Become a Kingpin and Scale Your Freelance Work

Freelancing rocks right?

You’re correct, but what rocks even more is being able to scale your freelance work!

Scaling freelance is something that you likely don’t think about all too often because you are too focused on creating enough work just to sustain your life. However, what if I told you that freelancing is actually quite scalable contrary to popular belief. In this article, I am going to help you lay the ground work to progress towards scaling your freelance so you can shut all of your friends up that think you are a slave to your time.

One of the biggest myths to the remote working freelance lifestyle is that you can only do as much work as you yourself can do. While none of us are freelancing superheroes, we do in fact have a network of freelancing friends.

As a freelancer, you quickly become friends with other freelancers that have totally different talents and professions. I am mainly an aviation digital marketing and writing freelancer, but I know my fair share of top notch graphic designers, videographers, photographers, business consultants, and IT freelancers in all different kinds of industries. This is not only great for helping me in having a support system in my ambitions, but it also allows me to become a kingpin if I choose to. Only if I choose to though.

So What is a Kingpin huh?

Yes, like the best of the best drug rings where there is always a drug lord or kingpin who hooks everyone up under him or her, freelancing kingpins can be the same way. Sadly the margins aren’t as good on freelancing as they are for the cocaine industry but we will make due.

Usually the more traditionally accepted term for sourcing your freelance work to other freelancers is called sub-contracting, but I like being weird.

When I first started my freelancing in Columbus, OH (my current city) I quickly became friends with someone who happened to be a great freelancer in the area as well. Even better, she loved helping other freelancers in getting more work. When her clients needed talent in other areas that she was no expert in, she hooked us up. She one times joked that she was like a freelancing kingpin for the Columbus area. She was so right, and the term stuck ever since.

I highly doubt she ever took large margins if any on the work that she sub-contracted out to me and others. That is just a testament to her huge heart for helping others. Nothing wrong with that at all, but this idea is where scaling is so exciting in my opinion.

Lately, I have had an influx of new clients. This is great but my new clients want work that either I don’t have time for or I don’t have expertise in. Most times, the unseasoned freelancer would turn away this new business. I however hate turning down new business so I outsource to my top-notch freelancing friends.

Here’s an example…

Just recently I got a video job from a client I have done work for in the past. Sadly, my schedule did not permit me to be able to make it happen this year. Instead of leaving them high and dry to find a completely new videographer for the event, I said I would make it happen for them.

I called up a friend in videography and he was all about taking on the job. So I gave it to him paying him a respectable $25/hr while the client was paying me $35/hr for my services. If you went to math school you can see that I make $10 per hour that my sub-contracted friend works. This is a win-win for my friend and I. Since my time to figure out travel logistics and such means something to me, I find this rate to be perfectly reasonable for the project.

This model for freelancing is what makes it totally scalable and perfect for anyone who wants to grow something that is a bit bigger than themselves. I love being able to get my friends more work and when clients love your work they are more than willing to pay a “premium” to know they will get that service. This is why everyone can win in the sub-contracting world.

This scalable model doesn’t come without some critical things you need to consider and be weary of

  1. You need to know and trust the breadth of your sub-contractor’s talent. In the end, your client rarely knows that you outsourced the work and so anything that happens, good or bad will fall on your shoulders and ultimately your reputation.
  2. You could lose MORE time and money if you aren’t careful. For example, if your client loves to have a lot of meetings (this is all you focus on as a Kingpin usually) than you could end up loosing your margin calculated in an hourly project rate.

It takes a semi-conscious business mind to make this model work because you must make sure that all of the margins make sense for everyone involved.

I know, you as a freelancer rarely find necessity to think in this way. That is why I am writing this article. You see I came from the business world first where I always was looking to scale products, then I came to the freelance world and love the freedom but hate that people think that this life is not a scalable career path. It totally is.

So are you super excited about adding this concept to your freelance life?

Okay I know you are fidgeting in your seat with excitement, but before you get started adding creatives to your kingpin ring make sure you practice or have these below traits ready:

Don’t be a control freak.

If you try to control your sub-contractors you run into problems. Primarily you will waste too much time on corresponding and less time using up your free time to do whatever it is you wanted to do in the first place. Also, you run into the possibility of them not being as creative as they need to be. Foster an atmosphere where they feel like they can take your brief and run with it. They are the professional in that industry, trust it.

Be able to fire quick.

Ultimately it is your reputation and personal brand on the line. If someone you sub-contract doesn’t hit the mark for you, be able to fire them (not do business with them in the future) quickly. Try not to make excuses for giving them multiple shots, it will only hurt your brand beyond repair and will make you look bad and you will lose more money.

Once you have those two traits locked down, you are on the track to making this a plausible addition to your freelancing empire. Let me be clear though, this scaling strategy is great but not for everyone. Some people start freelancing to work alone and that is okay. Some start freelancing to make just enough to get by so they can spend their time working on a hobby, music, or other special skill. However, for those who get into the service based industry to build something larger than themselves, this is how you can get started.

For me, I have started to scale my freelancing work. I love it, I am still figuring it all out, but it is working. In the long run I hope to one day create a remote working advertising and marketing agency specializing in aviation. This all starts with slowly building client relationships and practicing managing a team of sub-contractors. Embracing that an agency can be built out of growing and scaling freelance is the exciting aspect of this strategy.

Tools to use for scaling

When you start to scale, it is critical that you keep your process streamlined. You may not see it now, but when you have ten plus clients and a few sub-contracting projects going on at once, you need a way to manage your communications and financials.


Freshbooks Cloud Accounting

First and foremost, FreshBooks is the product to subscribe to when it comes to managing your client accounts, invoices, expenses, and team time tracking. This cloud accounting software is the freelancing industry standard and I use it religiously every single day. It is incredible and it is a must if you are looking to manage all that detail kind of stuff with a team (or alone). You can try it FREE for 30 days to see if it is something you too will love!


Honestly, I am still getting used to Slack but it bares being recommended for this. You can easily add your sub-contractors to a conversation and talk about the project instead of moving from iMessages, gChat, and Facebook Messages. Keep it all in one chat so you can cut down miscommunication, emails and such. Plus, Slack was made for this!

Shake App

Shake Law app Sub-contracting

When it comes to making legal agreements quickly as a freelancer, I recommend using the Shake App. This was made for freelance contracts and all the legal mumbo jumbo. You can make payment and deliverable contracts via the app so you and your sub-contractors can sign it. BUT, I am not a lawyer, and shame on you for taking this advice before first consulting your attorney.

A pair of really nice ear buds

You’ll likely start to fill the “Account executive” role with your clients. From taking meetings to corresponding between client and sub-contractors. You will be on the phone a bit more, and you will quickly get sick of holding your phone to your ear. I have the Apple earbuds with the microphone on it so I can easily talk while I do other work. I also own a bluetooth Jawbone but I find it just isn’t cool to use in public anymore. #WrongGeneration

Final Thoughts

You shouldn’t fear growth as a freelancer. This article hopefully has shown that you can easily scale if you want to. Remember, there are always freelancers in your area looking for more work, you can help them get it!

The last bit of advice I will give before I leave you to your day, is that freelancing is still volatile. If you had a sure thing, you would already be turning it into an agency and employing your sub-contractors. Remember this, and be diligent to not jump into agency creation prematurely. I obviously have never created an agency so I can’t give advice from that end, but I know for a fact that I desperately want to create one but know that my influx of work this month will likely follow with a dramatic wane next month. That can’t happen when you have employee’s livelihoods depending on it.

So test it out this week, give some freelance work to a friend and feel how awesome it is to make a form of passive income that gives you more free time to generate more new business.

I want to hear from you, comment below with any advice you have or questions about becoming a kingpin of freelance.