During a recent consultant led scoping session, we were asked, on a scale from zero to ten, how confident are we that the project will succeed. One-by-one, our answers ranged from three to six. Clearly a healthy dose of pessimism hung in the air. Then the consultant asked something extraordinary: why were we each even that high and not zero?

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James and Peter Provoking Us

The typical question asked is “Why aren’t you a ten?” The implication is to identify what’s missing or why you are skeptical of the project’s eventual success. Those questions create an echo chamber of negativity that is loud and reverberates…


2020 will go down in the history books on par with 1941, 1968 and 2001 as a year that changed the world forever. In most ways, this was a tragic year. But music in general continued to bring joy to millions of vinyl junkies who couldn’t be with their loved ones.

In 2019, I realized that I had to break out of my arena rock and alternative music prison. A Chicago music legend introduced me to the many great vinyl subscription services available where you receive a record every month. …


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?

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Embarrassing First Website

I heard the phone ring. Initially, I ignored…


My best friend as a kid was Eddie. He lived down the street from me. We both loved baseball, going to the park and riding our bikes around the block. The only difference was he was black and I was white. In our neighborhood, he was part of the majority and I of the minority.

My mother always told me to wash the dirt off of my hands. At the age of about four, I naturally asked my grandmother why Eddie’s skin was always “dirty”. At that time, I didn’t understand that his skin was naturally that color. …


Last year, I spent some time meeting entrepreneurs in Ljubljana, Slovenia. It is always energizing to speak with founders during their entrepreneurial journey. However, I was surprised to learn that founders struggle to maintain relationships with mentors. Whether the mentor is a founder, a leader or a peer, I believe that one tactic is to flip the table and ask what you can do for them.

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Junto Institute Session

A few years ago, I was assigned to a mentor team at the Junto Institute. If you aren’t familiar with them, the organization supports companies and founders that grow together. They do this by…


I walked into the office one morning to find a nice, shiny, laminated square card on my desk. Double the size of a postcard, it wasn’t there yesterday. Who purposefully set this square conspicuously for me to see this morning? What should I do with it and why was it square?

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A Square to Spare

About the size of a small laptop, this colorful square had the smell of a print shop. The colors seemed to match our corporate identity: orange, grey and blue. Actually, the blue was more navy, something I learned watching HGTV’s Property Brothers.

Words were printed all over the card…


The US has this crazy little constitutional right that befuddles people. Europeans wonder why the US is fascinated with guns. As an American who doesn’t own a gun, I too don’t understand the objectively strange fascination the some Americans have with guns, but gun ownership rights are written directly in the US Constitution since 1787. Before the internet. Before TV. Before women could vote. Before slavery was outlawed. In other words, back in a time when geographic groups of people formed militias to protect against foreign intruders.

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2nd Amendment of US Constitution

What can the 2nd Amendment teach us about global commerce? When engaging in…


Home office. Zoom socials. Live Instagram DJs. #AlwaysAvailable. That’s how fast the world changed between the beginning and end of March, 2020. When the lock down is over, how we work will never look the same. To adapt to the new normal, software will fill the gap in ways that were unexpected. Who will win is informed by who won past innovation events.

Who were winners in prior workplace revolutions?

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Starbucks Business Plan

The current sea change in how people work reminds me of the time when laptops first entered the workforce en masse. No longer was work only possible from your desk…


Coronavirus, the biggest global event in more than fifty years, put CEOs in position of balancing employee safety and business continuity. I know that I make different decisions now because of lessons that I’ve learned the hard way over the last ten years. I’m sharing the story where I learned that my business responsibilities begin with employee health responsibility in the hope that other leaders will avoid making the same mistake.

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Elevated Train in Chicago

In 2011, a historic snowstorm was predicted to bury Chicago with over 20 inches(0.5 meters) of snow. Having grown up in Chicago and living close to the Elevated train…


Today, my older brother, Brian, passed away at the age of 52. Brian and I were family, but we weren’t always brothers. For the past 20 years, I failed to look for Brian’s positive side. We weren’t brothers when we last spoke in 1997. We weren’t brothers when he pursued dreams out West. We weren’t brothers when news of his condition surfaced. But those 20 years are not the entire story and I want to share about the time when we were brothers.

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Brian and I Berry Picking in Canada

We explored Bellwood together in the 70's, mastered Dungeons and Dragons in the 80's and developed our…

Craig Vodnik

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

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