Copywriter Club and The Underground. And honestly, I just, I felt ready. I felt prepared. I felt like, ‘Heck yeah, man, you can do this. Let’s make this happen.’ So, yeah, there’s a moment of panic. But at the same time, there’s this lasting feeling of exhilaration. Like now’s the time. You can do it. Let’s go.

Rob:   So obviously there was a pretty big difference between the first time that you went freelance and this time you’ve been a lot more successful this time. What have you done to find clients and to really get your business moving?

Derek:            Yeah. So, how do I find clients to keep my business moving? I had had, think like a lot of us, I had a freelance side hustle going even while working the full time jobs, whether it be like one of the like for pocket money or something to keep things creative. So, I’d had that going along all the while. And for me in business and life really, relationships are so vital. Finding those connections and really treating relationships preciously. That applied to these freelance clients as well.

So, when I found out that I didn’t have a job anymore, I made the decision to build Cantilever Creative and go on my own. I was able to really comfortably go to those people. One of them is a major higher ed school in Atlanta, to that client and say, ‘Hey Angela, look, this is what happened. Do you have any hours you can give me?’ And she had my back. And she gave me the hours. She gave me more than I’d expected. But because we’d had that relationship, she knew my aspirations, she knew the caliber of my work. And so, she was able to not just provide the work for me, but also go to bat for me. Introduced me to other people who may have other work opportunities as well.

Kira:   Beyond leveraging those relationships that you’d already built, what else did you do that was really pivotal for you during those first few months where you were on your own and making it happen?

Derek:            I’d say, well of course there’s a bit of nervousness where you’re… For me at least it was like, let me just grab every hour that I can. And thankfully the hours were there. As far as what kept me going, I’d say I of course kept listening to y’all, got really involved with The Underground because I had a lot more time on my hands. I really sought to learn. Of course, I needed to do the work to bring the money in, but also felt I needed to really step up my game. So, that meant studying on my own. If I ran into a tough question, I’d ask it on our Facebook group. If I had a cool experience too, I shared it on our Facebook group because for me giving is a big part of this too.

Kira:   Let’s talk more about that, the giving piece of it. Do you have any specific examples of giving and how that actually pays off and it’s a good strategy or business growth?

Derek:            Yeah. It’s crazy because you really don’t think of altruism as a factor of ROI. Right? But yeah, in my experience, so it really is. And one example that really comes to mind, by word of mouth I’d just gotten wind of someone who needed some collateral, a long story short, talk with him, connected. Again, started building the relationship. Made a proposal for the work and in the end he said, no. He let me down in general. I really wanted to work with the guy. He had a really good thing going, building his business but it didn’t work out. That’s how it happens.

So, at that point I decided not just to drop it, but I said, ‘Hey look, it was good to get to know you. You’ve got a really cool business. Even though I can’t help you out, I know a few other copywriters who might be able to.’ And the reason I suggested that and presented that option to him was because it wasn’t a good match budget-wise, but still I wanted to help the guy.

So I said, ‘I can do that for you if you’d like. If you want to meet for coffee again, we can do another jam session, talk strategy, no charge.’ For me, this is just how I am. It’s like I want to help. I think that our world’s a lot better when we do. And it folds back to my modus operandi, which is work hard and be nice. So this is the be nice part, even though I wasn’t going to be able to work hard for that guy.

So anyway, I made this offer, right? No attachment to it, but just to put it out there. A little tidbit is that the proposal was right about $8,000 for all the collateral and the project. I’m not sure if it was a day, but definitely within the week of me getting to know from him and giving him this other option, out of the blue, I had a friend of mine present me with another lead, which turned out to be a proposal that this potential client said yes to.

The amazing thing for me is like the $8,000 that I did not get through that lost proposal was pretty much the same amount that I got the yes to for the second proposal. So for me, I don’t know, maybe some people will say that’s coincidence, Derek, whatever. But for me, if I take a step back and I look at it on the macro level, it’s like, did not get $8,000 here, still tried to help. And then you got $8,000 out of the blue.

For me, it was you can call it demonstration, manifestation, whatever we woo-woo term you want to use. For me it was a concrete experience that, ‘Hey, this idea of giving does work.’ So, it blew me out of the water when it happens, especially with the timing and the amounts lining up like it did. But yeah. So, that’s an experience I don’t think I’ll ever forget.

Rob:   Yeah. I like that. The universe tends to pay us back for the good things that we do. So, we’ve talked a little bit about your habit of giving, maybe giving more than what’s expected. Will you also just talk about how you work with your clients? What’s your process like?

Derek:            Yeah, sure. For me it’s important to learn as much as I can about the client. If they’re going to come to us with a need, some goals in mind and so forth. But for me, it’s all about education at the beginning. And like I said, developing that relationship. And the more you know, the better you can help them is what it boils down to. So like getting on the phone with them, meeting in person if at all possible. Just develop that relationship, but also then really digging into whatever problem they’re trying to solve or whatever goal they’re trying to reach. The more you know, the better you can help. But then it’s a matter of building trust too. So, let him know my processes, let him know how I work so that it’ll contribute to that relationship.

Kira:   Let’s dig into how you work with your clients as far as painting the picture of what your business looks like. Are you working with some of your clients, I know some of them are big brands too, long-term and more of a retainer model or how are you getting paid with most of your clients today? What does that look like?

Derek:            Yes. So as far as the way I’m working with my clients, I’m fortunate to work with some rather big names, but also able to work with some smaller outfits as well. I don’t have any retainers set up right now. It is something I’m looking into, some advantages to that. But my largest client right now has me working on an hourly basis. It’s just the way they do business. I would prefer to do project rate or something like that. I think it works out for everybody much more so than an hourly rate. One of my clients I’m talking to about doing a retainer, which I would certainly appreciate.

Rob:   So Derek, one of the things that I know that you did early on is you locked in on a niche. And I’m curious, first, why you chose the niche that you did, and second, how has that helped focus your business or has it hurt your business in some way?

Derek:            Yeah, the idea of a niche was, I’m not sure I liked it at first, Rob, but it was y’all’s advice. So hey, I went with it, I trusted you. But the niche I started out with was higher education. And I half jokingly say that the niche found me, right? Because one of my clients that I had been working with for a while on the side was the university in Atlanta. And it was great, it was fun work, good people to work with. Because I had developed that relationship with them and had a lot of momentum with them, when I lost the full-time job, that was where I gravitated. And that’s a client I went to and I said, ‘Hey, I need some help.’ And they helped me.

Because I knew I had them in my corner, I thought, ‘Well, this would be the natural next step, the natural place to focus.’ So for me, I felt it really did help me. I doubled down on it, not just in terms of the hours that I spent with them, but also my efforts to learn more about the industry. Jumped in on LinkedIn, making connections, reading articles and that kind of thing about higher education and just trying to learn more and be more knowledgeable so I could make those connections and sound like I knew what I was talking about.

The reason that I hesitated I think with really pouring myself into that niche was because there’s the FOMO, the fear of missing out, right? It’s like if I say yes to this niche and like say I’m going to go all in, then you’d be saying no to other opportunities. Which yeah, perhaps that’s true, but I feel that having the niche really benefited me because I was able to focus my thoughts rather than be completely scatterbrain and just grab areas wherever I could from whomever I could.

I did say no to a project or two so that I could focus on that one higher ed client. In addition to that, there’s also the stuff in the periphery, right? There’s just the effort that you make that’s not necessarily work, but it’s the energy that you spend. And I think I’ve benefited from keeping my focus that helped me grow my business, not just in terms of billable hours, but to think, you know, we talk about mindset in The Copywriter Club and The Underground, right? It really helped me develop that business mindset of this is my business, this is where I need to keep my focus. And if I do that then it’s going to pay off in the end.

Kira:   Yeah. And I definitely want to talk more about mindset, but first, for someone who’s listening and is interested in higher education and possibly exploring that niche for their business, what would be of your advice for that particular copywriter and what should they be aware of? Maybe even pros and cons of working within the higher education niche?

Derek:            The thing that pops out the most first at least is the money aspect, which let’s talk about it. My experiences are like the higher ed doesn’t always have the budgets to allow for full-time staff, right? But here’s the cool thing. And the things that advantageous for us, they recognize good writing and nine times out of 10, they’re willing to spend money on that. So, that’s something to be aware of.

What might be helpful is to share what’s helped me. Like I talked about relationships, of course. Having the degrees that I have help. I’ve got the two bachelor degrees. And I guess even the most concrete thing that would help people that are listening is just that you’ve got to have the chops regardless of the degree, or not or regardless of the relationships. Having the chops and being able to do the writing is core.

So that means for a higher ed, being able to write to, oftentimes, a lot of different audiences, having that capacity to write to their faculty, their staff, people who are very well-educated. But at the same time, then write to another audience, students. Write to the staff, write to the alumni. And as I think a lot of us know, it’s like it’s a matter of knowing who your audience is and culturing your writing to that audience.

Because for me, my higher ed clients, they had several, several audiences to write to. And when I was able to get in and start writing for them, they realized, ‘Okay, this guy writes pretty decently for this audience, let’s switch him over here and see how he does.’ And I was able to demonstrate writing to that particular audience. So, I’d say being able to match the messaging to the particular audience was really helpful.

I guess in that sense it’s not different from any other industry, or sector or business. It’s about being able to understand who you’re talking to, who they are, what they’re thinking, what they want, what they need, what they’re fearing and being able to write to them, not at them. Academia by nature, it is known for writing like academia, lofty, highfalutin as we say in the South. Stuff that’s not really relatable.

And I suppose there’s a place for that, but what I’ve found is interestingly enough is like higher education is catching on and grasping this fact that that kind of communication doesn’t reach people. They’ve got goals, and they’ve got aims, and they’ve got I don’t know. Anything that they need to do, they’ve got to have the writing that connects to people, that engages with people. And if you’re the kind of writer that can do that for several different audiences, you’ll be well-poised to jump into higher ed writing.

Rob:   And one of the things that strikes me about higher ed is that it’s probably similar in a lot of ways to big corporate enterprise clients. And finding the right person to pitch inside a big organization like that, finding the right person to pitch in higher ed feels like a big challenge. Is there something that you do in order to connect with the next client that you want to work with or to get referrals so that your business continues to grow? Or is it just a slog the entire time?

Derek:            A little bit of both, maybe. The nice thing about the big four firm that I worked with was I got in there, developed relationships and new people. So for me, I kind of had a leg up, Rob, that it wasn’t so difficult for me to jump back in, multiple times I have. And even now as a contractor, interestingly enough, I’m back working several engagements for that same firm. So, hey kids, relationships matter.

That said, I think that the thing that helped me out also beyond just having my name passed on doing pretty decent work was an ability, which I think is my X factor. We talk about X factors, super power or whatever, the sweet spot. For me, mine is mixing that creativity with credibility, the personal and the professional, the factual, the fun. That’s my playground. And I love riding in that space.

There’s plenty of space for everybody. So y’all try to come to the playground, we’ll have fun. But even in, I don’t want to use the word stodgy necessarily, but professional services, if you say that accounting, assurance, audit doesn’t necessarily seem like the kind of place that wants creative writing, but let me tell you, it is. At least the firm that I’m working with and many others, people are getting it. Like with academia, they’re getting it. You have to engage with your audiences.

But then there’s the challenge because you have on one side… and this really goes for any established brand that’s not fun by nature. Any established brand has that brand experience, credibility, to use another word. So for a firm you’ve got that on one hand, but then you have the need and it’s requisite to connect with people on the other.

So for me, I say developing your ability to mesh the two. To not go on, swing too far to the credibility side of the spectrum. Bring yourself back over to the creative side too, find a nice balance. And the cool and for me, the fun thing is figuring out where that is. So, that means asking a lot of questions. It’s also developing the trust that they’ll listen to you when you present an idea. You make it a marketing brief or a launching a new initiative. And they want to do X, Y and Z in this way for this audience.

Well, having the wherewithal and the confidence to say, ‘I understand what you’re saying. How about if we look at it through this perspective?’ Or, ‘Have you thought about doing the messaging in this way?’ Because at the end of the day, people are hiring us for our words, but the words are serving a purpose. The words are helping them reach a goal or solve a problem. So if for me, if I’m able to present to them that I’ve got the ability to think more broadly than just cranking out words, that’s what they want. And the trust is built, the relationship’s strengthened, and oftentimes I’m able to infuse a lot more personality, creativity into the work I’m doing.

Kira:   So, I have two questions about this. One is first about how to sell that to them. Everything you just shared that creativity matters, personality matters, fun matters. Are you attracting clients who already get that and they’re already sold on it or do you have to continue to educate them on why it matters? So, that’s the first part of the question. And the second part of the questions is just, how do you actually do that for your clients? How do you figure out where they fall in their voice and brand falls on that spectrum because some will lean more towards credibility and then others might lean more towards creativity. So do you have a process for determining that through your own questions that you ask?

Derek:            Yeah. So, the first question here was, do I find fun brands or do I-

Kira:   Well, are you selling… How are you selling them on the power of creativity and fun and that it’s important not to just focus on the credibility in the facts or are they just coming to you because they already get that. So what works for you?

Derek:            Yeah. A little bit of both. So, I’ve been fortunate to work with some local brands FORM yoga and Peachtree Bikes. They are fun to begin with. It’s a yoga studio, it’s a local bike shop and we just mesh. They’re looking for something that’s engaging. They’re looking for something that’s humorous. I mean, they’ve got personality to begin with. So, to me, it’s easy just to jump in there and run with it. That’s great.

But then on the flip side, you’ve got other, let’s say more reserved clients who do sometimes take some convincing. So, as an example, I was working on a newsletter. And I basically inherited it, picked up and ran with it for a while. And what I mean by that is I got the newsletter. This is the way that they’ve always been doing it. This is the way of writing that they’ve always used. And while I didn’t jump in and try to change the format, I said, you know, I echoed back, ‘Oh, this is really cool. This is an important topic. Okay, I can see why this is important.’

I echoed back what they knew about the channel, the newsletter. But then in conversations I said, ‘Well, what we might want to do is use the pronouns we, us, and our instead of the third person.’ This impersonal thing and shared some experience of why that’s a good thing, how it’s able to further engage people, which is what you need to do if you want them to do anything, right? If you want to influence them to think in a different way, take a particular action or just build awareness of something, you got to engage them. You can’t just inform them.

And so, getting them to think about the words that we choose and getting them to approve that and to really get behind it. Little things like that tend to help out as far as convincing them. I mean, I’m sure there’s statistics out there, I don’t know what they are, but as far as engagements concerned, I’m sure there’s some studies out there that look at different types of writing and can tell you like, yeah, people have more hang time on this page when it’s written in a more engaging way versus an informative way. I don’t know what they are.

So it takes, I’d say for me what works to get a client to really to buy in, if you will, and to infusing personality, even humor into their brand is just to tell them why. It really does revolve around engagement. And I think that we probably all could agree that brands are recognizing that we are in a more consumer-centric business environment, arguably consumer experience-driven environment. And so, we have to write to that accordingly.

Rob:   Derek, we mentioned mindset earlier and I’d like to dive into that. How has your mindset changed since the corporate job, being laid off, starting your business and as you’ve grown and become more comfortable and had some really productive months, what’s the change been like and how have you dealt with that?

Derek:            Initially when I started Cantilever Creative, I had to tell myself that, ‘Yes, this is no longer a side thing. This is what’s bringing home the bacon. This is what you have to make a success.’ So, for me it was a matter of taking it… I always took it seriously Rob, but, the side hustle is great. It’s a side hustle. It’s by nature, not front and center. Taking it front and center, I had to really shift my mindset, think like a business person, which The Underground has been so good in helping me develop that mindset.

And if somebody thinks, just even just process-wise, I mean, I got an accountant now y’all. I got a bookkeeper. I’m talking with a financial planner. The kind of things that grown up, big boys and big girls do who own businesses. It’s like I’m doing this. It started with that mindset, right? That this is no longer just a thing I do on the side. It’s like this is my business. I got to take care of it.

So I’d say that’s the biggest shift for me mindset-wise. The thing that I do want to add and dive back a little bit into the woo-woo is the idea of gratitude. What I mean by that is my take on things is everything’s good. Even if it sucks, there’s a lesson there, right? That’s just me. And I apply it to my business as well. Right? So the first time I tried to start a freelance business and failed miserably and imploded, it sucked.

I mean, it really did. But still tried to find the lesson in it. Still tried to be grateful for those really, really tough lessons. And I think that contributed to my growth, right? On the same token, I still try to be grateful for every little thing and express that too. The reason this is important for me to share is because I see it time and time play out that even if gratitude doesn’t show an ROI necessarily, like the experience I shared earlier, it puts you in a better place. And importantly, it puts others in a better place too. Somebody says, thank you to me, I feel good. So I make it a point of expressing that gratitude to my clients, to y’all, to other copywriters, to peers, to potential clients.

I think that that has actually… Having that attitude of gratitude, if you will, really informs my approach to my business and how I’m building it. So I’d say that it’s no matter what kind of crap we’re going through, there’s always something to be grateful for. And the ability to try to develop that no matter what, really it helps if nothing else just to develop your gumption and your ability to endure and to get up after you’re knocked down. That’s just a good thing.

Rob:   Yeah, that’s good advice. So, you mentioned The Underground, and I’m curious if belonging to communities the second time that you had to go off and freelance has made a difference. What has your experience been with The Underground and maybe even other communities?

Derek:            Oh yeah, man. The Underground is fantastic. I will be a poster child for The Underground as often as you want because honestly I went in there without any expectation but it doubles back to the idea of mindset. I knew that when I was starting my business, I needed to shift my mindset. And y’all were just, actually, I think y’all started The Underground prior to my getting laid off, but I knew that if my next chapter was doing my own thing, then I needed a community.

There’s this idea of finding your quorum, right? Like-minded peeps, if you’re either similarly driven or striving for something, people have different perspectives, but there’s some shared commonality. Like for me, The Underground was that. We may be doing in our different areas of copywriting, but there’s some shared space, right? So community was totally vital. I’m not really a member of other copywriting communities. I get what I need here, and it presents me with an opportunity to give as well. So like I said earlier, got a tough question, able to share it with a Facebook group and boom, you’ve got wisdom dropped on your question.

And I can grow through that so much quicker. So much quicker than trying to figure it out on my own. And on the flip side, I’m able to have a cool experience or have a neat perspective to help the client, I can jump on our Facebook group and say, ‘Hey y’all, check it out. This happened.’ So, it’s been really good. A lot of times we as copywriters it’s like you’re out on the range by yourself. But for me, having a community is being able to ride your horse into town or have somebody on the trail with you to share the journey. The lows and the highs. And I’d argue that we’re human, we need this. We need that connection. And I think now more than ever, but particularly among copywriters.

For me, I’m remote 100% of the time, working at home or a coffee shop or a library or whatnot, but being able to have that community, although it’s virtual, means so much and it really puts air in my water wings. It keeps me floating. But you have cool opportunities like a TCC IRL coming up in San Diego. Just chatting with a few copywriters earlier about that and just totally stoked to be able to meet these people in real life and it’s now I’m on a different level. It’s awesome. The community it’s totally, totally important for me.

Kira:   So just to dig into that more, there are other copywriters who join different communities, or even jump from community to community, or even course to course, membership to membership, not necessarily ours and they don’t get anything out of it. Right? So then they look for the next shiny object. So what advice would you give to other copywriters? So the next community or membership they join, they can get the most out of it?

Derek:            Wow, yeah. I guess it’s not dissimilar to deciding on a niche and just doubling or tripling down. You get out what you put in. Really it’s an adage, but it’s true. So for me, like The Copywriter Underground, I got in, made some posts, made an effort to really hear what people were saying and get into the conversation. And it comes back to relationships, developing those relationships. If I were to have joined The Underground and had some fun with that shiny object for a while and then onto the next, I wouldn’t have realized all the benefit that it offered.

I mean, there’s so much that y’all provide, right? I don’t need to tell you all, but I mean, The Underground is where it’s at, man. Templates, videos, the community which is dynamic and growing and evolving. It’s not like a book that’s there or a course and you take the course and it’s done. It’s living and it’s vibrant.

So, as you change or let’s say as I change and grow in my business and my ability so forth, I know that I can take that to our community, to The Underground and still get the same amount of benefit. And that’s a cool thing about it is like, no matter where you are in your copywriter journey, just starting out are like, ‘Hey, I think I want to do this. And I’m going to join in.’ Or whether you’re somebody who’s got tremendous experience and don’t have a lot of questions but got a lot to share, it’s a place for it. It’s where it’s at.

Rob:   So it feels like, as I listened to you tell your story and talk about your clients, that it’s been pretty smooth sailing since you launched this round of your freelance career. Have you stumbled at all? Have you made any mistakes? Will you share any of those with us?

Derek:            Yeah. I mean, it’s crazy, right? Because I’m preparing for our conversation today, I was making some notes, looking back and just thinking that it’s been really, really good y’all. I mean, really good on so many levels. I mean, however you term success, I’m very grateful that I can say that I think that I’ve met with it this entire past year. I’ve made just, talk about money again, I’ve made more than I ever have. I’ve been able to basically delineate my time so that I can spend time with the people that I love and dictate my terms.

I do not work on the weekends. So there’s a lot of successes, right? There’s a lot of thumbs up, that kind of thing that and the firing all these cylinders of a healthy, vibrant growing business, a really happy business owner, me who’s able to provide for the people he cares about, be part of the community, yada, yada, all these great things.

As far as stumbles, there have not been, thankfully, not a lot. Starting to work with a VA was a bit of a challenge. I got a lot of benefit out of it, but there are some challenges along the way. And it wasn’t a matter of like, not a lack of skill on their part. But for me, I think making sure that I give them my expectations and have a clear understanding of that. And that was a completely new area for me.

So let’s say that if you’re thinking of employing a VA I guess also go for any kind of like contractor, just really do your homework. I did reach out to The Underground, learned some things that helped me out, but I don’t think I really tapped that resource as much as I could.

Kira:   So again, it sounds like so much has gone well and maybe you learned a lot of your hard lessons earlier in your career and that’s why it’s been smoother the second time around. I’m just wondering what is next for you? How do you see the growth of your business based on where you are now? What do you want it to look like?

Derek:            Well, it’s funny Kira because when I started out, I just wanted to pay the bills, man. And thankfully did that and in The Underground, we’ve got this monthly amount of 10K a month that we bandy about. And thankfully that’s been my reality most months. It’s so grateful to succeed on that level, having that foundation. What’s next for Cantilever Creative is I’d say more of the same. I mean, I do want to grow it and like in our conversation we had last year, I am thinking about subcontractors. Okay. How would that look? What would that mean as far as me as a business owner managing people versus just managing my projects and clients, right? So it’s like a whole nother way of thinking about the business.

So, that’s what’s next is like taking the business, growing it to a comfortable level where I’m not stressed out because I’m trying to grow the dang thing. But to take it to the next level, bring some people into the Cantilever fold, junior copywriters, project managers perhaps, maybe designers, doing more collaborative projects. And always, like I said earlier, with an intent to help.

\What’s important for me is to work with people that don’t necessarily look like me, or have my experiences, or circumstances, that kind of thing. So as I build the business, I’m really seeking to give in that way to say, ‘Hey, you’re…’ A former coworker actually fell on some hard times and although I didn’t really need the help, I was able to connect with her and provide some hours. Don’t get me wrong it helped the business, but also helped her.

So, as I seek to grow Cantilever, I’m trying to grow it in a way that’s not just for the sake of growing. I mean, thankfully the bills are paid, not wanting for anything, not living ostentatiously but I want to grow it with an idea of helping. It’s fun to see something thrive, right? Garden, your child, the business. And you want to give more to it. So, I’d like to see how I can make that manifest in 2020. It’s going to be a fun journey. Not sure exactly where we’re going, but we’re going there.

Rob:   Derek, it’s been fun to follow along as you’ve gone through this journey since we were there when you were laid off or you reached out and told us about it and have been able to watch that. And so, this interview has been great just getting into the depths of your business and what you’ve done to succeed. If other people want to connect with you and maybe even have questions about your niche, what you’ve done this time to be more successful or just to reach out and have a coffee, whatever, where should they go?

Derek:            Yeah, you can reach me at I’m also on Facebook, Instagram as well, so just to connect with me as best suits your purpose. And love to connect. Always happy to help.

Kira:   All right. Thank you so much, Derek.

Rob:   Thanks Derek.

You’ve been listening to The Copywriter Club Podcast with Kira Hug and Rob Marsh. Music for the show is a clip from Gravity by Whitest Boy Alive available on iTunes. If you like what you’ve heard, you can help us spread the word by subscribing in iTunes and by leaving your review. For show notes, a full transcript and links to our free Facebook community, visit We’ll see you next episode.




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