Years in the making.

Made in the midwest.

Break Into Web was started by two self-employed web designers from the midwest, John & Kelly. We’re convinced web design is the best freelance opportunity for creatives because of the potential to generate wealth and recurring revenue (and ridiculously low expenses).

We first met at a local Jimmy John’s in 2010. We were both full-time freelancers and had heard of each other, so we decided to meet up.

Over the next few years we would occasionally talk about our businesses, successes and struggles. Something we both noticed was people who  desired our lifestyle. We would often hear something like…

I want to do what you do. I want the freedom to work when I want so I can _________.”

We also noticed there wasn’t a comprehensive course on how to be a self-employed web designer. There were courses on how to build websites … and other courses on how to start a business … but not a course that offered both with a freelancer in mind.

After several years of discussing and collaborating, Break Into Web was born.

Break Into Web provides a proven path to become a 6-figure self-employed web designer.

It’s been amazing to see students start their business, quit their full-time job, and gain the freelance lifestyle they always dreamed of.

What will your success story say?


Kelly Diekmann

Business Instructor

Kelly is owner of KDesign. She acquired an MBA because she thought she’d go work for some Fortune 500 company, but instead only lasted 6 weeks in the ‘real world’ at a soul-sucking insurance gig. Thankfully, her web design ‘hobby’ turned out to be a killer freelance career that allowed Kelly to stay home while raising babies. KDesign was established in 2004 and she’s been self-employed ever since.

Kelly enjoys working with small businesses and entrepreneurs, and they appreciate her honesty and excellent customer service. 

Kelly is the ringleader of the Diekmann circus which includes husband Casey, three daughters, two dogs, and any number of neighborhood kids at any given moment.




Freelance web designer since 2002


Retired pole vaulter


Almost astronomer

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. After 6 months he was able to quit his job and make the switch to being his own boss and never looked back.

Freelancing allowed John to tour full-time in a band for several years. He would build websites while traveling in the tour bus. He still tours occasionally with a couple artists.

He, his wife Corryne, and two daughters (Journey & Indi), love traveling the country … especially the mountains of Colorado. He loves talking entrepreneurship and everything drums.


Professional drummer


Freelance web designer since 2006


Breaks into song when no one is talking


Full of car analogies

Personal Support

When you join one of our programs you will get access to both John & Kelly via a private Facebook Group, live monthly Q&A calls, and/or direct 2:1 voxer access.

We’ll answer any questions you may have over the course material, give our advice on your business questions, as well as give encouragement & motivation for you to keep pushing through the course and grow your business.

Being able to directly access the instructors personally sets this course aside from most online programs. We want you to get the most value possible from our programs.

It’s time to Break Into Web

We’ll help you. We believe in you. It’s time for you to believe in yourself.
Let’s do this.