TCC Podcast #315: Building a Profitable Business without a Website, Email List, or Social Media with Rob Perry - The Copywriter Club
TCC Podcast #315: Building a Profitable Business without a Website, Email List, or Social Media with Rob Perry

Rob Perry is our guest on the 315th episode of The Copywriter Club Podcast. Rob Perry is a SaaS and B2B copywriter and consultant who has built a solid pipeline of clients without using a website, email list, or high-profile social media presence. In fact, he grew his business using a platform you may be familiar with: Upwork. How’d he do it? And could you do the same?

Stick around and find out:

  • How Rob went from President of sales to copywriter and how he leveraged his skills.
  • The struggles of abruptly moving your family overseas.
  • How he used Upwork to start copywriting and became a sought-after copywriter.
  • Standing out on a platform like Upwork and becoming the go-to choice.
  • Are 3 minutes of value worth your time?
  • Upwork 101: Setting yourself up for success in 3 steps.
  • Why you need to filter jobs on Upwork and cut out the noise and save time.
  • How to avoid clients who have unrealistic expectations.
  • Did Kira get kicked off Upwork?
  • How to tailor your proposals to each job.
  • The top reasons copywriters should use Upwork to fill their pipeline.
  • Can you build and make connections OFF the platform?
  • Finding the projects you actually want to work on.
  • How to dig up the pain points of your ideal client and create a solution.
  • Rob’s advice on closing sales calls and being a better salesperson.
  • What mistakes are copywriters making in the sales process?
  • How to step into different personas and voices as a copywriter.
  • Why it’s crucial to practice confidence and adjust (and take care of) your mindset.
  • What NOT to do when adding retainers to your client load.
  • Avoiding bad habits and thinking strategically about your business.
  • When to use Upwork and how to keep it from being your only lead source.
  • Thinking about building a team? Do this first.
  • How to get to where you want to go FASTER.

Press play or check out the transcript.


The people and stuff we mentioned on the show:

The Copywriter Think Tank
Kira’s website
Rob’s website
Rob Perry’s Free Upwork Workshop 
The Copywriter Club Facebook Group
The Copywriter Underground
Free month of Brain.FM
Episode 19
Episode 248
Episode 265

Full Transcript:

Rob Marsh:  In the past five years of interviewing successful copywriters on the podcast, I can only remember one who was running a successful business without a website or a social media presence, or an email list for that matter. And perhaps coincidentally, that person, I believe, is the highest-paid copywriter working in the world today. Now, I’m guessing at that assumption, but if he’s not the highest-paid, he’s definitely in the top five. And you might be thinking, “Well, sure, a copywriter with a good reputation and a steady flow of very high-paying clients can get away without a website or an email list or a social media presence. But what about an almost unknown copywriter working in places like Italy or Chile or Spain without any high-profile clients? In fact, a copywriter who might be getting the bulk of his clients in a place like Upwork?”

Our guest on the Copywriter Club Podcast today is copywriter Rob Perry, and he says that it’s not only possible to do that, but that he’s been doing it successfully for years. You’re going to want to stick around for this one and hear how he’s done it.

But before we get to our interview with Rob Perry, this podcast is sponsored by the Copywriter Think Tank. That’s our combination of coaching, training, and Mastermind for ambitious successful copywriters who are ready to take their businesses from where they are now, maybe somewhere around $5,000 a month and doubling, tripling, or doing even better with it. Or maybe they want to launch a new product or a podcast or create a course or membership or something different in their business, the Think Tank is the place that you can do it. And we’re just in the planning stages right now of our upcoming Think Tank Retreat. It’s going to be an in-person retreat this January. And so if you join before then, you’ll be able to jump in, meet everybody in person, and have a lot of fun with us at that retreat.

Anyway, if you want more information about the Copywriter Think Tank, check out There’s a little information there. There’s a short video there that you can watch. Just get a sense of what happens in Think Tank. And if you want to know more, you can just schedule a short information call with either Kira or me, and we will help you figure out if that’s a fit for you.

And then one more note, today, I am alone today. No co host. So this episode is just Kira, Rob Perry, and a double dose of me. Having said that, let’s get to the interview with Rob Perry.

Rob Perry:  We all feel like we have a similar story, right? None of us started as copywriters or most of us didn’t. But I was living in New York with my wife and had a job, working actually as a partner in a skateboard company, and my daughter was born. Life got immediately very complicated, very quickly because New York’s pretty expensive and my wife was actually from Italy so she was from out of the country and had a little bit of trouble adjusting to being there as well. So we decided to move back to Italy to her hometown to spend some time closer to her family.

Obviously, when we got there, I needed work and I couldn’t take my job with me, and I knew we probably weren’t going to be in Italy forever. So I decided, “Hey, I need to do something.” I need to create some sort of business that I can take with me because we may be moving again and I don’t want to have to look for a new job in a different country another time, maybe more than once.

So I started looking at a little bit of content writing initially because I knew I could write. I was an English major and a Theater minor. Writing was always something that was a passion of mine, not something I had worked on professionally. So I started looking into content writing. And as I dug into it a little bit more, I started exploring and discovered that copywriting was maybe a little bit more up my alley. I had a lot of experience in sales, particularly B2B sales and face-to-face sales. So moving into copyright kind of felt like a really sort of natural transition from that experience. But at the same time, I had no real-life work experience in copywriting. I had no real-life work experience in marketing really. I had overseen marketing teams, but I never worked in marketing. I was more on the sales side.

So I set up a profile and Upwork and just started looking for jobs. I sent a couple of proposals, I got lucky. One of my first few proposals got accepted and I was often running. Wrote a website, a couple pages of website copy for a hundred dollars for some guy, which at the time felt like it was perfectly fine, right? I was getting paid to write and it was always kind of a dream.

Rob Marsh:  Okay, so do you remember that first pitch, what you said or what you did in it?

Rob Perry:  I don’t remember the first pitch, but I remember the first job well, because I remember it was a clothing company and they were based in an east coast city, not New York. They wanted to kind of redo their brand, but they had a very specific feel and they didn’t want to completely redo everything. I guess they wanted to sound more professional, but they also were appealing to a younger segment. So I didn’t want to sound too professional.

So I wrote the copy. I tried to do the best that I could to make it grammatically correct at least while I was staying within the bounds of what I thought they wanted. And the first feedback I got from the client was, “Oh my God, what is this? You’re going to ruin my brand. What are you doing?” And I freaked out, right? We all do that the first time we get negative feedback. This was my first job ever. But it all worked out. I got on the phone with him. Fortunately, I took the feedback head-on, got the phone with him to figure out what was actually happening and realized that his changes weren’t so significant. It wasn’t so different. We just needed to change a few things up. At the end of the job, I got a five-star glowing review from him. And that was really, I think, the launching point for me on the platform was getting that first review under my belt and then other people could see what I was about in terms of what it was like to work with me.

Rob Marsh:  So I have a feeling we could talk about Upwork for the entire hour, but I’m curious how you go from that first project. I mean, you’ve basically grown your business on Upwork, but how do you turn that into a pipeline of projects coming to you?

Rob Perry:  Sure. I mean, it was one step at a time, right? The first year it was kind of piecemeal. I wasn’t working full-time either. I didn’t need to at that point. We were kind of in a family-focused stage, and I knew that I wasn’t going to dedicate 40 hours a week to it. So I kept pitching clients and I didn’t raise my prices immediately. I probably should have gone faster than I did. I think my initial hourly rate was around $40 an hour. I didn’t take hourly projects though, I worked on fixed-price projects. I would just find a job looked interesting to me that I thought that I could do that didn’t have too much competition or that had a specific reason that looked like I thought that I had some sort of an in, there was something I could offer to the job that I didn’t think somebody else could.And so that was really my opportunity. My strategy was looking for those strategic opportunities where I felt like I had an advantage. And so I would apply to jobs and give what I thought was a fair price and eventually worked my way up. As I got more reviews, it got easier. Pretty quickly, I became “Rising talent,” which is one of the badges they give you on the platform, which means that you start showing up in more searches and then you do start getting invited to some jobs. After about three months I was top-rated. And once you’re top rated, then you show up in more searches. The more active you are, the more proposals you’re sending, the more likely you are to show up on other people’s radar in their own searches as well.

So over time, I definitely started getting invited to more jobs, and that gave me the opportunity to pick and choose who I wanted to work with. I mean, you can go through and you can search and you can give out, put out proposals to the people you want to work with, but when people are coming to you, it makes that much easier to close those jobs and demand more money.

Kira Hug:  So you mentioned that you went after jobs early on before you even got your first badge, jobs where you had an advantage. So can you talk more about that? How do you identify that advantage? What does that look like?

Rob Perry:  Interesting question. I don’t remember exactly, but I think that a lot of what I was looking for were things that were in the B2B space because I had a lot of experience in B2B sales. And I feel like with startups as well, I can… I also had experience running a startup business or being a partner in a startup business so I understand the business owner’s perspective, I think a little bit better than your average copywriter who’s just quitting out a profile in Upwork. So that gives me an opportunity to ask questions and dig into things that other copywriters might not. And that, as we talk about all the time in the Think Tank and other places, allows you to position yourself as more of a consultant than simply a copywriter, right? And by asking the right questions, even in a proposal, asking questions in a proposal is a great way to show that you have some knowledge to offer and help you stand out.

Rob Marsh:  So I know you couldn’t remember the original pitch, but when you’re sending out pitches today or when you’re responding to projects, what does that look like? What are you sharing in that message? What does that communication look like so that people are hiring you?

Rob Perry:  Sure. I think the first thing is what I just talked about, you want to add value, right? You need to figure out some way that you can show them that you can do something for them that nobody else can, hopefully, the thing that they’re looking for.

And so when you get a proposal or you’re looking at a job posting, the first thing I do is try to get as much information as I can. Have they posted their website? Have they given you a link to an existing landing page? Have they given you an example of an email they’re trying to send? Is there anything, any information you can get from them? And in some cases, it might just be you see their name and you see the industry that they’re in, and you see that the city that they’re in through Upwork, and you can do a quick search and see if you can put A, B and C together and figure out who they are and what they do. And if you can do that, then you’re coming to them. You’re coming into the proposal with a little bit of information that maybe some other people don’t have that they’re not using as strategically.

So my first step is always, what can I find out about this person? What can I find out about this job and how can I offer value now? And that might be doing a quick two-minute audit of a homepage or a landing page and just saying, “Here are three things that I saw that I think we could work on right away.” And obviously, this isn’t everything. Some people might say, “Oh, this is doing free work” or, “You’re giving things away for free.” For me, that’s really just about me proving my value. And if it takes three minutes of my time to do that and that’s what’s going to be the difference between me getting an interview with that person or not and probably getting hired, then I’m absolutely going to do it 100% of the time.

Kira Hug:  So let’s just back up a little bit, and if I’m new to Upwork, a relatively new copywriter, what are some initial steps that I really need to focus on to do it right? And then alternatively, what are some things I should avoid early on that could possibly sabotage my experience on Upwork?

Rob Perry:  Right. I think two things that I’ll mention. The first is obviously your profile and getting your profile accepted. So there are people that do struggle to get their profiles set up and accepted. I’ve heard less of that recently, but I know in the past few years there have been issues with that. So create a profile, spend some time on it. Think about who the customer is you’re trying to serve and make sure your profile is set up to speak to your customer and not just about yourself. You’re not writing a resume, right? You’re trying to show why you have unique value and how you can add value for your customer. Basic copywriting stuff. If you’ve studied copywriting, that should be second nature. But a lot of people who are copywriters, even in their profiles, don’t do that. So think about how you can add value. That’s One.

Two, is mindset. And this one, I think I got lucky in that I landed one of my first two or three proposals. I have gone through periods early in my career where I had to send maybe 5, 7, 10 proposals to land a job that I was satisfied with, but I know a lot of people who have had to send more. So stick with it. Send proposals, search out jobs that look good for you that you’re pretty sure you would like to do and that you feel like would be a good fit and send detailed proposals, offer value where you can and stick with it because not everybody’s going to land one of the first three clients that they pitch even with a proposal, even with the best strategies out.

Not everybody’s the best fit for every client. So you need to stick with it. You need to keep the right mindset, understand that it will pay off over time. The hardest part is getting those first few jobs under your belt. So I think the third piece of advice I would offer is suck it up and do a little bit of work below your market value. Don’t give work away for free, but take a job that maybe won’t be so much of a time commitment, but it will allow you to get some history on the platform, because once you have a review under your belt or one or two or three, then people can see that you’re somebody that they might want to work with. When you have zero hit work history, it’s very hard. Those first few jobs are going to be tough and you might have to work at a pay level lower than you would expect to if you’re working off of a platform.

Rob Marsh:  Rob, I’ve heard you talk about this a couple of different times and it just feels to me not only are you’ve got your profile set up, but you’re doing something different on Upwork than maybe the vast majority. I don’t think you spend a lot of time with cold prospects. You seem to be able to find people who are ready to hire right now or they’re hotter. What else beyond the profile and the pitch that you send out are you doing to find these people?

Rob Perry:  I mean, I don’t know because I don’t know what everybody else is doing, but I do know that my experience has been significantly different than a lot of other people’s. And I think to me it boils down to a combination of things, right? Some of it is my work experience, off of the platform even. So when I came to the platform, I didn’t have any copywriting experience, but I did have extensive experience in sales. I do know how to present myself on a sales call. I am able to add value in certain scenarios. So I think that’s one thing in terms of getting hired.

In terms of finding jobs, I think it really comes down to understanding how to work a search function, a little bit of patience and understanding who you’re looking for. A little bit also of filtering out the noise because a lot of people get distracted, they get on the platform and they say, “Oh, here’s a job that looks interesting and this person says they want to pay $50 for a website copy for an entire website. Or this person says they want to pay 1 cent per word and they need a 10,000 word ebook,” right? You just need to filter that noise out. You need to set your filters. First of all, don’t search for any jobs at the beginner level. I mean, even if it’s your first copywriter job, if you’ve studied copywriting, you could probably work at the intermediate level in Upwork.

The people who are working at the beginner level who are looking for beginner level people, truthfully, most of them just aren’t going to be willing to pay you what it’s worth. And most of them are going to be unhappy even if you do a great job because their expectations are too high and they don’t really know what they’re looking for. So the better jobs you look for in terms of people who pay more and who are asking for a higher level of talent actually are going to be a better experience for you because those people have a little bit more idea what they’re looking for, they’re not going to have unrealistic expectations, and they’re willing to pay a decent price for good work. When you’re trying to work with somebody who’s really cheap, it becomes a challenge because not only are they not paying enough, but their expectations tend to be completely out of whack.

So I think those are a couple things that I’m doing differently. Aside from that, I don’t know. I mean, I do know what I do and I can’t teach people that, but I don’t know what a lot of other people are doing. I know that from the hiring side, when I get proposals, a lot of people just copy and paste proposals. And that’s the last thing you should ever do, is create a Steiner standard proposal, copy and paste. You need to make sure you’re personalizing it to them, not just adding their name, but telling them, showing them that you’ve read their job post and where you can offer specific value for the specific thing that they want, not like, “I would love to help you with…” That’s the last thing you want to say, right? It’s great that you would love to help me, but I’m not looking for somebody who’s passionate about working with me. I’m looking for somebody who can add value to my project.

Kira Hug:  Okay. I mean, we’ve heard you talk through this at TCC IRL, but what is the benefit of this? We know Upwork has been trashed in the copywriting space. I mean-

Rob Perry:  Sometimes by us.

Kira Hug:  Maybe Rob and I have trashed. I only trashed it because I got kicked off the platform way back in the day ago. I had to trash it. But-

Rob Perry:  What did you do to get kicked off, Kira?

Kira Hug:  I think it was when it was still Elance, right? It was Elance, and then it turned into Upwork. I think I was trying to modify my profile and add all these links outside of the platform, and then I got kicked off. So anyway, I was like

Rob Perry:  Don’t do it.

Kira Hug:  … “Okay.” Why should we use it? As copywriters, content writers, why is it a really smart decision for us to create this channel and focus on it and build it as a lead channel, as part of our business? Why does it make sense? So I guess, can you sell us on it?

Rob Perry:  I mean, I can. Although I will say that I’m not a paid spokesman for Upwork and I have spent my share of time trashing them as well. So it’s not that I love everything about Upwork. I’ve had bad experiences in Upwork, but I’ve had bad experiences with clients that I found other places as well, right? I’ve listened to people. I’ve read so many long posts on Facebook groups about people who have been ghosted by clients or can’t get paid, and all these things that Upwork actually kind of resolves for you in a lot of cases.

So a few things about Upwork that I think make it a really great opportunity for copywriters and content writers really at any level, the first thing is that there are what I call hot prospects, right? These people who have already put their credit card in the system, they know exactly what they want. They want to buy something, right? This isn’t going out to LinkedIn and contacting some people and trying to build relationships over the course of a few weeks or months and hope that maybe down the road they’re going to a lead magnet or they’re going to want to redo a funnel. There are people who are ready to buy. They’re going to hire a copywriter probably this week or next week or the week after. It’s just a matter of who is it going to be? And if you want it to be you, it’s easy enough to convince them.

Now there’s a little bit of work you can do on the front end, but definitely they’re ready to buy leads. And that’s something that’s really hard to find when you’re doing your only generation, starting from cold leads at least. Obviously, if you have inbound leads, it’s a whole different deal. But when you’re looking at that cold outreach, it takes time to warm those people up. And if you need a paycheck next week or the week after to pay your rent, Upwork is a place where you can find somebody realistically to land a job within a week, do a job within a week and get paid. Secondly, I think that there are a lot of people out there working on Upwork. So a lot of companies that work exclusively on Upwork and won’t look anywhere else. So that’s another thing that is obviously a big benefit.

Rob Marsh:  Rob, you mentioned one of your secrets is the ability to search function. Obviously, you sort out the beginner jobs. Are you also limiting by niche or by project type in order to find those jobs? I don’t know this because I haven’t been on… I don’t think I’ve opened up my Upwork account in eight years, so it’s been a while and I’ve never actually taken a job there. So how are you using the search function so that you’re really only finding the jobs that you want to work on?

Rob Perry:  Yeah, I think that you should definitely search for whatever you want to do, right? If you want to do copywriting for course funnels or for launches, then search launch copywriting or launch copywriter or launch emails or launch landing pages or sales page, right? Whatever the specific asset you is you want to work on, search for that. Particularly when I started out for the first couple of years, I was doing a lot in the SaaS space. So I would go in every morning and I would search SaaS, SaaS copywriter, to see if there was anything from SaaS copywriter or SaaS copywriting. And then just SaaS, and scroll through pages of SaaS posts. Most of them were looking for designers or developers or things that had nothing to do with copywriting. Once in a while, I would find one that was a copywriter, but hadn’t been written in a way that you would find it in a search if you’re looking for a SaaS copywriter, right?

So yeah, whatever it is that you want to do, be very clear and intentional with that when you’re designing your searches. And do searches every day because new jobs come up every day. So if you really are looking for work actively, then do searches every day. At this point, quite honestly, I don’t remember the last time I went on to Upwork and did a search because I get invitations for enough jobs that once in a while I’ll find one that’s interesting and I’ll just pick it up. And I’ve got a lot of recurring clients as well. So I haven’t needed to be doing consistent searches over the course of the last few months. But when I do, those are the techniques I use and I’m still successful at finding clients that way.

Kira Hug:  So how can we leverage Upwork and build our businesses? Beyond Upwork, what does that look like? What’s possible outside of… Especially since it sounds like you’ve brought some of your clients outside of Upwork and turned them into retainer clients.

Rob Perry:  Yeah. So you can’t actually bring an Upwork client outside of Upwork. So I’ll be clear that I haven’t done that. In case Upwork’s listening, I haven’t done that. But what I have done is I have made connections through Upwork with clients that I have then added to my network outside of Upwork, right? I might connect with them on LinkedIn and I know them personally because I’ve worked with them again and again, and they’ve referred me to people in their external network. So I have built a little bit of a professional network using Upwork, maybe not as much as I should have even, but I have built a professional network using Upwork that has helped me find clients off of the platform.

So you can’t legally, according to their terms of service, which I do suggest anybody respect, you can’t take a client off of Upwork unless you tell Upwork you’re doing it and then you have to pay Upwork a percentage of your work with them for the rest of your life in theory. So not something you can easily do. But that’s not to say you can’t grow a business without it. In fact, this year and last year, both, I will have invoiced more business off of the platform than I have on the platform, but I’ve done that without a website, without really any significant social media presence, without an email list, any of the things. I haven’t paid for ads. I have basically no lead outreach. I have no inbound leads coming to me from any other source. But through referrals and connections that I’ve made with clients that I’ve met on Upwork, I have been able to build a business outside of the platform as well.

Rob Marsh:  Okay. So I feel like, and it’s probably my fault, we jumped right into Upwork without talking about this experience that you had before you came to Upwork as sales manager, vice president of sales. I have a feeling that a lot of that may have contributed to your success as well. Like you said, you didn’t have any experience as a copywriter, but you did have sales experience. So I’m curious about your experience in the fashion industry, in the sales vertical, how that’s helped you as a copywriter and helped you grow your business.

Rob Perry:  Yes. I think that for me, copywriting is sales. Now, I know that it kind of walks that line of sales and marketing, and it depends on who you talk to. You have marketing copywriters, you have sales copywriters and maybe work through different beasts, but I think we both kind of walked that same line. And for me, the process of having sold people face to face for at least 10 years in different markets is something that has been invaluable in understanding how to approach copywriting, because we talk a lot about understanding your personas and doing your research to understand who people are and empathy, but there’s no way to get that experience better than actually sitting down at a table with somebody face to face and having done that over and over again.

So when I first started in sales, I was working for a clothing company. I’d actually been on the purchasing side first. I worked for a major department store as a buyer, and then I went and started and went to the other side of the table to sell men’s clothing to department stores essentially but department stores and specialty stores. So I had different types of clients, right? One of my clients was Macy’s. I had to sit down sometimes with a VP of Macy’s or maybe the VP of a major department store, a major regional department store, occasionally even somebody higher than that, occasionally even a CEO of a midsize department store.

So you had to be able to present and talk to them in a certain way and understand what their pain points were, right? Because these are people who are worried about their gross margins, they’re worried about their turnover, they’re worried about their markdown rate and all of these things that are very finance-based, right? But you also are selling to independent chain retailers. And these independent chain retailers, in certain cases, are much more concerned about the fashion, about the timeliness, about the advertising and marketing that you’re doing in the local market to reach their customer base, right?

So when you sit down, you’ve got two very different personas. And then beyond that, you get to the discounters. You start working with .J.Maxx and Ross stores and even local discounters who are even more aggressive, but the only thing they care about is getting the best price. So within my customer base there, I had at least three major personas, and each one of them had their own ticks and their own unique sort of personalities and wants and needs. And so you need to learn to understand what those are. And if it is something that you want, you can study. Obviously, you ask questions and you learn about them. I knew a lot of great salespeople that took notes and had extensive notebooks. I was more, let’s say, instinctive about it and maybe less disciplined we’ll call it, but you learn how to communicate with each one of these people and how to pitch them in a way that’s going to work for them.

And then when I left the clothing company and I went to help my friend with his longboard skateboard company in New York, we started working on wholesale distribution there as well. And then you meet a whole other range of types of retailers, from the people who are still chain-oriented and business-oriented in terms that they need to get their numbers right, to the guy who soon as you get in the shop, kicks the kids out and locks the door because he wants to go to the back and smoke. So it’s a whole range of different people. And that broad range of experience helped me to develop, one, the skill of using different voices and presenting myself in a different way when necessary to a different audience as well as to listen and understand where your audience is coming from so that you can try to give back to them what they’re giving to you.

Kira Hug:  So what advice would you give to a copywriter who struggles with sales or just doesn’t feel as confident, doesn’t have all the experience you have? I mean, there’s definitely practice. You mentioned repetition, listening. What else do you feel like could benefit us as copywriters to strengthen our sales calls?

Rob Perry:  That’s a great question. It’s interesting because I think I’m pretty good on sales calls. I close a lot of them and I’ve done a lot of sales over the years, so I know that that is something that I have a skill for. At the same time, I’m not outgoing. I wouldn’t call myself an extrovert, right? So a lot of people think of salespeople as bubbly and friends with everybody. I was never that person who built really intimate relationships with my clients, but at the same time, they enjoyed being in my presence, enjoyed working with me.

So I think that for me, a lot of it is about no matter how you’re feeling inside, you need to just push through it and present yourself in a certain way. Maybe this goes back to some of the theater experience I had in college, I don’t know. But for me, being on- selling has always been a little bit like being on stage. And so it is very comfortable for me to not necessarily… You want to be authentic, but it’s also a sense of a performance, right? So you need to enjoy it a little bit.

The second thing, which you mentioned, is listening. That’s really one of the most important parts, and it’s one of the hardest parts especially if you are trying to perform. If you have a script and you have this performance and you feel like you’re pulling off this performance, it can be hard to sit back and listen. But listening is absolutely essential. And along with listening, repeating back to your clients or your potential clients the things that they tell to you. It seems obvious and it might even seem too obvious, but it really isn’t. People like to hear their own words repeated back to them on a subconscious level, and it really helps you connect with them. It makes them feel like you understand them, even if you’re literally just telling them the exact same thing that they told you.

Rob Marsh:  And so aside from not doing those two things, there are mistakes, big mistakes that we make when we’re selling, whether it’s to our clients, maybe it’s other situations that are kind of sales oriented where we’re trying to get somebody to change their mind or to act in some ways? What mistakes do we make?

Rob Perry:  I think most sales mistakes, from my perspective, come down to mindset. It’s really about feeling inferior or feeling like you don’t have the right to ask for something or feeling that you’re in the wrong desk or something, whether that’s asking for an extension or standing up for your work, or if it is demanding the right price, right?

I think that everybody needs to try to be realistic about where they are in their business and don’t try to rip people off. You should be trying to add value wherever you can. But if that value is legitimate, then you need to display confidence and be confident about that. And again, even if you’re not feeling confident inside, you need to display it on the outside. And that does take practice, right? Because not everybody can jump on their first sales call and feel like they’re super confident and just smooth over those rough edges.

I still have sales calls where I get off and I’m like, “Oh, wow, that went really bad.” As many times as I’ve done it and as much as I’ve sold, there’s still times where it doesn’t work. But you need to get back on the horse and get back out there and do it again.

Rob Marsh:  Okay, so just jumping in here again. And remember, I’m alone here, so no one to bounce these ideas off with. But as I was listening back to Rob and the things that he was sharing in this interview, it really struck me just how much of a… I guess the word is a science. That’s what I want to say, how much of a science it is to use Upwork well and to do well with it. So many nightmare stories. We hear of copywriters who go there, they struggle, they can’t find clients. Maybe they find a client but they can’t find another client or they’re finding clients, but they’re paying literally pennies per word or less.

So much of making Upwork work for you is about the same things that we do when we’re creating websites for ourselves, when we’re out building our authority. You need to be adding value to your clients. You need to do things that make you stand out. Here Rob talked about adding value, finding out something about a client or the project or the job before he would even start talking to them. He talked about setting up the profile in a way that speaks to the customer, to the client that you’re trying to attract. There’s a lot of mindset things that go on here, sticking with it. This is all stuff that applies to setting up our own websites and competing on other places like Google or having a LinkedIn profile. We still need to do these kinds of things in those other spaces. And so in so many ways, Upwork is just a microcosm of the larger world of competition. And what works there will work off it, what works off it could work there. So just do those things that help you stand out.

I also really appreciated that Rob was talking about sending out lots of proposals and suggested the idea that especially as you’re just starting out, you’re trying to build a track record. Sometimes that requires taking a few jobs that you might not want to take or that might pay a little bit less than you would normally. Now, we’re not talking about the pennies per words kinds of projects, but in order to build that successful track record to get those five star reviews from some clients that you start getting invited onto projects on Upwork, you want to do those things that get you accepted. And sometimes, as Rob said, you just have to suck it up, go through that little bit of a difficult period and make it work.

He also was talking about when it comes to proposals, the copy and paste thing, don’t do it. Make each one unique. There are definitely ways that you can use a template and make it feel unique with different kinds of copy. But clients can tell when something is pulled from a template if you don’t really spend some time trying to personalize it. And getting to know the client, the project, as Rob was suggesting, is a really good way to do that.

Rob also is talking a lot about the power of filtering and searching, limiting the beginner jobs, even if you’re a beginner, because the level of beginner on Upwork is really beginner. You want to be looking at those intermediate and pro projects even if you’re just starting out. Of course you’ve got to be able to deliver if you get hired, but you can learn those skills, you can add those skills, you can develop them as you’re working on these projects if you’re dedicated to serving your client and solving the problem that they have.

And then I think a lot of people who go into Upwork, they jump in every couple of weeks or maybe only when they need additional work. And if you’re not making it a daily or maybe an every other day task for you, you’re going to miss a lot of what’s happening there because it’s such a big marketplace. There are new projects that are going up every day and projects that are being hired for every day. If you make it a habit of jumping in for 10 or 15 minutes just to scan through what’s available, maybe put in your search terms for your niche, your project levels, the kind of work that you want to do, you’ll find that you can have that success that Rob’s been talking about as he’s been teaching us about how uses Upwork.

I also want to just mention what Rob was talking about as far as at the very end of this segment, he was talking about confidence and practicing confidence. We’ve talked a little bit about this before, but it’s difficult to practice confidence because confidence comes from the doing. So many times we hold ourselves back from moving into something that feels uncomfortable or from doing that thing, like sending out a proposal or connecting with a client on Upwork or wherever, doing those things, because we want to be confident first and we want to practice that.

I’m going to be a little bit contrarian into what Rob was saying, we need to practice that. But confidence comes in doing. The way to practice confidence is doing the thing that you are afraid to do. And when you do it and you do it successfully or you do it, maybe you fail, but you come out not injured, there’s no real pain, there’s no real bad outcomes that come with that and we get through it, we’re like, “Oh, the worst thing that can happen is not a lot of bad stuff has happened to me. I just got a no from a client or I didn’t hear back.” Those kinds of things. That’s the thing that builds your confidence. And that’s true again on Upwork. It’s true if you’re pitching clients out in the real world. It’s true with anything that we do in our business. The way to practice confidence is by doing the stuff that you are afraid to do or that you’re waiting to be confident to do.

Okay, so that’s enough about that first part of the episode. If you are interested in working on Upwork, it probably wouldn’t be bad to go back and listen to this whole half of the episode again, because what Rob is talking about, what he’s teaching here, I think is so applicable. Using some of the tactics he’s teaching here, as well as what we’re going to talk about in the next half of this interview will make your experience in Upwork far better than most copywriters who are there. Let’s go back to our interview with Rob and find out how to make retainers work for us so that we don’t run into problems or pitfalls.

Kira Hug:  I would love to hear more about retainers because I know you have some retainer working relationships and they’re tricky at times. So how do you navigate through your retainers to make sure it’s working for you and not against you? Yeah, that’s the question.

Rob Perry:  Well, I think that this is one area where I still have a lot of work to do because I haven’t done a very good job of that. In fact, I think as of right now, I’m officially/unofficially not taking on more retainer clients because I’ve had a really hard time of managing retainer clients and still making room to bring on project work because I think I have a tendency, one, to maybe not define my retainers clearly enough in terms of what deliverables are going to be on a monthly basis.

So I would recommend anybody who wants to get into retainers to as much as possible make it deliverable based or hour based. I have gotten into some retainers that were a bit more flexible and that ends up with me not really ever knowing when I’m done and feeling guilty for not doing enough, or then probably overdelivering but still feeling like I’ve under-delivered. So that can be a complex thing. So I would say there’s some advice I would offer to people.

And for me, I think for the short term anyway, I’m planning to just not take on any new retainer clients. I prefer to work on a project basis. Even if it’s an ongoing client, set the deliverables, set the price, set a date, and I’ll deliver. But when I have to be trying to manage a project throughout the course of a month without understanding what the specific deliverables are, it’s been problematic for me, I’ll say that.

Rob Marsh:  So what does a typical project look like these days for you, Rob? What’s your favorite kind of copy to work on and what are you delivering for your clients?

Rob Perry:  Sure. I mean, at the moment I’m working on a B2B website with a little bit of some funnel activity in terms of lead generation. I tend to work on websites and then funnel assets, right? So landing pages, emails, maybe a little bit of ads to pull all of that together. So those are the biggest projects that I work on, whether it be lead gen funnels or sales funnels for B2B clients, and webpages. I have done some email based retainers as well, which I love email and I have had good success with that as well. But I think right now it’s been more on the website and total funnel strategy and assets.

Kira Hug:  How do you think strategically about your business? Because you’re on Upwork. You’re the king of Upwork and you can choose what you want, take the projects you want, so you could do everything. How do you decide what to take, what not to take? How do you think really big about your business so that you’re continuing to move in the direction you want to move and not taking those retainers and being really smart about what you’re doing?

Rob Perry:  Right. I mean, it’s a challenge for all of us to be as intentional as we would like to be about our business. I do think that that’s one area where Upwork has made it more challenging for me. And I think that I would recommend, as I have every time I’ve spoken about it, that nobody follows in my footsteps in terms of using Upwork as essentially my only lead generation channel. I think that Upwork is really great as a way to find clients, especially if you’re just getting started or if you’re running into some points where you’ve got weak spots in your schedule and you want to fill them up a little bit more. I think it has a lot to offer.

But if it is your only lead gen channel, then you are going to maybe fall into some bad habits, which are maybe not being as intentional as you should be about who you’re working with and when and taking on clients that fit maybe a little bit outside of what your ideal niche would be. For instance, it can be hard to find people in a niche consistently on Upwork. There’s a lot of clients there, but they don’t always align with exactly what you want to be doing. So you do end up sometimes working outside of your preferred niche maybe.

And also there is a tendency to stay inside the platform, think inside the platform, and not allow yourself to develop as much outside as you could. So I definitely still have work to do on my business to be more intentional about what I’m doing outside of the platform. Inside of the platform, I just choose jobs that appeal to me and where I know that I’m going to be able to make enough money to feel good about the job at the end of the day. I am being more intentional now about my business and in the process of getting my website out there and trying to be more intentional about the types of clients that I approach and types of jobs that I want to work on.

Rob Marsh: So Rob, I know over the past year or so you’ve kind of gone through a couple of different phases in your business where you thought about growing a team, bringing in some people to help with some stuff, and then maybe backed up a little bit after going through that experience. We talked a little bit about that and what you struggled with and what, if somebody’s thinking, “Okay, I’m going to grow a team,” maybe some of the things that they ought to be looking out for as they consider that as part of their business?

Rob Perry:  Yeah. I think that there are many things to look out for when you’re looking to build a team. The first is to make sure that it’s what you really want to do, right? I think that I had an opportunity to build a team based off of a specific client and a specific retainer deal that I wanted to take on. I did that for a year and I struggled to find the right people. I also struggled to discipline myself enough to give people work to do. I know this is something I’ve gone through in other points in my career too, not as a copywriter, right?

I’m the type of person who tends to want to do it all myself, and I need to learn to reduce that urge, but at the same time something I also need to be aware of, right? And so when I am looking at building a team, I need to be very conscious about what specifically are these people going to do and what deadlines do I need to hit on my end to be able to allow those people to do it. I got myself into a lot of situations where I ended up doing work myself, not because the person I hired was bad even, but because I didn’t give them what they needed in time to give me what I needed, which means that in order to get the client what they need, I have to do it myself.

So I think that was the biggest struggle that I had with building a team, was understanding how to manage my own time with a team in play. It requires a lot more organization. I think if I had to do it again, I would probably have invested more money on the front-end with not just a VA, but maybe an OBM, somebody to help me structure things because I obviously didn’t do the job that I needed to structure it myself to make it be successful.

Now, at the end of the day, the client was happy, we’re parting on good terms, but I’ve kind of winding down that arrangement that I had started to build because I discovered it wasn’t what I’d be happy, I wasn’t satisfied with how was that was working, and I would rather kind of put my individual attention on copy projects, which is where I have more fun and I think where my skills lie.

Rob Marsh: I appreciate you sharing that just because I think there are a lot of people who go through this kind of thing and we don’t talk a lot about that. Sometimes the team isn’t the right move forward. Sometimes we’re better off doing our own thing or maybe the situation isn’t correct. So I just want to say thanks for talking a little bit about this because I think it happens to a lot of us.

Rob Perry:  I’m sure it does. Absolutely we all make mistakes, right? And we all try things in our business. Sometimes they work, sometimes they don’t. I can’t say that I won’t ever try to build a team again, right? I probably will at some point if things continue to go the way that they are because I don’t think I’m going to get to where I want to be without having some sort of help. But that situation didn’t work for me, and I need to be more intentional next time around to ensure that I have a better result.

Kira Hug:  Okay. I respect… I feel like you have a more contrarian vibe sometimes. I don’t know, maybe you disagree. But I guess I’m wondering are there certain best practices that we talk about in the copywriter community or maybe even just in the small business, entrepreneurial, online marketing community that you feel like they just bug you every time you hear it, they annoy you, they drive you nuts. Anything that maybe even copywriters feel like they have to do? Like, “Okay, I have to hire a VA. I have to grow a team. I have to work in retainers”? Anything come to mind?

Rob Perry:  I think I’ve mellowed out a little bit over the last year. I don’t know. Actually, I’m intentionally trying to be less cynical about certain things, because honestly, in the industry we work in, there are certain things that rub me the wrong way sometimes. I mean, I think that for a lot of years, especially working in the B2B space, there are a lot of things about the classic direct response copywriting world that just kind of rubbed me the wrong way and made me feel icky. And they still do sometimes.

But I also realize that in my own work on the B2B side, I owe a lot to people on that side of the business because I can learn things from them, strategies and techniques that carry over and that are effective. Maybe I might not be 100% on board with what they’re selling with using those techniques sometimes, but that’s their personal choice as opposed to mine. I choose to use my skills in the way that I do.

And so I think that maybe a couple of years ago or even less than that, I might have had some different perspective on that, but I am trying to be more respectful of everybody else’s choices. Everybody else has power to make their own decisions on that front. I also am a little bit annoyed by frameworks, but-

Rob Marsh:  I think that’s what Kira wanted you to say.

Kira Hug:  I knew it! I knew it! Every time Rob and I mentioned frameworks, Rob Perry’s like, “Nope. Not doing it.”

Rob Perry:  Well, I’m trying to be less cynical on that front too, but I don’t feel like every business owner has to create these perfect little packages that are represented by some sort of an acronym. For me, I feel like that trend can go too far to the point where I go on some copywriters websites and I’m like, “This is just cheesy and silly. I’m not going to buy your product because of your lampshade formula. Just tell me how you’re going to help me. What are you going to do for me?”

Rob Marsh:  Yeah, I want to see what the lampshade formula is. That sounds great.

Kira Hug:  Well, as a follow-up, I’m curious why you decided a year ago or recently to not be cynical. What was the catalyst for that?

Rob Perry:  I mean, that’s an ongoing process of self-discovery and trying to figure out ways to be happier. Or if not to be happier, to be more at peace with certain aspects of my life. I think that in general, I’ve been a pretty cynical person throughout my entire life, my entire adult life. I don’t know that it’s served me particularly well. I told myself stories about how it was serving me. But it creates a lot of sense of separation from other people. And also it really kind of ramps up my anxiety when I really need to be lowering my anxiety, right? I had a little bit of a blood pressure scare a few months ago, maybe that has something to do with my sudden attention to trying to be a little more tranquil.

But just in general, I think that cynicism is something that, especially as a less outgoing writer type, it’s easy to fall into those types of habits of judgment and thinking that we know better. I’m really trying to get past that. I won’t say that I’m entirely successful at it. I’m definitely not and it varies from day to day. But across the board, it’s just something I’m working on. Yeah,

Rob Marsh:  I love that. So when we first met you, Rob, we were in a villa in Barcelona. You flew over from Italy where you were living. Since then, you’ve lived in Chile. You’re back in Europe again working. You’ve done, I guess what everybody calls the digital nomad thing or obviously working away from your home country while supporting your family, while raising kids, making it all work. Tell us about that experience and why you do it. Why don’t you hunker down in Cleveland, Ohio like most Americans? Not necessarily Cleveland, but yeah.

Kira Hug:  Rob is from Pennsylvania. Rob’s from Pennsylvania.

Rob Marsh:  Or Pennsylvania. Well, I wasn’t necessarily saying in your home place. I was trying to pick a place that maybe you wouldn’t want to hunker down, but I’m being unfair to Cleveland, I think.

Kira Hug:  You’re about to upset a lot of people.

Rob Marsh:  Yeah, I’m sure.

Rob Perry:  No, it’s fine. It’s fine. I’m a Pittsburgh fan, so you can talk trash about Cleveland a lot.

Rob Marsh:  Okay, there you go.

Rob Perry:  But I mean, it’s not something that was necessarily planned. I told a little bit about my work experience before. When I finished with the clothing company, I was about 31 years old. I paid off my college loans. For the first time in my life I had some money and I had never spent any real time outside of the United States. I got my passport at 30, so I had never been anywhere else. And I was like, I went to Spain for a week with a friend to visit. His sister was studying abroad. And then the next year, for the first time in my life, I had some money, I had no debt and I said, “You know what? I’m done.” I quit my job. I was burned out. I quit my job. I broke up with my girlfriend and I moved to Spain for a few months just to see what it was like.

While I was there, I took some Spanish classes. In my Spanish class. I met the woman who would become my wife. So that kind of shifted my entire life, right? I met this woman from Italy. I was living in New York. And so from there we traveled back and forth once in a while over the course of the next few years before we got married. Then she came to the US. Eventually, I went to Italy, the story I told earlier.

So that was really it. I mean, it wasn’t like we are sick of being here. It was like we went there for practical reasons. When I was there, I needed something to do so I started this business and that’s how this all came to be. We lived there for four years. And at the end, we decided that we had an opportunity to go to South America. My wife had an opportunity to teach in a school in Chile. So we left and we said, “All right, we left some stuff in Italy.” But for the most part we were just leaving and we went to see what was our next adventure and we stayed there through the pandemic, ended up being a blessing that we were there just randomly. We got there a month before the pandemic started and we got to spend a pandemic on a hill in the country, kind of co-quarantining with some other families. It was really the ideal experience for that period of time in this world. So super thankful for that.

But after that, we decided we wanted to get back closer to family. So I tell everybody now that I moved to Spain to get closer to my family. But Chile was really far away. And so from a “how did this happen?” standpoint, it was all very organic. My wife doesn’t really want to move back to Italy yet. We met in Spain and we already speak Spanish so we thought it was a good place to come and try to raise our kids.

It’s been challenging without a doubt. There are easier paths. Both are easier careers if you just want a stable income, right? We’re very dependent. All of us as freelancers or business owners are very dependent on what happens in our business. Sometimes it’s great and sometimes it’s less great. There are definitely systems to navigate if you want to live in different countries in terms of immigration system to Texas and all of that stuff gets complicated and complex. But at the end of the day, it’s been an incredible experience. My children at seven and four have seen so much more of the world than I had up until at least I was 30 years old. I wouldn’t trade it for anything. I missed my family. I do wish they got to visit more, but aside from that, it’s been an amazing experience. Hard at times, without a doubt, but all worth it.

Kira Hug:  I’m going back to mindset and reflection because it sounds like a theme that I’m hearing from this conversation as you’re taking more time to reflect and to even allow yourself to change your point of view on certain things. You also mentioned anxiety, which I think many of us can relate to. So how do you take care of yourself today knowing that you did just recently move? You do have young kids, like Rob said, you’ve been dealing with a lot in the business and outside of the business. How do you take time for your personal growth and reflection amid the craziness and chaos that you’re in that we can all relate to?

Rob Perry:  I mean, it’s certainly not easy. In fact, I don’t do a very good job of it, but I am trying to be more intentional about it. It means just making time to do it. And it’s easy enough to say that. Everybody says, “Just make time.” People were telling me that for decades, “Just make time” and I haven’t done it. And I still don’t do it as consistently as I would like. But I do try to find the opportunities when I can to do some things that might help me deal with some of that anxiety and the other stresses that my life brings.

Also trying to spend more time and be more present and conscious with my kids, with my wife. That’s a challenge for me and for a lot of different people, when I spend all my day in my office, focused on these things, and then I still have things coming out after hours and I want to be working when I’m supposed to be spending time with my family. So these are all things that I’m just trying to be more conscious about. I’m trying to be more aware of. I think meditation has helped a little bit, but I don’t meditate every day. I’m a disciplined person when it comes to that type of self-care, but I am trying to infuse it into my life a little bit more where it fits and figure out how that can be a part of my future.

Like I said, I did not have a big scare, but my blood pressure was a little bit high a couple of months ago, and it was something I’d never experienced before and it made me start thinking about, “What am I doing? I need to be exercising more, I need to be eating differently. I need to be thinking about how to manage this anxiety, which in some ways has become a part of my identity. The way that I see myself is as an anxious person.” I always took that as it was motivating me, but we know through science that we can’t be motivated all the time by anxiety if we’re actually sick. So I’m trying to figure out ways to deal with that with help of some external people sometimes and just through self-exploration as well.

Rob Marsh:  Rob, I’m curious, and this is a question I ask a lot on the podcast, but if you could go back to when you were just starting out as a copywriter, maybe logging into Upwork for the first time, what advice would you give yourself? Things you might do a little differently to get where you are a little faster?

Rob Perry:  Yeah, absolutely. I could have gotten to where I am a lot faster, I think. I mean, maybe not to where I am in terms of experience and skill. But the first thing is to trust yourself. If you’re doing the research and you’re trying to do this right, chances are you’re better than you think already. So I was really hard on myself at the beginning and I would spend days and days and days going over the same copy again and again and again. And really at some point, it just doesn’t get much better, right? Sometimes it gets worse. So trust yourself and ship the work.

The second thing is to not be afraid to raise your rates, right? Your clients will tell you if you’re charging too much. If your clients are happy, then you should be happy. And I’ve had a hard time accepting that over the course of the years. Even still sometimes. Even still my clients will be very happy and I’ll be like, “Yeah, but it wasn’t good enough.” So you need to learn to accept that you’re worth what your clients are willing to pay you. And if your clients are happy, that’s what you’re worth. So raise your rates. When your schedule is full, raise your rates. When it’s too easy and too many people are saying yes, raise your rates. Until you feel like you can’t add value, but you probably can still be adding value at a higher rate than what you think.

And the other thing I would say is build your network. This is one that I still struggle with today. Even being in the Think Tank and having a great network around me, I don’t rely on them nearly as much as I should. But I think that the people who have the most success quickly are the ones who are able to build their network, meet other people, get the help that they need, and also referrals and other things that come from that. So build your relationships and try to be as social as you can within the limitations that you have individually. Those are the three things I think I would point out.

Kira Hug:  And you’re working on a new product and workshop. Can you share a little bit about what’s coming up next?

Rob Perry:  Yeah, so it’s still in development, but yeah, it’s a surprise, surprise, focused around Upwork. So I have done something different on Upwork as you guys have mentioned before, and I’m trying to distill that into a program that I can help other copywriters replicate my success.

I really do believe that there are so many clients out there on Upwork that are looking for good copywriters, that there is no way that we can have too many copywriters on Upwork. So I really would like to help people figure out how to make it work for them, how to find the best clients, how to position themselves in a way that helps them find clients and use that as a part of their overall lead generation strategy. I think it’s great for beginners who don’t really have any experience. One of the great things is that you can get on and get paid to get that experience. You don’t have to be out there searching forever. You can get on there, find clients without really any history, maybe just a couple of samples that you write on your own, not for our client, and you can get work. And that’s a good way to learn. There’s no better way to learn than to work with clients.

The other thing is that it doesn’t require you setting up a website or doing a lot of these other things. I’ve seen beginner copywriters go through certain programs and they’ve got this entire business built and they’ve never had a client. They’ll have a website and they’ve done branded photo shoots and they’ve got merchandise, right? They’ve got their logo on a hat and they’ve never worked with a client. And then all of a sudden you talk to them a few months later and then you’re like, “How’s it going?””Oh, well, I’m not doing copywriting anymore. I couldn’t find clients.” The first step is to get a client. Get out there and work with somebody. Figure it out what this is all about. Maybe you don’t even like it. So the first place for me for a beginner is an easy way to get started without a low barrier to entry is Upwork.

But it’s also great for people who are further along in their journey and who have space on their schedule and need another way to infuse leads. I know several people in the Think Tank right now who just over the course of the last six months have either opened or started a profile or gone back into Upwork after years of being dormant because they have seen that it is legitimate. They are able to find clients that will pay their rates, that treat them well, that treat them with respect.

A lot of the things that people have heard about Upwork aren’t really true in terms of the negative things people have heard about Upwork. And if you learn how to work the platform the right way, position yourself the right way, talk to your clients like a professional, I believe that anyone can have success on the platform. So I’m working on a program called Hot Prospecting on Upwork. The idea being that you’re looking at hot prospects, not cold leads. These are people who are ready to buy and let’s get them into your funnel so you can start doing more business.

Kira Hug:  And you have a free workshop coming up on November 8th, right?

Rob Perry:  I do have a free workshop coming up on November 8th.

Kira Hug:  We’ll link to it. And so I’m just going to share it for you. 1:00 PM Eastern November 8th. It’s a free workshop all about how to use Upwork, and we’re going to link to it in the show notes.

Rob Perry:  Yeah, I would love for anybody to show up and hear a little bit more about how I was able to make this successful and some tips on what you can do to make this successful. Even if you’re not interested in a full course or a program, show up that day and I’ll give you some tips on how you can get started quickly and really stand out from the thousands of people that are out there already working on the platform.

Rob Marsh:  Will you be sharing your framework for working on Upwork, Rob?

Rob Perry:  I don’t know. My-

Kira Hug:  I want to see a visual of the framework. I need to see that!

Rob Perry:  My beach ball framework.

Rob Marsh:  Yes. I’m sure we’ll have more to share about that, but we’ll link to it in the show notes and we’ll share that workshop with our email list here in the future. So if you’re listening and you’re interested in this and you’re not on our email list, go to the and sign up and then we can make sure that you find out about Rob’s workshop.

That’s the end of our interview with Rob Perry. And before we wrap, I just want to just reiterate a couple of other things that we’re talking about in the second half of the interview as we like to do. Rob was talking about some of the mistakes that we make as we work on retainers. We’ve talked a bit about retainers on other episodes of the podcast as well. I know that Rob was talking about not making them deliverable-based, but rather focusing on hours, those kinds of things that can leave you feeling like you’re not doing enough, or maybe you’re not putting enough hours.

Retainers based on deliverables is an awesome way to do a retainer. And you basically sit down with a client at the beginning of the month, you agree on the projects that are going to be done that month. Of course, in the back of your mind, you’re thinking, “Okay, if I’m doing this for 10 or 20 hours, can I fit these projects into that allotted time?” so that you have time for your other clients or for whatever else you want to do with your day.

The other way to do retainers, of course, is just hours. Setting aside 20 hours and they pile on the work as it goes. I prefer the deliverable route simply because everything is clearly defined. You know what you have to do. If you run out of hours, you’re not going to be shorting your client on the projects that they need. Everything’s agreed to upfront and at the end of the month you deliver what you deliver and you hop back on a call and say, “Okay, what are we going to do this month?” and pick that up. I think this can be a really effective way for making retainers work if you’ve struggled with the hourly thing.

Sometimes if you’ve got an hourly retainer and the client only has five hours of work, maybe you’ve committed 10 to them or 20 and you feel guilty about not doing enough, or maybe the client starts to think, “Why am I paying for 20 hours when I don’t have enough work to fill the gap?” What can happen?

And then there’s this other thing that you can do when you’re on a retainer is rather than just being a copywriter filling the orders for copy and the client saying, “Hey, I need a website page, or I need an email sequence,” or whatever, you can start acting as that consultant, as a professional who shows up and says, “I noticed this about your business. We could use some kind of an email sequence or a sales page, or we could do something differently with this part of the marketing campaign.” And you can start to create that work for yourself and set aside time for it or add them to your deliverable list. But that’s some of the power of retainers and why they can work so well in your business. I like that Rob’s moving most of his to deliverable-based and not all-time-based. But maybe time-based works better for you. So just think about how you use retainers in your business.

We also talked a little bit about building a team. This is something that obviously we talk a lot about here on the podcast. Kira and I built a team in our business. We’ve worked with other teams in other businesses where we’ve worked before. Rob’s experience I think just really highlights the fact that teams aren’t always the right thing to move to next in your business. Of course, maybe you do need a team to help you, maybe you do need a VA to do pick up some of that work, but oftentimes it’s not about a team or we are not prepared with the processes and the systems in place to make a team effective or we’re not comfortable delegating work to the members of our team. And in those cases, if we’re not ready there, and that’s a mindset issue for us as the business owner, if we’re not ready for that, then building the team should be the farthest thing for what you do. I appreciated that Rob shared all of those lessons.

One or two other things that I just want to touch on before we left, I loved the conversation about Rob trying to be less cynical. I can totally relate to that myself. I’ve been incredibly cynical at different points in my life. Maybe some people would say I’m cynical today. I think that I’ve become a lot more optimistic as I’ve gotten older. But for me, and like Rob said, it just didn’t serve me to be cynical. Showing up a little bit more optimism in the world has helped me also like he did. And so I was appreciative that he brought that up.

And finally, we pointed out Rob doesn’t really like frameworks, the acronym thing. Obviously, Kira and I do like frameworks. We talk about them a lot in our programs. We’ve helped people develop programs. But I think when we talk about them, a lot of people get some bad ideas about what frameworks are. They’re always thinking, “Well, it needs to be an acronym. It needs to fit into a word that relates to the work that I’m doing or to the clients that I’m serving.” And we do see a lot of acronym-type frameworks especially that describe processes, but those are not the only frameworks. You can have idea frameworks, you can have frameworks that work through processes that aren’t acronyms, but go from step one to step two to step three. Those are fine too.

And the power of the framework isn’t in having something that’s necessarily your own or that you’ve got a cool name for it, but the power of the framework is that when you start talking about your framework with clients, they can see that you’ve got a defined process for the work that you do, and that helps you show up as a professional. You’re not just showing up and reinventing the will every single time or trying to figure it out from scratch every single time. Those kinds of approaches turn clients off. They don’t know what to expect at the end of it. But if you’ve got a set framework, whether it’s for a process that you’re going to go through, whether it’s for ideas that you’re going to share, whether it’s something else, clients can see that you’ve thought this through and you’ve done it before and there’s a beginning and an ending, and they know what to expect at the end.

And so it’s all just part of building trust and having that, especially if you want to build a business without a website, without social media, without an email list, when you’re communicating how you work to your clients on prospecting calls or at other times, having a framework that you can walk through can be really helpful.

And that’s about it for this episode. We want to thank Rob Perry for joining us on the podcast today. If you want to connect with him, you can find him on LinkedIn where he’s going to share details about his workshop here this week. We’re also going to link to his profile in the show notes so that you can find him pretty easily. There’s more than one Rob Perry in the world. And as we mentioned, he is running a workshop on how to use Upwork. It’s completely free later this week, so you’ll want to sign up for that if you can.

If you want to listen to more episodes like this one, check out episode 19. We recorded that one quite a while ago with Danny Marguiles. He talked about his experience on Upwork and how to succeed, and he shared even more ideas, especially about the content that you could be providing when you’re doing outreach to clients. Episode 265, we talked about Daniel Throssell and he also talked about some of his experiences in Upwork and how to succeed there. He also talked about his emailing strategies and a lot of the other things that he does in his business. And finally, check out episode 248 with Dayana Mayfield. We didn’t intend that one to be all about Upwork, but we talked quite a bit about how to succeed there along with a lot of other stuff. Those are three really great episodes, 19, 265, 248. Check them out.

And if you’re ready to take your business from where it is today, maybe you’re earning 3$,000 or $4,000 a month to something a little bit more like five figures a month, go to You’re going to find a link to that page in the show notes. You’ve probably heard us say that over and over as you’ve listened to the podcast in the last couple of months, maybe even over a couple of years, and you haven’t taken the opportunity to check that out yet. Do it now. Even if it’s just to find out information or to connect with Kira or myself, if it’s the right thing for your business in the coming year, January is the perfect time to start. Again, we’re getting together for our next Think Tank retreat at the end of that month. You could join us for that. So just click on the link, find out more. And if it’s right for you, move forward. And if it’s not, that’s cool too.

That’s the end of this episode of The Copywriter Club Podcast. The 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 or maybe forward this episode to somebody you know who could use it and would listen to it as well. Thanks for listening. We’ll see you next week.




  • David Kehler

    In addition to appreciating the many valuable tips, I loved Rob’s authenticity, humility, and vulnerability (self disclosure).

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