Brad Keywell

Chicago is poised to join the prestigious ranks of cities that host ideas festivals: multiday events built around A-list speakers and the collective hunt for the next big thing. Presiding over the first-ever Chicago Ideas Week is Brad Keywell, a 41-year-old venture capitalist who has had some fantastic ideas of his own. Keywell cofounded Groupon, arguably the fastest-growing business in the world. We asked for his take on CIW and innovation in general.

On Ideas Week:
“The Aspen Institute, the Renaissance Weekend, TED—these conferences are about bumping into somebody, then sharing what it is that you’re passionate about. That’s the magic that we’re trying to create in Chicago. Right now, in the city, in the Midwest, there’s just unfortunately not a pinnacle or a focal point around innovation.”

On his personal list of speakers to catch at CIW:
Segway inventor Dean Kamen talking about inventing and the emotion behind invention. Phil Zimbardo, Stanford professor and leader of the Stanford Prison Experiment, talking about heroes. Helen Fisher, noted anthropologist, talking about our brains and the science behind love. Majora Carter, the founder of Sustainable South Bronx, talking about urban sustainability and why we can’t let minority neighborhoods suffer from flawed urban policy.

What drew him to invest in Sprout Social, BenchPrep, BeachMint, Qwiki, and other recent ventures:
“I get very excited by businesses that couldn’t exist before now, for whatever reason: The technology didn’t exist, the usability didn’t exist, the connectivity didn’t exist, the accessibility didn’t exist. But right now is this magically perfect time to start that idea.”

Lesson learned:
“I just talked to the [investors] who passed on Google because the two guys who were working on Google were working in a garage, and the garage was dirty. My opinion is that great businesses, regardless of the pitch, find their capital, and that smart investors, regardless of the format of the pitch, need to be focused on the content and not the style. So it’s this never-ending balancing act.”

Book everyone should read:
Atlas Shrugged. It deals with the one thing that will certainly be a part of all of our lives—failure.”

GO Registration for Chicago Ideas Week is open at The event runs Oct. 10–16.


Photograph: G71/ZUMA Press/Newscom