Taking a Calculated Risk

It was a Friday. The build up lasted for weeks. After a year of prototyping, building, refining and testing, our Frankenstein creation was powered on directing us on a one-way path in the dark. The first email campaign pointing to our optimized customer commerce experience was launched.

Over a year earlier, we began discussing starting a business on both sides of the ocean. Headquartered in Germany with an outpost in Chicago, we challenged ourselves to pick a direction. Who would we be? What would we do different? Which market would we attack?

Embarrassing First Website

I heard the phone ring. Initially, I ignored the unfamiliar tone since it didn’t sound like my mobile phone. After a few more rings, I triangulated that it was coming from the living room. My computer was there in an early version of a virtual office! I sprinted across the apartment to answer the call.

In July 2005, we presented the first prototype of our platform at the Software Industry Conference in Denver. A shiny new administrative interface. More power into the users hands. The latest CSS technology for a less intrusive customer experience. A solution built by an experienced software commerce team for enterprise thinking organizations.

By the time that I reached the ringing phone, the call was in voicemail. I prepared for my first customer service call. As the customer answered the phone, I heard the raspy voice of an older gentleman from Oklahoma. His twang reminded me fondly of my time in Texas, where I learned about the internet. After listening to him describe his problem, I helped him install the purchased license key in just a few minutes. Success!

When it came time to name our baby in early 2005, we focused on the idea of optimizing the customer journey from beginning to end, but in a smarter way. Clearing the path so that the buyers get what they want as conveniently as possible was our guiding principle. Our earliest logo was a literal take on this concept where the customer strides effortlessly over the self-optimizing bridge. This, along with the view that we challenge ourselves to have creative solutions, is where the sideways ‘v’ as a symbol was born.

Ashampoo — Top Sellers of 2005!

That first customer I spoke with was one of less than one hundred first day visitors that traversed the bridge. Our first client, Ashampoo, rewarded us with another email campaign later that month, then moved their entire business to us as we developed additional features. One of the things I’m most proud of is that they are still a client to this day.

Taking risks is scary.

In 1993, I boarded a plane to Texas for graduate school. No internet. No mobile phone. And without a drivers license. I had to navigate a new part of the country without friends, on a tight budget and through only my own problem solving skills. I was scared on that flight to Houston and the subsequent bus ride to College Station.

Nearly two years later, after having discovered and immersing myself in the early world wide web, I flew home to launch the Chicago Tribune newspaper online. I described leaving weeks before I would have graduated as having jumping off the caboose of the nuclear industry onto the engine of the internet industry. Great risks have great rewards.

First Team Photo — July 2005

Thinking back to that first customer on November 11, 2005, I didn’t and couldn’t have imagined where we would be today, fifteen years later. The day that we decided to form cleverbridge was one of the most momentous days in my life, but at the time, it was just another calculated risk I’d taken in life. It’s certainly been one of the best as well.

Global flexible billing entrepreneur of @cleverbridge with a passion for recurring payments and customer experience. @hydeparkangels board

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