A Tale of Scale


How I make multiple 6-figures and work on less than 15% of the websites we create.

To scale or not to scale?

When I started my freelance business, I wanted it to be a part-time gig where I made part-time money to supplement my music dreams.  I mean, I was going to be a rockstar … playing drums and touring the world! (Turns out, most touring musicians do not make 6-figures, let alone $50k)

My plan worked.

While I was working my last 8-5 job (15 years ago) I built my web design freelance business to about $1,500-$2,000 per month.  Basically I was building 1-2 sites per month. It was great side-gig money!

My full-time job was one I even fought for! My buddy was moving to Austin and he put my name in for his job. It was a web designer position at a non-profit whose mission was to plant trees. They paid well, had great benefits, and promoted a great cause!

But, I was in a cubicle (blah), had a dress code (double blah), and I had friends out on the road living their music dreams.

One month into the job I realized a hard truth … I could not let my dreams die.

I doubled my efforts in my freelance web design business. You can see the schedule I used here.

VOTAThree months later my big break came.

I was asked to join a touring band called VOTA. I was so excited! I remember meeting with the singer to talk expectations and pay. Since I had graphic design experience, I would be making $25 more per show to occasionally help with graphic design needs (posters, CD artwowrk, etc). My total pay per show? $150.

Yes, $150 per show.

Like I mentioned above, touring musicians do not make much. Even today, guys on the biggest tours can make as little as $250 per show.

On average, the band would play about 10-20 shows per month.  $1,500 – $3,000 per month.

It only worked because I had grown my web design side-gig to $1,500-$2,000 per month.


That’s me on the left … emo hair and all.

You’d think this would be the end of the story. 

I’m on the road, touring, playing music professionally … all while still growing my web design business. Life is good!

But then I realized there’s probably a time limit on this rock-and-roll dream. What am I going to do when I’m 50 and have a family?

Then what happens to any solid freelancer starts to happen to me … word spreads … inquiries increase … I raise my prices … inquiries still increase.

I have a choice. Turn people away … or scale.

John at the apartment

Solo freelancing and touring … life was good!

Time to scale.

A few ways to scale…

– Hiring subcontractors
– Partnering with another freelancer
– Building a team

    Hiring subcontractors

    I used this method off-and-on for a few years while I was a solo freelancer. After trying a handful of developers and several designers, I ended up finding a couple subcontractors I would use frequently and could rely on.

    – Usually cheaper than an employee
    – No long-term overhead
    – You can scale up or down as needed based on workload
    – Can be specialists

    – Availabilty isn’t reliable
    – Their prices can fluctuate especially as they get better
    – They’re juggling your work with their own clients
    – Hard to keep them accountable to deadlines
    – Reliable subcontractors can be hard to find and pricey

    Team at Turbine Flats Coworking Space

    Jake, his wife Haley, and I at our co-working space.

      Partnering with another freelancer

      Eventually I needed more permanent help. I convinced my bandmate, Jake, to dive into web design. After Jake took Break Into Web, we worked together as two freelancers working on the same projects. I would handle onboarding, billing, and oversee design. Jake would handle content implementation, getting the site approved, and hosting.

      It worked well for a couple years. Eventually his wife came and worked with us.

      However, without anything legally binding you together, your separate businesses could outgrow the other and break the working relationship.

      – Usually cheaper than an employee
      – No long-term overhead
      – Availability is more reliable as you’re both committed to the same clients

      – The growth of your own business could break the working relationship
      – Clients can be confused on exactly who they’re working with
      – Splitting the payment can be tricky to figure out

      Team at Prescott Office

      Jake leading our team meeting.

        Building a team

        Eventually Jake and I got to the point where I needed to hire him (or else he was going to build his own freelance business), or we partner up and eventually hire employees.

        We partnered up and now have a team of 6 people.

        – You have a team working on projects
        – You can scale up or down as needed based on workload
        – Availability is not an issue
        – You can budget costs much better as your costs are fixed
        – You can appear more professional to clients which can translate into higher budgets
        – Eventually you’ve built a business that can run without you, making it sellable

        – Overhead … you now have a monthly “nut” to cover
        – Turnover … employees will leave and you’ll need to replace them
        – Firing … you may need to fire someone from time to time
        – Stress … you’re providing a way of living for people and that can weigh on you “Heavy is the head that wears the crown.”

        It’s up to you.

        The best of both worlds.

        How will you scale when the time comes? Will you partner-up and build a team like I’ve done? Or will you remain a solo freelancer and work with the occasional subcontractor like Kelly?

        That’s what’s great about Break Into Web, you get to see 2 examples of how each method could get you to multi-6 figures.

        No matter the route you choose…

          The sky is the limit.

          John Wooten

          Technical Instructor

          John is owner of Artillery. Frustrated with his 8-5 job, he started Artillery and began freelancing at night and on the weekends. Freelancing allowed John to tour full-time in a band for several years. Learn more about John