How to Go from Freelancing to Starting a Digital Agency and Growing it over 7 Figures

By Jason Swenk on June 8, 2016

In this episode, I’ll cover:

  • 3 steps for transitioning from freelancer to agency owner.
  • How to identify and overcome growth struggles.
  • How to hire when you’re ready.
  • #1 advice for newbie owners.

Rob Riggs has a great story to share about his digital agency journey, and it all begins with freelancing for a pretty awesome guy… ME 🙂

Seriously though, I met Rob through owning my digital agency and we frequently sent work his way. Over the years Rob has turned his freelance business into a thriving digital agency. In this interview, he tells us about the transition that began in 2004, from a one-man show to 12 person digital agency, Your Design Online. He shares how he overcomes challenges, how his role has evolved, and what he would tell his former self to do differently.

3 Steps to go from freelancer to digital agency owner

  1. Identify a narrow niche. Rob says he stopped taking on “just any project.” He drilled down to a specific niche and became a specialist.
  2. Go outside your comfort zone. In Rob’s case, he emerged himself in more complex projects that were beyond building websites. He took responsibility for delivering results and showing ROI to his clients.
  3. Be self aware. Know what you stand for, what you believe, and what you are (and aren’t) willing to work on. (For more on that check out this post on how to Quit Being a Prisoner to Your Agency, and read about an agency owner who created his agency around his life – not the other way around.)

Solving the biggest growth challenges

Rob says his biggest challenge, at first, was landing projects that were beyond what he could do himself. Once he got over that hurdle and grew to 3-4 people, then they were dropping the ball with details. As they grew even more, their issues were with delivery.

You’re always going to have issues, they just evolves as your business grows. The key is identifying the issue and the need for change. Then take action!

When project details were an issue, Rob says they starting using Basecamp. When they outgrew that tool, they adopted new PM software that did more in the backend. When delivery was an issue, they created standard operating procedures for delivery.

It seems counterintuitive but your need systems and processes that are made the be changed. Have a system in place for everything, but be able to identify when that system needs a makeover.

If you have an isolated problem, you get through it and you learn from it. But if there is an issue that becomes a repetitive problem, there needs to be a standard process for avoiding it. As Rob says, “I never want to type the same sentence twice.” And he’s right – if you have great processes in place, you shouldn’t have to!

How to find talent when you’re ready to hire

Rob’s first hire was a developer, who has been with him since the beginning. His role has evolved significantly over the past 12 years into project manager, problem solver and he’s now a key decision maker who runs things while Rob is out of the office procuring new business. Rob says he always looks to hire people who are sharers. Part of his process is to do a post-mortem after a project wraps. They talk about things that went right and things that went wrong. For this to be a successful process, everyone on the team has to be honest about their own mistakes. He also looks for a good fit with the agency culture – making sure to hire people who can get behind the company’s mission. He uses a lot of hypothetical situations in his interview process so he can look for creativity and problem solving skills.

And, you don’t have to pay top dollar for get great talent… Rob believes even coders making $200,000 are going to be unhappy and won’t work hard if they can’t get behind what they’re working on.

As the agency owner, you want to slowly replace yourself so you can be doing things that generate revenue. Often times that means being out of the office working prospects… not projects. (Not sure how to replace yourself? Check out this interview with an agency owner who fires himself at least once a year.)

#1 advice for starting out?

There’s a reason I say “systems outperform talent every time.” It’s true! In Rob’s case, there’s a delicate balance owning an agency of this size. They are just small enough to be agile and make quick moves and just big enough that they need standardization for consistency’s sake. If he had to do it all over again, Rob says he would tell his former self to this first.

Tired of Being Restricted in the Career Path You’re On?

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