Using Upwork to Build a Profitable Subscription Web Design Business: Part 1

Jan 4, 2023

As I work with students in the SWD Mentorship Program, I am delighted to find many people interested in scaling their businesses. 

I’m passionate about that topic anyway, but even more so as it relates to subscription web design. Why? 

Because it’s hard enough to build a subscription web design business, let alone build one with the power of scale built in. 

And by the grace of God alone, I have done both. 

One of the key tools in my Arsenal of Possibility is called Upwork. Our agency would not be what it is today without this incredible resource. 

So, how can you use it to build your own profitable subscription web design business? Let’s talk about it.

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The Philosophy of Upwork

Upwork was formerly oDesk and in the past few years merged with another company called Elance. 

These are companies that have embraced what has been called the “Gig Economy.” The idea, in short, is that you should be able to find and hire talented people to do small to medium size tasks for you online. 

This contrasts with the need to acquire a service provider, sign complex contracts, and pay exorbitant fees, only to have a small bit of work done. 

For example, I recently needed a podcast introduction recorded. In the past, how would I gave gotten that done? 

I would have had to: 

  • Somehow find a local recording studio that had access to great-sounding equipment

  • Find someone with a fantastic voice for doing this sort of thing, and that person would also have to be able to read intelligently and make the introduction “come alive” 

  • Engage the services of both those people, sign contracts, etc.

  • Hope and pray those people could also help with the mixing and producing of the intro

  • And more. 

The kicker is, because of my background in the recording studio industry, I would have had a way easier time than most people getting this done, and it STILL would have been a pain! 

The other day, I went to Fiverr (similar to Upwork) and typed in “Podcast intro for Christian podcast” and found the perfect person to do all of it in about 10 seconds. He’s a radio host on the West Coast of the United States. 

I paid him $50 and he did everything short of writing the script. Fiverr handled all the money for me.

That’s the gig economy.

What most don’t realize is that the gig economy can work in favor of business owners. It can big time work in favor of subscription web designers, too.

Now, over time, these platforms started allowing for the possibility of bigger and bigger jobs. 

There are now multiple ways to engage a worker on Upwork, for example: Hourly, Project-based, and even Weekly. 

There are multiple methods of discovery as well. You can search out talent and invite them to a job, hire them on the spot and wait for them to accept, or post your job and let them respond. 

Once you grasp the power of adding the gig economy into the back end of your business, you will never see it the same. 

Let me make one HUGE clarification right now, though, which we will discuss more below as well: This is NOT selling a job, telling people you’re doing the work and hiring someone to do it for you. I will not opine on whether that is ethical or not; it’s just important you realize that is not what I’m talking about. 

I’m talking about building an Avengers Team. Not pretending to be Iron Man.

Remote: An Opportunity, not a Concession

When COVID-19 first rocked the world, many learned of remote work for the first time. Even if they knew others had done it, many believed it could never be done in their role at their company in their industry. 

They quickly found that to be untrue. 

All over the world, teams and businesses made the adjustment because they were forced to.

By contrast, there are some companies (like 37signals, the makers of Basecamp) whose founders literally wrote the book on this way of working. They have been this way from the start. 

I am of the latter mindset. For me, remote is not a concession or a way to make my services more affordable or make the numbers work (although it does have those benefits). 

Remote is an opportunity. It is a way of business. It has unique advantages.

The easiest example is the minimization of distractions. Counterintuitively, many report they are able to stay more focused on their work and be more effective at home than at the office. 


Because while home has its distractions and, sure, boundaries are needed, the distractions are far fewer than those at the office. 

Bothersome bosses, busy water coolers, and regular cake breaks eat up so much time and account for so much context switching that getting work done is almost impossible. 

When I was working full-time in IT, even before we had to navigate COVID, some people would occasionally work from home (if they were allowed). Their reason? They had important work to do and didn’t want to be interrupted by the office.

Let that sink in. Read it again until it does. 

If you structure your business right, remote is an advantage. Everyone can get important work done, distraction-free, and be more impactful. 

Power Dynamics and Pocketbooks

To round out this introduction to using Upwork, let us address what is (rightly) a concern people often have. I am going to give an archetypal paraphrase of the “objection” as I’ve heard it from many: 

I have a hard enough time charging money for my services as it is. How can I justify hiring others at a fraction of what I am being paid to produce the work? My clients could just go hire them directly. Isn’t it unethical to be hired to perform a service and then pay someone else way less to do it?

Lots there. Can you relate to this thinking? There are two unspoken ideas lurking behind that paragraph that, once brought into the light, may help your thinking. 

Idea 1: Foreign vs. Domestic Hiring

When you use a Gig Economy service, at least as an American, almost always there is the assumption that you are going to be hiring someone from another country. 

And FWIW, this is true, although it is also true that Upwork, Fiverr, and sites like them are replete with domestic talent. You can absolutely do exactly what I am talking about here while keeping your Avengers Team in the U.S., if you believe strongly that is what you want to do. 

I am a proud American; I also do not hold the principled belief that I must hire only Americans. (In my next installment, I’ll tell you exactly what nationality I think you should hire and why.)

For now, I’ll say this: I and my wife are the only two North American teammates. Everyone else is from outside of the U.S. 

And the reality of this is, I pay far less for the same—if not better—talent than many U.S. citizens I’ve worked with. Not only do I pay less, but what I do pay is considered very nice in terms of the localities where I hire. 

Thus, my business is creating well-being in the world and providing a solid support structure for the families of those I hire. My customers are getting a better product. And, on top of it, it is a more economical way to run my business.

So while yes, it is true that almost everyone on my team is from another country, it is not true that my clients are getting less value. For reasons I will discuss next time, I would argue they are getting more. 

Idea 2: The “Employee” Mindset

Also lurking behind the archetypal paragraph above is the mindset that most new business owners have because they’ve only ever been an employee. 

The sheer reality of running any business is this: 

If you only charge the customer what it takes to pay the person doing the work, whether it’s you or another person, you will go out of business.

Why? Because you are not accounting for expenses, profitability, future growth, savings, or taxes

When I worked in IT full-time, the number I was paid as an employee is peanuts compared to what a person doing billable work was charging. Clients were paying, in some cases, 10-15x what it took to pay the people doing the work to make the result happen. 

Not because they are greedy and unethical! Quite contrary! They wanted to do the best work possible for clients, and that is impossible to do if you have no margin with which to build a successful Avengers Team and design systems they can use to deliver results. 

So here’s the mindset shift: Whether foreign or domestic, if you want to scale, you will have to become okay with paying employees far less than what clients are paying you. This is true if you’re a plumber, lawyer, course creator, or web designer.

Again, this is just the reality of business. 

But—where, then, is the value? Couldn’t your customers just hire your employees directly? 

We’ll answer that question—and many others—next time. 

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