FYI, my business is not Foursided, it's called Neighborly and features products sourced from Chicago and the Midwest. We're in the Ravenswood neighborhood not Lakeview, which is decently affluent but is more rental than ownership, median household income is $57k. I came to Chicago with nothing, but yes a college degree, and I started my business when Schulter was in the office, not Pawar, although I don't feel my local alderman had any effect on my ability to start a business in this city. It really is the cost of doing business, considering the space I need to make my product, that is what makes Chicago so accommodating, from a business owners perspective, besides the supportive community.
Jenny Beorkrem commented on a link
I own two small businesses in Chicago and believe that if you DO head out beyond the lakefront (i.e. Gold Coast and Lincoln Park), I'm proud to say that most of our neighborhood business districts do still have a Main Street - like landscape. Sure they might be dotted with Dunkin or Starbucks (of course) but the mainstays tend to be locally owned and/or family businesses that have been there for decades. As compared to other cities of its size and density (NY and LA) Chicago offers affordable living and work space. Although my first business is largely online, I wouldn't have been able to afford starting a business in either NY or LA. Sure, working with the city has not always been easy, but I truly believe that thanks to affordable space and an underlying Midwest attitude to "help your neighbor", the entrepreneurial and small business community in Chicago is unmatched elsewhere. I agree that yes, there are social issues that Chicago may be trailing other cities of its size, namely gang violence and public education but I do think Chicago is a great place to live and do business and is headed in the right direction.
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