Building an Agency: Find Clients or Hire Freelancers First?

If you're seriously considering owning a content agency, one of the first things you have to address is a conundrum. Should you find clients or hire freelancers first? It's a real concern to ponder. It's a chicken or egg thing and how I did things is not necessarily the way to do it.

Although things turned out okay, I have come to believe I didn't do things the best way. I started my agency 9 years ago and it wasn't my first choice. Looking back, I think I would have done exactly the opposite from what I did.

I wasn't even thinking about becoming an agency owner when I became one. Two of my clients asked me to produce more content than I could do on my own, thus forcing me to either stop working for them or hire writers to help. Because I liked both clients, I opted for the latter.

Feeling the pressure to make my clients happy, I quickly assembled a team. Initially I hadn't even considered going to Elance (the predecessor to Upwork). I asked friends for referrals and I posted jobs on Craig's List.

The Best Way to Hire Freelancers for Your Agency

Although I had supervised people in my previous jobs in the corporate world, I had no experience hiring anyone, let alone an understanding of how to hire freelancers—which I came to learn isn't the same as hiring in the corporate world.

In the corporate world, face-to-face interactions make it easier to determine whether someone is reliable or a flake, has a personality that works well with yours or grates on you, has the expertise needed and one more thing people aren't supposed to discuss but may be the biggest overall determining factor.

Let's talk about the obvious ones first.

If you want to hire freelancers to round out your team, here are some things you have to screen for up front.

How to Hire Freelancers Who Aren't Flakes

Any potential freelancer for your team can have all the expertise in the world but if they aren't reliable, what good will it to do to hire them? I learned this the absolute hard way my first month after I started to hire freelancers.

The very first freelancer I hired was recommended to me by a family member. Jason was a a gifted writer. From the first writing sample he sent me, I was bowled over by his ability. And damn did his writing chops put mine to shame.

The first big job we got was to write 20 articles about reggae music legend Bob Marley. What a fun job, right? The best part was that Jason and I were able to choose the topics. He chose the ten he wanted and I chose my ten.

We had a week to write them. I started mine that night. I didn't bother to ask Jason when he would start his because I had already told him two of my philosophies:

  1. On time is late and early is on time
  2. Under promise and over deliver

By day three I was finished with mine. I asked Jason to proofread my word and closed the email with, "make sure to send me yours to proofread before we send them to the client." Jason proofread mine and promptly returned them. "Ready for delivery," he said in his email.

I sent the first ten and the client was pleased.

I waited. I waited some more and finally the night before they were due I checked in with Jason to see where his were. "I have two completed and I've just been given tickets to the sold our Slash concert. I'll be gone for a few days. The concert is in California." Jason lives in Portland. "I'm leaving in an hour and driving down there. I'm really sorry. You'd do the same in my position."

"No, I wouldn't. I wouldn't leave you stranded the night before a job's deadline. Why didn't you write them the last few days?"

I honestly don't even remember the answer. I remember thinking several things: "What an asshole to dump his work on me." "Why the fuck hadn't I checked in with him two or three days ago?" "I guess I'm staying up all night and writing his remaining 8." And I thought one more thing, which I verbalized to him.

"You fucker! You're fired! I'll send you payment for these two after I get paid and don't fucking call or write me again you mother fucker!"

I stayed up all night, pulling my first of many 15-hour work days, wrote them all and turned them in. The client was very happy with them, paid me and gave me a bonus. I think you already know I didn't offer to share it with Jason.

I learned an extremely valuable lesson. Prioritize reliability over talent/expertise the next time I decide to hire freelancers. And to be honest, although that was a huge learning lesson for me, I have had to learn it a few more times because unlike face-to-face interactions where I can see people's facial and body expressions, folks can talk a good game. And in my experience having hired well over 200 freelancers in the last 9 years is something that will blow your mind.

75% of freelancers of flakes and it may be completely unavoidable hiring them. I shit you not. 75! I used to keep a spreadsheet. I stopped. The only difference is that now when I hire freelancers, I expect it. It's happens less frequently than it used to but I can't avoid it now that I know the odds. The other difference is I no longer feel badly letting flakes go. I used to agonize all night over the decision to let someone go. Flakey or not, people need to eat.

Personality is Crucial If You Want to Hire Freelancers

This is pretty simple. Don't hire freelancers who are jerks, have large egos and are selfish. I don't care how talented and reliable they are, you will regret it. Their needs will always come before yours.

Freelancers don't have to be talkative. Most writers are introverts. I am one of the few writers I know who's an extrovert. This may be why I do well in the role I'm in. I love chatting people up, which is the one complaint I hear from many introverted writers. Their shyness can make it difficult to feel comfortable interacting with clients. Many have told me they like the fact that I do all the interacting and all they need to do is show up and write.

And writers don't need to be friendly to be team players. Because I have a team of freelancers, all of us spread throughout the world, having people who can follow my simple rules of being courteous to others isn't dependent upon them being outgoing.

I've learned in my life that jerks are present in all races/ethnicities and countries. They span all political and ideological beliefs. Nobody corners the market on being nice and nobody corners it being jerks.

You Are Bound to Hire Freelancers with Untreated Mental Illness

Perhaps not politically correct to write this but it's a fact. I have hired some incredible people in my time. The National Institute of Health of Health estimates one in five people has mental illness of some kind. This can include mild to severe, such as mild depression and panic disorders to borderline personality disorder and bipolar and more.

Forbes estimates 57 million people in the U.S. freelances for their work. This means 36 percent of adults who can work are freelancing. Doing the math, it seems conceivable when you interview and hire freelancers, a percentage will have mental illness.

And having a form of mental illness in and of itself isn't a big deal. For it's not a deal breaker at all. But I can tell you from personal and professional experience that when a person doesn't treat their mental illness, it's a huge problem. And I personally don't care how it's treated. I have a panic disorder and I smoke a lot of marijuana, which helps keep it controlled by an incredible amount. Others I know and have working with me use either weed or one of Big Pharma's meds. As long as it's addressed and treated, I don't care.

If this sounds callous, consider this: I get all the reasons why people don't want to treat mental illness. The side effects of Big Pharma's drugs are many and some of them range from a pain in the ass to dangerous. But untreated mental illness will impact so many areas of your business. It can be stressful on you, your team members and your clients.

Erratic behavior, lashing out, extreme highs followed by extreme lows can have all sorts of repercussions. I once hired someone who was with me for three years. She was an integral part of my team. She was yin to my yang and what I couldn't do, she could and vice versa.

I knew early on she had bipolar disorder. I didn't care because she said she was treating it. About year two I noticed she'd be superwoman for six months and become despondent and disappear for six months.

In her down period, I couldn't find her anywhere. I would call, email, try her on Facebook, even call her sister. When she came out of it, I begged her to treat it. She would and then feel amazing through her euphoria phase and stop taking them, and thus the cycle started up again.

I suppose I could have hired her for six months out of the year except in this case with each low, the lows were deeper and more difficult to recover from. In the end, she disappeared and I haven't heard from her in two years. I know she's alive, which is all I care about.

The weeks leading up to her final disappearance were extremely challenging as three of our clients noticed her repeated fuckups. I found myself struggling between telling them the truth and bearing the brunt of her issues.

In the end I chose the latter. A team is only as strong as its leader. No matter what happens you can't throw your people under a bus. And because your name on the line, you have to step up and just handle it. And believe me, your clients will ultimately appreciate that approach.

I'm not suggesting you shouldn't hire freelancers with mental illness, but look out for signs and consider talking very seriously with them—as a friend, not a client/boss. Ask them to consider meds, but beyond that you just have to determine what you can do and how much you can take. When it's impacting other people on the team, your clients and/or you, it's not being insensitive or discriminatory to want what's best for the majority—even if you want to be supportive to the person struggling.

To be clear, I won't not hire a freelancer with mental illness. If I start to notice signs and behavior that could indicate a pattern, I have inquired, again as a friend, and decided things on a case-by-case basis.

The irony is I've noticed the freelancers I've hired with mental illness have turned out to be among the most talented. There are theories that mental illness and high intelligence and brilliantly talented often coexist in the same body. I have seen this.

In Summary

It's been a journey being an agency owner. If you decide to become an agency owner and hire freelancers, I can tell you one thing with absolute certainty: ensuring your clients have the reliable expertise needed to complete their jobs will be both amazing and gut wrenching.

Fortunately the longer I'm in business, the gut wrenching times are fewer and farther between than when I first opened my business 9 years ago. I don't know if there's a tried and true method for hiring people. I know what has worked for me. My goal is to give you things to think about.


I started freelance ghostwriting in September 2009. A little late by some standards, given my age at the time (42) but I was reinventing myself after serving a 20 to life sentence in corporate America. I didn’t have any professional writing experience when I started and I had to do a lot of on-the-job training. Every time I learned something, I made note of it and tried not to make the same mistake twice.

While I was registered with Elance (an online bidding platform that matched clients with freelancers that no longer exists) I was very active and visible. I was a member of their 10-person panel they tested new features on before they rolled them out site wide. I wrote a regular column for their blog designed to help freelancing newbies.

I established my content writing agency a year after I started freelancing and went from a freelance force of one to an agency owner.

None of this means I'm an expert. It just means I have many years' experience as a freelancer and I'm hoping some of my advice can be helpful to you.

If you have a question ask here.