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Hire First? or Get Clients First?

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Expanding beyond solopreneur capacity often requires hiring help. But should you wait until you land bigger clients, or bring on support early to free up selling time to secure those clients?

It’s the classic chicken and egg dilemma of hiring vs. growth. In this episode, Zach asks whether he should hire a contractor before or after he lands his ideal high-revenue clients.

Here are a few of the key considerations we discussed:

Key Takeaways from this Episode:

  • Evaluate cash flow sustainability before hiring to avoid risk if revenues are inconsistent.
  • Precisely track your current workload and capacity to validate the need for help right now.
  • Consider starting with a freelancer for flexible temporary bandwidth versus full-time roles.
  • Weigh personal lifestyle factors like family time that may suffer from overwork.
  • Structure initial trial periods when onboarding contractors to ensure fit before long-term agreements.

Read on for our full advice to Zach on the pros and cons of hiring help vs. waiting for growth first.

Freelance to Founder Cover Art 2023

Zach’s Hiring Dilemma

Zach explains he currently handles all projects solo in his web and branding agency. But he feels overwhelmed juggling sales, fulfillment and internal roles alone.

His goal is to secure a few high-budget “anchor” clients in the $5000-$8000 range. But Zach worries he lacks the capacity to properly court these accounts while executing existing work.

At what point should Zach hire help? He wonders whether to:

  1. Add a contractor now to free up selling time to land bigger clients
  2. Hold off on hiring and push himself to get larger clients first

On one hand, waiting may allow Zach to stay lean a bit longer. But he also risks burning out without support. What’s the right order of operations?

Key Considerations for Hiring vs. Growth

We explained why there’s merits to both approaches. The right call depends on Zach’s unique situation across a few factors:

Cash flow

Can he sustainably afford hiring help if revenue is inconsistent? Locking in a few large clients first provides stability.


How much additional capacity does Zach have solo? Will his spouse support extra evening/weekend work? If so, he may be able to push harder temporarily.

Personal lifestyle

Is preserving family time and work/life balance paramount? If so, brought on help earlier may be best.

Existing capacity

Is Zach truly maxed out currently? Precisely tracking time often reveals hidden bandwidth.


Gradually hiring contractors first allows Zach to vet team members before long-term commitments.

Essentially, Zach should consider his clients, cash, time, lifestyle needs and current workload. With this full context, the ideal hiring cadence becomes clearer.

Our Final Take: Prioritize Flexibility

Ultimately, we stopped short of endorsing one approach for Zach. His circumstances and priorities must drive the decision.

But some compromise options exist too. Zach could:

  • Bring on a freelancer for just 10 flexible hours per week.
  • Hire for specific administrative tasks versus core project work.
  • Structure an initial trial period to test compatibility.

Maintaining flexibility allows Zach to get help without major disruption or commitment. It likely prolongs his transition from solopreneur to larger team. But it also reduces risk amid inconsistent revenues.

In closing, remember hiring is simply a tactic, not a goal. Define your ideal client first, then determine the least risky approach to secure them. With revenue stability, team expansion naturally follows.

Episode Transcript

This transcript was auto-generated and may have grammatical errors.

Preston (00:01.191)
Hello and welcome back to another episode of Freelance to Founder. My name is Preston Lee with and joining me on the air today as always is my good friend Clay Mosley from Hey Clay. Going well man. How about you? Hey Clay.

Clay (00:13.311)
Hey, how’s it going?

Clay (00:18.385)
It’s going good, going good, you know.

Preston (00:19.239)
What are you up to? It’s been a minute since we’ve talked. What are you up to lately?

Preston (00:36.658)
There’s a little above in there. How’s business?

Preston (00:45.659)
Yeah, we can hear you in your co-working space there. So if people are wondering what that background noise is, every once in a while it’ll spike up. It’s not a big deal. Most of it, Willie, we will edit out. But if you do hear through there, Clay is in a cool new co-working space. Not really a co-working space. It’s an office, but there’s just lots of people around.

Clay (00:54.86)

Clay (01:02.918)
Yeah, it’s a private office inside of a co-working space, but you know, I’m going to go back and listen to this episode. And if it’s so bad, I’ll go to, all right, we actually have a podcast studio we can, we can, I can use, but, you know, it’s, it’s a shared studio. So I only got so many hours I can use.

Preston (01:15.603)
Yeah, that’s cool.

Preston (01:22.831)
Yeah, you know, listeners, if you like the ambiance of having people in the background, let us know. If you’d prefer that we’re a little more quiet, let us know, I don’t know. Different people like different things. So yeah, you know you can reach us at slash ask. You can send us anything you want there. Of course we use that also for our Tuesday episodes, which are Q&A episodes. But today is Thursday, which means we are chatting with a guest also joining us on the air today calling from Pennsylvania, right?

Zach (01:52.299)
Yep. Yeah. Out of Lancaster.

Preston (01:52.995)
is Zach. Yeah, wonderful Zach. Welcome to the show.

Zach (01:57.335)
Thank you guys, appreciate you guys having me.

Preston (01:59.655)
Absolutely, we’re excited to have you. We were chatting here before we hit record. All set to go to talk about your business. Why don’t you introduce us and the listeners to you and your business, what you’re working on, who your clients are. Just give us kind of a quick picture of what’s going on.

Zach (02:11.435)
Yeah, so my name’s Zach Johnson-Medland. I started a small studio out of Lancaster, Pennsylvania called Gumption Design Company. So I have a background in a small agency setting and then in-house at a fly fishing e-commerce store. And then I started doing some small freelance businesses on the side.

doing branding, websites, and content creation. And then eventually that kind of led me to creating my own company and all that entails. And eventually I kind of tapered off of working for someone else and then started my own thing. And I’ve been doing that for about a year and a half, full time, yeah. And it’s really fun, really great to work for yourself and be able to work with small businesses around here. Some…

Preston (02:53.075)

Zach (03:04.955)
agency offshoot work where agencies are offloading some of their work to me, and then some consulting as well. So a little bit of everything. I think what I wanted to kind of talk about was streamlining some of the services that they feed into each other a little bit better, and then kind of getting outside of the word of mouth sphere and advertising and marketing yourself.

Preston (03:21.672)

Preston (03:30.047)
Cool, very nice. So it sounds like you’ve done a ton of different things, different kinds of work. What would you say is like your specialty? What do you really focus on? Or are you more of like a broad, do you offer a more broad service to your clients?

Zach (03:44.811)
Yeah, so I think one of the things I really like is doing branding and logo design. I think what kind of happened is I have the ability to work on websites and like working on them, so I kind of was like, okay, well, it makes sense to be able to show them how to incorporate it into a website. You hand over these logo files, and a lot of times the companies don’t.

necessarily know how to use them, so I wanted to make sure they were used correctly. So if they had the budget, I’d piggyback a project on top of that to kind of roll out their brand into the website. And that’s kind of where it started. And then eventually I had some clients come back to me and say, hey, we saw you do some social media stuff, some email marketing, could you do those for us as well? So it’s kind of grown naturally. And I think that is great.

But growth itself can kind of be its own challenge of like, how do you focus the growth then and make sure that you continue to get clients in certain places instead of all over the place.

Preston (04:51.771)
Yeah, this presents such a common and interesting problem, right, which is like, who’s deciding what I offer? Is it the people who are willing to pay me to do work? Or is it me? Am I deciding what I’m actually going to do, right? And in the beginning, I feel like we all are kind of in this place where it’s like, I’ll just take… Yeah, yeah, that’s right.

Zach (05:00.136)
Yep. Yeah.

Clay (05:09.002)
You just take whatever money you can get. And I gotta pay bills, right?

Zach (05:13.138)
Yeah. Exactly.

Preston (05:14.215)
And then at some point you sort of start to go, no, I think I really excel at this and maybe this pays the bills better and I enjoy it more and I’m getting this flow state, like there’s all these things to consider. So it sounds like you’re maybe in that transition period almost like thinking to yourself, like, okay, how do I merge what I do all into one specific streamlined process and make sure that I’m really getting the most out of the time that I put into my work.

Zach (05:29.473)

Preston (05:39.879)
So that’s a cool place to be because you’re not like scrambling anymore. Hopefully you’re not scrambling anymore. Like where am I going to get my next dollar? How am I going to buy my next meal? Right. You’re, you’re sort of past that very, very beginner stage. And now you’re thinking maybe a little more strategically about your business. So I love that.

Zach (05:47.968)

Zach (05:54.215)
Yeah, I feel like I’ve gotten to a point where I think in the beginning you kind of, yeah, you’re saying yes to everything. And then at a certain point you start to realize, I mean maybe like a year in I started keeping track of everything and you can see that it, whether you know that a project is going to happen or not, as long as you’re doing your marketing, talking and networking and all of that, that projects tend to go along so you start to get a little bit more comfortable saying no to certain things. And then…

As I did that, I realized, okay, there’s something to this. I have to keep doing this. It’s just, yeah, kind of doing the forethought before that.

Preston (06:29.575)

Preston (06:33.887)
It’s actually such a good feeling, right, Clay? Like when you go from, will I get more work or any work to, yeah, if I just keep doing what I’m doing, I’m at least gonna get some work.

Clay (06:37.723)

Zach (06:44.93)

Clay (06:45.054)
Yeah, yeah, that’s a really, really good feeling. It’s, you know, you get past that, again, you get past that startup mode phase. I mean, technically you’re still in startup, but that early startup mode of, I just need to put food on the table kind of mode. Yes.

Preston (07:02.935)
Yeah, there’s a lot of fear, I feel like in that stage and you finally get to get to begin to brush that off a little bit.

Zach (07:06.257)

Clay (07:10.762)
I think it’s a mind shift change, right? It’s like there’s this natural progression that happens whenever you first start a business where there’s a lot of fear and you’re avoiding a certain situation, you’re avoiding starving yourself, you’re avoiding being homeless to a point where now your mind is like now proactive versus avoiding a reactive state. Does that make sense?

Preston (07:38.063)
Ah, yeah, yeah. It’s sort of like at some point you get to switch to this like abundance mentality where you’re just like, no, there’s plenty of work, there’s plenty of business. If I’ve done it once, I can do it over again, as opposed to like, will there be enough clients? Will there be enough money? Can I make this work? All those questions that you ask before you start and then for your first few months or maybe a year, you’re kind of asking those questions too.

Zach (07:39.66)

Zach (08:01.867)
Yeah, that’s a perfect way of putting it. I think one thing I’ve encountered too is that when I started, so I tapered off from a full-time job, which was really lucky that they allowed me to just go part-time and then slowly, as they didn’t need me anymore, I could taper off and kind of really put my toes in the water and like feel it out before. But I noticed that I think when you first jump off, you can…

Preston (08:16.945)

Zach (08:30.103)
I had this expectation of like, I’ll give it a year. If it doesn’t work, you know, we’ll move on, whatever. I just know that I have to try it because it’s happening now. And I think you get past that. I hit a year and kind of was like, oh crap. Like I didn’t really plan beyond a year. I just kept saying, I’m gonna make it to a year. And then you’re like, I keep hitting goals, which is great. It’s its own problem when you’re kind of like,

Preston (08:36.144)

Clay (08:41.076)

Preston (08:50.987)
I’m sorry.

Clay (08:56.266)

Zach (08:59.923)
Oh shoot, I wasn’t thinking big enough to like grow past that, you know?

Clay (09:02.483)

I did the same thing. When I first started, I was like, I’m going to give it a year. Same until, I went through the same, it’s a very similar journey. And then a year passed and I was like, huh, I actually did make this a thing. And people actually like me enough to keep paying me.

Zach (09:19.484)

Preston (09:19.927)

Preston (09:24.871)
Yeah, we had something very similar. You’ve heard my story, which is, did it on the side forever, got laid off from a job, was so excited to give it a try and sat down and crunched the numbers. And we had something like 18 months financial runway, which is ridiculous. And so I said, I’ll give it 18 months, right? And my wife and I kind of decided we’ll give it 18 months.

Zach (09:41.451)
Yep. Yeah.

Preston (09:49.395)
Well, actually, I think I said we’ll give it six months or maybe 12 months, right? And then you still have some time to find a job. And yeah, we’ve never even had that conversation again, right? Six years later, seven years later almost, and we’ve never had the conversation of like, well, is this working? Because it is. And it’s a really good feeling to finally be out of that stage of wondering and staying up at night and wondering if it’s going to work out. So…

Zach (10:06.22)

Preston (10:16.007)
Let’s talk a little bit about where your business is headed, Zach. So listeners of the show know that we have this questionnaire that you fill out when you come on. If you want to join us on the show like Zach is joining us today, we’re going to help him power through a couple issues he’s facing in his business, hopefully help him have a breakthrough, take his business to the next level. We’d love to do that for you as well. You can visit where we can have you fill out a… find a time on our calendar and then fill out a questionnaire. In the questionnaire, we ask a few questions. It’s really quick, really easy.

And one of those questions is on a scale of one to 10, one being a freelancer, 10 being a founder, one being working entirely on your own, your business relies on you, you can’t ever take a vacation to 10 being, your business has systems and processes set up, you maybe have some people working with you or for you, and it’s a lot easier to step away from your business and it’ll still continue to generate revenue. Where do you fall on that scale? And Zach, you put that you’re currently at a three, but a year from now or so, you would like to be more at an eight.

So could you walk us through what an eight looks like in your mind like a year from now, as we’re talking about this idea of growing past where you had planned originally, what does an eight look like for you a year from now?

Zach (11:23.763)
Yeah, I think one of the main things is being able to work with other freelancers and maybe hiring out some of the work, especially with things like websites where there’s a developer involved and then having like some processes around making sure everything gets checked before it goes out the door. Some of the things that you benefit from when you get more people in is having a little bit more eyes on things.

and just, yeah, I think a lot of it revolves around being able to hire someone else out and have the processes that stay in place because I think as one person, yeah, I can theorize about having processes, but it really starts to come into play when you have two people or more.

Preston (12:14.107)
Yeah. So, okay, so let’s talk about that then. What is, what do you feel like is sort of standing in your way or what’s a hurdle that you’re facing when it comes to getting to that point where you’re at an eight, you maybe have one or two or more people working for you, you’ve developed some processes in there. What can we help you with today, Zach?

Zach (12:31.787)
Yeah, I think some of it is about at what point do you hire that person? It’s kind of like a chicken and egg problem of like, do you wait for the big client, you know, that helps you fund that? Or do you hire them and then you have more time and then you can go out? And then I think I am not confident that the current clients I have will fulfill enough to…

hire that person right now. And I want to make sure I get some like, I have one or two reoccurring clients, but I’d like to get like three or four and then maybe like one large gig before I would hire someone else.

Preston (13:13.519)
Yeah, yeah. Well, let me ask this question and then I’d love to Clay’s take on like this chicken and egg issue, which is, you know, do I wait till I have the big client to hire people or do I hire people and then that frees up time to get the big client? My question is, Zach, do you find right now that you don’t have time to go out and find those big clients because you’re so busy executing on the deliverables for clients or is that not an issue?

Zach (13:38.983)
It’s, I mean, the classic like feast and famine thing happens a lot of times where, um, this past year was a really good example. I had booked out maybe three months in advance and I was working, um, pretty heavily throughout the summer. And then I submitted a bunch of stuff, had a couple of clients sign on and I had this large gap of time where I realized, okay, I haven’t been marking myself. I had all this time booked out. So now you have to go back and.

And I feel like it kind of goes in those cycles if you get really busy, I stop going to networking events I stop emailing and posting on social media, and then you come out of that fog and are kind of like okay I Need to be doing these things and when you’re doing those things projects happen and pretty consistently, but just making sure that is Continuing throughout the busy seasons

Preston (14:32.591)
Right, that’s classic feast famine, right? It’s like you have no work, and so you have plenty of marketing time, sales time, and then you get lots of work, so you have no sales or marketing time, and then that leads to no work, and that’s literally why it’s a cycle, right? It’s because we’re trying to do it all. So Clay, what’s your take? If he’s looking at hiring, does he hire in anticipation of freeing up some time to have bigger or more clients, or does he?

Zach (14:46.803)
Yeah. Yep.

Preston (15:01.927)
maybe like double down, pull a few late nights, extend his own hours, get those clients and then hire someone.

Clay (15:09.058)
Hmm, yeah, this is a really good topic to discuss. We’ve talked about it before. I don’t think either way is incorrect. I don’t think there’s one solution to this. So I’m just gonna preface what I’m saying with this. It all really depends on your own personal situation. If you have the time to be able to just put in a few extra hours and you want to stay lean.

Zach (15:25.494)

Clay (15:38.954)
Like maybe that’s the way to go. But if you do have, like, if you, let’s just say, and I don’t know your personal situation, but let’s just say you have kids and a family and stuff and maybe that time is just off limits, you know? And you don’t have that time to be able to put in the extra hustle, then hiring might make more sense. The only thing, so like, I think it’s just going to really depend on your situation. So like,

Zach (16:00.844)

Clay (16:07.478)
Tell me a bit more about that.

Zach (16:09.535)
Yeah, yeah. So I had the privilege of my wife has a full-time job as well. So when I came off of my part-time work into full-time freelancing or working for myself, I did have the benefit of that. And we don’t have kids, so that’s really nice. We have one dog, but not the same at all, I understand. It feels a lot like the same.

Clay (16:34.114)

Clay (16:38.167)

Zach (16:39.131)
nothing and having to walk him all the time, but I know it’s not. So.

Preston (16:42.293)

Clay (16:42.514)
Yeah. So do you have the… So two things. Would your wife be okay with the extra hours? Because they would probably be in the evening sometime or maybe a weekend. So that’s question one and two. And you don’t have to answer that. This is just a rhetorical question. But number two, do you have… A thing that can affect this is do you have the extra cash flow?

Zach (17:04.043)

Clay (17:12.77)
that could cover hiring somebody, you know? Because the answer to both of those questions, and I’ll throw in a third question, I think that’s very, something that people don’t think about, but the answer to those two questions will affect your answer. The third question I would say is, how much capacity are you actually at currently? Because some people think they’re a lot busier than they actually are.

but if you actually track your time, you may have spent like an hour or hour and a half just scrolling on social media during lunch, you know what I mean? So it’s like how much actual capacity you have. So my rule of thumb is that before you hire, you need to make sure that your capacity is pretty close to full, not full, not past full, but close to it.

Zach (17:44.428)

Clay (18:11.782)
I’d say probably like 85, 90%. So the reason why you don’t want to do it when you’re at 100% is because now you’re going to rush hire. And what happens when you rush hire is you probably going to hire like a bad quality employee or contractor. You can’t take the time to fully vet the people. So that’s why I like somewhere between 80, 90% capacity.

Zach (18:16.043)

Zach (18:21.791)
Yep, yes.

Clay (18:40.646)
enough time to vet people properly and go through a slower hiring process. So with all those three factors in mind, you can go either way. I don’t think there’s any right way or wrong way. It just depends on your personal situation.

Zach (18:58.803)
Yeah, no, that makes a lot of sense. Yeah, I think this past year or two, I’ve tried to… After I hit a year, I wanted to kind of push myself. So I’ve been trying to feel it closer to reality, you know, making sure I’m keeping track of my time and saying like, okay, how much of that is actually billable? How much of that are you, you know, taking a walk with the dog because you think that you don’t need to be working right now or something like that?

and then being honest with myself about that. And I completely agree with what you’re saying. Once you start looking at the numbers, sometimes you’re like, oh, I was not actually that busy as I felt.

Preston (19:41.103)
I think though, keeping that in mind, and I agree with everything you and Clay have said, it’s important also to ask yourself, like we’re saying, make sure that your spouse or your partner or whatever feels good about you spending the extra time or make sure your cash flow looks good. You also have to ask yourself, most of us are trying to not only build a business but build a lifestyle around our business. Not a lot of us are trying to build like multi-million dollar startups or tech companies, right?

Zach (20:07.681)

Preston (20:11.415)
Yes, maybe I am taking the dog on a walk every afternoon, but is that something that I’m willing to give up now in exchange for more clients? Or is that something I wanna hold onto, right? All of those, it’s maybe a little bit of a silly example, but like all those lifestyle decisions, right? As kids, if they end up coming into the picture, you know, just all those questions, it’s like, am I willing to give up time with my kids or with my spouse or with my friends or with my hobbies or with my church or whatever it is you have going on in your life?

Zach (20:25.718)

Preston (20:39.559)
Am I willing to sacrifice some of that time to build my business or am I not willing to sacrifice that extra time? All of those kinds of questions I think will inform that decision.

Zach (20:52.115)
Yeah, yeah, because I know that was part of the reason I wanted to go full time by myself was benefit of being able to, you know, do some, you know, whatever you want with your own time and be at home and looking into the future at maybe having kids of like, if I have this job while I have kids, it’s a lot more flexible than if I was working at a desk job. Yeah.

Preston (21:13.659)
Right. Yeah.

Zach (21:17.443)
That’s a really good point.

Preston (21:18.543)
Yeah, so, you know, unfortunately I wish we could answer this question for you. Those are the kinds of questions that listeners, if you’re wondering the same thing, which comes first, the chicken or the egg, the hiring or the client, you know, those are the kinds of questions you have to ask yourself. I don’t know, Zach, are you, um, what are you after thinking through those kinds of questions, what are you thinking would be a better fit for your business? Are you thinking hire first or try to find those bigger clients first?

Zach (21:21.952)

Zach (21:44.975)
I think I want to try and hire someone. I do think if I got a little bit extra time that I could start to get some bigger clients and really follow those leads. I think it’s something that I underestimate how much time it takes to build those relationships and follow up with people and grab coffee and all of that. And I know there’s some work like working on a website that I am…

Preston (21:58.782)

Zach (22:13.079)
definitely not the most effective at, you know, and doesn’t keep me interested, so it takes a lot longer. And I think if I was hiring someone else out, there’s the possibility it would kind of even out, if not be better anyway.

Preston (22:29.051)
Yeah, and the nice thing we’ve talked about this on the show before too. The nice thing is you could hire just a contractor subcontractor right now Um and just book them for like one or two projects, right? There’s no long-term commitment or clay and I will say I think clay has a 30-day rule I typically do like a 90-day rule where it’s like after 30 or 90 days we’re going to reevaluate and see if this is working and there’s a lot less like onboarding time or You know legal paperwork all that stuff that you might deal with a full-time employee

Zach (22:35.543)

Preston (22:58.155)
And you can limit those hours. So it’s like, look, I have a budget for, you know, 10 hours a week or something. So you can really start small and ease into it and make sure that that’s the right fit for you as well, without blowing all of your cashflow on it.

Zach (23:04.098)

Zach (23:11.423)
Yeah, that makes a lot of sense. I didn’t even think of, you know, telling them I only have this many. I always kind of assumed like, uh, they’re gonna have to take whatever they take, but that makes sense.

Preston (23:21.447)
Yeah, no, you decide, right? You’re the client. And so, you know, it’s weird because on the one hand, we tell freelancers, no, you decide your rates. And then on the other hand, you as the client, we’re like, no, you decide, right? But in reality, you have to come to an agreement, right? If a client can’t afford you as the freelancer, Zach, then you guys can’t work together, right? And if you can’t…

Zach (23:29.324)

Zach (23:33.58)

Preston (23:45.371)
afford a certain freelancer or contractor as the client, then you guys also can’t work together. It’s the exact same relationship. So it’s kind of weird because you’ll start to live in this duplicitous, you start to just live in both roles. On some days you’ll be the freelancer or the contractor with a client, and on the other hand you’ll be the client to a subcontractor. And so it can get a little tricky. But definitely, yeah, you can 100% set those boundaries for your business knowing what your cash flow is.

Zach (23:59.543)

Zach (24:06.071)

Preston (24:14.479)
You can say, look, I’ve got $1,500 this month, that’s it. And here’s what I’d like to have your work on. Does that sound like something that you could do for that amount? And there will be some freelancers that will just be out of your budget, and that’s fine. That’s just how business works. And there will be some that are within your budget. And the trick is finding the really good ones who are also within your budget, like the very best you can get for the right budget.

Zach (24:37.409)

Preston (24:37.659)
Let’s, let’s, let’s talk a little bit about your, I know you had a second question and I’ve forgotten it. So we talked about hiring. What was, what was the other issue we wanted to tackle today? I want to make sure we cover everything you came for today.

Zach (24:48.195)
I think kind of looking at getting clients outside of word of mouth and reaching those larger clients, I think I don’t think I’ve exhausted the pool of word of mouth clients, but looking ahead and realizing, okay, at some point it’ll get lower from word of mouth and like really trying to push nailing some bigger clients that are like not…

I get a lot of local clientele from small businesses. I work out of a co-working space as well, so I get a lot of referrals that way. And I love working with those businesses, but a lot of times working with a few larger clients that are doing a full brand project with a website, with the content creation like monthly retainer kind of thing going on is what keeps…

me able to work with the smaller people and have some time to do those lower revenue projects.

Clay (25:52.418)
Can we define large client because it’s, the way you’re describing this is that you work with smaller, quote unquote, local businesses, but is it smaller because they’re only doing one service with you or because of the actual business is only a mom and pop shop versus a corporation, right?

Zach (25:54.722)
Yeah, yeah.

Zach (26:18.707)
Yeah, no, that’s a good point. Probably a little bit of both. So they’re usually pretty small businesses like mom and pop owned. A couple of them have like employees. Sometimes I get like some manufacturing clients and then usually what happens is someone will come in for a website. I’ll usually tell them that I also offer branding services.

if they want to redo their logo before we do the website or after. And then once we’re through, usually I’ll follow up with them and say, Hey, it looks like you could use some email marketing, general content creation services. Um, yeah.

Clay (26:59.414)
Got it. Can we talk numbers though? Like how much is a small client to you and how much is a large client to you? Revenue.

Zach (27:05.951)
I think like a small client, typical client that I’m getting now is maybe like 1800 to like maybe $2,500 a project. And then larger, I would say like I had a client that was branding website and then the whole kind of kit and caboodle and that turned out to be like $5,000 to $8,000.

And then I have a couple reoccurring clients that are monthly retainers and those are like $700 a month so those are nice because they kind of keep everything going So that’s general content services, which is usually updating their website With a blog I usually sit down with them talk about what they’re doing for marketing then give them a blog from that talk turn it into for

Clay (27:47.33)
What do they pay you for?

Zach (28:05.731)
to six social media posts, and then pump out an email for them as well for that.

Clay (28:11.278)
Do you want more of those clients or do you want more of the $5,000 to $10,000 one time project clients?

Zach (28:19.199)
This is a hard, I always, I think this is where some of the struggle lies is the, it’s comfy to get the content creation ones because they’re reoccurring, but I like the five to $8,000 ones and I think I do those better.

Clay (28:35.373)

Preston (28:36.415)
Do you like them better because of the numbers higher? Do you like the work better?

Zach (28:41.843)
I like the work better. I’ve done a lot of content creation services in past jobs, so it’s kind of something that comes along with a lot of in-house positions. You end up making a lot of emails and stuff, and I get it, but it’s not really exciting to me. It’s kind of just plug and play.

Preston (28:43.304)

Preston (28:55.218)

Clay (29:06.982)
Okay, so the recurring stuff I will tell you is going to allow you to grow.

Preston (29:18.943)
Mm-hmm. Predictably and without that fear, right? That chicken and egg fear.

Zach (29:19.201)

Clay (29:20.982)
Predictably, yeah.

Yeah. So I’m wondering if, and I totally get the five to $8,000 projects. Like if that’s what you enjoy doing, I totally get that that’s what you want to do more of. So I’m just curious, remind me again of what that would include. Like if it’s a $8,000 job, what would that include?

Zach (29:38.452)

Zach (29:50.743)
So that would usually be like branding redesign. So we’d go through brand identity, a little bit of strategy in the beginning to kind of set that up, get the brand identity done. Then go through a web creation process and kind of set up a five page website. And then usually with brand identity, I give them like a couple pieces that would be helpful for them. So usually I limit it.

Clay (30:16.376)

Zach (30:17.359)
three, so maybe like a business card, letterhead, social media, template, something like that.

Clay (30:22.422)
What happens with the website? Do they just… who hosts that? Do you host it? They host it? What?

Zach (30:28.499)
Yeah, so previously I was, I don’t, I would use like Bluehost and then they would host it. So they would do all of that. What I started realizing and I’m trying to figure out this pricing as well for switching over to, I have someone in the co-working facility that’s

Zach (30:57.771)
better service and a lot faster hosting and customer service. So I’m trying to work whether to go from like a one-time plan. He costs a little bit more, but it’s so much more worth it than dealing with like blue hosts and all of the different customer service things. And yeah, so the answer is they do it currently. I’m looking at trying to turn the website into a reoccurring model because I think they get a lot.

Clay (31:02.231)

Clay (31:14.752)

Zach (31:27.531)
better quality out of it too. Someone will usually end up, I noticed a lot of clients will say, can we edit this ourselves? And my answer is usually technically you can, yes, but I will not be responsible for changes made. And what ends up happening

Clay (31:44.238)

Clay (31:47.869)
How do you charge people if they want you to do it?

Zach (31:52.189)
I usually do hourly. I started doing like packages of hours and then


Clay (31:59.65)
This is why they ask if they can make the changes. I never understood this by the way. Websites, so websites by the way, are a very, very easy monthly recurring thing to offer. Even if you don’t do it and you want to partner with this other person, you can just kind of white label that if you wanted to and just kind of charge up charge over that. But like,

Zach (32:13.685)

Clay (32:26.658)
The reason why people want to, and this is just my eight years of web experience, the reason why people want to update their websites themselves is because their web provider is charging hourly for a service that’s super technical that the client has absolutely no idea how long it’s going to take and therefore they don’t know how much it’s going to cost and therefore they’re going to say, I’ll just update it myself. And what happens with that is that…

Zach (32:47.265)

Zach (32:51.517)

Clay (32:54.958)
Now your credibility is terrible because they paid you for something that they have to do themselves. And then they get frustrated and then they move over to the next web person.

Zach (33:10.611)
Yeah, no, that makes a lot of sense. Yeah.

Clay (33:14.302)
So yeah, I don’t know. Preston, you’re about to try it.

Preston (33:16.647)
Well, in my mind, in my mind, I think, I think maybe there, I think you could tie in these two clients, these two types of clients, like I assume, I assume the sale, getting the, getting the sale, closing the deal on the $700 a month thing is quite a bit easier than closing the deal on a $8,000. And so like, yeah. So, so imagine, imagine if you, um, instead offered, because they’re very, like they’re very related, right? What if the service was.

Clay (33:23.798)
I think so too.

Zach (33:32.531)
Yes. Yep, so much easier.

Preston (33:45.079)
I will help you rebrand and rebuild your website. And then I will publish frequent content on your website and your social media. And this will cost $750 a month. We’ll sign a 24-month contract. And in the first three months, we will do your brand and website. And then every month after that, it’ll just be new, fresh content, any updates you need on the site. It’s all included. I mean…

Clay (34:14.954)
Yeah, that’s exactly what I was gonna say. You know.

Preston (34:15.163)
It just feels like, yeah, and it’s so easy to hire. You need like three of those clients to hire someone to start helping with updates. And then you can completely hire out that other stuff that you don’t enjoy as much, the content updates, the social posts and all that. And you can focus on the front end, the first three months that you love to do. And then you can still reap the financial benefit of the remaining, you know, 21 months plus.

Zach (34:17.44)

Clay (34:40.922)

Zach (34:41.972)

Preston (34:43.203)
of having that client and it’s an easier sell. Like I don’t see a downside to trying that.

Zach (34:49.887)
No, I’ve, yeah, I love that. I think that’s something I’ve been trying to figure out how the pieces fit together, yeah. And what you’re. Yeah.

Clay (34:49.933)

Clay (34:57.058)
You just lump it all into one package and you spread it out over 24 months. That’s what you do. Like just exactly what Preston said. Cause like if it’s a, let’s just say it’s a $7,500 package, right? I’m just doing the math here. Sorry. You’re going to hear some clicks guys. Preston.

Preston (35:13.486)
I was getting mad at Clay before we hit record because he was clicking his mouse. I’ll just click my mouse while you talk.

Clay (35:19.047)
Yeah, so a $7,500 package that over 24 months, that’s $312.50 a month. And then you add on the $700 a month for the other stuff. So it’s $1,012.50. I would just say you get all of this for $995 a month over 24 months and call it a day. Like that’s so much simpler to sell.

Zach (35:30.208)

Zach (35:41.331)
Yeah, yeah, no, that’s.

Clay (35:41.95)
If somebody’s willing to pay $700 a month, they’re willing to pay for $995. And the benefit is they get so much more, right? The only caveat is that it is a 24-month agreement, but from my experience, that’s not difficult to sell. And so you just have to lock it in. And I know what a lot of graphic designers are saying right now. They’re probably saying, well, I did all this like…

Zach (35:51.7)

Clay (36:09.81)
work on the front end, what happens if they like quit or whatever. To me, this is where you lock in your agreement. So pay a lawyer, lock in your agreement to where it is a 24-month agreement, and transfer of ownership doesn’t happen until the 24th month.

Zach (36:31.072)
Uh, yeah, no, that’s a, yeah.

Clay (36:33.462)
That’s how you lock this in. So over the branding assets. That’s the way I would do it. And I think you could sell that all day long.

Zach (36:48.288)
blowing my mind a little bit because it’s like something that’s just been like sitting similar you know and it’s coming together and you’re like oh shoot like

Clay (36:51.026)
I mean like, yeah like…

Clay (36:56.634)
Well, it’s so funny because I mean, think about it like if you’re pitching somebody a full menu of services and you’re saying, hey, I could do a website, I can do a branding package for like this, this is going to cost $3,000, this is going to cost $4,000, this is going to cost another $2,000. Also on top of that, we can add on web hosting for $99 a month. Plus, on top of that, we can do email and blogs for $700.

Zach (37:15.135)

Clay (37:24.13)
Dude that’s so f-ing complicated.

Zach (37:26.735)
It feels like, it’s funny you say this, because the other day I was getting really frustrated because I went to a diner, and you know they give you those menus that have like 500 options on them. But I was saying to my friend, I was like, this is what I feel like sometimes, because I have to like, I have a document that literally just says like every possible thing, and what hour allotment it might have, and what price it might be. And I was like, every time I look at a project, yeah, no, that makes sense.

Clay (37:37.458)
Yep. Mm-hmm.

Clay (37:41.567)

Preston (37:50.883)
Yeah and they don’t want that either. Yeah.

Clay (37:51.947)

Clay (37:55.37)
I mean, you know, you could offer all of this stuff a la carte. But as far as marketing and sales and like what you’re pitching, you just make it this package. It’s like $9.95 for everything.

Preston (38:09.447)
And you think about too, like the opportunity cost here, right? They can either do it all themselves, which for most businesses is well worth less than $1,000 to not have to deal with it because most of them are not in web, they’re not in tech, they don’t understand content, they don’t get it, but they know they should be doing it. And so you’re talking about $12,000 a year, right? So the other alternative would be for them to hire someone. And who are you going to hire for $12,000 a year?

Zach (38:25.036)

Zach (38:35.203)
And that’s, I mean, honestly, that’s kind of where it, this actually makes a lot of sense because when I was coming out of my full-time job, essentially the experience I had was working in an agency where they were kind of doing that for people where, and I was seeing that, you know, there’s that in-between client who cannot afford large agency services of like 20,000, $30,000 plus, but there’s also.

Like there’s a space for it somewhere in there where and that was kind of what I was realizing is that these clients have A lot of these small businesses have room for a marketing budget But they really don’t understand how to use it So they end up spending it on all these little bits and pieces that don’t end up doing them any good So then they end up never doing any marketing, you know

Preston (39:26.523)
Yeah, yeah, I mean, what you’d be selling is for less than $1,000 a month, your website, your social, and your email will all align. The content will all match. It will all drive leads and new customers. It will all look well together. It will all have the same voice. It’s all going to be cohesive instead of, yeah, one Upwork freelancer doing your email and one Fiverr freelancer doing your social and someone else doing your website. It’s going to be all in one place.

You could not, there’s no way you could hire, you know, a web developer, a social media strategist, an email copywriter for less than a thousand dollars a month. I think it becomes a really easy sell.

Clay (40:09.92)

Zach (40:10.015)
Yeah. Do you think, and maybe this is beyond the scope of this podcast, but do you think selling wise that it should be focused on return on investment as something in the contract or kind of brand identity or does it not matter, do you think?

Clay (40:32.694)
That is a good question.

Preston (40:33.667)
That’s a great question. To me, that’s gonna depend a lot on conversations you have with your clients. Right, I think there are some clients who are willing to pay for sort of that brand awareness. And there are some clients who are like, I’m not gonna spend a penny unless I get a positive ROI out of it. So it’s really just gonna depend on what kind of clients you wanna attract and what they’re telling you. And I think you’ll start to find one or the other. In my experience, there’s literally those two types of clients where it’s like.

Zach (40:34.679)
No, no, no.

Zach (40:38.707)

Clay (40:55.042)

Preston (41:02.471)
You know, one of them is willing to pay whatever just to have their brand look great and have brand awareness and they believe in brand awareness. And if they have good brand awareness, they believe the sales will come. And then the other people who like know every little piece of data, they know where every sale comes from, how many clicks it takes, how many emails subscribes, like they know the whole funnel, you know, like the back of their hand. And you’re just going to have to figure out which client you work best with and which ones are easiest for you to close. I think, I don’t know, Clay, do you have anything to add?

Zach (41:21.459)
Yeah. Yep.

Clay (41:28.71)
I think either way you’re selling the same thing. You’re selling right this list of services, but I agree with Preston. I think it’s whoever you’re talking to. This is where sales training comes into play. It depends on who you’re talking to and how the conversation goes. If you’re talking to like a super data analytics person, talk to them, talk to, talk their language, talk data, right?

Zach (41:40.642)

Clay (41:56.29)
If you’re talking about somebody who’s like big on the look and the visuals and things like that, then talk brand aesthetics. You know, if you’re talking about, if you’re talking to somebody who, uh, who is doing this to increase their own client experience, right? Then talk that language, right? At the end of the day, you’re still pitching the same thing. Just just.

Zach (42:19.575)

Preston (42:23.027)

Clay (42:25.339)
Use different words according to who you’re talking to.

Zach (42:28.159)
No, that makes a lot of sense, yeah.

Clay (42:31.274)
You know, you know…

Preston (42:31.303)
Yeah, you think about selling things like if you sell a car, right? Some people are going to really care about the engine. Some people are going to care about the color. Some people are going to care about the mileage. Like you sell it based on what people care most about. I like that approach.

Clay (42:44.29)
Mm-hmm. I think a really good question to ask prospects as you’re having those conversation is, is what is what is the thing that’s the most priority for you right now?

Zach (42:57.919)
Yeah, no, that makes a lot of sense.

Clay (42:58.522)
Like, because that answer is going to vary. You know, and I think that’s going to help steer the conversation.

Zach (43:08.863)
Yeah, I was kind of thinking that makes a lot of sense. I was not thinking at the beginning of the sales funnel. I was thinking process wise of like, making sure that they’re happy those 24 months and like showing either return on investment or, but that makes a lot of sense too of like asking at the beginning.

Clay (43:29.202)
That’s the second part of the conversation. You have that part of the conversation after they give you buying signals. Yeah, like, because this is where people mess up and this is why people like lose sales is because they go right into what they’re getting, right? But you hadn’t even sold the damn thing yet. You know what I mean? Like you got to know what’s important to them.

Zach (43:31.989)

Zach (43:37.69)
Okay, yeah.

Clay (43:57.502)
and what’s priority for them, and then talk about that, and then when they give you buying signals, an example would be, oh, okay, well, how would you do help me with this, or what does that include? How much does this cost, right? That is when you go into that part of the conversation.

Zach (44:20.523)
Yeah, reassuring them with showing them.

Preston (44:23.211)
Yeah, and I think too, like, if you don’t know, if you can’t prove ROI, then don’t take that angle. You know what I mean? Like, some of your work, you may not be able to prove ROI on it.

Zach (44:30.487)
Yeah. I think that’s the hardest part I’ve had is… I mean, I’ve definitely had clients. Yeah.

Preston (44:36.015)
Yeah, and there will be some clients who demand that and they just might not be a good fit for you um, it’ll depend and maybe Maybe maybe like over time you can you can start to get a feel for what roi looks like and you can give case studies And things clay, what were you saying? You you wouldn’t do what?

Zach (44:41.825)

Clay (44:43.359)
I would not do that.

Clay (44:55.655)
I would not guarantee ROI.

Preston (44:57.615)
Yeah, no, I wouldn’t either, especially on a 24-month contract.

Clay (45:01.198)
Mm-mm. Yeah, like if you That’s just because what’s gonna happen is you’re gonna get people that’s gonna come back in on the back end and Ask for a bunch of refunds like that’s Yeah now that Yeah, that that’s not to say you can’t have an ROI conversation But I would not guarantee it

Preston (45:12.679)
Yep. You guaranteed this. You said this was accomplished that and there’s so much out of your control, right?

Zach (45:13.004)

Zach (45:24.883)
Yeah, what I’ve done in the past is like given them the tools to track what they think is like a… Like I say like, talk to me about if you think this is not worth it during those meetings. You know, bring it up so we can address the concerns, but I don’t necessarily… Because it’s just so hard to measure on my end of like every week, what am I going to do? Ask them for their sales and then compare it to like, you know, that it just gets really… Yeah.

Preston (45:25.296)
I… Go ahead.

Preston (45:49.778)

Clay (45:52.17)
It’s uncontrollable. It’s uncontrollable on your part.

Preston (45:53.863)
Yeah, it’s outside of your control. It’s not fair for them to ask that of you, things that you can’t control, right? What you can guarantee is like, look, we can guarantee we will have a fresh new blog post on your website every week or whatever that is. We will have new social media content twice a week. We will update your website within 36 hours of you sending a request. Like whatever you decide, the things that are 100% within your control.

Zach (46:09.059)
Yeah, yeah.

Preston (46:23.303)
Those are the things you can guarantee. And then you can say things like, and for most of our clients, they tend to see an uptick in traffic and a da da. But what we can guarantee is we can do this. And if, and you know, depending on what you do on your end, we do this with, uh, with clients all the time where I say like, look, for some clients, this works really well and for other clients, this works really well. And so it’s going to depend on what’s set up on your side. Right. Um, but here’s what we can do and what, and what we typically see, uh, and it’ll just depend again on what, what you’re doing on your end on the other half of the equation.

Zach (46:54.015)
Yeah, no, that makes a lot of sense.

Preston (46:58.343)
Well, Zach, this has been a fun conversation today. Thank you so much for calling in. Hopefully it’s been helpful for you.

Zach (47:03.571)
Yeah, this is super helpful. I appreciate it so much guys. Yeah, it’s really cemented a lot of ideas together, finally.

Clay (47:08.972)

Preston (47:11.379)
Good, good, great. Why don’t you let people know really quickly where they can find you and then we’ll sign out.

Zach (47:15.967)
Yeah, so you can find me on line at or on Instagram at gumptiondesigncompany.

Preston (47:25.811)
Perfect, I love it. Zach, thank you so much for joining us. I’ve been Preston Lee with and of course, Clay Mosley from Thanks, Clay. All right, we’ll see you guys.

Clay (47:33.214)
Yeah, thanks a lot guys. See ya.

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'Freelance to Founder' Podcast

Freelance to Founder is a unique call-in show helping real-life freelancers grow their businesses and escape the feast-famine lifestyle. The podcast is co-hosted by Clay and Preston, two former freelancers who have started, built, and even sold six- and seven-figure businesses of their own. Catch the Tuesday Q&A episodes, dive deeper with Thursday's call-in episodes, or join us on the air and take the next step on your journey from ... freelance to founder.

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