Using Upwork to Build a Profitable Subscription Web Design Business: Part 2

Jan 17, 2023

Last time, we began discussing how to use Upwork to scale up and build a successful business. 

I attempted to break some false beliefs you may have and point you to the reality of becoming a business owner: A successful business involves paying people less to do work than you are being paid for not doing the work. 

As counterintuitive as it sounds to anyone with the employee mindset, it is the only way. 

With most of the philosophy out of the way, let’s get a bit more practical.

Hey by the way…get subscribed if you’re not already! 🙂

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The Filipino Secret 

When I go looking for new employees, I ALWAYS start in the Philippines. 

Not because I have a particular obsession with the Philippines or its culture. I’ve never even been there before. 

But because there are some interesting things about the Philippines that make it particularly conducive to working with their people as an American businessperson. 

First things first — I cannot speak in the abstract before I speak in the personal. 

love my team. Every one of them is so special and important to me. They are not “the help”. They are not servants or slaves. They are not underpaid. They are not forced to do “the dirty work” or any other nonsense you may hear from people. 

My people are first class, and I would go to the mat for them. And I have. And I’ll continue to. 

At the end of the day, it does come down to the person. I have some of the most amazing people on my team, regardless of culture. 

Let me also say, I also use people outside the Philippines. My designer is from Mexico and my advanced developer is Dutch but lives in Brazil! 

So, what makes the Philippines special? Why look there first? 

A Culture of Loyalty 

Filipinos are intensely loyal. If you treat them well, are sensitive to their needs, and simply care about them…they will do everything in their power—and I mean that—to ensure that you are happy. 

They don’t want to steal your money, your time, or your clients. 

They are not entrepreneurial in that way. They are proud of the work they do for you. They brag about their job to their family if they have a good boss. 

Because remote work/virtual assistance is the #1 Filipino export, they are very accommodating. My project manager, Brian, even works hours that put him up late at night/early in the morning for him, but they are normal work hours for me. 

That overlap is significant; even so, though, not a deal breaker if you become used to adopting asynchronous communication (which we do). 

Fantastic English

There are many different native dialects in the Philippines. 

Because of this, many/most Filipinos end up being taught English from a very early age, because it is a way of communicating across relationships with people that may come from different areas. 

Their primary languages are Filipino (basically an updated version of Tagalog) and English. 

Admittedly, some have better English than others. Some can type it better than they speak it and vice versa. 

My SEO copywriter is from the Philippines and writes incredible English. I’ve never heard her speak, but she probably speaks incredible English as well. 

This makes a huge difference considering that, if you’re reading this, chances are you work with primarily English-speaking clients. 


This will not matter to everyone, which is fine. But I am a Christian and we do a lot of work for churches and religious organizations. 

It is helpful when the entire team can be “on mission” together. And chances are high that when you engage a Filipino, they come from a Christian upbringing/worldview. 

So if that matters to you, it is a huge plus. Even if that doesn’t matter to me, it should be a comfort that they have a religious worldview that asks of them to be morally upstanding and honest in their endeavors.

They are very trustworthy and it shows in their actions. 

The Right and Wrong Way to Use Upwork

Primarily, there are two ways you can use Upwork to find talent: 

  1. Know what you’re looking for and seek out the talent

  2. Post a job post out there and wait for responses

Within those, there are lots of different options: 

  1. Hiring on the spot

  2. Inviting to a project

  3. Hourly pay

  4. Project pay

  5. Weekly pay

  6. ETC 

Lots of options, which is great!

…and a little overwhelming. 

This is just my opinion, it is not science. But what I like to do is seek out the talent for myself and extend an hourly contract offer right away. 

The main reasons I do this are: 

  1. I don’t want to field responses from people. 

  2. I know what I am looking for, which has a lot to do with communication style and skill, which can often be told from the profile alone

  3. It shows commitment – project invites don’t get responded to a lot of times. I want the worker to feel like I have searched them out and found them, and I’m committed to making something work if they are. Because it’s true!

A student of mine, Victor, is taking a different approach. 

He started by hiring two different workers to complete the same project. Found one he likes to work with, and plans to work with that one on future projects. 

And that’s just fine!

That worked really well for him, and it could work really well for you too. 

One big difference is the project was relatively simple and did not require specialists in any area. My team works on projects that usually require specialists in a different area (SEO, design, development, etc). 

Plus, we need a project manager because we have so many plates spinning. 

Not every team dynamic is going to look or work the same — but dive in and start seeing what works for you. It’s never too soon to start down this path.

Next up…

We’re going to close out this series next time, where we’re going to talk through two very important things. 

  1. How do make enough money with subscription web design to scale? That’s one of my favorite topics, and we’re going to dive deep into it. 

  2. I mentioned that we have specialists on our team. That is true. But it’s not always about the skills of the people…more sometimes it’s about the system itself. We’ll dig into how to build a system that works. 

Hope you’re enjoying this mini-series! 

If you want to work with me in a more intimate setting to discuss how some of these principles apply to your business, consider my mentorship program at