After Historic Election, Chicago Can Be the Only Winner

    The City of Chicago leaves many from the outside and frankly those within with a lot of questions. Chicago’s Mayoral Elect Lori Lightfoot will have to have a lot of answers. I write this article from the perspective of someone that was raised in Chicago, that moved away for a dozen years and that ultimately returned in hopes of contributing to a better city and better region. Like many I watched the election with interest, however, with two days left on the trail, I found myself oversaturated with the promises of potential campaign hopefuls. Not that I didn’t care about the issues the city is currently facing, it’s just that there are some issues that I realize that if they were a priority to be fixed by the city and the state … then they probably would have been fixed by now or at a minimum improved to some measurable degree. These issues include but are not limited to:


    Since the days of Al Capone, the name Chicago and the State of Illinois has been synonymous with organized crime and crooked politics. How does a city that is known for pay to play, aldermanic privilege, under the table lobbyist money, and nepotism among other things, begin to implement structural political reform? It has to start with transparency at city hall and its top office.


    Looking to the future, Chicago has many projects set to come online in the next few years and it must find ways outside of high-interest debt or raising property taxes to fund them. Did I mention that Chicago has the second highest property taxes in the nation? Add to that imbalance massive retirement payments, hundreds of millions paid out in wrongful death police lawsuits (among other things) and the city might be facing a budget shortfall last reported at some $700 million. Yet somehow the new mayor will have to find a way to do the impossible.


    What does criminal justice reform look like?  How to tackle the high rates of recidivism? How do we enact tougher gun laws and keep more guns off of the streets? What is the root cause of the persistent violence that the city is facing? Why are we only solving around 15% of the city’s homicides? Why do we have twice the number of violent crimes as New York and Los Angeles combined? How do we gain better police collaboration at the community level? All questions that no one to date has had the answers for.
    Despite my now suburban life, I was born in the city, I still work, play, contribute and have family and friends here and so I will forever be connected to Chicago. In my twelve years away, the once industrial looking city of my youth has undergone some pretty dramatic changes. We have a growing startup culture centered around the efforts of 1871. The race for academic excellence that was once led by the city’s Ivy Leaguers has now opened up to a host of world-class institutions. The city has become the #1 corporate relocation city in the US. We now have our own park in the middle of the city, take that New York and San Francisco. In addition, Chicago has managed to add to its world-class architecture and has enough museums and eateries to keep tourist and Chicagoans alike busy for a lifetime. Yet something interesting happens when you stay away for a while you gain some objectivity. You not only see the city in all of its grandeur but you’re able to also acknowledge it’s many faults. The more things have changed in this amazing city, unfortunately, the more things have stayed the same.
    In Mayor Lori Lightfoot’s inaugural address she spoke of a future of inclusion for all Chicago residents. Yet despite all of the issues that need addressing, one of the most effective ways to create an equal playing field among all Chicagoans is by spreading opportunities and economic development to all neighborhoods. The following are my top five economic development areas that Chicago must get right in order to begin leveling the playing field all taken from the Lightfoot for Chicago Campaign Website.
    1. Make Chicago Friendly to Small Businesses and Startups:  Small businesses are the lifeblood of our economy, and if Chicago is to thrive and its neighborhoods are to grow, then Chicago must do more to attract and support small businesses and entrepreneurs. As many of Chicago’s small business owners can attest, it can be difficult to navigate the maze of small business regulations and requirements.
    2. Change the Existing Capital Program: Chicago must change its capital programs from matching grants to straight grant and loan-based programs. This means money is available typically to businesses and entrepreneurs who already have raised money through traditional sources of capital like banks, private investors, friends, and family. Small business owners and entrepreneurs who cannot tap traditional sources of capital often do not qualify for matching grants.
    3. Expand Opportunities for Minority, Disabled and Women-Owned Businesses: It is vitally important that minority, disabled, and women-owned business enterprises (MBEs, DBEs, and WBEs, respectively), and small businesses have a fair shot to do business with the city. Chicago currently sets a goal that 26% of construction contracts will go to MBEs and 6% will go to WBEs. While other cities, including Philadelphia, set goals for M/WBE participation at 35% or higher.
    4. Offer More Small Business Planning Advice & Technical Support: Small businesses in Chicago often struggle to obtain the business guidance and technical support they need to expand. There is no reason that these entrepreneurs cannot access this expertise.
    5. Grow Professional Apprenticeship Programs: There is a direct inverse correlation between crime and employment opportunities. Apprenticeship programs — in which younger employees learn career skills through the on-the-job experience before starting a full-time, white-collar position — are growing in popularity around the United States. Chicago will need to continue to engage and find opportunities for young people, particularly young African American Males ages 18-24 which have the highest unemployment rate of any group.   
    At the time of this article is Chicago is set to undergo an $8.5B O’Hare Airport expansion project. Developer Sterling Bay is investing $6B in the Lincoln Yards Project along the Chicago River. Another $7B is being used in the development of ‘The 78’ a mixed-use development between the South Loop and Chinatown. More than 100 new low-income homes are set to go up on the south and west sides of the city. Add to that mix the future of the Obama Presidential Library, a proposed Tiger Woods golf course, the fate of the Michael Reese Hospital site in Bronzeville and whatever may come of the troubled South Works location. When you take all of those things into account, it translates into a Chicago landscape that might look radically different from the image that we have of the city.
    In addition, it translates into an unbelievable amount of business opportunity for all of those involved. Yet despite what is on the horizon, Chicago’s greatness and opportunities are all concentrated. This means that some 80% of the city’s population are struggling to take advantage of these opportunities which only widens the financial disparity and economic divide. The new mayor must find a way to implement more technology training, spur economic development and reduce some of the obstacles for plugging into the local economy such as starting a business. Only then can will the citizens of Chicago begin to be the true winners of the election and only then will the City of Chicago begin to live up to its world-class title.


    Cavanaugh L. Gray is the founder of The Entrepreneur Café, LLC. As a small business development specialist, he brings two decades of experience implementing entrepreneurial-based business strategies that help startups scale. He has served as a business advisor to Innovation Award Winners and is the author of The Entrepreneurial Spirit Lives (An Amazon Top Read) and Bridging the Entrepreneurial Divide. With more than a decade as an academic, he currently serves as Adjunct Professor of Entrepreneurship at Loyola University Chicago. For more information on how to start, grow and succeed in small business Connect With Us at, 877-511-4820 or on social media @TheECafeLLC. Copyright 2019.


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