People Changing the Conversation in Chicago’s Startup Community

A couple months ago, I wrote a post challenging Chicago’s startup community to elevate the conversation, to go beyond the same topics and pronouncements that get recycled over and over again.

In that time, I’ve taken an even keener interest in discovering and reading content I find to be refreshing and thought-provoking, yet relevant to entrepreneurship. It’s easy to find blog posts, longform articles, and videos that fit this criteria across the internet in general, but it gets a bit more challenging when you zoom in on Chicago’s startup community.

So starting today, I’m going to periodically share a handful of discoveries, along with a brief description and a quote from the piece. Between posts, I’ll also tweet some with the hashtag #FreshConvos. And as you discover (or create them yourself!) such pieces by people in Chicago’s ecosystem, please send them my way to freshconvos [at] ramanations [dot] com.

I hope you enjoy these and that, over time, they may inspire you to change your own conversations.



Heroes in Our Failures, by Matt McCall of New World Ventures. This gets inclusion not because it’s a fresh topic but because it comes from someone on the venture side, which isn’t exactly known for talking about the human aspect of startups. “Here’s what makes the hero’s journey scary: evolution always occurs on the fringe. It never occurs in the middle.”

The One Who Cares the Most Wins, by Howard Tullman of Tribeca Flashpoint Media Arts Academy. A thoughtful and logical explanation of why and how the a laser focus on customers is even more critical in today’s “whatever” society. “No one cares how much you know or how good you are at your job…until they know how much you care about them.”

The Pivot = Overhyped + Dangerous, by Seyi Fabode of Power2Switch. A provocative discussion of the collision between the art and science of entrepreneurship: executing a vision with persistence while following lean startup principles of adaptations and efficiency. “Businesses that pivot too frequently and fail to deliver on their promises to customers will continue to fail. Pivot your way out of that one.”

Why 80% of Female Entrepreneurs Were Once Girl Scouts, by Maria Wynne of the Girl Scouts of Greater Chicago and Northwest Indiana (featured on Technori). Quite a surprising statistic but one that makes a lot of sense after you read this piece. “Girl Scouts is providing girls with a better understanding of what it takes to be an entrepreneur…building girls of courage, confidence, and character to make the world a better place.”

Why Politeness Is Your Worst Enemy, and What You Can Do about It, by Sharon Schneider of MoxieJean. Entrepreneurs love asking others what they think of their startup ideas. Problem is, most people are too kind. Sharon presents why this is problematic and what to do about it. “YOU, the founder, the CEO…can’t ask people directly for feedback.”


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  2. Pingback: Fresh Convos, Vol. II: People Changing the Conversation in Chicago | ramanations

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