The Strange Trail I wandered down...


I started thinking about it about two years ago. Like most entrepreneurs, I felt like I had identified a problem in the market place. I'd been working in Digital Marketing for more than a few years at this point and kept coming across the same client-related issues.

Digital marketing projects can be lengthy journeys. In the throes of a project, near the beginning, I would ask my clients questions about their brand. I wasn't all that surprised when I got a mixed bag of resulting replies. No one...not the executive teams, the employees, the clients, or the vendors...would tell the same story about how they viewed their business's brand.

Every time, I'd think to myself, "how can we deliver their brand to the marketplace if we don't even know what the brand is? And what a waste of time, energy and over-all effort!"

Meanwhile, I'd also recall previous branding projects I was involved in: excellent opportunities for me to put my best skills on display. These projects spark difficult conversations; the risk of offending business owners / colleagues is usually high. I enjoyed being the diplomat and carefully guiding the process along. After each project's completion, what I always walked away with was how deeply it involved people...and how invested they were. Everyone has lots of opinions on various projects, but branding projects are a special breed because they bring out passion. People spend most of their lives working. They want to feel proud and invested in their companies and the purpose at the core of their business. A branding project gave everyone an opportunity to be heard and feel connected to their employer.

What I thought was interesting was that I was making all sorts of noise on the digital marketing front. It was the hot topic. Everyone was hungry for as much information as possible. So I gave people what they wanted (and still am) through my digital marketing services (

I just wasn't sure if people would be as excited about a branding company, though.

I've often mentioned that, in order to shake people out of apathy, you need to hit them up the side of the head with a sledgehammer. Don't be fooled...people like being comfortable. That was it. I felt I was on to something. If I could make people uncomfortable, I could get their attention...and if it had a great design behind it, I could keep their attention.

Before one of my daily runs, I loaded up the iPod with a bunch of David Bowie. "Cat People" came on after about mile 1. I felt like a sledgehammer hit me! I couldn't get enough and was plowing through mile after mile with bursts of energy. I kept envisioning a concrete jungle with neon lights everywhere. A Blade Runner-like world that people would want to explore.

I was also struck by how the song made me feel. I was slightly weirded out by it. The line, "Those who feel me near, pull the blinds and change their minds!" along with "Just be still with me. You wouldn't believe what I've been through!" wouldn't leave my head. I've listened to the song about 100 times since then and it still has failed to get old.

Now I needed a name. It came much easier than I imagined it would. I thought the whole thing was rather strange so I knew I wanted that in the name. I went back to the digital marketing idea then and how long a brand can take to revise, refresh, and implement. I kept toying with the word journey. Strange Journey didn't mesh, though, so eventually I replaced it with Trails.

I actually found myself scared of the I knew I was on to something.

The last part: convincing some people to join me. The first person I shared it with was Katie Robleski, one of the best designers I've worked with in the Milwaukee area. She was into it. Yes!

I entrusted everything to her to help make the brand and the methodology. I hoped it would feel just as much hers as mine. I'm still excited about what we're doing. We're either really on to something...or just delusional! Either way, thanks for being with us so far. Let's keep walking...


James Pellizzi