So You Want to Be an Agency Owner

Something I'm frequently asked about is how to become an agency owner. It seems a natural progression to go from a freelance force of one to managing a team of freelancers, doesn't it? Well, actually no. They're extremely different and not every freelancer is built to be an agency owner—and vice versa. For some it can be a natural segue. For others it can feel like you're in some grade B Science Fiction film from the 1950s.

I'll lay it all out and you decide what's best for you.

I started writing in 2009. Less than a year later I was managing a team of six writers. I wasn't looking to manage writers and I certainly had no designs on being an agency owner. It just happened.

From the moment I started freelancing I used bidding sites to get work. Soon after I joined Elance (the predecessor to Upwork), I was invited to bid on two interesting jobs. One was to write about boomers and seniors and the other was a survivalist site (also commonly referred to as off the grid).

Both clients indicated to me that if things worked out, they'd "give me more work than I can handle." I am a skeptic by nature and assumed they were trying to reel me in so I would give them a discount. It turns out they were both very serious. And soon I had to make a decision to either stop writing for them or find other writers to work with me.

I chose the latter, seeing it as a temporary situation. I had no designs on owning a company and managing a team of writers forever. At first I hired one writer, then two and before I knew it I was managing a team. What's crazier is that I found myself liking it. I even solicited the two clients for more work. But there was a problem.

I knew nothing about owning an agency. I had supervised people in my previous corporate jobs and previously owned an event planning business, but neither prepared me for being an agency owner.

In my event planning business I hired people for events but otherwise I did everything myself. And in my corporate work, I wasn't the one hiring. I just supervised their work.

Agency Owner: Trial By Fire

Still brand new to freelancing and suddenly thrust into something I only jumped into because I hadn't considered every angle first, on the fly I had to figure out how to (in no specific order):

  • Come up with a company name
  • Hire freelancers
  • Manage projects vs. single deliverables
  • Know the difference between farming out work and being upfront with clients*
  • Pay people remotely (I live in Puerto Rico and most of the online accounting programs don't recognize Puerto Rico and/or don't allow me to pay people in every country)
  • Know when to walk away from assholes masquerading as clients
  • Continue writing (whether with my team or separate clients)
  • When and how often to raise my rates
  • Figure out how much to charge so that my freelancers got paid, there was enough to run the business and feed my family and me
  • Be pushy (not to the point of getting fired) when clients paid late
  • Manage cash flow problems (freelancers completed the work but I'm waiting on a client's payment to clear)
  • Let shit roll off my back more easily and accept that some may see me as a bitch because women who push back are always bitches!
  • Resist the urge to respond to everything and everyone who annoys me or tests my patience (including freelancers calling me a farmer)
  • Deal with flakey freelancers and learn how to minimize that going forward
  • Manage freelancers' work (including editing before delivering to clients)
  • Create a contract with non-disclosure agreement that spell out everything in easy-to-understand English
  • Learn the art of diplomacy with clients (especially when I needed to fall on my sword for one reason or another)
  • Walk the fine line between agency owner, mentor and friend
  • Know when to coach and when to let someone go
  • Learn not to be fucked up for a week or two when I've had to let people go (no matter the reason, taking away someone's livelihood is not fun!)
  • Research my competition and benchmark myself against them
  • Write a business plan
  • Create an LLC where I have to comply with Puerto Rico's local rules and the U.S.'s (because Puerto Rico is a colony) in a language that isn't my first or even my second
  • Market us and make sure I had enough work coming in to feed everyone

In other words, I had to learn to be:

  • Human resources
  • Managing editor
  • Supervisor
  • Mentor
  • Accounts payable
  • Accounts receivable
  • A marketer (something I had done in my previous life but this was a whole new industry)
  • Paralegal
  • Secretary
  • Recruiter
  • Diplomat
  • And a CEO who is taken seriously

And the craziest part is that I had to learn all of this while not fucking up what I was doing, such that good clients or freelancers didn't leave. I had a HUGE learning curve!

*Regarding farming work out vs. being upfront: a mistake many overwhelmed freelancers make is farming out work to other freelancers without being upfront with their clients. This causes a situation where the freelancer is biting their nails, hoping the second freelancer gets the work done on time. It's a recipe for disaster and sets everyone up for failure.

For one thing, many new-to-farming freelancers set extremely unrealistic expectations for delivery dates, oftentimes not allowing enough time to look over the work before submitting to their client. And in my experience, more than 75% of freelancers are flakes, so this scenario wouldn't work for me.

I'm personally not a fan of farming out work because of the potential for disaster.

Initially I sought out a mentor but got many doors shut in my face. Some told me (without bothering to read my emails or listen to me) they couldn't help my company because I'm in Puerto Rico and don't speak English (yeah, seriously). The other issue was would other agency owners really want to groom potential competitor to them? I would but I doubt most would.

So I went mentorless for months, and by the time one agreed to mentor me, I'd already spent several sleepless nights figuring it all out.

And this isn't to suggest I knew it all. I continued making mistakes—especially hiring. It took me a while to get the hang of how to look for freelancers. What I learned about hiring is that it runs counter to what you might expect.

This first blog is to get you to look at all that goes in to being an agency owner. I've given you a lot to think about. There's a lot that goes into being an agency owner. I'm happy to spend the next several weeks dissecting one facet a week.

So stay tuned!

Photo credit: Association Zavata

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.