23 consultants were in a restaurant. . . 

The leadership team of our consulting practice were enjoying wine and canapes. (Yes, consultants eat well).  My buddy and I were talking and when we looked out the window into the January Chicago night, someone was staring back at us. Not something you expect.   

In a winter coat, sketching on piece of paper 

We realized that the gentleman was drawing us. Outside – in the cold – he was drawing our caricatures on his notepad. Fascinating, odd, endearing, perhaps a little sad. After going outside to check it out, of course we invited

This is what he drew in 30 minutes on a simple sketchbook with a marker.  

Team Cartoon

Amazing, right?  

Beyond the fun of the story, believe there are several lessons to learn something from this guy:

1) Here, let me show you

This definitely takes some chutzpah to start drawing without prompting. No guarantee of a pay-off.  Just doing good work. As Seth Godin says, “shipping art.”

2) Confident in my skills

My work is good enough for these random people to buy from me.

3) Knows the target market

He was not randomly painting people on the street, instead targeting big corporate dinners at upscale restaurants.

4) Pricing to value

When we asked how much, he said $0-40, whatever you “wanted to pay”.  We loved it. We paid $60.

5) Creates mystery

He drew this remotely, not interfering with event, sitting as far as 30 feet (10 meters) from the people farthest away.  Some of the attendees did not even know this happened, until I showed it on PowerPoint the next day

6) Delighting us

When we asked him to put our company name on the bottom of the picture (redacted here), he asked, “which font do you want it in?”  Whoa!

7) Strong brand

All the servers knew this guy.  He’s been doing this for a while.

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