Calling Your Own Shots

Going out on your own as a solo developer can be terrifying! That's why I made this 1-hour video: to share with you the things I did to scale myself from a solo developer to a successful online...


In 2001 the company I worked for (and partially owned) went belly up with the rest of the internet consulting agencies out there. We had just enough work for myself and the original founder so I decided to sign my part of the company over to him and go out on my own. We ended things in an amicable way, for the most part, and I decided that I could probably do just fine if I did little contracts with him and for other companies.

Within a year we worked out a great arrangement where he would arrange contracts for me through the clients we used to have. He would keep a cut of what I made and I could eat and pay rent.

A year or so after that I began to raise my rates as the work began to pick up, and one of my friends said something that changed my career:

You really should establish yourself as a business. Let me set it up for you.

Scaling Me

I fought this idea. I had just ejected myself from the mess of running (and losing) a business and I was not keen to jump back in. My friend, who’s also a CPA, convinced me otherwise and he set me up with an S-Corp and showed me how to do my books.

Looking back on this now a number of things jump to mind. I can still feel the anxiety associated with running a company and having to fire your friends. Of staring at your books and wondering how deep your credit line runs so you can make payroll. I hated this. On the flip side: knowledge is power or, as Peter Drucker says: what gets measured gets managed.

We apply patterns to the code we write. Run tests, wrap it in all kinds of processes and basically make sure it’s structured as well as possible for the future. Why wouldnt I do the same for my solo career?

Refining The Process

Over the years I’ve tweaked and nudged what I do. I took a break from the solo thing in 2006 (through 2009) to work at Microsoft. I enjoyed it, but when I left I remember having a feeling along the lines of “right, let’s rev this up again”. I feel like I have the process down and I can scaled myself from a solo contractor on up to a full blown company.

I thought this might be valuable to others, so doing what I do I decided to wrap up what I’ve learned over the years into a one hour video which you can preview here. If you’re thinking of going out on your own and/or maybe someday selling something on the side, you might be interested in this.

I designed this video as a “nuts and bolts” blueprint, leaving the “you can do it!” type of inspiration to your friends and family. To that end, the video is divided into the following sections:

I should add that it’s largely based on my career experience here in the US. Other countries will have different requirements so all of the information might not apply.

Missing PeepCode

I’m hoping to do more small, polished, < $20 1-hour videos like this one. If you’re in to the idea, hit me up on twitter and let me know! I miss the monthly drops from Geoffrey Grosenbach and friends - it was so much fun to take a break over the weekend and learn something new!