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Dispatches from the early days of Chicago's tech scene

From 2009-13, I wrote a weekly Q&A series for chicagobusiness.com (the online home of Crain's Chicago Business) that featured many of the entrepreneurs powering the emergence of the city's tech scene. My favorite part was the sense of optimism and boundless potential that pervaded the tech community then, even as it was still small, as was the likelihood of a breakthrough startup. I've collected a few of the more notable conversations below. 

Crain's Chicago Business •

2013 Q&A with ContextMedia's/Outcome Health's Shradha Agarwal and Steve Svec

"When we opened the New York office, it felt like we were building a startup within a startup, having to build a culture again — hiring the right people, then getting them to understand and buy into and embody the culture we have in Chicago. We wanted everyone to feel a part of one family and not to sort of be associated with the more important part or the less important part. ... "
Crain's Chicago Business •

2011 Q&A with Centro's Shawn Riegsecker

"You start with a brand hoping to engage a customer who looks like so-and-so, and then you figure out what customer's journey through media looks like. They wake up in the morning and grab their cellphone or maybe turn on the TV; they drive to work and there are billboards all around; they see a digital display in the elevator at their office building. In the afternoon they check their social account, and then at the end of the night they've got their iPad and they're reading in bed...."
Crain's Chicago Business •

2011 Q&A with New World Ventures' J.B. Pritzker and Matt McCall

JP: If you have $20 million at risk in a company that’s doing well, you still might spend zero time on it. If you have $4 million at risk in a company that’s not doing well, you spend a huge amount of time on that. So it’s not necessarily rational, but it is what it is. These (companies) are all our children. I feel that way about all the investments, that these are ours, and we can’t let any of them suffer. And so that’s where you spend your time, on the problems, not on the successful rising stars.
Crain's Chicago Business •

2010 Q&A with Lightbank's/Groupon's Eric Lefkofsky

I don't think it's right to say, "If I go to the coast, then I can be creative and swing for the fences." I think of it as, no matter what you do, or how risky you want to be in launching a business, if you're not truthful with yourself, if you're not self-aware of what's really going on, then you're just wasting your own time and other people's money. So the real issue in my opinion isn't revenue, it's value. We look at tons of businesses that got seed funding from (Silicon) Valley. ...
Crain's Chicago Business •

2010 Q&A with Sprout Social's Justyn Howard

"That’s another way in which the timing of this is very good. We’re starting to see more of the places where these conversations take place open up their data. A year or two ago, you would have had to go do some black-hat scraping, a lot of parsing of data to get these conversations in front of your users. Now a lot more platforms like Yelp, Twitter, and even recently Facebook, are starting to open up their data and give us access to it. ..."