Three years ago this August, I quit my job. The 10th also marks my 30th birthday. It might come as no surprise, then, that I’ve started to do a little reflecting about that time.

At no point growing up did I ever expect be an entrepreneur. I didn’t even know I wanted to be one until I realized what I really wanted was creative freedom, and the ability to consistently create things with meaning and value.

To truly do those things with consistency, it required taking my own path – not following the one bosses had given me.

Fast forward three years later, and I’m now running what seems to be a successful content marketing agency, Siege Media. We’re creating content that tens of thousands of people view each day. Every month we’re putting out something slightly better than we had ever created. ….


I was initially introduced to Dreyfus model of skill acquisition by Merlin Mann, one of my favorite go-to’s for anything around productivity and the world of work. This concept changed the way I thought about problems and about expertise. The model basically describes a stage in the learning cycle where we are “advanced beginners”, which follows the novice stage. The advanced beginner stage is best described as a period where we have a lack of situational awareness.

This means that you’ve built enough expertise to the point that you believe you’re an expert, without the true experience to know where your deficiencies lie. This period is incredibly dangerous because it causes people to quit jobs, take risks, and overall do things that they simply shouldn’t because of a false arrogance about their true skills in whatever they call a career.

As with anything, I, in many stages of my career and life, reached this stage. I particularly reached this stage as it comes to three aspects of building a company and overall building a life, with strong associations to starting an agency that others might empathize with (or be glad to know before it happens). ….


It’s been almost two years since Siege Media originally came to life. It’s been a wild two years, where I’ve moved from Seattle, to Long Beach, to San Diego, where Siege Media is doing great and continuing to grow. We are now a team of seven people and business is booming – but that’s not to say that the first two years have been without speed bumps and lessons learned. Among those lessons is one pivotal one that I want to reiterate with this post: be extremely meticulous when choosing clients.

When starting out – or at any stage of the process, inquiries are going to come that look attractive, but in the end, really aren’t – but you won’t really know the size of your mistake until months to years down the line. These choices end up seeming good, and especially good in the early stages, for one reason and one reason only: they have money to give you. But these clients have fundamental problems that will impact the long term growth of your company, and ironically cost you down the line. ….


Making the jump. Quitting your job. Making a living outside of your 9-5. These things are difficult to do, and one of the things that prevents most from ever doing it is the risk. The risk of being stuck out in the cold and suddenly unable to find work. That’s a scary thing, and for good reason – nobody wants to have faced that fear and failed.

Mitigating the risk of this situation is something that’s worth considering, and worth putting long, deliberate thought to. Many startups have the opportunity to blow up in your face, and one of the great benefits of a consulting company is that it can be run in an efficient fashion that isn’t nearly as volatile. ….

The Danger of I vs We When Building a Company

June 6, 2013 Entrepreneurship

The habit I’ve most wanted to break in the early stages of having others work at Siege relates to problems with differentiating between “I vs We”. I vs we is the pronoun choice that says very little, but also says a whole lot. The use of one versus the other can happen more than you […]

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Early Lessons From Building a Consulting Company

May 20, 2013 Entrepreneurship