TCC Podcast #166: Getting More from Your Copywriting Business with Ashlee Berghoff - The Copywriter Club
TCC Podcast #166: Getting More from Your Copywriting Business with Ashlee Berghoff

Online Business Manager, Ashlee Berghoff, is our guest for the 166th episode of The Copywriter Club Podcast. Ashlee has helped a bunch of copywriters we know and like figure out how to make their businesses more profitable… and just as importantly, helped them focus on the work they are best at (while shifting other work to a VA or OBM). That sounded like something we needed to hear more about. So we asked Ashee about …..
•  how she became an independent business manager/COO for copywriters
•  the 10 months she spent working to prevent human trafficking at IJM
•  when you should get help in your copywriting business
•  the different kinds of VAs and other help you might consider hiring
•  some examples of how she works with copywriters to grow
•  the systems she helps her clients develop as they start working together
•  the importance of discipline as you set up processes in your biz
•  what it really costs to work with an integrator versus a VA (and what you get)
•  the easiest systems to build that almost everyone needs right now
•  the return on investment when you spend money on a VA or OBM
•  the true cost of doing the work that others could be doing for less
•  how to keep your VA relationship from falling apart
•  some of the problems you should anticipate to keep the relationship working
•  where to find the best VAs… the answer may surprise you
•  what you need to put into a contract versus email
•  how to deal with problems when thing inevitably go wrong
•  the tools Ashlee uses in her business

If you have a sneaky suspicion that your business could be doing better and that you need help to make that happen, you’ll want to listen to this episode now. Click the play button below or subscribe using your favorite podcast app. Or scroll down to read a full transcript.


The people and stuff we mentioned on the show:

International Justice Mission
Global Fund to End Modern Slavery
Angie Colie
April Dykman
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
The Copywriter Underground


Full Transcript:

Kira:   What if you’re going to hang out with seriously talented copywriters and other experts, ask them about their successes and failures, their work processes and their habits, then steal an idea or  two  to inspire your own work? That’s what Rob and I do every week at The Copywriter Club Podcast.

Rob:   You’re invited to join the Club for Episode 166 as we chat with business integrator Ashlee Berghoff about how to know when you’re ready to bring in help for your business, the systems and processes copywriters need to grow, practical ways copywriters can expand their capacity and exactly what a VA or OBM can help you do in your business.

Kira:   Welcome, Ashlee.

Rob:   Hey Ashlee.

Ashlee:          Thank you so much for inviting me. It’s wonderful to be here.

Kira:   Yes, we’re excited to have you here because you worked with, I don’t know-

Rob:   Everybody.

Kira:   …six to eight, maybe even more copywriters. You don’t have to name drop all the copywriters, but you’ve worked with a lot of well-known, successful copywriters that we’ve hung out with and we know really well too. So, we’ll get a behind the scenes look at the type of work that you’re doing with them. But before we dig into that, let’s start with your story. How did you end up as an integrator, OBM? I know there are multiple titles for it. Yes, how did this all happen?

Ashlee:          Yes, so I think as is the case for so many people, it was not a straight line at all. I actually graduated with an English degree and no idea what to do with my life. And in my first major job, I ended up in the Philippines actually working as kind of a de facto recruiter for an anti-trafficking field office there, did that for about 10 months, built out their recruiting program from scratch, which was really fun for me, but I didn’t know why, just that it was a really amazing experience. And then, when I came back to the States, I worked in staffing for and then ended up at a publicly traded financial services consulting firm for a couple of years working in operations and project management there.

And as I was doing that, I realized that I loved the type of work that I was doing and I was good at it, but it wasn’t the right industry for me and it wasn’t the right kind of work culture for me. And I was going to school for my MBA at Georgetown in the evenings and as I was getting close to graduating from that, kind of all the pieces started coming together for me. I kind of started realizing, wait, I organized for fun as a kid and I made lesson plans and report cards for my stuffed animals. And that’s not normal for 12-year olds to do. And I loved taking things that were really messy and organizing them and bringing order and calm to them. And the reason I loved my job at IJM was because I got to build templates and checklists and trackers and plans, and all of these things, and I’m sure I overwhelmed the poor intern coming after me with all of that stuff.

And so, I started realizing, wait, this is something that comes really naturally to me and that I really love, but that a lot of people don’t love. And maybe there’s an opportunity here. I wanted the autonomy, I wanted to build something for myself, I wanted to have the flexibility to adjust my business and my career around the needs of our family as it grew. And so it seemed like the perfect opportunity to try it out, see if I could do what I was doing at the consulting firm, but for small businesses, basically just helping them run everything, make things happen, and kind of take that weight of running everything themselves off their shoulders.

So, a couple of years ago, I essentially started out as a souped up VA, I called myself an independent business manager. Found my first three clients on Facebook after failing to find anything clients on Upwork. And after doing that for a while, I realized that really the area that I was providing the most support and value was in helping them design their processes and build out the structure they needed to kind of mature as a business and expand their capacity without having to add a bunch more hours or overhead. So that’s where I’ve really focused a lot of my energy and in my programs this year and going into next year are all about making that transition from kind of a scrappy freelancer to bonafide business, and organizing all of the pieces that go into that.

Rob:   So, before we get into all the stuff that we teased in the intro and how you help copywriters, you mentioned your experience with trafficking, anti-trafficking, and I’m assuming you’re talking about human trafficking. Will you tell us a little bit about that experience because first of all, we’ve never talked about that. Obviously, it’s this crazy thing that’s going on in the world and such an important thing, but tell us a little bit about your experience there and what you did?

Ashlee:          Yes, so the organization I was with was called International Justice Mission. They’re the largest anti-slavery organization in the world. And they purposely go to countries where the law enforcement kind of structures there are failing to protect the poor from violence. And so, they do different kinds of casework depending on the needs of those places, but in the Philippines, we focused on sexual exploitation of minors and commercial sexual exploitation of minors. And it was right around the time that they were realizing that that was happening much, much less on the street and much, much more online, so they were beginning to make the transition towards focusing on cyber trafficking issues, which was a really, really hard time to be there because no one really expected that, the age of the clients that we were working with was much, much younger, we were dealing with families and things like that. And so it was a very hard kind of casework to be getting into and it was a very, very hard year for me to see that. It rocked a little bit. My sense of the world and what evil is and what it takes to combat that effectively.

But what was really incredible was working with the colleagues that I had there. All of the kind of full-time staff in our office were Filipino locals, or lawyers, or social workers, everyone who was there and just watching them continue to show up every day was incredible. And so I got the opportunity because we were expanding so much as an office to help them hire 20 more people. It was already an office of 20 and so they were doubling the size of their team. And so my boss was also managing all of the HR and an office move and payroll and insurance and everything that he was doing, and so I had kind of free rein to set this thing up and start trying to find more people for the team.

And so I got on the phone with people, confused them quite a bit, they were trying to figure out why they were talking to an American at this company, getting them in for interviews, scheduling that and helping them get on board and sharing my passion for the work with them and getting them excited about joining IJM. And just last year, I got to meet some of them in person again, because they came to the US for a big conference and they were celebrating five years in the office, which was just really, really amazing and fulfilling for me to know that even though I was only there for 10 months, I got to be part of something bigger, helping them join the team so that they could then keep the work going for so much longer. So it was very, very tough and I came back with a lot of stuff I needed to process, but it was one of the best experiences in terms of getting the chance to be on the front lines like that.

Kira:   Can you share a couple of resources that… for anyone listening who does want to learn more about the topic or wants to support an organization or get involved in any way. Are there any go to resources or foundations that you think are worth supporting?

Ashlee:          So IJM, I would definitely say is a great one, their website is They’re really on the front lines of doing this kind of work globally and some of the first kind of front runners of showing that it can be possible to work with local law enforcement and see systemic change and improvement there. Another great thing that just was passed a couple of years ago is called the Global Fun to End Modern Day Slavery. It’s a partnership between the US and the Netherlands and several other countries to bring together funding and resources and information about combating slavery globally. And so a lot of what IJM is having all of us, who are here in the US do is kind of help make sure that stays funded and stays a priority. So that’s a really interesting thing to check out as well to see how different countries are coming together to talk about this problem, address this problem, combat this problem, because especially as it’s going online, there has to be a lot of collaboration between countries to combat it.

Rob:   Yes. So, thank you for sharing that. I know that wasn’t what you were thinking we would ask you about when you came on to the podcast, but it is such an important thing and so we appreciate what you’ve done there. So let’s switch the conversation into what you did come to talk about and that is, when do we as copywriters need to start thinking about getting help with our business and what kind of help is it that we should be looking at?

Ashlee:          Yes, that’s a great question. So I think a lot of times in the first place couple of years of running a business, you’re just trying to throw stuff against the wall and see what sticks, figure out what projects fit, where you provide the most value, what kind of work you want to do, who your ideal client is, but once you start figuring those pieces out, it’s really time to start thinking about yourself as a business and maturing as a business. And so that’s when it’s good to start stepping back, building structure into your business and thinking about outsourcing so you can expand your capacity and move up to the next level in your business without having to just throw more hours at the problem. And I think a lot of times people get to the point where they’re just way over capacity before they start thinking about it, they’re just like, ‘Whoa, I’m working way more than I wanted. I’m still not making quite as much money as I want. I could keep raising prices, but is there another way for me to grow this business and maybe bring my hours back down and get rid of some of this just stress and overwhelm I’m experiencing?’

And so it’s good to start thinking about it kind of before you hit that point of saying, I see that more clients are coming in. I’m going to hit capacity at 10 clients. I would love to grow beyond that. Let me start thinking about how I can streamline this business, automate pieces of this and delegate pieces of it so I can really start to focus on what I’m best at and grow past that capacity point.

Kira:   And Ashlee, can you tell us the difference between all the terminology. I know there’s the virtual assistants, there’s office business managers, there’s COOs, there’s integrators, like there’s so many different terms thrown out and it’s really confusing to know which one you need and what they all do and how much they charge and the differences. Can you just kind of give us a quick mini workshop on like, what do they do, all the differences?

Ashlee:          Yes. And it’s still a pretty new industry and so there’s not a ton of definition around it yet in terms change and things like that, but kind of at its base level, the virtual assistant or the VA is what you hear about the most often. Because there’s so many of them, they tend to be less expensive, so feel like a really good kind of first hire and they can do a little bit of everything right. And so, a good way to think of a virtual assistant is essentially an administrative assistant or an executive assistant, so they can help you with recurring tasks, data management, inbox management, managing your calendar, communicating with clients, helping you with your bookkeeping, helping you with your social media, kind of all of those miscellaneous tasks in your business. And some of them specialize on specific areas of that and then others are more generalists. And that’s kind of on the least expensive end of the spectrum. And then when you move up a little bit with VAs who’ve been maybe in the industry for several years and are ready to move up, that’s when you start hearing the term OBM or online business manager kind of being thrown around. And virtual COO is kind of a synonym for that level of person.

And so, really, if you think about a virtual assistant coming to you and saying, ‘Hey, how can I help you? Where can I help you take the load off in your business?’ An online business manager is coming in and saying, ‘Hey, tell me what your goals are, tell me what your problems are, where do you want to take this business?’ And then they’re actually coming in and saying, ‘This is what I can do for you. This is where I can step in, take more kind of substantial chunks of the business off your shoulders.’ A lot of OBMs manage teams of their own or manage the teams of their clients, and so they’re kind of stepping in a more strategic role to say, ‘Where do you want to go? Let’s work together to get there.’ So they have more experience, they have more of an ability to kind of have that leadership role within the business.

And a lot of times companies when they’re reaching that maybe six figure mark, maybe bumping past that, might start finding that really attractive especially if they don’t want to go through the work of telling someone else what to do. They can hand that process off to someone else and its entirety. So that’s kind of what I started out as it was kind of in that business manager role with my clients of just saying, ‘Hey, tell me what hurts, what’s going on and then we’ll figure out together how to get you to where you want to go.

Integrator is, I think it came from the book Rocket Fuel initially. And it kind of shows the personality of that kind of person who would be drawn to that kind of work. So I am 100% an integrator and part of the reason I never saw myself was an entrepreneur originally was because I thought of entrepreneurs as visionaries, which is the kind of the other side of the coin from integrator. And so a lot of entrepreneurs are visionaries. They have the big ideas, things they want to do, they’re really excited about a lot of different things, but they might struggle to finish what they’re starting, to bring things into life, and to kind of be realistic around what it’s going to really take to implement those things and that’s where the integrator can come in alongside a visionary and say, you want to do this thing, let’s talk about all the pieces that need to go into making that happen and then let’s actually get that stuff done so it does happen. So a lot of entrepreneurs when they’re hitting that point where they’re creative and they’re visionary of finding someone who has that integrator way of seeing the world can be really, really helpful.

Rob:   So as we’re talking about these different roles and the state of readiness that we need to be in when we’re ready to hire some of these people. I wonder if we can talk through some very specific examples. So, I know you’ve worked with copywriters. Can you just give us a couple of examples of how you would jump into a copywriter’s business and start to help them either with the extra work that they’ve got or to figure out processes and systems so that we can maybe get a really practical understanding of what it is that you help us do?

Ashlee:          Yes. So, this is shifted a little bit. When I first started in my business, it was very broad. So, I would come in and just say, ‘Hey, what’s going on?’ And they would say, ‘Hey, I want to launch a course.’ And so, we would just start working on that together, making a project plan, making it happen. Now that I’ve been doing it for a while, I’m recognizing kind of the main elements that need to happen first for a business to kind of make that shift. So one being setting up your core processes, the customer experience is a great one to start with to say, this is the offer I’m committing to, this is how I’m going to bring on clients, this is how I’m going to deliver what I do, this is how I’m going to be able to do that consistently, and these are the software tools I’m going to use to get there.

So we get really specific about those things in our process and systems design intensive, because what we found is that if you jump straight to the VA or straight to the software tool without kind of thinking very systematically about, what do I do when a client first walks through the door, then what happens after that, what happens after that, if you don’t have definition around that, the software tool or the VA are not going to be as effective as they could be. And so we start with the processes and just kind of bringing definition to those things and saying, I commit to onboarding my clients this way every time and kind of locking those pieces in is a really good kind of first thing that we work on together, then bringing in the software to enable that and then helping them bring on a VA to help them out long term.

So after the intensive, people can then move into our program around hiring a VA, so we help them go through the process of identifying exactly what it is that they need, finding that person, interviewing, training, all of the pieces about really setting up that relationship for success. And then we’re also going to launch a program next year around helping people create the disciplines and habits around their project management so that they are sitting down at the computer every day and saying, here are the four things that I’m doing today. I know these are the most important high value tasks for me and being able to kind of sort through the barrage of things coming at them and know how to spend their time and how to manage their business effectively. And so those are kind of the three pieces that we start with and then if we keep working with clients long term, then it becomes more general again of saying, now we’ve done all of that groundwork and you want to build out a new arm of your business. Let’s now use all those tools that we have in place to build that out to expand your business and to grow your capacity further.

Rob:   Yes, sign me up for the discipline piece because that… immediately I’m like, I need that for sure.

Ashlee:          Yes, it’s tough when you have… I think most people start a business and it’s like, wait, I’m sitting here and I could be doing anything. And so what should I focus on? And so a lot of people when I first start working with them, they’re like, I spend the first hour of the day trying to figure out what to do with the rest of my day, which gets tough.

Kira:   Yes, I mean, when in doubt, just go on Facebook and start searching [crosstalk 00:19:39]. That always helps me. So when you’re talking to the intensive and these different stages you work through with your clients, are you ultimately like almost… it sounds like you’re replacing yourself by finding that VA so that you could step out and they have everything they need, or they could continue working with you long term, but is the idea that you give them everything they need, so they don’t need you anymore?

Ashlee:          Yes, exactly. I mean, I love working with people long term. It’s really fulfilling for me and really fun and the people I work with are just incredible and getting to watch their businesses grow as fun. But I’m more expensive than a VA. And so I wanted to set up a way for people to work with me, where if the work that they need done long-term is stuff that they don’t need me to do, they have someone in place to do that for them, and they’re not having to pay OBM prices for VA work. And so my goal is to set it up where they have the structure, they have everything they need, and they can then decide, you know what, am I going to be really expanding this and growing quickly and adding a lot of new things where I still need that strategic support, or do I now have the structure in place where having a great VA who knows how to work with me and I know how to work with them will help me move forward a lot more affordably. So I wanted to have that option available for people too.

Kira:   Because you mentioned prices, can we talk about prices and rough ideas? You don’t have to share exactly what you charge, but like to work with an integrator at your level, can you give us some ballpark numbers and then as opposed to working with a VA, just so copywriters have an idea of what to expect?

Ashlee:          I have a lot of opinions about VA pricing. I think over time, it will change quite a bit and there’s just a lot of confusion among VAs about how much to charge and it’s very price competitive. So I’ll start with the VA side. Because since I started out as a VA and I kind of saw how the economics actually worked out, I realized that one of the reasons why a lot of times people struggle with the VA is that they’re undercharging, taking on too many clients to try to make the numbers work and then struggling to deliver the at a high level for that many clients at the same time. And so kind of the benchmarks that I put together that I feel are kind of helpful for people to think about are to make that kind of connection with the corporate world.

So if you think of an entry level, kind of recent college grad who might be going into an administrative role at a company, they might be making $10 to $20 an hour in the corporate world. They’re still young, they still have some things to learn about how to be in that kind of professional environment, they need some training, some mentorship. That would kind of translate in the freelance space to around the $25 an hour range for a freelance VA. And the reason it’s so much higher is because they still have non billable work, they’re having to juggle a few clients and things like that. And so those guys still need some teaching and some training.

You can have that number go down quite a bit if you do a couple of things I can talk about to kind of help make that make sense for both sides, but if you’re working with kind of a freelance very part time, very variable role with somebody, 25 for kind of a very entry level person makes sense. Once you move towards kind of an experienced VA, maybe someone who would be serving as an executive assistant in the corporate world, they would be making maybe $40 to $60,000 in a corporate job. That translates into more like $50 to $75 an hour for a freelancer doing that level of work. So, they’re going to be more proactive, professional, at the level where you would be comfortable with them being client facing and very reliable, they’ve been doing it longer. And then if you’re looking at more of the OBM level, the virtual COO level, you could be bumping into $100 or more an hour at that level. Some OBMs will do more just monthly fixed retainer rates. I’ve heard everything from kind of $1,000 to $2,500 a month for that, just to kind of have that relationship with the business owner long-term.

So, there’s a lot of range there. And especially with the kind of more junior level VAs, you can help make it makes sense financially at lower levels than 25 by making it really consistent in terms of when you need them, the kind of work that they’re doing for you, working really well within the wheelhouse of what they already know how to do, so they’re not having to spend a lot of time learning something new. And so that’s where it’s hard to kind of give hard numbers, but it kind of can give you at least a benchmark in terms of at least US-based business support of what you might see out in the market.

Rob:   So, a quick follow up on reducing the cost of working with a VA. You’re not necessarily reducing the hourly rate by making those processes really tight, or are you reducing the hourly rate? I’m thinking it probably reflects more in the hours that they take to get to speed on something. Is that right?

Ashlee:          Both. Yes. So absolutely, if you have your processes really well defined, you’re going to have so much less time taken in training them, in them coming back for a clarification, in the back and forth that it takes to make something happen, because if, for example, you onboard someone that exact same way every time, you don’t have to go back and forth and say, ‘Hey, for this person, can we do this a little bit differently, and this is how we’re going to charge them and we need to follow up with them some other different time than normal.’ You can cut all of that stuff out and so it becomes a lot less expensive overall to do those pieces of your business. But even in terms of the VA you’re working with, sometimes if you have someone joining you at $25 an hour, but you need them to be able to drop everything at a moment’s notice to get something done that’s urgent, or hop on the phone immediately when you need them, or be doing a wide, wide variety of tasks for you, that’s going to be a lot harder for them to deliver at that rate in a way that makes sense.

So, I think that’s where people run into issues where they’ll be like, ‘Oh, I’m paying this amount. So this person should be available to do these wide variety of things for me’, but what that happens with the VA is they’re trying to also juggle five other clients to make a basic living, and if all of their clients are doing that at the same time, then they start dropping the ball. And that’s where I think people have really bad experiences with VAs because they’re like they weren’t there when they were supposed to be and I tried to get in touch with them and they weren’t there and what’s going on. And so I think a lot of times if someone has those really strong processes in place and can also then plan ahead and say, ‘Hey, I’d love for you to be online for an hour a day and on Tuesdays, I want you to do this, and on Wednesdays, I want you to do this, and on Thursdays, I want you to do this, that’s a lot easier for that VA to deliver. And so they might be more than happy to do that at even a lower rate than they would otherwise. So it can actually affect the hourly rate as well in terms of how you’re structuring the role and what makes sense for both of you.

Rob:   Okay, yes, that makes sense. So as you’ve worked with copywriters and before we started recording, you mentioned several who you had helped systematized the businesses. Have you noticed across the board that there’s low hanging fruit, several systems or processes that all of us really should have and that maybe when we’re struggling, we don’t have and that we can move towards those first?

Ashlee:          I almost always start with a customer experience for people because it has a very direct connection to the quality of the work they’re delivering, the amount of time they’re spending in their business and the ability that they have to start raising their prices as well. So it has this just broad impact across their business. So we start a lot with how they’re onboarding their clients. How are they sending out proposals? What expectations are they setting? What information are they gathering? How are they getting paid? All of those things. And it’s not even just the structure of it, but also kind of the… I don’t know if you’d call it kind of the emotional weight of that process, but I kind of the philosophy of the business that runs into that. So, for example, a lot of my clients will ask for 50% of their payment at the beginning of a project and 50% at the end. And then they find themselves with cash flow issues because the end the project keeps moving, right?

A lot of clients, there’s delays, the scope grows, things happen, and then all of a sudden, they’re getting that last 50%, much, much later than they had originally planned on or hoped. And so one of the things that we will build into their process is saying, that last 50%, let’s lock that in on the date that you’re planning to end the project, so then even if the client’s delaying, even if something’s happening on their side, where the project’s not going to be done on that day, your invoice is still happening on that date. And that slight tiny shifts will change the way they’re approaching their client and the way their cash flow is working. And so we look at things like that too and how they’re delivering what they deliver. So we start there. And then after that, for a lot of our clients, we start looking at very, very basic bookkeeping. I am by no means a CFO and I always tell them that before we even get started, but it’s really important for them to know how much money they’re making, when’s money coming in, when’s it going out, how much in taxes do they need to be paying, all that stuff and at the very base level, we want to get them set up in something that’s going to work for them for that piece. So that’s usually step two.

Kira:   So because you’ve worked with these copywriters, you see how what makes us extra special as Copywriters, and also slightly frustrating too. What surprised you the most about our strengths? Let’s start with the positive. What are copywriters? I mean, this is generalizing, but like what surprised you the most about what we’re really good at and then what surprised you the most about how we struggle, and maybe some trends you’ve noticed as far as like, ‘Oh my goodness, five out of eight people I’ve worked with release suck at this thing’? Just be honest. Just talk about both positive and negative.

Ashlee:          Okay. I started out working with Copywriters by connecting with Angie Coley and I kept working with Copywriters because I love them so much. And part of the reason Copywriters are really amazing is that they’re incredibly creative and ambitious and excited about learning and building really incredible businesses. Usually, their goals and their visions extend far beyond freelance copywriting. Some of them do, but a lot of them have a much bigger idea of where they want to go with it in the long-term, so it’s just been really fun because there’s a lot of change that happens over five years of working with a copywriter. You see their business transform in so many major ways, which is really, really fun for me to see. I haven’t worked with anyone that long yet, but just knowing that these people today are not at all the same as they were when we first started working together, and hopefully, for working together three years from now their business will look entirely different. And that’s pretty… it’s fun. I love lifestyle businesses. I believe they’re really important. I started my business to be a lifestyle business and I think they don’t get the attention they deserve in the broader small business and startup community. So that’s really fun for me and kind of working with Copywriters and seeing that.

On the challenge side, I would say that a lot of the copywriters I meet don’t want to write copy forever. And so, they at some point hit this wall where they’re like, ‘I do not want to do this thing anymore. So, what do I do now?’ And that’s a fun challenge, but it’s a very real and difficult one. And I’ve worked with people in kind of other online services as well and it’s not necessarily as common. So, for example, one of my clients is a graphic designer. She loves graphic design. Five years from now, she wants to keep doing graphic design. And so, when we start putting structure into our business, it’s to make that sustainable for her as her life changes and things grow and develop. But for copywriters, it’s more of helping them make a much, much bigger shift away from doing direct copy. And I know you guys have made… added things like this podcast and The Copywriter Underground and things like that to expand your business beyond kind of direct client services, and there are a variety of ways to do that, but that shift is really challenging and so that’s been something that’s kind of unique that we kind of have to work through together with a lot of the copywriters I work with.

Rob:   And now I want to explore why copywriters don’t want to write copy forever. This seems like a really, really-

Kira:   We all want to stop writing copies.

Rob:   There’s some psychological thing going on here that maybe needs to be understood more deeply.

Ashlee:          And I don’t know the answer to that.

Rob:   I’d love to talk through the ROI on an investment like this because I think a lot of people maybe wait to make the investment because it feels very expensive. In fact, when you were talking earlier, $100 an hour or retainers, 1200 or $2,000 a month, like give us some examples of how that pays off in the end because yes, hiring somebody for a year at $2,000 a month is a pretty big expense and maybe for some copywriters it’s even most of their profit. So what does that look like?

Ashlee:          When I first started doing this, that was one of the hardest things for me, was kind of quantifying the impact to their business in numerical terms, because people were coming back and saying, ‘Wow, I feel more confident. I feel more in control’, which is all amazing, but it’s hard to quantify that in terms of here’s the ROI in the business. So what I’ve started doing is kind of measuring when we first start working together. What’s your capacity right now? How many clients can you feasibly take on and the number of hours that you want to work each week? And how many hours are you working each week and are you happy with the revenue that you’re making with those metrics right now. And then we set goals and then measure afterwards to make sure that we’re hitting those goals in terms of expanding their capacity, lowering their hours and getting the revenue to where it needs to be, so that if they want to make $10,000 a month, working 20 hours a week, we want to get them there. So, adding those metrics to it to quantify that.

And it’s not as straight of a line as sales is or marketing is where you ramp up the sales engine and clients come in, but it’s more of an indirect thing where when your capacity for taking on good clients expands from seven clients that you can deliver at a high level to 14. If your sales engines then growing at the same rate, now your income has doubled in the same amount of time. And so, it’s enabling your business to grow without having to pour hours on it on this kind of exponential way, where if you want to double your revenue, you have to double your hours. And so that’s where, kind of at the more strategic level, you see the ROI, on the more kind of virtual assistant level, April Deichmann, who I got the chance to speak with a few weeks ago, had a really great analogy of it where she said, you kind of also have to look at the cost of your own time as a real expense and understanding if the work that you’re doing is actually worth that cost because a lot of times we think, oh, if I’m doing it myself, I’m doing it for free. If I give it to someone else now I have to spend money, but your own time has a cost to it as well, especially if that same time could be put into revenue generating things.

And so, if you say, hey, a billable hour, I can make $75. I should not be spending an hour transcribing a video or something when I could get that done for $15. And so it actually shows that it’s saving you money in the long term to outsource things that other people can do for you and much less expensively than you doing them for yourself. But it’s a big mindset shift at that level.

Kira:   Yes, these are things we constantly… Rob and I are constantly saying to each other and conversations we have around, ‘Rob, you shouldn’t be doing this work here because it’s a $15 an hour job.’ So my question is when you’re looking to hire a VA or an OBM, I’m just going to put them together for now, what should you really look for as far as characteristics or like even do you have any specific questions you should ask so you can weed out maybe people who aren’t a good fit or maybe aren’t trained? What do you recommend asking? And then also, as an add on to that, where do you find them? Because that’s where everyone asks us. Where do you find them?

Rob:   Yes, I like this question because I think a lot of people have nightmare stories where they tried and now they don’t want to do it because it didn’t work.

Ashlee:          100%.

Kira:   And that’s the next question I want to ask you, but let’s start with like, what should we look for before things actually fall apart even though they don’t always fall apart?

Ashlee:          Right. Yes, one of the questions I think is really important to ask at the beginning, that people might not necessarily think about is, what is your capacity and what do you want this business to look like? So, if you’re working with someone who’s a virtual assistant and they say, ‘I want to work 15 hours a week. I already have a client who I’m working with for five hours a week and now you’re wanting to hire me for 10, so you’ll be my two clients.’ That is a drastically different experience you’re going to have than if you’re hiring someone for 10 hours a week, but they want a full-time growing business, because then you’ll be one of multiple clients potentially and your relationship with them is going to look different. And so asking them kind of what their capacity is and when they’re working and how they’re working is really important. If it’s kind of a side hustle for them, you’re going to have a much different experience than if you’re their one client and they’re setting aside time every day to work with you. And it also can help if they have a lot of clarity around that or they don’t.

So, if someone’s like, ‘Oh, yes, I’ll work around my work schedule. It’ll be fine’, that’s probably going to be a little bit more challenging than someone who says, ‘Hey, I’m going to be sitting down from 5:00 to 7:00 every single day and I’m going to be working on your business, because you know that they’ve thought about this, they’ve set aside the time and you know exactly what to expect from them. I think a lot of the challenges people have with VAs is that they have a mismatch in terms of how the VA is working and expecting to work versus what the business owner needs. So asking about that, I think is really important.

And then also understanding kind of what rhythms they have for communication. Because I think a lot of the times the reason that relationship falls apart isn’t because the person is making mistakes on the actual work. It’s because they’re disappearing. They’re not getting things done when they said they would, or you don’t know what’s going on. I think those are kind of the three big things that that hit people. And so really understanding, do you have a rhythm for communicating with your clients where they know what you’re working on? What’s your system for tracking everything? What can be our system for tracking things together and kind of figuring out some of those things beforehand and ideally working with someone who’s already figured that out in a way that works really well can be really, really helpful.

And for me, at the OBM level, if you’re paying a little bit more, the big promises I made to my clients and I think the things that you want to look for are basically this attitude of, it is not you, the business owner’s job to tell that person what they promise to do, to remind them like, ‘Hey, remember you told me you were going to get me that thing today.’ It’s the VA or the OBM’s job to remember what they’ve promised and when they’ve promised it to get it done in that timeframe. And so, kind of making sure they have that attitude towards your relationship is really important instead of saying, ‘Oh, well, you didn’t remind me to do that. I forgot.’

And another thing I always promise people is kind of along the same lines. Like if you ever have to follow up with me about anything, then I’ve let you down. And that was something that I took really seriously and wanted to make sure that on my side as their business support person, they could throw something at me and forget about it entirely because they know I’ve got it. And I’m going to take care of it and it’s going to get done and it’s going to get done right and they’re going to know when it’s done. And so a lot really of the relationship with the VA is around that communication piece and that trust that they’ve got it, whatever it is that you’ve asked them to do.

And in terms of where to find them, I found my team on Facebook, which is kind of a strange place to be, but most VAs are not really on the traditional job boards. And so it’s hard to find them that way.

Rob:   Will you talk a little bit about contracts? How much of this stuff should be laid out in agreement? What’s okay to just communicate through email and should we be talking to people who aren’t able to… who are bonded or who are insured against loss because we might be trusting them with some pretty important details with our business?

Ashlee:          That’s a really good question. From what I’ve seen, insurance among VAs is relatively rare. And so I think for kind of those more sensitive items, and especially anything financial, it might be worth kind of looking at more professional, kind of financial managers. I know kind of a contract CFO whose [inaudible 00:43:37] certified and works with businesses, small businesses on that side. And so she has more of that kind of official business focused on the financial piece and has the protections in place as far as I understand for that.

But among VAs in general, a lot of times it’s hard to find that kind of additional protection. So when I hired people, it was making sure that my own contracts were really, really strong and that I had set the right expectation for them. And it can be especially challenging. I know people have run into this if you’re working with a VA who might also be working with a competitor, because then it’s, even if you have strong confidentiality agreements, then the boundary between those two things can be kind of thin, in terms of the suggestions they’re giving to the other guy based on what they’re doing with you.

I’ve seen sometimes if people have more of that sensitive information, they want to make sure it’s protected. They’ll either bring someone in house where they’re the only client, or they have a provision in their contract that that person won’t work with a competitor, and they kind of have that agreement going in, where both of them kind of agree to that to kind of help avoid that problem. And for me, I actually brought in Jen who’s on my team as a W-2 employee, so we’re going full W-2 with her because of the relationship I wanted to have with her. But for contractors, I think having that really, really strong agreement is really important around confidentiality. around conflicts of interest, and things like that. So you have something enforceable if, God forbid, they go where they shouldn’t go with your confidential information.

Rob:   Yes. Okay. So that’s awesome. What is your advice for dealing with something when it goes wrong? Let’s say the VA isn’t doing what they’re supposed to be doing, or they’re out of contact, rather than just sort of giving up, firing somebody, how do we deal with that stuff and make it work?

Ashlee:          Yes. It was interesting for me hiring my first team because I kind of realized for myself how hard this relationship can be because as a small business owner, I didn’t necessarily see myself as a boss at first or as a leader in my business. And Carey who was my first hire, I’m sure she could testify to this, I go to her and be like, ‘Oh, I’m working on this stuff, do you want to do this? Does this sound fun to you?’ She’s probably like, ‘Yes, just give me work to do. I’m here to work for you.’ So learning how to become a leader and a mentor and a manager is a bit of a brain shift when you first bring someone on, and I think one of the challenges people have when they bring on a VA is they’re like, well, you’re a contractor, you have this business. I shouldn’t have to teach you any of this stuff. I shouldn’t have to train you on any of this stuff. But a lot of times for those more junior level VAs, you do. And so that’s where, as a leader, kind of taking responsibility for that relationship can really help to say, the first time something goes wrong, I’m going to automatically assume it was my fault. I didn’t communicate something clearly, I didn’t set the right expectation with them, I didn’t give them what they needed to succeed at this thing. I’m going to work from that assumption for this first time and then if we remedy all of that, and then they do it again, then I can come to them and say, ‘Hey, we’ve had this conversation, what’s going on? Why isn’t this happening?’

And I think sometimes as part of that conversation, you can almost mutually recognize if maybe this role is not the right fit for them, the kind of work that you need them to do is not something that they’re good at, or things like that, where they might say, ‘You know what, I’m just really bad at this thing that you’re asking me to do’, and then maybe they need to be in a different role within your company, or maybe it’s not the right fit. But I think a lot of VAs are still in need of that kind of leadership and training and mentorship and clarity, where a lot of business owners want to be able to say, ‘Hey, here’s this problem’ and the VA doesn’t have quite the level of experience or skills to actively solve that for them or fill in all of the gaps or kind of figure out what they want.

I think for me making that mental transition from doer to manager and recognizing that it’s my responsibility to be the best leader I can possibly be, has been one of the hardest shifts in my business, but really helpful and kind of saying, hey, we messed up here, especially right before I went on maternity leave, I brought in two people and we were figuring all this out and there were mistakes with our clients, and I was mortified. But kind of coming alongside my team and saying, ‘This is not okay, you know that’s not okay, I know it’s not okay, how can we fix this? How can we make this better? And what is it that you need for me to help make this work?’ And so we were able to kind of sort that out together, but it’s tough. It’s really hard to learn how to do that.

Kira:   Yes, maybe I’m just pushing this a little bit more, but what else can we do, because this is an area I struggled too, is around managing a team, leading a team, same struggle as you and I don’t like micromanaging and I don’t think that’s what you need to do, so I just back off completely. What other resources have you used or what could you recommend we start? Maybe there’s some basic action steps we can take to start showing up as a leader, a manager on a team rather than the doer.

Ashlee:          Yes, I think… something I’m still learning, but one of the things that’s been really helpful for us as a team was to kind of set up rhythms in our business for that kind of become the spot where problems get caught before they become major problems. I did the exact same thing here. I was wanting to step away to give them leeway because I was about to have a baby and disappear for six weeks. And so I needed them to have the sense of autonomy and ownership to be able to operate for over a month without me, but I stepped back too far. So we started implementing these rhythms where we were coming in and going through everything that was on their plate, to understand where the status of things were and then we could identify as part of that conversation like, ‘Oh, this isn’t moving forward. Why isn’t it?’ And they’re like, ‘Oh, well, I’m confused about this thing, or I need this from you.’ And it’s like, ‘Oh, okay, great. Let me get that to you.’ And so rather than waiting until it’s due, and it’s not showing up, trying to kind of catch it in the process.

And one of the things that I have done for previous clients and my previous manager when I was working at Navigant was a daily email which sounds of obnoxious, but it’s very important for the VA to do, especially when you’re in those early phases and they’re juggling more than a few things at a time to say, this is what I did today, this is what I’m doing tomorrow, and this is what I need from you every single day. Because then it can also help you identify early like, hey, the priority here is wrong. I want you to do this thing first. Or great. Now I know these things are done. Thank you so much. That’s awesome. Oh, you need this for me. I forgot. Thanks for reminding me. I’ll get that to you. So it kind of becomes that ongoing communication rhythm with your team, especially because for a lot of us, they’re not in the same city.

For Jen, we’ve worked together for almost a year. I’ve never met her in person. And so having those rhythms where I know at a basic level what’s going on, but at this point, she’s worked with me long enough. I don’t need that from her. I know she’s got it. But it’s really helpful in the beginning phases to make sure that they’re keeping on top of things and they are letting you know when they’re getting stuck and things like that, that can help prevent some of those problems and then also, gradually, over time, give you the chance to kind of backup from things because you know very clearly and have evidence that they can handle it on their own.

Rob:   Yes, the communication piece feels really, really important to actually make this thing work. So aside from email, are there other tools that you use with your clients in order to make sure that projects happen and things still going on time?

Ashlee:          Depending on the client, some of them have a project management tool of their own and I work within that with them. Asana is a major one for a lot of clients because it’s free and it has all of the stuff that most people need for managing everything going on in their business. For us internally, we brought out the big dogs, we use JIRA, which is created by software developers and it is ugly, but it is effective. We have-

Rob:   I hate it. I hate JIRA. It’s my least favorite one.

Ashlee:          It is so ugly. But we manage 400 live tasks and the tool for 10 ongoing clients and all of the stuff that’s going on for the business because not only are we managing our own stuff, but we’re managing all of the stuff our clients are throwing at us, and sometimes it’s stuff like, ‘Hey, would you remind me six months from now to do this thing?’ And so we need to have really rock solid project management on our side to remember in six months to remind them to do that thing. And so, that’s what we use on our side and we kind of have all of the pieces to make sure that happens. And so Jen’s in there, I’m in there, and it helps us track back and forth as we’re growing the business, but most people don’t need anything like that. I’m just ridiculously nerdy about project management and throw every idea I ever had in there, so that’s why there’s so much stuff.

Rob:   But that’s what you want to know BM. You need somebody who’s ridiculously nerdy about this stuff in order to make this work.

Ashlee:          We get so excited if we’re talking to someone and they’re like, ‘Oh, everything’s a mess. We’re so disorganized.’ I’m like, ‘Oh, yes, this is fun.’ So yes, we’re nerds like that, but we have learned to embrace it. And especially with a tool, having something where everything is in one place for both of you is really, really important, because then you can see what they’re working on, they can see communications back and forth with you about those things, and so Asana works really well for that first team member to make sure you’re organized together.

Kira:   Wow. All right. Yes, JIRA is hardcore. I am impressed. You’re just so dreamy from the first moment you start speaking on this in interview. You’re just… Yes, I mean, I am the mess that needs people like you to help me, so I appreciate what you do. And this has been a really, really helpful conversation because we’ve covered every question that has popped up in our membership group and in our communities. So thank you so much for just sharing everything and giving it to us straight. Really appreciate it. And where can people find you if they want to work with you? How can they find you?

Ashlee:          Yes, so our website is and squared is spelled out. And we also have kind of a quiz on there if people enjoy quizzes on kind of are you ready to hire a VA, just kind of going through the questions and then we have kind of just some fun free materials around helping set up that relationship and get ready for your first person. But kind of our intensive is on the website there, all the details for that and so that’s where they can find me. I’m also on all the things Facebook, Instagram, LinkedIn.

Rob:   Thanks, Ashlee. This is incredibly eye-opening and helpful. Thanks for your time.

Ashlee:          Thank you both. I really appreciate getting to talk with you and you’re both amazing. Thank you.

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



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