TCC Podcast #227: Writing Content with Jacob McMillen - The Copywriter Club
TCC Podcast #227: Writing Content with Jacob McMillen

On the 227th episode of The Copywriter Club Podcast, we’re joined by content writer Jacob McMillen, who as you’ll see towards the end of the episode is an SEO master. Jacob shares his insights on writing great copy and running a content business. Through actively listening and really wanting to help others in his door-to-door sales job, he decided to take the world of copywriting for a spin. Having scaled to 6 figures, we talked about the stages of business as a freelancer and what it really takes to make it. What’s more… he’s the #1 search result for “copywriter” on Google. We break down:

•   how copywriting can be the good of sales without the ick
•   how Jacob went from accounting student (who didn’t want to be an accountant) to copy expert
•   Jacob’s natural talent for connecting a solution to a problem
•   the perfect lucrative combination of marketing
•   how batting 5% is crushing the pitching game
•   how persistence is necessary in the beginning
•   how to get your ideal customer to agitate their own problems
•   the ropes of reeling in clients during the early stages
•   why putting your eggs in one basket can leave you scrambled
•   how Jacob went from 3k months to 20k
•   how pitches can be the bread and butter when in need
•   how flirting with SEO paid off & created 30+ monthly leads
•   how to stand out in 2021 as a new copywriter
•   why not to compare yourself to other copywriters
•   building a copywriting agency and how it’s not for everyone
•   if flipping websites could be the new real estate?
•   how new technology cannot replace copywriting geniuses

If you’re ready to go from side-hustle to business owner, this episode is worth checking out. Grab a cup of coffee, hit play & start taking notes.

The people and stuff we mentioned on the show:


Full Transcript:

Kira:   This week we talked about the different stages of business as a freelancer with our guest, copywriter, and entrepreneur, Jacob McMillen. Jacob is currently the number one US search result for the search term copywriter, which means we should all team up and up our SEO game and challenge his number one spot.

Rob:   We’ll come back to Jacob’s interview in just a moment, but first you should know that this interview is brought to you by The Copywriter Underground. That’s our incredibly valuable membership for copywriters who are done figuring out things by themselves and want to surround themselves with an awesome community of copywriters. It includes our perfect proposal training, our persuasion course, our new sales course, plus more than 20 templates and dozens of presentations all designed to help you make progress in your business. You can learn more about it at

Kira:   Now let’s get to our conversation with Jacob. Jacob, we would love to just start with your story, a very detailed story of how you got into copywriting. Do not leave anything out.

Jacob McMillen:   Okay. I think it’s a relatively fun story. I think you have to start back when I got into sales and unlike a normal person, my start in sales was door to door sales in college. I got roped into doing it one summer. I needed a lot of money. It sounded a little ridiculous, but the numbers made sense to me. So I was like, I’m just going to do it. And I made enough to pay for three years of school in 16 weeks… Not 16 weeks, yes, 12 weeks. And I really enjoyed the sales process. I enjoyed sitting down with someone talking to them, hearing about their needs, connecting what they needed to the solutions I was selling. There were also a lot of things about direct sales that I hated.

So after college, I graduated with an accounting degree. Only thing I knew was I’m not going into accounting. So I was like, what’s next? Started to discover the online marketing world, SEO, stuff like that. And then I fell into copywriting and realized it was everything I loved about sales, minus everything I hated about sales. And I never really thought of myself as loving writing, but it would always come fairly easily. And once I started applying it and directions I actually cared about versus the writing you do in school, I realized I actually enjoyed it. So it just seemed like this great convergence of something that I was relatively talented at naturally, something I was learning to enjoy. And I quickly tapped into just how lucrative the demand was for it.

And so, that’s the perfect combination of things in terms of skillset to build your career around. So I just ran with it and yeah, started with blog writing and then went into landing pages. I just went full speed on the freelancing end of things, did that for a few years. I applied… I think doing that door to door sales job, my mentality towards sales was very volume-based, very hustle-based. I knew you got to knock on enough doors before you find someone who’s going to say, yes, it’s not about batting 90%. If you bat 5%, you’re crushing it. And so, that helped me do pretty well in freelancing pretty quickly, did that for four, five years, and then started thinking, “Hey, wait a second, if all these people are paying me so much money for this writing, that must mean they’re making more off of it. So I should try to make more off of it through my own businesses.”

So I started experimenting with that and building some side businesses and then that’s… I still do freelancing work, but I’ve mostly started to transition into building some of these side businesses, including the one that I have through my website where I help other copywriters follow my freelancing path. And yeah, that’s been the last, maybe three years that I’ve been doing some side businesses on that. And yeah, it all connects back to those original skills of writing and selling and been doing… Overall the career’s now been about nine years and it’s still a blast. I don’t know if it’s a mixture of luck or just progressively eliminating other options that I didn’t like, but I’m super glad I found this career and that’s where I am now.

Rob:   Sweet. You maybe block out little chunks of that path and talk a little bit about them. Going back to the whole door-to-door sales gig, it’s funny that you mentioned that because we’ve talked to quite a few copywriters who have had some door to door sales experience, or even retail sales experience, but a lot of people who learn how to do the sales thing one-on-one, however that was. So what was it about you that made you so good at it? Because so many people wash out after a week or two and can’t do sales. Why did that work for you? And what were your biggest takeaways from that experience?

Jacob McMillen:   Yeah, I think maybe the two biggest things, the first was the persistence. I think my first through my third week, maybe my fourth week, I had full on panic attacks every day from 11:00 AM to 12:00 PM. And most of it I think wasn’t really around what was actually happening in the field. It was the fact that I knew I was committed to the full 12-week-period I was going to do this. And so I felt trapped, the day-to-day was tough and I knew I wasn’t going to quit. And knowing I wasn’t going to quit created these panic attacks, which is obviously a whole other side of things, but it was coming in just like pre-committing. I’m just one of those people who, if I commit to something, I do it. And so, if you go into something and your mentality is no matter what I’m figuring this out, you just tend to brute force your way past the things that trip up a lot of other people who are looking for an exit strategy.

I think that was probably the first big piece. I don’t know how healthy that is, but it is what it is. And then on the back end too, when it comes to the actual sales process, I actually didn’t like… The people I was working with, the organization I was working in, they tracked the stats on everything. And my actual percentage of getting in and talking with people was very low. Not a lot of people would let me in the door to talk with them about what I was selling, but my close rate was through the roof. I think it came down mostly to just listening. Once we started, I knew what I needed to get to at some point, but instead of trying to rush to it or trying to sell, I just asked them good questions and let them sell themselves. Just sat back and listened and let them spend as long as they wanted to talk about the challenges they were feeling because I mean, as much as it’s great to try to agitate the issues that people are dealing with, if they can do it themselves even better.

That’s the nice thing with direct sales. You can just ask the right question and let them spend 20 minutes agitating their own problems. And then it’s just a matter of, if you’re selling something that has a great product market fit, then it’s just a matter of just very clearly showing how it’s going to solve the things that they just spent 20, 30 minutes agitating. And so I wouldn’t rush that. I would let it take its time. Part of the things I hated about sales was how emotionally invested I get in any particular conversation. I mean, it was a two-edged sword in the sense of people could feel that I really cared and that I was actually genuinely interested in the challenges they were facing and genuinely looking to see if what I was selling could help. And the upside of that is that, when you are able to communicate that authenticity and make people feel seen and their problems are real and important then they’re more likely to purchase from you.

Kira:   Maybe you already said this, Jacob, but what were you selling?

Jacob McMillen:   Educational handbooks, the company was called Southwestern, and you might’ve heard of them, but basically it was the way that schools are teaching various curriculum across decades changes. And so it was designed to help parents bridge the gap between how they learn stuff when they were in school, and how their kids are being taught at now. Because the classic little anecdote, they hammered into us in the sales training was like, you have the dad, who’s been an engineer for 40 years and can’t help his elementary school kid do a math problem because they’re using this cube method or something. Basically just bridging that gap and helping parents transition their knowledge of how to tackle these various concepts from the old way it was taught, to the new way it was taught.

Rob:   I hate the cube method, I got to say it.

Jacob McMillen:   It’s a real pain point.

Rob:   Oh my gosh, I would buy that book any day here.

Jacob McMillen:   Right?

Kira:   Sell Rob the book. Sell him the book, he will buy it. Well, so your audience is mostly parents. What did you learn from that time about parenting that prepared you for your own parenting experience years later?

Jacob McMillen:   Man, I don’t know if I learned anything about parenting from that, except from maybe like… Just that so many parents genuinely care about their kids and just absolutely genuinely want the best for their kids. Yeah, I mean, it’s crazy because you come in to certain neighborhoods that were really run down and you’d have some people think I’m not going to sell anything here, but you can walk into a house that’s worth 50 K or a house that’s worth 5 million. And oftentimes you’re going to get the exact level of care and love for the kids that translates into what they’re investing their available money in. Which I hate to frame it from a monetary view, but at the time that was my lens. And I think if there’s any takeaway on the parenting side, it was just that love for kids has nothing to do with money.

Kira:   Yeah. Okay, cool. And when you got into copywriting and made that transition, it almost sounds like it was really easy for you to just take off in the copywriting freelance space. So what were you doing to attract your first few clients? It sounds like the sales side was easy for you, but were you pitching clients, were you doing something else to build your authority? What did that look like?

Jacob McMillen:   Yeah. I mean, and this is what I teach my own students is, I think reliably when you’re first getting started, it has to be outbound. It’s the only reliable way. It definitely has been true for me through all of the students that I’ve worked with up. Just getting out and getting in front of people, putting the numbers in, that’s how it was for me. Before I really had the mental model of freelancing, it started with I was just looking for part-time jobs to fill up my schedule. So I did on Craigslist and I’d look up jobs connected to things that I might be able to do. And that’s how I landed my first job, which was in my first client who was an SEO. And they were basically having me write articles on pest control and it was a used car repair and all sorts of local SEO type stuff.

And so for me, I was just like, okay, I have this one person they’re paying me a fixed amount. So let me go see if I can find more people that look like this through Craigslist, which is how I’d found them. So every day I would just hop in and see if there were any new postings. And then I started to discover that, hey, Craigslist, isn’t the only spot for this, started finding some of the different job boards. Every day I’d just open up the various places that had a potential for new listings and look through and see if there’s anything relevant and pitch it if it was.

I wasn’t really on the clock to make any particular amounts of money at the time. So at first it was very passive, very casual, just a habit that I would look for any place that potential new gig could be posted. And then maybe probably like two years into this, I added a few one or two other clients, but it was still like one client who was paying probably 60 to 75% of what I was making on any given month. We were about four months away from my wedding which I was paying for and that client just out of the blue dropped off. A lot of the budgeting and bills that had gone up to that point depended on that client being there. That really lit the fire to actually go real hard with the pitching.

I just started pitching everything that moved, was probably sending out a few hundred pitches a week. At one point, I got super annoyed that I wasn’t hearing back from any editors, even on free guest posts. So I started writing full articles and sending them out even though it was a lot of work. Over about a course of a month doing that, I landed a gig writing for Crazy Egg, which ended up opening a lot more doors down the road and was even a good paying gig by itself. I landed up a website copywriting project that ended up paying about 14,000 and then another one that paid 5,000, which at the time, I think the most I had made prior to that, because I was working very part-time at the time, was maybe 3 K in a month. So it had jumped up to landing over 20 K worth of gigs in about a month or two of this really heavy-duty pitching.

I think that was the moment where for me I knew this is a long-term career. At that point, I knew if I ever need money, all I have to do is send out some number of pitches and I’ll have money. And so I think that’s when mentally, it transitioned to me from just being something I was doing to make some money, kill some time while I was focused on other things too. This is a full-time career. And then about a year later is when I went full-time.

Rob:   I definitely would love to talk a little bit more about that pitching. It’s been a theme of a few of our recent episodes on the podcast. But I also heard you say that you went to school, studied accounting, and then you didn’t want to be an accountant. At risk of losing the flow of where we are, am curious, why did you study accounting not wanting to become an accountant? And has that changed the way that you look at your business because of your background with numbers, with books, bookkeeping, being able to do the debit-credit thing. Does that give you a unique view on a copywriting business that maybe a lot of the rest of us who came from say humanities or some other place, what we would look at our business from?

Jacob McMillen:   Yeah. So the answer to why I chose accounting, I think up until that point, I mean, I think a lot of us do this. I was just living my life on default. You graduate high school, you go to college, you pick a major, you know you don’t have any clue what you’re actually going to want to do. So you’re just picking something. For me, business school just seemed like the practical choice. Then within business school, accounting, and finance both were interesting to me. They were the two more prestigious majors. And accounting, we had top 10 nationally accounting program at University of Georgia. It was what the business school was known for and it was supposed to be the really hard major.

So I think that for me, it was just what’s going to look the best on the resume. What’s going to give me the most options and when it came down to it, if I had wanted to go the public accounting direction, it would have been a lot more difficult going that direction with a finance major. If I had wanted to go into finance with an accounting major, it would have been easy. So I was like, well, this route gives me one more option. It was a very practical, very uninteresting uninspiring choice, like many of my life choices. And in the end, how much of an edge has it given me in the numbers department? I’m not sure. I will say it was very easy for me to do my taxes for the five years that I did them myself. So that was definitely a bonus.

And I think maybe it’s hard to know whether this was due to the major or just due to me being a little more of an analytical person, but definitely, when I talk to even other freelancers who are more experienced than I am, I definitely seem sometimes to feel like I have a better grasp of personal finance and long-term, even just like leveraging tax advantage, savings accounts and stuff like that. Has nothing to do with getting an accounting major it’s just maybe I’m less intimidated to look into some of those directions because I’m aware of how straightforward it is. So that would probably be the biggest thing. And I think too, this might be an accounting thing, but just being very metrics focused.

One thing I do with my students is when I ask them like, “Hey, what’s your goal?” A lot of times writers tend to have very vague goals or very vague milestones they want ahead. So I’m always trying to transition concepts into numbers because I think going after a clear number, especially a number that’s fully within your control is what has the most impact on forward growth and business growth.

Kira:   So to get back to the pitching, I wonder if there’s a way… what your perspective is on marketing over time as a freelance copywriter. And the initial stage is really outbound, you shared and that worked well for you and works well for many, pitching clients, reaching out to them, when did you feel you moved into the next phase of marketing and putting yourself out there where maybe focus less on, sending cold emails and more on speaking on podcasts or something else? Can you break that up for us and describe your perspective on that type of authority building in the marketplace?

Jacob McMillen:   Yeah. I don’t think anyone wants to spend the rest of their life pitching. So that was definitely looking to move to that next phase I think is definitely important. For me, it was through finding some recurring distribution, which for me was SEO. I would say maybe two years into me being full-time, I got really serious about trying to learn SEO. I’ve been flirting with it a bit and even ranking for some things, but it was like, I’d identify a term I thought ranking for would have a big impact and then I’d rank for it and it would be meaningless. So I was like, okay, I need to actually get serious about this. So I really dove into trying to understand keyword research and things of that nature. I would say that took about a year of trial and error, very intentional.

It was almost like I learned more by osmosis than by actually anything clicking. And then I started getting some SEO results. I was ranking for professional copywriter, expert copywriter or something like that. And then website copywriter and they get… Those terms brought in less traffic than you might expect, but it was enough to start getting some good lead flow and on a month to month basis. And then at a certain point when I was probably getting the most copywriting leads through my site, it was like between 30 to 40 a month. And at that point, there’s just no reason to pitch now because you’re getting these warm inbound leads, which are higher quality anyway. SEO is the route for me, I’ve seen people do this through just building a massive audience on LinkedIn. I’ve seen people do… They’re just like really strategically connecting with people on Twitter constantly.

You can do it if you’re focused around building an email list, you can do it the JV route of doing little partnerships with other people who have lists of people who might be interested in hiring you, lists of entrepreneurs, things of that nature. So I’ve seen it work in a lot of ways. I think every copywriter, if you work long enough, you get to a point, some sooner than others, where referrals will take off a big chunk of that. Just almost organically, but at the same time, I don’t think there’s any truly passively jen, even when we talk about SEO, these other things, there’s always some active, ongoing work involved. And I equate it to if any Fortune 500 company told their sales team to take a month off, the company would just crash and burn in a month.

I think it’s the same with freelancers. Whether you doing cold outreach, whether you’re doing branding marketing or some combination of the two, you just have to accept from the beginning that it’s going to be a monthly part of building your business. And so whether you do the outbound early, which I think is the faster results or find some channel that you want to commit to ongoing to get that more inbound eyeballs, the key is just that you’re doing something every month.

Rob:   Yeah. When you mentioned earlier, as part of some of your pitches that you started actually sending out full articles, I’m guessing that’s not something that you would recommend to people that you’re coaching or talking to now, but what was the result of that? I mean, in some ways I almost like the idea because it stands out, it’s really different, and if it gets results doing those things that don’t scale early on in your business can be pretty effective, even if you can’t keep doing it. But tell us a little bit about how that worked out and why you stopped.

Jacob McMillen:   There’s this website that’s pretty big in Australia called SitePoint. That led to me getting a publication on SitePoint. And that was actually the funny thing is, up until that point, most of the stuff I was getting paid for was from working with an SEO client who wanted to get a link from an article out of your byline. You are guest posting on behalf of the client. That’s what I was expecting to happen here. I was only expecting to make maybe 20, 30 bucks from a piece on that and they responded like, “Hey, we loved it.” You can bill us at our standard rate of 150 and that was the light bulb of like, oh, I can actually get paid for the writing itself not just the fact that I’m including a link to the brand in my byline.

And so that was a revelation for me, not necessarily because of the specific tactic, but just how it played out. And yeah, I think I may be sent out six or seven full length articles and got two of them accepted, which at the time, I wasn’t even getting a response from other pitches. I felt like it was a win. You can also too… I think once you hit a certain point where you really know what a lot of the businesses you’re pitching are looking for, my friend, Aaron Orendorff, he would do a lot of that when he was still freelancing. He would pre-write an article that was based on a trend, and he would write it specifically with the first brand he was going to pitch in mind, but he would do a type of article that if that first brand said, no, he could retool it a little bit and then look to sell it to another brand.

I think it’s a viable strategy. I think it’s better for more experienced writers, just because a lot of newer writers aren’t good at blog writing. It takes a while to get good at it. And so, writing a whole bunch of crappy articles, practice is never lost because, but if you’re looking for a more… it’s definitely not the most efficient way. I think pitching, writing out headlines and pitching two to three different headlines to any individual client is probably a good mix of it just being a completely copy paste pitch and doing a full article to pitch them. It middle grounds that a little bit. And I had the most success doing that strategy. But at the end of the day, it’s never a bad thing to practice the craft you’re trying to get good at.

Rob:   Yeah, sure. That makes sense. Were there other things at this point in your business that you were doing that wouldn’t scale today, that were just getting you in front of the right clients or helping move your business forward?

Jacob McMillen:   So I was doing a lot of guest posting. And I didn’t care if I didn’t make any money from a lot of the writing I was doing. And at the time, some of those were connected to someone paying me to throw a link in my byline. A lot of them were. I just wanted to get my name out in the marketing space and a lot of those ended up translating to other gigs. I think at a certain point, you get to the point of diminishing returns when it comes to having your byline out there. But when you’re first getting started, I definitely think that’s a non-scalable thing that can have a big impact, for so many reasons too, you can get your byline out in front of potential clients, if you’re a guest blogging in a niche you want to target, you are connecting with editors in the space. Ideally editors who can help you become a better writer by critiquing the work you’re sending them or just making it better.

And you can evaluate what they changed to make your content better. But it was to the point where I had one client who I was working with, telling me that my name had come up while there their editor was talking with an editor from some other marketing blog at a conference. If you’re doing so much of this that your name starting to pop up when editors are talking, you’re on the fast track to be getting a lot of paid work. It doubles as a networking thing. If you do a really good job and something you give them for free performs well, you can always follow right back up and try to upsell them on a paid gig. So I just think if we’re talking about non-scalable stuff that’s really effective for newer writers, that would probably be the number one.

Kira:   Okay. And then, I was going to ask you what else you would recommend today, 2021, it’s getting to be really competitive in the copywriting space as more people move into freelancing. What else do you think copywriters need to do today to stand out in a crowded marketplace, especially if they are new, they’re a little less well-known, other than what you shared already around, getting published and creating guest articles?

Jacob McMillen:   One place where I would differ from the prevailing advice that I see a lot for newer writers is, I don’t actually think you need to niche down in your first year or two. If you come into the field with a specific niche that you really want to target, then great. I think it can definitely help. But I see a lot of new writers really get hung up on trying to find a niche. And to be honest, I don’t really think having niche expertise helps you a whole lot until it’s been stacking for like three, four, five plus years. So to me, I think, especially when we talk about saturated places where most of the niches being recommended are very busy and do have a lot of established experts. I think coming in and just taking a wide range, anything that interests you, pursuing opportunities in it, taking a wide range of gigs and letting the niche and even the writing type itself come to you, find the Avenue that you most enjoy, where the opportunities are opening up for you.

And then, if you wait two years to really let the niche come to you and then really specialize in it, you’re not going to lose a whole lot of ground in terms of your career trajectory. And you might end up finding certain avenues that aren’t in really crowded spaces. Because “crowded” as the freelancing market is becoming, it’s all relative, we’re talking about 100% year over year e-commerce sales growth. The supply, in my opinion, isn’t even close to catching up with the demand. So I think there are hundreds of industries and niches and specialties that still people are struggling to find, great writers and those niches, even in… I’m in a fairly saturated one, which is the B2B Marketing blog content and copywriting. And I have clients coming to me who are really wanting to do more work with me because they’ve been sampling out lots of other writers and are still struggling to find a good fit.

So I think it’s, let the niche come to you and then once you do, I think prioritizing mastery over income earlier on is really advantageous. That’s another thing I see a lot of is as much as I agree with the idea of charging what you’re worth, and there are people being underpaid. Especially in the beginning stages, I see a lot of writers who are rate chasing. They got paid more than their writing was really worth this one time. And so every future client they’re trying to land at that rate, instead of more looking to drive demand to their work and price based on demand. And so that’d be the other thing is, and I go through this process with my students.

I would much rather see them work on 100 projects in their first few months that are paying 50 bucks a project, than land like two 5 K gigs where they only get two practice rounds. So that’s another thing, that’s definitely something I’ve done in numerous places throughout my career is, any place where I felt like, hey, this is going to give me this gig or this direction is going to give me an opportunity to increase my mastery, I’ll take it, even if it’s a pay cut. And I definitely recommend that if you’re in the newer stages. If five years plus, 10 years plus, then probably the mantra of charge what you’re worth done, except the low ballers is much more applicable to where you’re at.

Rob:   Yeah. Anytime you’re talking about mastery and trying to get better at stuff, you’re talking my language. So-

Jacob McMillen:   Anytime you’re investing in yourself, this is why Kira and I talk all the time about joining masterminds and surrounding yourself with people who can help you grow. I’m all about that. So I’m 100% agree with a lot of what you’re saying there.

Kira:   Let’s jump in here and talk about one or two things that stood out to us. So, Rob, what did you take away from this conversation?

Rob:   So there’s a few things here that I started making notes about. Number one, going back to his early experience with the sales process and just asking questions and that was his secret. We talk to copywriters all the time who were saying, “Okay, how can I sell myself to my clients? I’m about to have a sales call. What do I need to say?” And our advice is almost always just ask questions, ask questions about the business, ask questions about how they find customers, ask questions about where they’re doing their marketing today. What are the hot buttons? What are the features, the benefits, all that stuff and you’re always asking questions to try to understand the business.

And ironically, when you do that, when you’re asking all the questions about what you don’t know, it shows the prospect that you’re interested in their business, that you’re trying to figure out the best ways to help them as opposed to selling yourself where you’re just talking about all the great things that you can do, it actually is more effective at selling them on you. Just because again, you’re showing interest, you’re learning about the business and you’re starting to identify some of the problems and the things that they need help with.

Kira:   Yeah, I love that idea of allowing your prospect to agitate their own pain points. And even though we’re not necessarily doing direct sales here, but we can sit with a prospect on a sales call and zoom, and we can take as long as we want on those calls. I think oftentimes we might rush those calls and feel like we have to get them in and out in 30 minutes, but we can give ourselves space and time just like Jacob did in his direct sales position. So that we can cover all the questions and allow the prospect to really agitate their own pain points and realize that you ideally are the best solution.

Rob:   Yeah. And I think I had another thing that stood out to me, the question that I was asking about doing things that don’t scale. Jacob was obviously doing stuff that you can’t do for everybody in order to grow your business. You can’t write an entire article for every potential client that would come along. But when you have more time than you have projects, or more time than you have money, you need to use that time in order to do things that stand out. And so it’s impressive when he’s talking about how he would write the whole article doing spec work, which is not something that we would usually recommend, but doing these things that don’t scale in order to stand out.

And I think that there are other ways that we can do that too, that we need to be aware of when we do have a six-figure business or when you do have enough clients coming through that they’re taking up all of your time, you can’t spend your time doing that stuff, but again, when you have a lot of time and not a lot of money projects, clients, it’s smart to do those things that you can’t do at other times in your business.

Kira:   Yeah. And that’s why I like thinking about the different phases of your business in marketing and how you put yourself out there, because there are these really distinct phases, just like Jacob mentioned, how he started pitching and he focused heavily on pitching at the beginning. And that’s not something that is necessarily… I guess it’s sustainable, but most people don’t want to continue pitching. But you evolve out of that eventually, and then you get referrals and then you can focus on something else, which he then went and focused on SEO, but there’s no one right way or one way to do things as you start marketing and evolving.

I think that’s why it’s important not to compare yourself to all the other copywriters and content writers out there because they might just be in a different phase. So while they need to do something else, maybe they need to focus on pitching. You may be past that stage and need to focus on building your authority in a totally different way. So I think it all goes back to just knowing what works for you and where you are in your business growth and not comparing yourself to others.

Rob:   Yeah. And I think that’s why it’s fun to interview copywriters on the podcast from different stages of their business. Because when we’re talking to somebody in their first year, they’re doing things very differently than people who have built six-figure businesses and are talking about your building agencies and the products that they’ve developed. And so to me, it’s interesting to see all of those phases play out with the people that we get to talk to every week.

Kira:   Yeah. So anything else stand out to you?

Rob:   Maybe one other thing, Jacob mentioned the niche question, and this is something, again, that comes up a ton. In fact, you and I were talking this morning, and I think you said that you’re tired of talking about niching, should we niche or whatever. But I think as he recommends, that it’s not always the best thing to choose a niche right out of the gate, you don’t necessarily need to launch your copywriting business without a niche. But there are things that choosing a niche does help you do. When you’re talking about a particular niche that starts to attract people who are in that niche, you’re able to demonstrate that expertise.

And so while it is okay to launch without a niche, it is okay to explore several different niches to see if one’s a better fit for you than another or if you connect with those clients. He is right. You don’t necessarily need a niche to succeed at the beginning, but it can help you focus your business as you start to grow. And like you were saying, go through some of those other phases in the business. When you get to phase three or four, you oftentimes, almost always would niche into something or other whether it’s a particular industry, whether it’s deliverable that we create or whether it’s the problem that we solve for our clients.

Kira:   Yes. And I have nothing to add. I think you’ve covered it. And I’m going to take the week off from talking about niching.

Rob:   Awesome. So let’s go back to our interview with Jacob and ask him about starting a content agency. If I’m remembering this right, Jacob, you also started an agency at this point in your career track. Tell us a little bit about the thinking that led to that and why you also ended that experiment.

Jacob McMillen:   Yeah. So basically what happened there was I had a client that I had just gotten them so big that just to continue growing the blog, I needed more people. So to tackle this bigger budget and vision I had to create a team. And so I went through the process of creating that team. And then, once you have the team, initially the capacity of that team was higher than what the one client needed. So I started looking to add some more clients and started building a small agency, mostly built around a contract work team. And I did that for, I think it was about a year, maybe a year and a half. And I just got to the point with it where I realized quickly all my time was going to hiring and editing.

And it just, wasn’t fun. At this point, I really do enjoy writing. I really do enjoy creating. And so for me to be in a situation, even though it was fairly lucrative to be in a situation where I was spending most of my time trying to hire, train, manage, and edit work just wasn’t appealing to me. I started experimenting too with… I brought in a project manager to help with that, to see if that would solve it. But I realized too, at a certain point that you can’t really build a business around contract workers like freelancers. I love freelancers. I am a freelancer. We are not the most reliable of individuals, and not to say we can’t be, and there aren’t very hyper professional freelancers, but just as a general rule, if you’re trying to build a 10-year company, you bring in a freelancer, you find a great freelancer who you can bring in at $0.10 per word.

If they’re a good freelancer, they’re going to be charging $0.20 per word within the next six to 12 months. So it’s just like whether it was you go through the process of bringing a writer onto the team and then three months in, you can’t really afford them anymore. There are a lot of freelancers who just are aren’t great with deadlines and things of that nature. So it was just one of those things where I realized if I was going to continue growing it, I really needed to transition into full-time hiring.

Even with the freelancers, I realized I didn’t like the anxiety of having other people’s livelihoods on my mind all the time. Of like, hey, if I lose this client, I’m going to need to… At that point, I’m not just hustling for my own income. I’m hustling for five people’s incomes, 10 people’s incomes. And I realized that’s not why I got into solopreneurship and freelancing to have other people’s wellbeing on my conscience. So it was between that and not enjoying the day-to-day work of managing and editing and things of that nature. I just realize agency running was not for me.

Kira:   Yeah. And I love this conversation because Rob and I are possibly creating an agency together. I’m just trying to find more ways for Rob and I to partner.

Jacob McMillen:   Totally.

Rob:   …So basically, you want Rob coming at you from every direction. (laughing)

Kira:   What else can I do with Rob? Let’s do this. Okay. So what would be your advice? I mean, to someone maybe like me who is interested in building the agency model based off what you’ve learned. I mean, clearly it sounds like it wasn’t a good fit for your goals and what you enjoyed. But for someone who wants to do it, what advice would you give them maybe based on what didn’t work for you or what you would do differently if you were to jump in again?

Jacob McMillen:   Yeah. I think, the biggest thing I’d recommend is having a real specific vision of what you want your personal involvement to be, and making immediate full-time hires for the positions that for the key objectives and roles that you don’t want to do. Because I think you can make the freelance contracting model work if you’re not necessarily wanting to go to a full-time writing hires. But you really want to have someone who wants to handle all that. Who’s good at it. Who’s a good editor, fully invested in that. That was probably the single best hire I made was bringing in the project manager. They were fantastic to work with. And it made a huge difference. It just didn’t change some of the other things that I didn’t like about the experience.

So that would be the big thing. And then obviously that’s the fulfillment side, then obviously you need to have a really clear understanding of how you’re going to be growing the lead pipeline to facilitate the rollercoaster of client inflow and outflow as you build the team. Because I think that’s even just from the copywriting and one of the things I’ve noticed a lot in talking and getting to know entrepreneurs over the years is, in a service-based business model, you deal with this… You’re constantly in this state of not having a big enough team to fulfill, the amount of work you have or not, or having too big of a team for the work you have. There’s never a perfect equilibrium on that note until you just get massive. So, pre understanding that challenge, going in and having a clear idea of how you’re going to tackle that would probably be my biggest recommendation.

Rob:   So Jacob, let’s talk about where you are in your business today. I know you’re not doing the same stuff. Obviously, you’re not doing the agency thing anymore. But I think you’re not writing for clients quite as much as you do. You have some programs. Tell us a little bit more about where your money comes in and how that all breaks down.

Jacob McMillen:   Yeah. So about 18 months ago now, I stopped taking on new freelance work for a season and I was like, I’m going to give myself 12 years to just try to grow my own blog and email list. And I was planning on making a freelance copywriting course. That was something that, over the years, a lot of the real popular courses that had been around since I was in the field in 2012, I just was constantly hearing poor feedback on some of these really super well-known brand names. And with the big piece being that they didn’t really teach how to land clients. And so, that was something I’d wanted to take some time to do for a while. So finally, I was like, hey… We actually found out my second child was on the way.

So I was like, I have about nine months here to potentially start something new. And after that, it’s probably going to be like a decade before I even want to think about doing anything new which I was definitely right on that end, at my productivity went off a cliff when that second kiddo came around. So I spent nine months just working on creating lots of content, building my email list and pre-sold that course and started building that course. And it ended up being super well received and the email list has grown a lot. So that’s become probably the biggest part of what I’m doing right now is working with students in that course. And then we also have a community as well called Right Minds, it’s exclusively for writers who are more in the intermediate plus stage of running their business.

And so between those two things and creating content, that’s my main business at the moment. I also do quite a bit in terms of investing and I’m working right now, there’s a new company called CopyAI. You might’ve heard of it, they’re utilizing GPT3 to help entrepreneurs in particular work out the baseline for new copy. So I’ve been working with them as well. And then I’ve bought some websites on the side. They were low revenue generating and then working on improving their SEO and it was an alternative to real estate play, something where had a pretty stable income stream coming in and had a much higher revenue to investment ratio versus purchasing and renting. And so I’ve been experimenting with that over the last two years and have some of those going on the side and just anything where it’s like, “Hey, how can I create reusable assets through the writing skills I’ve developed?”

Kira:   Okay. I want to ask two questions, I’m going to hog the mic for a little bit. So first one is, productivity because you mentioned productivity plummeting after your second child. I am expecting my third in June. And so I’m just assuming I’m just going to just crash and burn. I’m always looking for ways to kill my productivity. And this is the way-

Rob:   It’s a great time to start an agency too by the way.

Kira:   Yeah. So we’re going to start an agency and I’m going to leave Rob in the business by himself. So I would love to just hear how you are juggling that as far as schedules and work times with two young children. So that’s question one, and then I’ll wait on question two.

Jacob McMillen:   Okay. So, I mean, I think my first answer would be I’m not well. This definitely the last, let’s see, he’s about nine months old now. So this is definitely been a very challenging nine months. And I don’t know that there’s any good way to approach it. For me, it’s been finding what are the smaller things that I can commit to? So I noticed right off the bat my ability to focus and writing long form was gone, just absolutely gone. And so instead I was like, “Well, why don’t I do 10-minute podcast episodes? And I can post one of those a week. And that will be my ongoing, the maximum thing that I can commit to in place of these 40-hour work blog posts.

So just having something that’s like, hey, this is not ideal, but it’s something that I can actually commit to. That’s been big for me. And then two, I think just being realistic. There was a time where I was trying to like force my old work schedule into my new circumstances. And once I stopped trying to do that, I realized that if I could even just find one or two hours a day where I could really focus in without interruption, that I could actually get a pretty good chunk of what I needed to get done, done in that time period instead of maybe my normal process, which was to be moderately focused for six hours.

That was a big thing for me, just not trying to force any unrealistic milestone or expectation into my new environment and just build around what was available and find the opportunities in the new circumstance, in the new season. And just look for those ways where I could still be consistent, even if realistically the output was not significant. At this point, I’ve had virtually zero return on the effort I’ve put into the podcast and YouTube episodes. But it’s something that’s building and that’s going to potentially be a recurring payoff down the road. And it was all I could realistically commit to in the short term.

Kira:   Okay. I appreciate that. That’s great to hear. And second question, I love this idea of investing in other websites and that’s something that I have not done. I wouldn’t necessarily focus on SEO, but I could see we all have our unique expertise we could add and purchase it and give it an uplift. So what are maybe some basic resources for someone who’s also interested in purchasing other business websites and flipping them?

Jacob McMillen:   Yeah. I definitely would not consider myself an expert at this point. I’m still relatively new to it. What I opted to do was go through, there’s a site called Empire Flippers. And you pay more to get the sites through them, but they do a pretty extensive vetting process, have a pretty in-depth escrow based transition process. So it was like I felt safe with what I was going to get there. And so then for me, it was just about being patient and looking for the sites, waiting for sites where I felt like I looked at the site, I looked at how they were monetized and I just compared it to businesses I’d worked on the past, my understanding of various spaces and just waited for the opportunity to say, here’s something that feels a bit under monetized or here’s something where they’re bringing in some money through content, but the content could be a lot better.

And so, like you said, looking for ways that I could add my unique expertise to those sites. I don’t necessarily have any specific resources that I could… or tips. It really depends on how you’re going to improve the site. If you’re someone coming at it from an affiliate marketing angle, the criteria you’re going to use, and the steps you’re going to take will be drastically different than if you’re looking for ad revenue, or if you’re looking to sell products or things like that, but just approaching it on a very case-by-case basis and being patient, and just looking for something where you really feel like, “Hey, I can make a move on this.” Would probably be the best thing I can recommend.

Kira:   This site is so cool. I’m getting lost in all these businesses I can buy for-

Jacob McMillen:   Isn’t it cool?

Kira:   It’s so cool. Probably should list The Copywriter Club and just see how much we can get for it.

Rob:   There are a couple of sites that are like it, being in the SAS space and having done a startup I’ve played around in there before and seen some of these businesses that are for sale there. So, Jacob, you also mentioned that you’ve been working with an AI tool, AI client. Let’s talk about that for just a second. Are you on board with the idea that AI is going to take away all the copywriter jobs in the world three years from now, or what is that going to look like?

Jacob McMillen:   Not at all. I don’t think it could be any further from the truth. I think if the right iterations can be created, I think that the AI GPT-3 in particular, can be utilized as almost like a productivity tool for copywriters because obviously everyone has their own unique process, but for me, one of the most time-consuming parts of copywriting is the brainstorming phase where you’re trying to find just different ways to say stuff, trying to find different phraseology, just trying to find anything that’s going to spur ideas and cascading ideas for different ways of expressing concepts, expressing them concisely, things of that nature. For me, that’s always the most time-consuming part of copywriting. And it’s so easy to get in your own little mental rut where your ideas sink into this one channel and it’s tough to break out of it.

So with GPT-3 and the way CopyAI is doing it, and I’m helping them build a tool specifically for value propositions right now. But the idea is basically that you can put the core ideas in, and then this AI is going to spit out a bunch of just raw ways of saying things connected to this concept. Just like you do with your own brainstorming, you’re not really looking to brainstorm the perfect idea that’ll hit the final draft. You’re just looking for little seeds. You’re looking for pieces that you can then build around and create into something polished. And I think that’s where GPT-3 excels and has the potential to excel, even in terms of being a tool for writers is just that vein of idea generation of spinning out new ways of saying things, new phraseologies, things like that you can then incorporate into your own copy.

The biggest reason that I don’t think writers have anything to worry about with GPT-3. And when I say writers, I mean good writers. In my opinion, the real low end of the market was always vulnerable and was often just being cannibalized into other things. So definitely the low end of the spectrum, people who just aren’t good writers and just the demand is so high, they’re still managed to land some work that might be vulnerable. But for people who are being brought in for companies actually making money to write copy, that it’s actually going to be read by an audience that they paid to bring to the site, it’s never going to be able to create the core and strategic substance that makes writing so special.

I think there’s definitely some formulaic aspects of copywriting that will be able to be implemented by AI. But in terms of just the finished product, there’s just so much that goes past the formula. There’s so much even in terms of identifying the core value and substance that needs to come into the writing to actually make on impact readers. Yeah, I’m definitely not worried. Even being at the forefront and working with some of these tools that are being used by actual entrepreneurs, in some cases, even to put coffee on their end website. I definitely don’t see it being a threat as a general rule.

Kira:   All right, Jacob. So I’m leaving this conversation feeling very energized to be a copywriter, thanks for that. Feeling excited about an agency and excited about flipping businesses on empire flippers. So I feel like you’ve given us a lot to think about and look forward to where can our listeners find out more information about what you’re up to. And along with that, what are you doing next that we should know about?

Jacob McMillen:   Yeah. So I’d say, if you head to you can find my blog, which has several hundred thousand words of free content there. I have the podcast I mentioned, every week I try to do like a 10-minute YouTube video/podcast episode on writing, marketing, and freelancing to get the flex in there. If you Google copywriter, you’ll find me at the top result. And then-

Kira:   Wait, what?

Jacob McMillen:   Yeah. I guess I never slipped in my party track in our episode yet, but that’s what I’ve been mostly working on the last year is getting rankings for copywriter, website copywriting, email copywriting, copywriting books, I think-

Kira:   That’s right. You are top of the list. That’s crazy.

Jacob McMillen:   Yeah. I think I’m jostling with one of your guys’ articles for copywriting books. We trade places one and two every few days.

Rob:   All right, we’re going to take you down, Jacob.

Kira:   Oh, wow. Game on, Jacob. I don’t know anything about SEO but I’ll do it.

Rob:   Yeah. I mean, it depends a little bit I think on search settings or whatever because Google’s personalization sometimes will drop things under people’s search results that are related to them. Right? So it may not come up for every single person, but yeah, you’re right.

Kira:   It came out first for me, Jacob, you’re top…

Rob:   We’re definitely taking you down.

Kira:   Everyone listening should take down Jacob.

Rob:   Link me to your own blogs and your own sites. Yes. Please help us take him down.

Jacob McMillen:   But yeah, I mean there’s not really anything at the moment, any particularly new projects, just focused on creating the best training I can for people trying to grow their freelance writing businesses. And that’s about it for the time being.

Rob:   That’s awesome. Well, thanks Jacob, for coming on, sharing your wisdom. Maybe we need to have you pop into The Copywriter Club group and share how you attain the number one position at some point.

Jacob McMillen:   Totally. I’d love to.

Rob:   Thanks for coming in and just talking about your business, we appreciate it.

Kira:   That wraps up our interview with Jacob, but before we go, it might be worth talking about how Jacob started his agency and a little bit more about that.

Rob:   Yeah. So, as I think about this, I mean, obviously we said that we’re thinking about doing this ourselves. There are definitely pros and cons here. When we talk about starting an agency, when you have people working for you, whether they’re contractors or employees, now you’re suddenly responsible for the income as Jacob mentioned. You’re responsible to make sure that that work comes through and that they’ve got things to do. And that’s a pressure that’s very different from the work that we do when we’re working one-on-one with clients. And you’re responsible for coaching them for copy chiefing, for editing or proofreading. And while some of those kinds of roles can be assigned out to other contractors, that stuff still has to happen.

And when you do build an agency, it changes your job very dramatically from working one-on-one with clients to create content or copy to one where you’re managing a team, that’s doing those kinds of things for your clients. And so, something I think that’s pretty important to understand. And a lot of the people that we’ve talked to on the podcast who have started agencies have backed down and decided that it’s not the way to go. So it’s definitely not right for everybody, but it’s right for the right people.

Kira:   Yeah, we talked with Jamie Jensen about her agency and how she built it up. And then she shut it down and pivoted in her business and is doing really well in the new direction of her business. So I do think there’s a lot to the agency space that probably a lot of us don’t think about or realize until we’re in it. And so I think it was a good conversation with Jacob and he offered some great advice about figuring out what role you want to play and being really clear about what you want to do and what you don’t want to do in that agency.

Because I think that’s what happens, is you end up stuck doing something that you didn’t really go into business to do anyway. So as we’re slowly brainstorming what that could look like for us, we are taking our time and just experimenting and thinking about it because it’s not worth rushing into without a plan. And I know for me, I love copy chiefing. To me, that would be wonderful to copy chief and sell new clients into the agency. But without that clarity, it could get really messy along the way.

Rob:   Yeah. So again, I’m definitely not slagging the idea of starting an agency. If agency is the goal for you, build into that and start to develop that. And if it’s not, if you’re the person that just wants to write for clients and work that one-on-one have those personal relationships, then there’s other ways to build a successful copywriting business that maybe gives you more of what you’re looking for. So those are the things to think about there. And then, I know you mentioned this in the introduction and we buried it to the very end of the interview, but I mean, his ability to show up as number one for the term copywriter is pretty freaking amazing in my opinion. I’m not exactly sure what Jacob did to earn that, but I’m jealous.

Kira:   Yeah. I think it’s really impressive. And I love that he left that till the end of the interview, too, to share that and the competitor in me wants to challenge him and take him down, which I think is a fun challenge. But yeah, that’s really impressive. So well done, Jacob.

Rob:   Yeah, exactly. And then maybe finally, some of the other investments that he’s making, the Empire Flippers site that he mentioned and buying sites and doing interesting things with them, again, this is something that we really haven’t talked about on the podcast before, when we’ve talked about the different kinds of things that copywriters can do as far as developing products or the different services, different packages that they can offer. But resurrecting old sites like what he’s doing or finding sites that have poor SEO, but a really good sales opportunity and fixing the copy, making the sales copy work better. That’s something that copywriters can do. And I know people who have purchased sites for $1,000, $1,200 and then have flipped them later for multiples of six and even seven figures. And so at some point, we should probably have a podcast that goes into how people do that and what they’re doing, and how they’re applying those copywriting skills. But I am glad that he mentioned that because it got me thinking about things that we haven’t actually talked about before.

Kira:   Yeah. It was a really fun new conversation. And I could probably tell during the conversation, I was so excited about it because it just is such a great reminder that there are so many different possibilities out there for us as copywriters and what we can do and other businesses. So it’s definitely something I would like to revisit at some point and buy one of those businesses on that site.

Rob:   Yeah. You said we should put The Copywriter Club up for sale just to see what we could get. I actually got an email from somebody this morning offering to buy the copywriter club for $2,000. So we have our starting bid for our-

Kira:   I am very curious to find out who that is and how they came up with $2,000.

Rob:   Yeah, exactly.

Kira:   Cool. We’ll consider it. We’ll think about it.

Rob:   We want to thank Jacob McMillen for joining us to talk about copywriting and his business and all of the things. If you want to find out more about Jacob, you can visit his website where you’ll find several hundred thousand words of free content at His last name is spelled M-C-M-I-L-L-E-N .com. And you can also find his podcast there. It’s called Write Bites. It’s also at Apple podcasts, Stitcher, and Spotify. And finally, if you search for him, you can find him on YouTube talking about marketing, writing, and freelancing. And I guess actually really finally, we did mention that just type copywriter into Google and you’ll see him at the top or near the top of the page.

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 is composed by copywriter and songwriter, David Muntner. If you’ve enjoyed what you’ve heard, please visit Apple podcasts to leave a review of the show, to learn more about our programs like The Copywriter Underground and The Copywriter Think Tank mastermind, visit Thanks for listening and we’ll see you next week.




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