The Key Habit of Disruptive Entrepreneurs

Pat Ryan
Cooler By The Lake
Published in
2 min readMar 17, 2017

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Rishi Shah and Shradha Agarwal of Outcome Health (formerly ContextMedia)

As we prepared to kick off Chicago Founders’ Stories® in 2013 with Siri Founder Dag Kittlaus, my INCISENT Labs teammates pointed out that the videos and post on our most recent guests, Outcome Health (formerly ContextMedia) Founders Rishi and Shradha, had been viewed over 2,000 times on Built in Chicago (their story is a great one — once again I was reminded of important lessons to keep in mind as we build our next company).

As I reflected on how many people turn out to be interested in such great entrepreneurial stories, one of our Labs’ guys mentioned that his first time founder friends like the idea of Chicago Founders’ Stories® but have just been too buried in their companies to check out any of the interviews. I’m a big believer in the criticality of focus and hustle in making start-ups work yet a couple of conversations later that week reminded me that there is a price to being purely heads down.

A few days later I connected with two legendary founders — both still very active and busy entrepreneurs — who have kindly agreed to join us for Founders’ Stories later this year. I was surprised to hear that both had already watched several Chicago Founders’ Stories’ interviews on their own. The contrast made me wonder:

“Why do these highly successful entrepreneurs make a priority of hearing other founders’ stories even though they are no less busy than other founders who are buried in their business?”

I realized that innovation guru Clay Christensen addressed this question in his most recent book — The Innovator’s DNA — which identifies the traits of “disruptive innovators”. Clay’s research identified the skill of “Associating” — applying ideas and practices from one context to another — as the critical differentiator separating disruptive innovators from the pack. This skill is very similar to that most often associated with the greatest venture capitalists — “pattern recognition”. The prerequisite to developing both of these skills: Exposure to a significant number of high quality learnings from other contexts. In mathematical terms: increasing your “n”.

The most successful founders are unrelenting in their desire to increase their “n”, which increases the quality of their insights and decisions. The incredibly successful founders we are privileged to host on Chicago Founders’ Stories® got there by being learning machines — what better way to continue to learn than to hear about the experiences of the creators of the Grub Hubs, Open Tables and Braintrees of the world? Like those deep in their first start-up, highly successful founders didn’t realize this right away — they developed the habit along the way. The good news is that the videos of their stories will live on at www.coolerbythelake.com for whenever founders are looking to increase their “n”.

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