Whether to Freelance or to Run a Company?

Published on in Director's Cut

by featured blog contributor, Jeremy Pinckert

In working as a director and also as an owner of a video production company for 10 years, there are many different categories of relationships I have experienced. There is the all-crucial client relationship. Then there’s the relationship between collaborating colleagues. There is a certain dynamic between myself and staff employees. And finally, there is the relationship I develop with vendors and freelancers. This last relationship with freelancers is one I want to look at from the perspective of my experiences from both sides of the coin.

I started my career as a staff associate producer for a broadcast storytelling production company in Indianapolis. Our clients were large networks on the coasts like the History Channel, Discovery Channel, and ESPN Original Entertainment. These networks would sub out the entire video production of longer storytelling specials to our production team. I eventually worked my way up to staff producer, and in this role would plan, direct, and work with freelance video crews on shoots. In the edit, producers would work with either the staff editor, or a variety of freelance editors who had the creative chops to enhance our vision for projects.


As most creative jobs go, I got paid peanuts to work long hours, travel, and jump through hoops to establish my career. But my future changed when I met a freelance producer we had to hire because we were so busy. She was older, established, and most importantly, made money doing the same thing I was doing. This idea kept festering in my mind, and before long I decided to go freelance and move closer to Chicago, where I could find work for other production companies producing & directing similar entertainment television stories. I had to travel more, but as a freelancer I was able to make more money and control my schedule, all very important to me in my mid-twenties.

The next decision I made would be the one I want to discuss today, where the distinction between freelancer and production company had to be made. After working as a freelance producer for a while, I came to a point in my life where I was starting a family and didn’t want to travel as much.  I didn’t have the experience to transition to directing advertising campaigns at that point, so I decided to focus on becoming a production company.  Instead of freelancing for other production companies in Chicago, I would focus on my small neck of the woods just outside the city, and provide the level of broadcast storytelling I had been taught on entertainment television for corporations and small advertising campaigns.

How to work with freelancers if you’re a company

As an owner of a video production company, rather than wear many hats like other small companies I had observed, where the internal staff shoots, edits, directs, does motion graphics, and makes $.05 per DVD making dubs, I decided my model would be to focus on what I was good at: directing, producing, and managing clients. I used freelancers for all of my shoot crew, my editing, motion graphics, narration, music licensing, finish and replication work.

A few years went by, and I grew to the point where I could hire some producing staff, but still develop key freelance relationships with DPs and other crew. I looked for talented videographers who had access to equipment, a good eye, and who were geographically close so I could be flexible in setting up shoots. One Director of Photography I ended up working with almost exclusively was a freelancer who had his own video production company, but he seemed to be working on smaller projects I didn’t want. Trusting this dynamic, I was able to introduce him to my biggest advertising client at the time, who themselves had given me a great opportunity to direct larger advertising campaigns. We had no written agreement to define our freelancer - video production company relationship, only what I thought was an understood ethical boundary code.


You can probably guess where this is headed…the agency relationship with my company soured after a few years, and the freelance DP who also owned his own small production company decided to use this to his advantage and work with my client directly.

Many, many companies have similar stories, but luckily, unfortunate experiences generally lead to learning opportunities. For our company, we couldn’t cut off all freelance relationships, and quite frankly, in our smaller market we didn’t have a large enough freelance talent base to choose from. So we decided to protect ourselves the only way a business can: legal non-compete contracts. This worked like a charm, in the 5 years since we haven’t had any similar issues.


What do you do if you are a freelancer and you also have a production company?

After ten years in business as a production company, I am finding myself wanting to focus more on the Directing side of the business. I’m working to get my name out in New York, LA, and of course, Chicago, but this time as a Director for advertising agencies and production companies.  The time is right to leverage my experience and work on exciting new projects.

Recently I met with some potential clients in Chicago who could use me as a freelance Director for big-brand TV commercials. At one of the meetings, the video production company was structured as an in-house crew, and the idea of using an outside freelance director was appealing, but the fact I also have a video production company (albeit one 100 miles away) was a source of potential anxiety for them. They asked me questions like, “What if their client called me directly?” “What’s stopping me from just moving my production company to Chicago and taking their leads?”

Having been through this before as a video production company from their point of view, I completely understood the anxiety, and I told them exactly what I would do if I were them: have me sign non-compete contracts. Essentially, any client they introduce me to, and any client they are currently quoting, is off limits for a set period of time.  

I’m not in the market to open a video production company in Chicago.  But even if I was, if you’re going to be a freelancer and still be a video production company, or if you’re a company looking for freelance talent, you should operate under these simple rules:

Tips for smooth freelancer - hiring company relationships:

  1. Sign a non-compete outlining the limits of the relationship between freelancer and hiring company.
  2. When working for a company, work as an extension of that company to the client.
  3. Your company name should never be communicated in front of a client if you’re a freelancer.
  4. Never break trust for personal gain. What goes around comes around, and if you climb to the top on the backs of those who trusted you and gave you an opportunity, you can be sure the same karma will come back around to eventually hurt you in the end.
  5. Pay people what they are worth.  If you’re a hiring company, and you are gaining on the backs of freelance talent shoot after shoot, pay them their rate.  Honor the relationship with loyalty and you’ll be surprised how many ideas and production tips you’ll receive in return.

Jeremy Pinckert is an award-winning freelance Director and the owner of Explore Media.  You can follow him on Twitter @videocompany, see him on LinkedIN, check out his video portfolio reel, or download his free manual: How to Produce for Video!  


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