030: How To Build A Freelance Business (Brennan Dunn)

Brennan Dunn

What does it take to make the transition from being a skilled freelancer to being a savvy business owner? Quite a lot actually, and here to tell us is Brennan Dunn.

Brennan is a former programmer employee turned freelancer turned agency owner and now savvy business man. He’s been in almost every role you can be in while in the working world: employee, contractor, freelancer and chief owner. What he’s learned about creating a successful business he now shares with other freelancers and potential freelancers. Have a listen as he spills the beans on the 30th episode of How’d You Get Into That?.


Born and raised in Fort Lauderdale, Florida Brennan always had an interest in technology and web-related things. He did miscellaneous projects for family and friends. His first non-family or friend gig was for his high school. While in still in school there, he was asked to create the web site for the school. He agreed. Even though he knew nothing about creating infrastructure for the site, he learned it all as he went along.

That was a theme that would play a significant role in Brennan’s professional life from that point on.

Worried he would grow to hate technology and web development, Brennan went to college for liberal arts. He studied the classics and envisioned becoming a professor at a university somewhere or perhaps a high school English literature teacher. Although he loved his studies, he soon saw the frivolity in what he was doing. Why was he spending $50,000 a year at college just so he could get a $35,000 a year job when he got out?

And when he started earning real money – far more than he had ever earned before – doing web work, he left school to pursue his technology and web interests.

His next step was taking a job at a software company and continue to look for moonlighting gigs on Craigslist. But he soon discovered he was terrible at closing! It was easy if he was talking to a family or friend, but if it was anyone else he seemed to botch it somehow and so his freelancing career didn’t grow until later on.


  • What was one of the best lessons he learned from his first agency experience?
  • If he were starting fresh, what would he do differently?
  • How to think of yourself as an expert, even if you don’t think you are.
  • What does he love about consulting?
  • The biggest mistake freelancers make, according to Brennan.
  • And so much more!

Brennan left the software company awhile later to build a start-up. The company created lead generation for mortgage brokers. Little did he know the real estate bubble was about to burst. Even though the product they created was great, the company folded when the sub-prime mortgage crisis hit. The company simply couldn’t weather the poor economic climate and they closed.

He was back on the job hunt and soon landed a programming job with an agency in Miami, Florida. Although he didn’t necessarily agree with how the agency landed their clients, he was happy for the work. He stayed put til his wife became pregnant and wanted to move to be closer to her family in Virginia.

So off they went. Brennan kept his job at the agency and worked remotely. That only lasted a few months, they weren’t used to remote clients and wanted his physical presence in their offices. He gave his notice and began looking around for work.

Not finding anything in their remote region, he decided to get his own clients and freelance. He found one and that company wanted him to do a lot of different things for them, so he started partnering with people he knew who could help him with various tasks for that client. He and his partners agreed on a split of the fees and they ventured on.

The system worked until Brennan’s client didn’t want to work with anyone else but him. So it was back to freelancing on his own. But that didn’t feel right to him so he invested in office space, furnishing an office and hired a business developer – all so he could do it right this time. He wanted his own agency and wanted to hire staff, employee people and build a company together.

Within two years, there was a staff of 11 people working for him and he had a payroll of $100,000 every month. He was traveling, meeting with his clients all over the world and generally feeling the challenges of it all. There was no recurring revenue so every month he was faced with making payroll plus his other expenses.

It didn’t take much longer for Brennan to know this wasn’t his dream either. He was away from his wife and two kids a lot, and he didn’t want to be. He was also enamored with the product creation concept and the lifestyle it offered. He realized he had the technical know-how, the equipment and everything else he needed to create products for himself. In fact, he was doing that now for his clients but not for his own business.

So he devised a plan to let his employees go by giving them the clients they were working on to take on as their own clients. They were also given first preference for any new work that came in. Everyone who had worked for him was given this offer and many of them built their own companies without missing a beat.

Brennan was then free to create and build his own products, which he did. Today he is the successful owner of the Freelancers Weekly site and has launched multiple products; he also continues to consult on a limited basis.

And happily, he has plenty of time to play with his kids and see his wife too!

Please join me in thanking Brennan for sharing his knowledge biscuits on the show; he’s an awesome guest and it was great to chat with him. Leave him a comment or send him a Tweet.

Tweetable: “I looked at myself as an engineer first.” Brennan Dunn


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