TCC Podcast 18: Hiring and Working with a VA with Hillary Weiss - The Copywriter Club
TCC Podcast 18: Hiring and Working with a VA with Hillary Weiss

Hillary Weiss is in the house for the 18th episode of The Copywriter Club Podcast. Rob, Kira and Hillary chat about finding confidence, hiring and working with a VA, Hillary’s love for Andre3000 and hip hop, the lessons she’s learned from building a course and where she’s taking her business in 2017. We tried to find links to her Star Wars Romance Fan Fiction, but so far Google has failed us. If you know where she’s hiding these nuggets, add the link in the comments. Don’t miss this fantastic episode with freelance copywriter Hillary Weiss.

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

The people and stuff we mentioned on the show:

Sponsor: AirStory

Don’t write words. Write Music.
Michael Bolton and Tupac Blog
The NextWeb
Buffer Blog
Art of becoming indispensible (Business Insider)
Hillary’s old site
Are you the icing or the cake?
Alexandra Franzen
Danielle Laporte
Amy Harrison
Hillary’s Website
Hillary’s Twitter
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
Intro: Content (for now)
Outro: Gravity

Full Transcript:

Rob: 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

Kira: 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 and idea or two to inspire your own work? That’s what Rob and I do every week at the Copywriter Club Podcast.

Rob: You’re invited to join the club for episode 18 as we chat with copywriter Hillary Weiss about how she got started as a writer writing for publications like Business Insider and the New York Observer, teaching what she knows, and the art of being indispensable.

Kira: Hey Rob. Hey Hillary. How’s it going?

Rob: Hey Hillary.

Hillary: It’s going awesome. Thank you so much for having me guys. I’m so excited to be here.

Kira: We’re excited to have you. Hillary is a friend, and I was just trying to go back to when I first heard about you and our first meeting, and so, to reflect a little bit, I think I heard about you originally on the Unemployable Woman podcast.

Hillary: Oh, yeah.

Kira: A couple of years ago.

Hillary: Yeah, I remember that.

Kira: I had seen you online before that, but I remember listening to that show, and I’m pretty sure on that show you talk about how you got your start as a copywriter and that you had originally reached out to Alexandra Franzen about being her apprentice, or just getting into the industry, and how that really helped you. And I remember listening to the podcast, and I was like, “Ooh, that’s a good idea,” and I’m going to do that to you Hillary. I was like, “I’m going to get you.” I immediately reached out to you, and somehow we set up a meeting, and I remember meeting you in New York City, and I was super pregnant at the time, and just liking you, liking you very much.

Hillary: Yeah, I remember that. You organized that whole lunch, I think, and gosh, it was awesome. Memories. Yeah, and I believe the word I used for Alex was not apprentice. I believe it was actually minion.

Kira: Oh, right, right.

Hillary: She was generous to let me in, so yeah, that’s one of my favorite stories, actually, in terms of how I got started in the sphere. It’s just reaching out and asking.

Kira: Yes. I think a good place to start is with confidence, because I know that’s what we talked about recently when we met up, and I want to hear about the course that you’ve been creating and how you’re helping copywriters cultivate their confidence, which is a challenge for all of us, including myself.

Hillary: Yeah, absolutely. For me, it’s not just to copywriters. The course I’m working on is for entrepreneurs and online creatives, and generally anyone who wants to not just learn to write better, but figure out how to develop their own style and have the confidence to say things the way they want to say them, how they want to say them, and when. Because, especially with the current political climate, in my opinion, more than ever we need people who aren’t hiding their ideas behind their own anxieties. We need people to step forward and whatever it is they were going to do, you know, to call bullshit, to present a new way of being in the world, to spread their ideas and philosophies, and I think we need that more now than ever. And there’s also more opportunities to do so, now more than ever, not just with your website and blog content, but also on social media and Facebook Live. Everywhere is live streaming now.

The course itself is about writing content, but overall it’s about helping people develop creative confidence in every aspect of their content. And for how I’m working on doing that, I’m still in the final stages of creating the course right now, but basically I’m showing enough examples and enough structures so that people learn the rules and then they can figure out how to break them.

Rob: Hillary, I really like that approach to thinking about copywriting. If I were in that course, what sort of things would I be learning? What are the things that I need to do to become more confident?

Hillary: For me, actually, where I was, I interviewed I think probably close to 15 people before I even started writing the course. A big challenge for most people was figuring out just how to get started and how to stay inspired. Because for me, I think I’m naturally kind of a sponge for information and style. I find inspiration everywhere. I have a zip file, I’m sorry, a swipe file of photos, and quotes that I hear, and all of this stuff that I save and refer back to.

The starting point of the course is not only teaching people the principles of copywriting, but also teaching people how to get and stay inspired, how to listen, how to interview themselves, how to notice when and why they’re reacting to certain things that they see, so that they can try to recreate the same kind of experience with their own content.

Kira: And I know you’ve written about the power of music, and I think your blog post was called Don’t Write Words, Write Music. Can you just speak to the power of music and how you’ve really used that to improve your copywriting?

Hillary: Absolutely, and this is going to, as a white girl living in Brooklyn this sounds like the most cliché thing ever, but for me hip hop has been a huge influencer for my content, because there is no better resource to listen in on the rhythm of language, how you can play with it, and also some of the best one-liners that for close off, for sign offs for emails, et cetera, actually come directly from hip hop music, and also R&B, pop music in general. I’m a big indie listener as well. André 3000, I think, is actually my biggest inspiration in terms of how he figures out how to play with language and express ideas beyond traditional, “This is x because y and z.”

I think music, in that sense, music can teach us a lot as writers, because when you get to a certain point with your writing and your craft, it doesn’t necessarily become about the individual words or even the sentences. It’s about texture and rhythm, and you see things more in block form. You’re thinking about it in a sense of how people are going to react to these ideas, not just the ideas themselves, and I think hip hop is a great example of how to do that.

Rob: I’ve got this picture in my head now of Michael Bolton in Office Space, rapping to Tupac, and instead with Hillary, you know, her headphones on maybe in the New York subway.

Hillary: Yes. Damn it feels good to be a gangster. It really does. It really does.

Rob: Hey, Hillary…

Hillary: But, yeah.

Rob: … you’ve written for some really big publications. I think a lot of writers would look at this and say, “Wow, how do I get my stuff there?” How did you connect with the editors there and make that part of your platform?

Hillary: Well, I have to make a confession here, that it is not necessarily my individual doing. Basically, I started writing for the blog a couple of years ago. We’re currently on hiatus right now because they’re doing some restructuring, but they’re a blast to write for. And not only do I have an amazing audience, not only is their editor Jory one of the best editors on the planet, we have a great time working together, but they also have a number of syndication partners, which I did not know about at the time.

I wrote these pieces for them, and they were well received, and they were kind of making the rounds, and then I think the first day I realized that they had syndication partners, again, nobody told me about this, was when I started getting a lot of hits from The Next Web. The cool thing about that is The Next Web editors tend to follow blogs like Crew, and I’m sure they probably do it with the Buffer blog too as well, where they look for pieces that they’re interested in and then they repost them. The only awkward thing about that is I don’t find out about it till either I check my analytics or someone sends me a link. I think when I made it onto Business Insider, a friend of a friend found it and tagged me on Facebook saying, “This is so awesome. Your quest is to be a writer and it’s really taking off, and I’m so proud of you.” And I was just sitting there like, “Oh my god, I’m on Business Insider. I have to call my mom.”

But that’s also an alternate route for finding your way onto publications like that. The interesting thing about it is, it’s also less intimidating. Because I think if I had set out to write, I forget the piece that was shared on Business Insider, I think it may have been The Art of Becoming Indispensable. But I think if I had been writing for Business Insider in the first place, I probably would have been extremely nervous and overthought the whole thing. But, if you are looking to pitch blogs to be a regular guest poster on, I would make that one of the criteria, finding out who their syndication partners are and what the possibility is for your work to expand into other arenas like that. Kind of like a little hack.

Kira: Yeah. Well, Hillary, I personally know that you work really hard. And like you said, you write your ass off basically. And that’s a big part of your success today is you’re a hard worker. I want to know specifically though if there’s anything that really helped you pick up steam, like anything that was the catalyst to your success as a copywriter?

Hillary: I think the biggest change for me was probably, the biggest shift in my business was probably when I … Well, I switched my business and models before this happened, but I did a rebrand in 2015 that really changed the game for me. Because, at the time, my website at the time, it wasn’t really me. I don’t know, Kira, if you saw it, but it was like-

Kira: I did see it. Of course I saw it. I was all over it.

Hillary: It was something that my former, I had a business partner for a time who was a graphic designer, and she threw it together for me in 24 hours. It had like a bunch of, I was really into sunflowers at the time. I was working mostly in the female sphere, so I was like, “All right, let’s just throw up a girly, super girly website. And so I will, and then I’ll just figure it out later down the line.” She made me this website and it was like yellows and pinks and curly script and all that stuff. If you know me, that’s not really my vibe at this stage of my life.

When I did the rebrand, I decided a few things. That I was not going to go by the traditional structure for websites at the time, which was your face big and bold in the header with your opt-in and then the information below the fold. I kind of wanted to do things my way. Another thing I did was I took things a little edgier, and I also wanted to go more gender-neutral. Because I feel like women copywriters in particular can sometimes get, stick themselves into a women-only space, that doesn’t necessarily give them the opportunity to flourish in the way that it would if they diversified their client base, basically.

So I wanted to work with more men. I also wanted to sort of, I was working in the coaching space at the time and the creative space, and I still love working my coaches and creatives. But making that move attracted a lot more tech clients. I worked with a lot more startups and agencies. The new brand for me was very honest. It was a little more gender-neutral, it was a little edgier, and it was something that I was really proud of. When I made that move, I started attracting the kind of clientele that I really wanted to work with. The tech companies, the agencies, and again, coaches and creatives I still love working with, so they were in the door too. But more people were able to self-select out because I had shifted out of that super girly, super I guess, I don’t know what the word for it, like ultra cheerful kind of style, and into more of who I really am.

Kira: It was happy. It was very happy.

Hillary: Yeah, it was very happy, and I’m a happy person, but I also have an attitude. That was able to come through a little more, and it comes through in all of my work too. It just felt like it made me bolder, it made me more confident because I felt like I was finally representing who I really am in the online space.

Rob: So Hillary, let’s talk a little bit about the business side of the copywriting business. You mentioned all of these different clients that you’re trying to attract in the tech space, and the coaching as well. How does a typical client find you? What does that funnel look like? And what does your onboarding process look like? How do you identify a client that’s worth working for, or working with? You know they can pay your fee, you know that it’s a project that you’re interested in. What does that process look like?

Hillary: I’ve been fortunate enough that I’ve never had to pay a cent for advertising for my work, which has been awesome. It’s been exclusively word of mouth. And actually, the way a lot of my higher level tech and agency clients have found me is through my articles and my writing online. I always stress that to copywriters that I speak to, that if you can find yourself a platform outside of your own blog to write for, that’s really ideal and will surprisingly work wonders for you. But a number of them found me from my Next Web post, from the Business Insiders post. Also I’m very friendly with all of my clients. I tend not to work with people I wouldn’t get along with personally. My philosophy is kind of don’t work with someone that you wouldn’t get a beer with, even if they don’t drink. Because I think if you’re going to be spending so much time speaking with them and learning about their ideas, and most importantly, representing them, you have to like them.

Fortunately it’s created a relationship that has made people want to talk about the work they do with me, because I know sometimes when people work with copywriters they’re a little clandestine about it. They don’t necessarily want people to know that they’re outsourcing. They don’t necessarily want people to know that someone has been ghostwriting their blog on behalf of the CDO. Like it’s a whole thing. But the wonderful thing about the online space is that people talk. That’s been a great way to get referrals, just by word of mouth and by my articles.

My onboarding process is actually quite simple. I will never take anyone on without doing an interview call first, and this is where that would I get a beer with you comes in. The criteria for that phone call is usually people who I feel confident can pay the fee, I try to avoid at this stage of my career working with people who are total newbies, because that tends to send a project spiraling into infinity. Just because if they’re not completely clear on who they are, what they want, and what they’re offering the world, there are people who that, there are people who will help them get clear on that. I personally, it’s not where I love to devote my energy. I will have a conversation with a client and learn about them, and I’m always upfront with my fees.

I also send them a number of samples of my work in the initial email discussion back and forth, I’ll send them my portfolio. And if they feel like we’re a fit to work together, we’ll jump on the phone. Usually the phone calls are where I talk to them about what their goals are for the content, for our work together, what their long-term vision is. Because, as Kira might have told you, I work almost exclusively in long-term retainer style with clients, so I prefer long-term relationships over one-off. Because A, it means I have to hustle a lot less, and B, it really gives me a chance to sink my teeth into their online content and strategy and really play in their world and develop their content and voice for the long-term, for the long haul, which is something I really enjoy.

So it’s rare that I take on new clients right now, but when I do, the onboarding process is really simple. We’ll do the call and then I send them something called the brand voice brief, where they give me all the details about their brand voice, their audience, how they want to sound, who inspires them, what their general deal is. And then from there, I also send them a product outline guide or a blog post outline guide, depending on their needs and what they’re going to be working on. Because I find, when you have surveys and intake forms for people, they feel a lot more comfortable. Because before they talk to you, for my bigger projects I’ll do interview calls before we start, which last one to two hours. But before people get there, I want them to get their ideas in order first, so that’s why I begin with the surveys, then we go through the interview calls, and then I hit the ground running with the content.

Kira: So Hillary, you mentioned the retainer. I know switching to the retainer model changed your business and it made a big impact. I guess I have two questions. How has it really impacted your business as far as numbers? And then, what does it really take to have a retainer client? Because it’s intimidating and I have not had retainer clients. I would not be against it, I also have heard horror stories about it, I’ve also heard great stories about it. Can you just paint the picture of what it actually takes, the good and the bad?

Hillary: Absolutely. I once said, I took on a retainer client who I should not have taken on for the first time in I think 2012, when I first moved to New York. It was a whole disaster. I sort of likened retainer clients to losing your virginity when you just really want to lose your virginity. Where you’re like, “Okay, I gotta wait for the perfect person.” Then time goes on and you’re like, “All right, like you wanna do this? So like let’s make it work.” That was a huge mistake. One of the biggest mistakes I ever made in my business. It was a whole mess, but essentially, I made the decision to switch to retainer structure because, as you remember, Kira, at the time I was doing, this is back in 2014. No, 2015. I just can’t believe we’re in 2017 already. God, where does the time go?

Rob: Time flies.

Hillary: Seriously. So it was 2015 and I had been working intensive style with clients for two years. Which means I had been working with clients over one, three, and five days, depending on their needs. It was great because I got a lot of people in the door. I got a lot of great experience. I became very fast at what I do. But it also was very, very, very taxing on me. I found myself working six or seven days a week because I’d get through the five days and then I would have some things to finish up, so I’d be working every Sunday, sometimes Saturdays, so I could just be done with the work before I got to jump on the next client.

I was like, “This is madness. I can’t do this. But project to project doesn’t sound super exciting either, so let me see if I can switch to retainers.” And how I did it was, at that phase I had had enough clients in the door that I knew who I could approach for this. I did the numbers and I decided I wanted to make a certain amount per year. It was a pretty modest, by business success story standards. I think I set myself up. I was like, “What do I need to live comfortably in New York?” I estimated it to be about 80 grand, so I worked backwards and I said, “How many clients do I want to work with per month? How do I wanna structure this retainer? How many hours do I wanna work?” I ended up narrowing it down. I narrowed down a list of maybe 10 to 12 clients who I knew had the budget, who I knew had the need for long-term content support, and who I really, really enjoyed working with.

So I narrowed it down to this list and I ended up signing on with, I want to say, six or seven of them at the time. I set a retainer minimum, so at the time my retainer minimum was $1,000 per month. Should’ve been higher, but anyway. $1,000 per month, which translated into about 10 hours. I really hate doing hourly work, but sometimes you need to give people that reference point so they understand what they’re getting. Because you don’t want to say, “It’s $1,000 a month for a single blog post, oops.” Even though I’ve encouraged people to do that too if that’s what you’re worth and that’s what you can get paid, awesome.

Rob: So you identified these companies that you wanted to work with. What was the outreach that you used to get them?

Hillary: It was very simple. I came up with an email and I said, “Hey, I just wanna let you know.” Because I actually shut down my intensives. I gave myself a date, it was May 1st of that year that I would be shutting down intensives and would be working exclusively with clients long-term. Basically I sent out a group email to all of my clients saying, “Hey guys, just so you know, the intensives are shutting down. Book them if you can.” That brought a nice surge of income. But to these specific clients I said, “I’m shutting them down, I want to work with you one-on-one with this for the long haul, and here’s what I can do for you.” Because I knew what their needs were, I was able to sort of pinpoint areas that I could be of great use.

For example, one of my clients I knew needed consistent blog support and also consistent support on nurture sequences for their challenges. So I said, “Give it to me so you can free yourself up to write your book. Focus on your other stuff and we can keep your content engine running while you take on whatever this year has to offer you.” The great thing about these clients was they were all growing at such a massive rate, I knew they needed the support. And if I didn’t step in to offer myself up, chances are they’d find somebody else.

So that ended up being the key strategy. Knowing these clients very well, knowing what they needed, and offering it before they even thought to ask.

Rob: We interrupt this interview for a special message from our sponsor, Airstory.

Kira: We are really excited. I’ve got a big smile on my face. We’re so excited for our first sponsor of the show, Airstory, which Rob and I got to experience in beta a couple months ago. So Rob, I know you’ve been in there, can you tell me a little bit about what you like and what the experience is like so far?

Rob: Yeah, so with Airstory, there’s actually a lot to like. I’m just going to share one thing that I like the most about it. We could talk about the awesome design, we could talk about the tools that are there for writers and how it helps you speed up, but the thing that I love is that when I’m working on a project, let’s say that I have a client that needs me to ghost a blog article, and it’s on, say, internet security. When I’m doing the research for that, instead of having 20 browser windows open and copying and pasting things into a Word document or into a Google document, and having all of this information scattered all around, Airstory allows me to clip little pieces of research, or even large pieces of research. It adds it to the document that I’m working in and it basically creates a card file that then I can mix and match and move around in order to create the document that I want.

It’s sort of like Scrivener, but with a much easier to use interface. It makes working on a document a real pleasure. It’s something that I think any writer who’s listening ought to give it a try and see how it goes for them.

Kira: And you can get more done in half the time. Go to to get started.

Rob: Hillary, I want to shift gears a little bit. Earlier, or I guess late last year, you wrote an article in your blog that I think got some pretty good attention about becoming indispensable. I think it was the result of having lost one of your retainer clients-

Hillary: Yes, I got fired.

Rob: Talk about that. Because this is, I think, maybe the key challenge that, once a writer has a business up and going, as a freelancer you have to make yourself indispensable to your clients, otherwise it becomes a career of one-off projects. How do you do that?

Hillary: Well, in the article, it just makes me hungry every time I think about it because the title of the article is Are You the Icing or the Cake? At the time, basically, the risk of retainer clients is that if somebody drops you then you are out a few grand a month, and that is a big challenge. So you should always have people waiting in the pipeline. But for me, the issue at the time, why I got fired was essentially because the client was capable of doing their own content. They were downsizing their budget to focus on some other stuff so they had to let me go. The worst part though was that they let me go on, they called me on a Wednesday and were like, “We need everything wrapped by Friday.” And I was like, “Whoa, whoa, whoa, whoa, whoa. Okay.” So now I have a clause in my contract that I need a 30-day lead time. Anyway.

But as far as being indispensable goes, I find, and this is kind of what I was talking about in terms of how I was reaching out to retainer clients, is being able to anticipate the needs of your clients, coming up with ideas frequently for them, keeping things fresh, and not just waiting for the order. I think that has been a huge shift for me in terms of not being passive about my clients. Because if I’m working with somebody for the long-term and I’m truly invested in their business, I need to be looking for problems to solve. I need to be looking for concepts that are going to make them stand out in their space and be original. This is what I enjoy, I’m a huge nerd about it. I need to have my eyes open for places where things can be more efficient, where they could be using different platforms, where they could be putting themselves out there to a different audience.

I think if you tend to be looking for that for your clients, you are going to make yourself absolutely invaluable, because they don’t have time to look for all that stuff. That’s your job. And making things your job that aren’t necessarily in your job description, i.e. coming up with different strategies, brainstorming on your own, looking for, as I said, inefficiencies or places where they could be doing more, that’s really the key and that’s what makes you completely indispensable.

Kira: That’s like such a good reminder, even if you’re working with retainer clients, just with project-based clients to get them, to go above and beyond and be active, not passive. That will help you get those next projects and those referrals. I know this kind of a personal question because I struggle with this, so it’s really boundaries. Like you said, you were working with those intensives. It was intense and you were working six day weeks and really crazy hours, and I think that is the trap that I fall into often. It’s just, I’m like not sleeping and busting out these projects. It’s hard, and it’s not sustainable. My concern going into this new year is that I’ll fall back into that. So how do you manage that and how do you avoid falling back into those bad habits?

Hillary: I think it’s something that any freelance worker, any subcontractor will kind of struggle with because you have in the back of your mind at all times that if you don’t get the work done, if you don’t take the seven p.m. on a Friday night phone call for the emergency project that they’re going to find someone else who will. This is kind of, again, if you’re working with clients, you’re developing relationships, that’s important. But in terms of boundaries, what’s been a big lesson for me was when my partner actually got a 9-5 job, because I was stuck in that zone, that freelance zone of waking up at noon every day and going to bed at three o’clock in the morning. I think everyone kind of gets stuck in that loop, especially, I know you have some wonderful kids Kira, but if you don’t have children you tend to be like, “All right, there’s no reason for me to get up.”

I had to get back in control of my hours, but I also had to get back in control of my weekends. It was something I tell all of my clients is that my weekends are sacred. If there is a huge issue and you need me on board, I will reach out to you. Sorry, you can reach out to me and I will take care of it. But for me, it’s come down to, first of all, learning my own lessons. If I say, if someone calls me about a project on Wednesday and I can complete it by Friday, but in order to get it competed by Friday I end up working till 11 p.m. on Thursday, then I have to remember to give myself more lead time. I have to take note of where I’m making promises that I can’t fulfill without crushing myself.

I think that’s been the biggest help for me, even though I can work quickly, even though I’m highly efficient, I need to understand when I make promises that I just can’t keep, which is where I think a lot of writers find themselves stuck in the loop. Because you have to deliver, again, or someone else will. But the key is just figuring out what it really takes, how much time you need, and what’s important to you so you can work around that.

Rob: That is really great advice in my opinion, and something in fact, before we were talking with you Hillary, Kira and I were sort of taking about how we have this problem with procrastination. The morning gets lost and suddenly you start to feel the stress, and now you’re writing into the evenings and you kill all of the time that you had hoped to spend binging on TV or going to the movies or hanging out with your kids. So anyway, fantastic advice. What would you say is your copywriting superpower? What is it that you do insanely well?

Hillary: For me I would say, not to toot my own horn, but I would say I do style-

Kira: Toot it, toot it!

Hillary: Toot, toot. I would say I do stylized writing extremely well, and also deeply personal scripts that sound like the client. Content that stands out because it is, I find ways to talk to my clientele and understand the way they speak so I can recreate it. What’s interesting about the effect that that seems to have is that, again, I talked about this with my rebrand, when you help a client find out what their exact voice is and help them come across the way they want to come across, like the person they are, everything changes for them because they start attracting the right people. They start magnetizing opportunities that make sense for who they are and their goals. It’s just really, really awesome to see.

And my other superpower I think is my speed. I am freakishly fast at what I do after two years of doing intensives, which I would never do it again, but man. It taught me how to work with great alacrity, as the saying goes.

Kira: So to get that speed, do you have to just do those intensives for two years? Is there any way I could get that speed without doing intensives?

Rob: Maybe you can get a bottle of…

Kira: Please, yeah, bottle that up.

Hillary: The thing is I’m a jack of all trades, so I don’t really restrict myself. Because I started so young, my modus operandi at the time was like, if I haven’t done something I’m going to figure out how to do it. I’m going to be honest with my clients and I’m just going to find ways to make it happen. So when it comes to writing, I do everything. I’ve done everything enough times to where there is a pre-ordained kind of structure in my head for the best way to do things. I’m actually working on taking these structures out of my head and putting them into my course. But I’ve just had enough practice at this stage to where I’ve been able to be highly efficient, and also I’ve mastered the art of the shitty first draft. I am so good at it because I am not afraid to put something on paper that sucks, but I know I’m going to come back to it.

So it comes down to, when I’m sitting there writing something and I’m on a time crunch, I’m like, “All right. Let’s just get these ideas down there, even if they kinda suck, even if they don’t flow right now, because I will have a chance to go back and fix them into something that’s a little more shapely, a little more smartly styled, and a little better. But first, I just have to get all my concepts out here.” I’m a big fan of the split screen, so I’ll have my notes on one side and the document on the other and I’m just copy pasting direct quotes from the client in there where they’re going to fit. And then I go back and refine it and turn it into something that’s beautiful, that I can actually submit to the client.

Kira: We’ve talked a lot about your course, or we’ve mentioned your course a couple of times. You know, I want to hear more about how you’re teaching what you know, what you’ve learned over the past however many years and now you’re actually sharing it. I know that takes confidence, it takes organization to figure that out and pull those frameworks, those formulas that you’ve learned. So what is one thing that you would tell yourself if you could go back to the beginning of that process, because I know you’re already deep into it. I know there are a lot of people listening that want to create courses or programs.

Hillary: So go back to the beginning of when I started creating the course, or the beginning of my career?

Kira: Before you created the course, if there’s any advice you could give yourself then that would alleviate some pain maybe you’ve faced.

Hillary: Yeah, god, the pain that I’m facing. First of all, it takes a long time to create a course, especially your first one. I was told 100 times that the first one is the hardest. And I was like, “Meh, I’ll figure it out, like whatever.” But no, it’s absolutely true. So I think if I were to talk to myself at the beginning of this, I would say to keep going no matter what, because I started, how I’ve been working on the course is I’ve carved out an hour of my day every morning that I just commit to working on the course. I don’t do anything else, and I don’t take any phone calls, and I put my phone away. Of course, I’m not good at doing this every single day because things get crazy, but on days when I don’t have a launch deadline breathing down my neck, I work on it a little bit every day.

That sort of allows me to both put ideas down on paper and shape ideas, because my biggest fear was that I’m entirely self-taught as a copywriter. I never took a course. I barely knew what copywriting was before I got into the industry. My greatest challenge was how to reverse engineer what I do and how I think. And giving myself so much time over a long period to figure it out, to reference my own blog posts, my own journal entries, my own concepts, I was able to formulate it into something that I think is going to work. And I’ve also sent it to some beta readers who agree with me, which is super exciting.

But I think if I was to give myself advice going back to the beginning I would just say, “Be patient. Don’t rush it. But get working and keep working.”

Rob: I love that you mentioned you’re self-taught. I think that’s actually a pretty common thing for writers. Let’s talk a little bit about how you did that. What were the resources that you used? Was it just a matter of practicing? How did you self-teach yourself to write?

Hillary: Well I’ve been writing since I was but a wee babe, as I think all of us were. I actually got my start writing in the online space by writing fan fiction in my teen years, and editing fan fiction, so that was a fun way to get my start.

Rob: It’s funny you mention that because you’re not the first person that we’ve talked to who started out fan fiction writing.

Hillary: Before I get into the copywriting piece, the fan fiction piece is so interesting because it is so tied to the experience of copywriting. Because with fan fiction, you get a chance to play with characters and storylines and an entire universe that are already created for you. And with copywriting you are working with clients who have created their own character and ideas and concepts that are already there waiting to be rewritten and developed in a way with your writing skills. That’s kind of an interesting parallel there.

For me, in terms of teaching myself, I was very honest and open with all of my clients. But I think my first go to resource is probably Copyblogger and ProBlogger, because Copyblogger just has some amazing free resources and they still do, and I send everyone there who’s trying to get their start in copywriting, just because it’s such a good beginning point. But I also had some great inspiration in front of me. I had Alexandra Franzen, Danielle LaPorte, Andy Harrison, and a bunch of people who were at the top of their game at the time and are such generous spirits. They were just sharing, sharing, sharing.

And another technique that I started applying was, and it’s not really a technique at all, it’s just good groundwork, is I would ask clients to send me examples of sales pages, about pages, home pages, whatever it is they needed that they liked and felt applied to them. Then I would take a look at that, I would reverse engineer how it worked, and I would find a way to apply the client’s ideas in a similar way.

Kira: So Hillary, my last question for you is just, I know you mentioned you have a VA. I’ve read that she’s a huge part of your team. I just brought on a VA. It’s hard to-

Hillary: Oh, congrats.

Kira: Yes and no, it’s like I haven’t fully given her the opportunity to help me yet because I, that takes time, that takes some strategy. If you could speak to people that are thinking about growing their team, or just at least bringing on that first person so that they can grow or just ease the pain, what advice would you give me just to help make this easier so I can actually use this person and take advantage of this opportunity, rather than just missing it because I don’t know how to help them help me?

Hillary: Absolutely. I think what I was clear on before I reached out … Emily’s my VA, shout out girl. If you’re listening, you’re the best. I came to Emily at the end of my rope with a lot of things and I was figuring out, I had a list of things that were really annoying me in my business that I wanted someone else to take care of because I did not have the time. So for me that was actually pretty simple. That was my email, that was proofing my pieces, that was uploading things to WordPress and Medium, and generally scheduling my social media posts and all that stuff. Those were things that we’re clear on and that are simple to teach, but what’s not simple is how to teach someone how to do that for you. Is that the issue you’re running into?

Kira: I think at this point it’s just prioritizing and then figuring out the plan, the onboarding plan, how to make this simple.

Hillary: Basically, I think I’m kind of a goofball when it comes to my emails, so I think the first email I sent over to her was, “Please help me, I’m dying.”

Kira: I’m sure that’s like the first email that most VAs [crosstalk 00:37:29].

Rob: That’s a pretty good headline though. There’s got to be a pretty solid open rate for “Please help me, I’m dying.”

Hillary: That is an impactful subject line.

Rob: That’s right.

Hillary: But no, I basically, the great thing about Emily as well is that she, what drew me to her as a VA is that she has a knack for solving other people’s problems. So I sent her a list, I was like, “I need help with my email. I need help with x, y, z.” And she came back at me saying, “Okay, here’s what I can do. I can organize your Gmail. I can setup canned responses. I can clean out your inbox once a week. I can, if you send me your proofing, I’ll get it back to you in this and this span of time.” So then it became a issue of me creating canned responses for her to help me respond to my email, figuring out systems of having her accept or reject clients, figuring out when she was going to be available for uploads and getting on a schedule there. What was really useful was that she forced me to create some structure in my business that I didn’t have before because I was just kind of like an octopus with my arms all over the place and not really getting much done.

So I think the biggest challenge for me was that the onboarding forced me to create structure that hadn’t been there before, and I think that’s the biggest challenge. But it’s just really about setting aside the time and figuring out, “Okay, what systems are going to make this run on its own? How can I help you work independently? What feels best for you? And what is going to be, what are the most necessary pieces going forward?”

Rob: My last question for you Hillary is what’s next? You’ve hit six figures, you’ve got a course, you’ve got a VA. So is it just a matter of sitting back and watching the cash roll in?

Hillary: God, I wish. No, I’m actually in the process of shrinking, which is interesting. I am going to be, I’m working with retainer clients right now, but ideally in the next year I will be working with fewer clients at a higher point, and also at a director position in terms of their creative strategy and content strategy and all that stuff, which is exciting. That’s kind of part of what’s in motion right now. But again, it takes time to get there. I need to release my damn course and send the beta testers in. I’m looking to eventually also adapt my course to attract other writers to me and other copywriters so I can get a team going, so I can start attracting more people. And also giving work to other copywriters so I can take on more projects that I have to turn down because I just don’t have the bandwidth. And these are good folks, these are awesome people who I really wish I would have had a chance to work with, but I just can’t at that stage, at the stage where I am.

So ideally I’ll have a little agency, but that’s more of a 2018 project. Right now what I’m really focused on this year is teaching. I’m going to shrink my business a little bit so I have more space to create my course. I’m going to be doing a number of live events on behalf of a client or two, potentially, where I’m going to be teaching hot seats and speaking at conferences and just getting myself out there in a way that I was comfortable doing before.

This yeah, I don’t want to make it so much about the money. I have made the money. This is going to be figuring out what I want to do in the long-term to make an impact on the writer world and on the world of online business in the way that I’ve always dreamed of, which is helping people find the courage to be more of themselves and share ideas that they may not have shared otherwise, that they not have the tools to know how to say it.

Rob: Sounds like we need to have you come back maybe in six or seven months and tell us how all that went.

Hillary: God, I’ll probably be at the same place I am now. I’m like well, I got really busy, man. So we’ll see.

Kira: Thank you, Hillary. Thanks for taking time to join us.

Rob: Thanks so much.

Hillary: It was an absolute pleasure, thank you for having me guys.

Kira: Oh, and we forgot to ask you, where can we find you online?

Hillary: Oh, you can find me at, that is a two Ls Hillary. You can also find me on social media pretty much anywhere, on Twitter, Instagram, Snapchat, @hcweiss, W-E-I-S-S. So yeah, come say hi, give me a little wave. I would love to say I’d love to chat with you.

Kira: Sounds great.

Rob: Thank you so much.

Hillary: Thanks guys, take care.

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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