TCC Podcast 19: Succeeding on UpWork with Danny Marguiles - The Copywriter Club
TCC Podcast 19: Succeeding on UpWork with Danny Marguiles

Upwork specialist Danny Maguiles joins Kira and Rob for the 19th episode of The Copywriter Club Podcast, where they talk about how to create a six-figure freelance writing career working with clients on Upwork, Danny’s Crystal Ball technique for winning clients, and three things copywriters can do to separate themselves from all of the other writers out there. We didn’t hold back in this one—we grill Danny on the truth about working on platforms like Upwork. And honestly, we were surprised by what he had to say. Don’t miss this one…

Click the play button below, or scroll down for a full transcript.

The people and stuff we mentioned on the show:

Sponsor: AirStory Danny Interview at Bloomberg’s Benchmark Podcast
That Medium Post
That Medium Post, Part II
That Medium Post, Part III
Freelance to Win
Secrets of a Six Figure Upworker
The Copywriter’s Handbook by Bob Bly
Decisive by Dan and Chip Heath
Start With Why by Simon Sinek
Simon Sinek’s TED Talk
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
Intro: Content (for now)
Outro: Gravity

Full Transcript:

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

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 on The Copywriter Club Podcast.

Kira: You’re invited to join the club for episode 19, as we chat with copywriter Danny Margulies about his six figure success in Upwork, how copywriters can use job platforms to gain experience and grow their businesses, what he teaches other writers in his community and the shift from being overworked to running his own business.

Rob: Hey, Kira and Danny.

Danny: Hey, guys.

Rob: Thanks for being here, Danny. So, I think a good place to start is your story before you started writing for Upwork and taking clients on Upwork and you really made a name for yourself. What were you doing before that?

Danny: Not much is the short answer. It’s funny you should ask because people send me emails all the time and they’ll be like, “Oh, it’s so obvious you’re a great copywriter and you must have all this experience and I don’t have that much experience, so I can’t do this.” I’m like, “Whoa, take a step back, okay?” That’s like 10 assumptions too many. I’ll tell you, I was on Bloomberg News talking about freelancing about maybe six months ago and after the segment, I was talking to somebody who worked there. They were like, “Wow, I can totally see why you are able to take this to this level.” In my head, it’s kind of like one of those cartoons where my head is … I got this bubbling image of me five years earlier, which is really not a very long time, picture this, sitting at my kitchen table unemployed. my wife and I both unemployed, expecting a baby. I have no college education. I have no real skills.

The job I just quit was working for an insurance services company for 15 bucks an hour and by the way, just a spoiler for anyone listening, they really do pay you to lie. It is an awful, awful industry. All the stereotypes are true. Before that, I was working at a car dealership, another place where a lot of people get paid to lie. I made like 15 bucks an hour there. Before that I was doing telephone surveys. I would call people in the middle of dinner and say, basically, beg them for 10 minutes of their time, to take a survey.

I had a series of really awful, non-career dead-end jobs and now I found myself … it was Friday, July 20th of 2012 and I was just desperate. I had maybe a months worth of bills that I could pay with the tiny amount of money in my savings account. I mean, this is all very embarrassing, but I say it for a purpose, I want people to understand. I had many disadvantages and so wherever you’re at, chances are you can do this too. That was pretty much my story, is just a story of what most people would look at at that time and they would just shake their head and go, “Wow, that Danny, you know, he seemed like he had potential but he never really did anything.”

It was really a dark time in my life beforehand. I really just want to give people hope. If you have anything more than I did, which is no college education, no real marketable skills, no real work experience. You can do this.

Rob: Danny, what was the real catalyst for change? How did you come about to find Upwork?

Danny: Oh, yeah. Right. So, I was sitting there that morning and I had no way to make money and we’re expecting a baby. I didn’t know we’re expecting a baby at that time but I would find out about two weeks later. I was sitting there, just kind of desperate and I didn’t want to get another crappy dead-end job and so, I didn’t know what to do. I was sitting there at my kitchen table drinking coffee and just on a lark, I decided to Google, how to make money writing. Just so you understand, I had no business doing that Google search. I had no experience writing. I had never been paid to write. I didn’t even know what copywriting was, not really. I certainly didn’t know there was a such thing as a freelance copywriter and I certainly, definitely didn’t know that I had any business doing that. It was just total long shot, total lark I Googled that.

Then one thing led to another. I found Upwork either through that search or through a link after reading a blog post after that search or whatever. I found Upwork and I’m looking at the jobs and I’m like, “You know what, I don’t understand what 90% of these are.” Like, I didn’t know what an autoresponder series was and I didn’t know what even like a sales page was but there were some things on there that I was like, “You know, I think I can do that.” I know what a 300 or 500 word blog post was, right? Everyone’s read a blog post. I said to myself, “I could write a freaking blog post.” So, I was off to the races.

Kira: Danny, what worked really well for you early on, if anything did? I mean, how did you really start to gain traction as you took on those early projects?

Danny: The first thing I did is I realized that it … It hit me early on that what clients are … There’s a lot of people applying for jobs, that’s the nature of jobs. Right? A friend of mine is a recruiter for a big company and he said when they post a job, they might get 400 resumes in the first 30 minutes or something like that. Everything’s competitive. It occurred to me early on that clients are probably looking for something … In other words, when you apply to a job and you want to show a client, I can do this job, they probably would love to see a piece of work that’s very similar to what they’re looking for.

It hit me early on, that most copywriters, even if they have a lot of work that they’ve done in the past, there’s probably only a very small chance that they have an example of a piece of work that is virtually identical to what the client needs. Here’s what I mean by that, let’s say a client posts a job and says, “I’m looking for a blog post about the health benefits of red wine.” Okay, let’s be honest, I have a big portfolio now, but I don’t have any articles about red wine. If I had to apply to that job, my portfolio wouldn’t help me any more than a copywriter who just started a month ago. It occurred to me that what I would do, is I would go away from the job post and I would create a writing sample that was similar to what the client needed. Not identical because you don’t want to tempt them to steal it from you but you want to create something similar.

For something like the health benefits of red wine, I might go away and write an article about the health benefits of apples or something like that. Right? Something that they can’t use but they can start to imagine like, “Oh, you know what, this guy totally gets it.” I later started calling this my crystal ball technique because it’s the equivalent of showing clients a crystal ball and saying look, “This is your future if you hire me. You can imagine that I will easily finish this job for you.” When somebody else is … You know, you might have another copywriter with 10 times my experience but he doesn’t have anything as relevant to show the client.

What I figured out too is, it’s not even wasted effort, even if you don’t get the job because if you don’t get the job, you take that piece that you wrote and you file that away and now you start to build a portfolio. That was the number one— again, I call this the crystal ball technique—that was the number one action that spurred my career forward when I was trying to break in.

Rob: I think that’s really good advice. Although, a part of me is like, “Wow, you’re writing really two articles for every job that you’re taking on.” You’re working really hard but at the same time, you have nothing else, if you don’t have a portfolio, what else are you going to do, right?

Danny: Exactly and the really cool thing is … The one thing I found along the lines of what you just said, Rob, what I found is, let’s say like I’ll give you an example, I wrote an email about the fitness industry to try to get a job writing emails about the fitness industry. Right? It took me maybe an hour to write this piece and I didn’t end up getting the job. One way to look at it is, “Wow, that’s a wasted hour.” Here’s the amazing thing. I got other jobs later, using that same piece. I actually probably got over probably 5-10 jobs in the next year using that piece. It’s an industry that a lot of people are looking for.

If you stick to things that are relatively popular like health, fitness, make money online, even though that’s kind of a skeezy industry, but there’s still a lot of good stuff going on there, dating and relationships, personal development. As long as you’re working within those kind of big demand fields, you’ll probably end up with something that you will land work with at some point, even if it’s not today.

Rob: Danny, I’m going to ask the question that probably you hear over and over and over and that is, “Really, Upwork, or what was Elance?” There are so many small, tiny jobs there. There’s so much competition that pushes the prices down. How in the world in you succeed in building a business using Upwork and I guess, the second part of the question is, are you sort of a one of a kind guy? Is this something that every writer can do or is it just one or two writers that can succeed like this?

Danny: That’s a great question. I’ll answer the second part first and then we’ll go to the first part. A friend of mine, this guy named Chris, he started working on Upwork a few months back. In his first month, he took on a small job, I think he made a hundred bucks for his first job. Now, this is an experienced guy so a hundred dollar small job is not so exciting to him but at the same time, he wanted to get his foot in the door, so why not?

His first month he made, I think maybe, I want to say $1500, which is about the same amount of money that I made in my first month. He called me up and he goes like this, he goes, “Dude, look, no bullshit. Do you think that you could start out on Upwork again today from nothing, from scratch, no profile and pull a hundred grand again within one to two years?” I was like, “What, really, are you kidding me? It would be easier today.” There was more clients today. More people know about copywriting. The economy is better. Everything is better today than it was in 2013, the first year that I made over 100,000 there. I was like, “Yeah, you know, go get ‘em.” He just really needed to hear me say that.

I’ll tell you something, his first month, I told you he made $1500, and in his second month or … I don’t know if it was his second month but it was the month after we had that conversation, he went on Upwork on earned $8800 in one month. Then the next month he earned more than that and the next month he earned more than that. He’s probably going to pull six figures too and we have others too. Definitely what we found is, that I’m not a unicorn. Even though when I first did this and I first started writing about it, everyone’s like, “Oh, you know, yeah, sure, he did it but can anyone else do it?” We’ve seen over and over again, many more people doing very similar things.

Now, let me answer the first part of your question. I have found a very different experience on Upwork than what some other people have found. What I’ve found is, you can look at anything and you can see negative or you can see positive. For example, somebody who starts a blog or a podcast, like you guys, you could say, “Oh, look at Google, you know. You got nine billion search results for any search but only one lucky dude or one lucky lady gets to be on top.” Right? Another way to look at it is like, “Holy shit, if I work really hard, I could get to the top of Google.” Right? Of course, that’s what the winners do.

I’ll tell you, I have discovered an iron clad way to kind of do like a reality distortion check when people start saying things like, “Oh, all the jobs on Upwork are this,” or whatever. You just replace the word Upwork with the word everything or the entire world. Here, this is how it works, “Oh, Upwork is very competitive.” Okay, replace that with the entire world is very competitive. Or, “Oh, on Upwork, there’s a lot of small jobs.” Okay, in the entire world, there’s a lot of small copywriting jobs. What I found with Upwork is, it’s really just a microcosm of the entire world of copywriting.

If you go knocking door to door, just knocking on businesses doors, you’ll have the same percentage who are willing to pay a lot of money in the “offline” world as you will on Upwork. A lot of people say like, “Oh, I don’t want to compete on Upwork because it’s too competitive.” But the reality of it is, you’re competing on Upwork no matter what because clients know it exists, you know what I mean? I’ve found it to be a great place to work.

Kira: Well, I love the way you put that. I mean, we’re talking about Upwork with you but really this represents everything, the entire industry, and just getting work in general as a copywriter, is just competitive period. I really want to know what it takes to make the six figures in a year on Upwork? When I hear that, I’m like, “That’s cool.” I’m also imagining you working crazy hours in order to take on enough projects, in order to make that amount and that is probably incorrect. If you could paint the picture of what it took during that first year to hit six figures in your business. If you can share how many projects it really took and even how much you ended up charging per project, what types of projects you were taking on.

Danny: That’s a great question. My first full time year on Upwork, I started in July of 2012, and then if you look at 2013, I think I earned about 55 or $60,000, that was basically my first year. Then in my second year, I more than doubled that and earned over 115,000. What’s interesting is that I worked less hard my second year, by far, than I did in the first year because A, I was charging more, B, I had plenty of repeat clients going into the year. I still took on a good number of new clients and I’ll tell you more about that but I already went into 2014 with a lot of repeat business, a lot of people banging down my door going, “Hey, Danny, great working with you last year. Let’s do more.”

I always say it’s kind of a three part formula. Part one, I’ve already talked about is … Well, I’ve talked about parts one and two. Part one is charging enough. You need to charge enough if you really want to make six figures and by the way, not everyone wants to make six figures. I get people, a lot of people who come to my site, who are like, “You know what, I just want to make a couple of thousand dollars extra every few months or a thousand extra dollars a month or whatever.” So, you see a range of things.

If you want to get to six figures, and I think six figures is a great goal, because we’re in a time where let’s face it, the middle class is shrinking. Obviously, 50 grand a year is fine when you’re first starting. It’s not something you might want to … You might not be aspiring to make that 10 years from now. Six figures’ a great goal. You need to charge enough so that you’re not killing yourself. There’s this cycle of charging too little, I see copywriters end up in.

Here’s how it goes, they charge let’s say, I don’t know, $20 an hour, $30 an hour, even 35, $40 an hour, in some cases, and they’ll go like this, “In order to make six figures with this amount of money, I have to work a ton.” Then they work a ton and then they’re tired and they’re burnt out and they don’t have time to work on their skills and they don’t have time to recharge and then their work suffers and then their reviews aren’t that good and then they have to lower their rates. That’s not what you want to do. You want make sure you’re charging enough.

For the entire year of 2014, I never charged less than $100 per hour, no exceptions. That’s the first thing. You got to make sure you’re charging enough, so that you’re not doing what you said, which is killing yourself. Right? Anyone can make a hundred grand a year if you’re willing to work 20 hours a day. We don’t want you to do that and it’s not going to be sustainable. So, that’s number one.

Number two, you got to … Well, we talked about this already, I touched on it a bit but you have to get repeat business. If you’re spending 20 hours every week looking for clients, it’s going to be very hard to hit a hundred grand a year. Repeat business is key. Fortunately for us, other than the cocaine industry, copywriting is the only industry I know of, where you can create your own demand. If you do a great job of, let’s say, I hire you to write blog posts for me, for SEO or engagement or whatever. If you do an amazing job, do you think I’m going to be like, “Oh, okay, Cool. Peace out. Here’s your money”? I’m going to be like, “Holy shit! How much more can you write? Do you have friends who can do this too?” More content is better. Right?

If you write me a great sales page and we make a lot of sales, do you think I’m just going to lose your phone number? No. I’m going to be like, “Okay, I’m need to create more product so I can get this person to write more sales pages for me.” By the way, what else can you write? Can you do my opt-in copy? Can you do my landing page copy? Do you do Facebook ads? You’re literally creating your own demand. If you’re not creating your own demand, then that means you need to brush up on your skills but maybe we’ll talk about that later. That’s part two. Okay?

Part one is charge enough so you’re not destroying your life. Number two is make sure you’re getting that repeat business. Number three is something that I call the hidden Upwork economy. What I mean by that is this, when most people think of Upwork, they think of, “I’m going to go on Upwork. I’m going to find these jobs that are posted publicly and I’m going to apply to them.” By the way, that’s fine and you can make a lot of money that way but if you want to maximize your income on Upwork, what you really want is, you want to get clients to invite you to jobs because that’s passive leads, right? Those come in passively.

Clients will send me messages, I can show you screenshots, they will send me messages and they’ll go, “Hey, Danny, I was browsing the freelancers on Upwork and I was looking for a copywriter and I stumbled upon your profile and it sounds like you are the exact person that we’re looking for. We would love to hire you, are you available?” Now, wow, I did no work to get that client. Right? You need to tap in that, what I call the hidden economy. Which is, you need to get those invites if you want to maximize your income. Now, we have a lot of people who are not getting a ton of invites, for whatever reason, and they’re still doing very well but obviously they could be doing better if they were getting those targeted invites.

That to me, is the kind of three part system. Did you know want to know more details like what kind of jobs I did that year, how many clients I had?

Rob: I’d love to hear more about that hidden economy piece that you’re talking about. I mean, that only happens when you’ve built a strong profile, I assume, and have a portfolio, that kind of a thing. Tell us a little bit more about that.

Danny: That’s great. A lot of people actually assume what you just said. They assume that you got to built up a big history and a big portfolio, etc. Of course, it does help if you have a previous history and if you have portfolio items in your portfolio, that will help. You can do a lot of stuff to help push it along. I also want to tell you, we have one person … We did a case study on this in my course, we actually have a person who went on Upwork, created a profile, used the right keywords, really understood what her target clients were looking for and really just filled out a great profile with a great title, great overview, excellent photo, really just did everything right, right from the start.

Then she didn’t even log back in for two weeks because she got busy with other things. After two weeks she got an invite and it was targeted right at her, using her first name, and it was like, “Hey, we love the way your profile sounds. We’d love to talk about hiring you.”

Yeah, if you do a lot of work, that can help but the truth is, there’s so many clients on Upwork, millions and millions and millions of clients and probably thousands of new clients every day. It’s really not that hard to get found, if you have a profile that really stands out. You know, your average copywriter on there, their profiles are really dull. They kind of all say the same thing. It’s really not that hard to stand out, if you do a little bit of thinking about it. It’s not as hard to get those invites as most people think.

Rob: We interrupt this program for a message from our sponsor. As we noted at the top of the program, The Copywriter Club Podcast is sponsored by Airstory. Recently, Kira had a chance to talk to copywriter Lisa Pierson about how she uses Airstory in her business. This is just a part of that discussion.

Kira: What should other copywriters know about Airstory?

Lisa: Some of us are a little ADD or our minds wander and it really helps you focus. You can do all of your research ahead of time. You can add it all to cards, so it’s right there in your document. You don’t need to leave your document once you start writing. I love that I can do all of my research, have it in my cards, and focus on the work. My name’s Lisa Pierson, I’m a conversion copywriter and strategist and I love using Airstory to keep me focused and on task, when I’m working on my projects.

Kira: I want to hear a little bit more about that second year. The first year, that you hit the six figures, like you said, I do want to dive into like how many projects and what type of projects were you taking in your business, to hit that mark?

Danny: Okay, great. I’ll give you a few examples. I was doing some diverse stuff. What I like to do is, I like to keep things fresh. I don’t like to work on the same every day, I’m not that guy. I don’t like to work on emails every single day. I had one client who runs a video marketing company, they make whiteboard videos. I would write the scripts for their videos. At that time, they had so many video scripts, I could’ve probably just been busy full time, writing their scripts, but I didn’t want to freelance like that. I didn’t want to just have one big client. What I did was, I only wrote for them for several hours per week. Then I referred friends of mine, who are copywriters, to write the rest of their scripts.

That would be a portion of my week, every week, would be spent writing a few scripts for them and we did that at a flat rate. I think I charged them at that time, I want to say it was $165 per script. The scripts were very short so it was actually a pretty decent price. I used to bang those out fairly quickly, so that was a really good deal. That was one thing. I always tell people, “Try to look for clients who will be able to give you ongoing work.” Right? When you have a video marketing company that’s growing, well, guess what, they’re going to need you more and more. So, that’s a really great client to have.

Another client that I had, he was a serial entrepreneur. He would start these web businesses. Again, you have a guy who’s always going to be starting a different business and so, he’s going to have a lot of work for you. For that person, he had so much work for me, that I just charged him just a flat, I think it was $130 an hour. Not a flat, I’m sorry, an hourly rate, because every day he would just come up with something new. He might email me on a Tuesday and say, “Oh, I need four landing pages for this new thing.” Or then he might on a Wednesday and be like, “Oh, I need three press releases,” or whatever. There was no time to sit around and negotiate a flat fee for each piece. He just paid me per hour.

I had other clients going into that year who were actually paying me less and then I had to drop those clients, which was kind of difficult, but luckily I was able to refer them to other copywriters, who were a little less experienced than me and were happy to get paid 50 bucks an hour or so. Then the rest, honestly, were just small business that I met on Upwork. People who just wanted a good copywriter. A lot of them had tried other copywriters and were kind of frustrated that they weren’t getting great results.

We could talk more about this too and it’s something I talk about often but the average copywriter, even professional copywriter, is not as good as most people think. What ends up happening is, you might have a small business, they might hire a copywriter for 50 bucks an hour and they might think, “Wow, we’re going to increase our sales by 20%. We’re going to increase our opt-ins by 30%.” Whatever picture they have in their head. Then most of the time, that’s not going to happen.

I really dedicated myself to, okay, how can I think like a businessperson and how can I help clients accomplish a business goal? When they met me, they were pretty relieved to find someone who really devoted themselves to the craft and really took it seriously. I didn’t find it very hard to get clients who would pay the kind of money that I was charging.

Rob: Danny, I want to kind of come back to that idea, in a minute, about the average copywriter not being as good as people think, but before we leave Upwork, obviously you’re telling a really rosy story about the success that can be had at Upwork but there are others who have had really negative experiences. I’m sure you’ve seen them. There was recently an article on Medium, it wasn’t a writer but a developer, who had a run in with a client and lost his business, that kind of thing. He was complaining about Upwork raising the fees that they charge and some other things. What do you say to people who are critical of Upwork? Are they completely wrong? Are they doing something wrong? Or is there a dark side of Upwork that we still need to be aware of.

Danny: What I found, like I said earlier, I’ve just found a totally different experience on Upwork. At the same time, when people say they raised their fees, what actually happened, and a lot of people don’t talk about this, they also lowered their fees at the same time. For example, they raised their fee for the first $500 that you earn from a client. If I were to hire a new copywriter today, for the first $500, he would pay more of a percentage. That is true. But after $500, he would pay the same amount as before and if he got to $10,000 or above, he would now only pay 5%.

That day, when they raised their prices, and there were a lot of people online going, “Oh, they raised the fee.” What you didn’t see and what I did see, is all the people behind the scenes, doing high fives, because they were about to … including myself, by the way, because I have many clients on Upwork, with whom I’ve reached that $10,000 threshold. Right?

We were all doing high fives because our story, our story, our headline, was Upwork cuts their fee in half. There’s multiple perspectives and different ways to look at things. If you’re someone who does a lot of one off jobs, then yeah, that’s going to hurt, right? My recommendation is not to be ever be the person who does a lot of one off jobs for 500 bucks, that’s just not how to make good money freelancing. If my son grew up to be a freelance copywriter and he told me, “Dad, my business plan is to find a million clients every year on Upwork and charge each one of them $500 or less,” I’d be like, “Can you please do something else?” Right? That’s not good advice.

Yeah, some people were not happy with that but to me, if you’re doing what you’re supposed to do, which is find clients who can give you lots of repeat business, charge them a really good hourly rate, and then you’re going make more money overall. It’s funny because I’m also a client on Upwork now because my site, FreelanceToWin, I have freelancers helping me build that site now. I have multiple freelancers with whom I’ve either reached the $10,000 threshold already, in terms of how much I’ve paid them, or we’re about to reach the threshold. They were high fiving each other. I did a podcast about it and I’ve got so many emails, hundreds and hundreds of emails that day, from people who were like, “Wow, you know, I went online and I was so scared because I was reading all this negative stuff and you really helped me kind of reframe this in my head.”

By the way, the Medium post, a lot of people don’t realize, that guy, as far as I know, I don’t really know the whole story, but here’s from my perspective, and I could have the facts not straight so check the facts for yourself if you’re listening to this, but what I read is, he said he was never going to work on Upwork again. Then there was a part two and a part three to that post, where he said that he resolved his issues with Upwork and he was back on there working and he appreciated their service and helping him fix the problem.

To me, it’s just a great place to work. Like I said, you can find negative in literally anything. I’m sure there’s people living in Maui right who will tell you all about the negatives of living in Maui but as somebody who’s in the middle of Nebraska and it’s zero degrees outside, I’m sure that I would love it. Similarly, I feel like, when I first found Upwork, I was like, “Holy cow, this is a real thing?” I still to this day wake up and I feel like, wait a minute, somebody’s find out I have no college degree and they’re going to delete my Upwork account.

Yeah, do I wear the rose-colored glasses for Upwork? I’m sure that I do but I really just love it from the bottom of my heart. I think that for copywriters, I think it’s the best opportunity out there, bar none.

Rob: It’s good to hear that other side of the negative story because the negative story gets out there a lot.

Kira: You mentioned FreelanceToWin and that you are now hiring other copywriters and I want to get into that and how you manage that side of your business. I just want to connect the dots between your hitting the six figures and having your successful year in 2014 and how do you get to where you are today? What was that transition like? Usually it’s like the middle ground that we don’t talk about as much. How did you navigate through that?

Danny: Oh, yeah, sure. Are we talking about from my six figure year on Upwork to my FreelanceToWin business?

Kira: Yeah, yeah. Taking on and hiring other copywriters to support your business. How did you get there? Did you know that you wanted to build almost an agency model? Is that what you built? Just if you could talk about that transition and then lead into where you are today. What does your business look like today?

Danny: Okay, great. Okay, let’s clarify. There’s a few things going on here, I want to make sure we’re clear. When I say that I have freelancers helping me build my business, that’s my FreelanceToWin business, which is a blog and an information business when I sell my course. That’s separate from my freelance copywriting business, does that make sense?

Kira: Yes. Yeah.

Danny: I’ve never had freelance copywriters working for me in my freelancing business. I’ve always just done everything myself. I mean, I did dabble in it but I just really like being the writer. When I was just freelancing full time, it was just me writing for clients and getting paid. Then what ended up happening was, in 2014, I was having a great year. I started connecting with lots of people on Upwork because what I found is I had so much work and so much interest in my work, that I needed people to refer my clients to because I was getting too many invites and too much demand. I wanted to have other good … not only copywriters by the way but designers, programmers, you name it.

This is a good tip for copywriters who are listening, you want to have other people that you can refer clients to. Like if you have a client who says, “Oh, this is a great piece of copy you wrote for me. Who do you know who can help me build the landing page? You know, the hosting, put it online and get it live and do the design and email opt-ins.” You want to have names where you could say, “Hey, I know this person who will help you build your email list,” and this person will do this and this person who’ll do that.

I started reaching out on LinkedIn and other places. I started reaching out to people on Upwork just making friends. Okay? Over that time, people start asking me for advice. They’d go, “oh, hey, Danny, I see you’re doing really well. You got so many jobs. What’s going on? Can you give me advice? Can you give me coaching? Can you do this? Can you do that?” I was like, “I really don’t have time for coaching. I really just want to do freelance copywriting.” I just kind of stuck to that, and I help people here and there. At the same time, I noticed articles popping up by people. They were writing about how to make money on Upwork but they hadn’t really done well on Upwork. When I would read their articles, I would be like, “Oh, you know what, that’s kind of bullshit.” They were saying you should do this and they were saying you should do that. They were saying, “Oh, don’t charge more than $30 an hour.” I’m like, “What is …” Like this is the opposite of good advice.

I kind of held my nose for a little while and then I was like “You know what, (beep) this. I’m going to start my own blog and I’m just going to tell people the truth of what’s going on.” I started a blog, right? I basically just started blogging about what does it really take to make money on Upwork, it’s not what most people think. The response was unreal. People start subscribing to my email list. They wanted to know more and they were reading and sharing. Then I said, okay. You know what, there was so much demand for my coaching and I just didn’t want to do coaching, so I just made a course. I was like, “All right, let’s compromise. I’m not going to coach you one on one but I’ll make a course, cool?” Everyone was like, “Yeah, yeah. Make a course, we’ll buy it.”

I made my course, it’s called Secrets of the Six Figure Upworker, I released that to a small group of people in October of 2014. If you had said to me, “Will this turn into a multi-hundred thousand dollar a year business?” I would’ve said, “No freaking way.” This is a side project. I’m doing it just as an experiment and then wouldn’t you know it, this thing just took off like crazy. In 2015, I sold the course all year, it was open all year. I didn’t close it. I just had it sitting there with a sales page and we did over a hundred thousand dollars in sales that year for the course. Now we just wrapped up 2016 and we’ve done multiple hundreds of thousands of dollars in revenue, this last year.

What I found is, you can only get so far in an information business if you’re just working by yourself, at least in my experience. When I made a hundred thousand dollars in sales from the course, it was relatively … I don’t want to say it was easy, it was a lot of work, but I did all the work myself. Then I realized, if I want to grow it bigger, I really need some help. The first person I hired is just a great guy, I hired him just to help me with Google Analytics, because I couldn’t figure that out, because I’m a little bit of a technophobe. One thing led to another and he just started helping me with more and more stuff. Then he started learning and we both learned together and now he does a lot of the marketing for us. Then later I hired someone to write case studies. The great thing is, I was able to hire students from my course because it was easy to connect with them. They would just present themselves to me as very talented people.

Now, we’re trying to grow the team. We just hired a marketing assistant. We’re really just trying to grow and have a much bigger year in 2017. Yeah, it was a very slow transition. It really just went from side project, earning a couple extra hundred dollars a month, to this gradual … I started having to give away my clients because the business was so demanding. For a while, it was like doing half and half. Then I was doing three quarters FreelanceToWin and 25% freelancing and now I haven’t had a client in months just because this business just really … There’s a lot of people out there who really need our help and I want to focus on those people. There’s a lot of people out there who can write a great sales page and so I feel comfortable referring my clients to other people who can do that.

What I found is, there’s not a lot of people out there who can really help freelancers earn more, make more money, especially make more money on Upwork, and just really knock it out of the park and do well. I feel really called to put all my time into helping people and we create a lot of free material too. It’s not just the course. That’s been really gratifying to me to just be able to help people raise their rates, do work they enjoy, and have the freedom to really control their own schedule, which is what we all started freelance copywriting to begin with for.

Kira: That’s interesting. I was actually going to ask you if you’re still taking on projects through Upwork but it sounds like you’re focused on building this platform to support other freelancers build their businesses. Is that right?

Danny: At the moment, yeah. The beautiful thing is, at any time, I can go back on Upwork and take a client. For instance, about six months ago, I just felt like, “You know what, I really just want to do some freelance copywriting.” I just went on there and found a client. I raised my rate to $250 an hour. The client hired me at that rate and that went really well. I feel like that’s always there. I can always go back to that. I may very well go back to that. I may do that next month. I may do that next week. I may do that next year but it’s great to have options.

Kira: The question I really want to ask you because it keeps popping into my head is just, when you’re on Upwork and you’re doing well, what prevents you from leaving the platform and pulling those clients? Say your clients love you, you’re doing well, and taking them outside of the platform to grow your business, what really keeps you within that platform, once you hit that success point and you’re doing really well?

Danny: Well, I mean, for one thing, it is against Upwork’s terms of service to do that. They do have parameters and don’t quote me on this but I think if you’ve been working with a client for like two years or more, I think you can take them off. I think there’s also a buyout option. There are options for doing that in an ethical and kosher way. It’s not always against the rules. I just want to point that out for anyone listening.

Honestly, the real thing is, I’ve always kept my clients on Upwork just … Even if you look at the threat of getting my account deleted aside, which to me is just not worth it, why would I want my Upwork account deleted for a few bucks? The main thing is, the more you keep clients on there, the more money you’re going to make because what’s going to happen is, first of all, they have payment protection and all this other great stuff, but this is all stuff that you can find out on Upwork’s website. What I want to give you is the behind the scenes that nobody talks about. Okay?

When you stay on with a client, your reputation becomes better. Rob touched on this earlier. The more of a history you have, the more good reviews you’ll have, the more invites you’ll get. What I’ve found is that, the amount of invites you get and by the way, not just the invites, but the ability to close those deals. Do you know I’ve how many people I’ve had come to me and say, “Danny, I want to hire you right now. I’m willing to pay your full fee.” I would literally say to them, later I would ask them, I’d be like, “Hey, Joe, how come I didn’t even have to sell you at all? What was it about my profile that made you just want to hire me?” They’d be like, “Oh, that’s easy. You had like 85 reviews that were all just glowing. It was so easy to understand that you’re just going to be a great person work with.”

I could’ve shot myself in the foot by taking clients off the platform and having a shitty history but I chose to invest in my history. His is an old model. This is not a new model. Right? The same thing goes for eBay and all these other sites, you know? Yeah, you could take people off the platform, you could break the rules, but to me, you’re just shooting yourself in the foot. You’ll make way more money if you just stick with it than you will if you try to skirt the rules and it’s just unethical too. You’re not going to sleep as well at night. Honestly, I’m just going to appeal to everyone’s selfishness. Keep the work on Upwork because you’ll do better.

Rob: Danny, earlier you mentioned that the average copywriter isn’t as good as you think they should be or maybe as they think they are, what did you mean by that? What does it take to become above average?

Danny: Great question. What I’ve found, when you talk to most copywriters around the 50 to $65 an hour range or I would say, up to $65 an hour, even to some extent, up to $75 an hour and in some cases even more, what I’ve found is when you say to them … If you say like, “What makes you a great copywriter?” They’ll say like, “Oh, you know, I understand how to talk to an audience or how to specify my message for a particular audience,” or, “I understand how to focus on features versus benefits,” or, “I know what makes an eye catching headline.” To me, I don’t think that any of those things are particularly advanced these days. I think a lot of the clients who are hiring you, already have a good idea of that kind of stuff.

You need to have a bit more stuff in your arsenal, right? I’ve seen freelance copywriters who are earning like 30, 40 grand a year, and they’ll have a blog and the blog will be like, “Oh, let me teach you about features versus benefits.” Okay, people were writing in copywriting books about features versus benefits literally like 50 years ago. Right? That’s not cutting edge stuff. What I always tell people is go with cutting edge stuff, right? For example, I look for things that can’t be duplicated, can’t be copied.

If I read a copy of Bob Bly’s The Copywriter’s Handbook … and by the way, that’s a great book, everyone who’s listening to this should absolutely read that but any copywriter can read that. You’re not going to have an enormous advantage. It’ll give you some advantage, especially over the copywriters who didn’t read it and there is many but you’re not going to get an enormous advantage by reading that book, right? I’ll tell you what would give you an enormous advantage. Every time you see something weird or interesting or counterintuitive or funny or unexpected, write that down. I have a file called writing prompts. In that file, I have hundreds and hundreds and hundreds of weird little things.

I’ll just give you an example. One day I was sitting there playing Super Mario Kart with my wife and kids and I noticed that when my wife plays Super Mario Kart, she turns into like basically a wild animal. She’ll do whatever it takes to win. She’ll elbow you to win. I thought to myself, “Wow, that’s weird and it’s kind of funny.” I wrote it down. Then later I used it in an email. Right? Nobody else will have that. If you interview a hundred copywriters and you say, “Oh, do you have a million writing prompts?” I’ll say yes, they’ll all say no. That’s something that you can’t … not everyone’s going to have. That’s going to give you an enormous advantage.

I could give you some more examples. If you, for example, if you study decision making and you read books like, you know the Heath brothers wrote a book called Decisive. Right? If you read that book, you will understand things about the human brain and how we make decisions, that the average copywriter would just not be able to talk about.

I’ll give you one more example because I don’t want to bore everyone to death but if you read the book Start With Why by Simon Sinek, or hell, don’t even read the book, go and watch Simon’s Ted Talk. It’s 17 minutes long. That guy will teach you more about the human brain and the way we make decisions than a hundred copywriting books and you’ll have an enormous advantage. You got to kind of go beyond the obvious and don’t … Most people, they just stick with copywriting books. That’s not really going to give you the big advantage you’re looking for.

Kira: Danny, before we wrap this conversation, I want to know if you could go back in time to 2013 and maybe even when you were doing that Google search and just kicking off your career as a copywriter, what advice would you give yourself?

Danny: That’s a great question. I don’t think I would say anything. I think it worked out perfectly. If there had to be one thing, I would say this, I would say, “Expect there to be struggles.” Okay, because this is the big thing that I see is people go, “Oh, you know, it’s hard to find clients.” Yeah, well no shit it’s hard to find clients. You know what I mean? You’re trying to live the dream of being a freelance copywriter. It’s not going to be easy to find clients. Be comfortable with things sucking, okay?

I guess the other thing I would say is, “look for opportunities to fail.” Okay? Here’s what happens is, we start copywriting and we get good at let’s say, writing emails. We’re like, “Okay, that’s my wheelhouse. I’m going to write marketing emails.” Then somebody says, “Hey, can you write a sales page for me?” You’re like, “Wow, that’s out of my comfort zone. So, I might fail if I do that.” Okay, fine. You might fail if you do that but you also might do really well and get to the next level. A failure in copywriting is not the end of the world. I’ve had clients say to me, “This sucks. I don’t want this.” Okay? I’ve had to navigate those waters. You learn more when you’re doing that. If you make a mistake and you screw up, you’ll learn 10 times more than you will by just doing what’s in your comfort zone.

Rob: Danny, this has been an awesome interview. Unfortunately, we’re out of time but there’s tons of other things we’d love to talk to you about. How do you build a platform on a platform, that kind of stuff. We definitely need to have you back but until then, where would people find you online? Where would they find you and where would they find your course, in case they’re interested in this kind of thing?

Danny: Oh, thank you. Thank you. Yeah, I’d love to be back. It was great chatting with you guys. If people want to find me, they can contact me, they can read my blog. They can do it all through my site, which is It’s easy to find my course through the site too. We also have lots of free materials, so you don’t need to jump into the course. We have tons of free stuff, you’ll see it if you start looking on there. We have a free tools page and then the blog has tons of information. I have some copywriter specific articles as well as some other general freelancing articles. Really just lots of free stuff. If people are particularly interested in Upwork, they can sign up to my email list. I have several free sign ups. Probably the best one for copywriters to start with is, I just call it My Top Upwork Hacks. They can sign up for that right on basically any page of the site.

Kira: Thank you, Danny.

Rob: 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 in iTunes. If you like what you’ve heard, you can help us spread the word by subscribing in iTunes and by leaving a review. For show notes, and full transcript, and links to our free Facebook community, visit We’ll see you next episode.

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