In 2011 I attended an event called FutureMidwest at the Eastern Market. It was backed/funded by Gilbert and he gave away $1M to a startup at the event. I had several conversations with locals about how attractive Detroit is to a Chicagoan. They didn't believe me. Lo and behold, a Chicago based agency gave one of the last talks of the conference and said exactly that, urging locals not to abandon Detroit but instead to embrace the city, see it through the lens of an outsider. There's great freedom in being in a place with lots of people and low rents. You can't find that in Chicago. And the nights out in Detroit are far and away more charming and creative. Chicago's forgotten what it means to be "cool", if it ever knew in the first place. Detroit, on the other hand, has "cool" locked down.