Successfully Navigating Chicago’s Bureaucracy

By Beth Kregor

Being an entrepreneur rarely goes according to plan.

Just ask IJ Clinic on Entrepreneurship client Amanda Scotese. Her business, Chicago Detours, just celebrated its fifth anniversary. Chicago Detours is a creative and fun tour-guide business that teaches guests about the history, creativity, political maneuvering and hard work of the people who built Chicago. The tours are fun and unique for both visitors and residents. But it takes years of hard work behind the scenes to become a successful small business, like Amanda’s.

Since 2011, the IJ Clinic has worked with Amanda to guide her through the legal twists and turns of opening up a small business in Chicago. Thankfully, Chicago does not have onerous licensing restrictions for tour guides like the ones that IJ has challenged in Washington, D.C., New Orleans, Savannah and Philadelphia. But the legal requirements of employment law and corporate governance are often overwhelming.

When we asked Amanda where her business would be without our help, she said, “I can’t imagine actually! I had no idea how much legal help I needed. It has been invaluable.” Clinic attorneys and law students analyzed trademark questions, tax questions, employment questions and much more. We have written the agreements that the business uses with tour guides, customers and contractors. We have even mapped out the copyright protection for maps. Because Amanda is so creative and entrepreneurial, she keeps us busy. Her new business plans and her insightful questions have been a training ground for many law students over the years. We have seen firsthand the hard work of Amanda and other entrepreneurs like her, whose businesses build our city.

But fun was at the forefront in August, when I was lucky enough to attend the Fifth Anniversary Bash for Chicago Detours. Part of the party was getting a sneak peek of its new “Big Shoulders Bar and Food Bus Tour.” We drove through historic neighborhoods, learning about the waves of immigrants who marked their neighborhoods with their architectural styles and culinary traditions. We hopped out to look in old speakeasies, meet local entrepreneurs and taste local flavors. We imagined the lives of the people who worked in the stockyards when Chicago was the “Hog Butcher to the World.” At the end, we gathered at a mansion from the Gilded Age and toasted the success and growth of Chicago Detours over these five years.

We are so proud that Chicago Detours has reached this milestone on its journey. Only 50 percent of businesses survive for five years, and Chicago Detours has overcome many obstacles to make this business work on a small budget in a tough economy. The creativity and hard work of people like Amanda are invaluable to their customers, their community and their economy. Chicago may not be the Hog Butcher to the World anymore, but when strong, persistent entrepreneurs like Amanda team up with the IJ Clinic, we can still be the City of Big Shoulders.

Beth Kregor is the director of the IJ Clinic on Entrepreneurship.