Thank you to everyone who attended South Side Pitch 2020! Congratulations to this year’s winners:

1st PlaceThe Black Mall

2nd PlaceNew Magnolia Garden Center

3rd PlaceThe Lemonade Land

United Airlines Community Favorite AwardThe Black Mall

South Side Pitch is a shark-tank style pitch competition that showcases incredible South Side businesses. In prior years, we focused on early-stage companies and business ideas. This year, we are switching it up and focusing on established businesses. We want to highlight how important South Side businesses are and the incredible companies that exist south of the skyline. This year, on November 5th, our virtual pitch event will celebrate the South Side businesses that have contributed positively to the lives of their customers, employees, community members, or individual business owners. South Side Pitch will offer small business owners an opportunity to pitch in front of a virtual, city-wide audience and a panel of judges to share their success story and for the chance to win cash prizes. The winner(s) will be determined based on the judge evaluations and the audience votes. We are also excited to announce that this year we will award the “Community Favorite” award to the finalist that receives the most votes from the public in the night of the event.

South Side Pitch is hosted by the Institute for Justice Clinic on Entrepreneurship in partnership with the Polsky Center for Entrepreneurship and Innovation and the University of Chicago Office of Civic Engagement.

Event Details:

South Side Pitch 2020
Thursday, November 5, 6:00PM – 8:00PM
Virtual Platform (Livestreamed on Facebook and Youtube)

This Year’s Judges: Peggy A. Davis, VP of Community Impact, Chicago Community Trust || Vincent Williams, President and CEO, Chicago Minority Supplier Development Council || Susana L. Vasquez, Associate Vice President, The University of Chicago Office of Civic Engagement|| Elizabeth Kregor, Director, IJ Clinic on Entrepreneurship

This Year’s Finalists:

Children’s shop focused on representation and inclusivity.

Maestri Tutoring
Bilingual tutoring center for working class families.

New Magnolia Garden Center
A U-pick farm and garden center located in Back of the Yards.
A marketplace of Black-owned businesses that includes an online business directory and a brick and mortar shop in Chatham.

The Lemonade Land
Pop-up market for micro Black-owned businesses in the South Shore, Greater Grand Crossing, and Woodlawn area.

Wesley’s Shoes
Sit and fit family shoe store serving customers since 1970.


Members of the media: if you are interested in hearing more about South Side Pitch, please contact Erik Castelan at

How do I apply to be a contestant?
Applications for South Side Pitch 2020 are now closed. Thank you to all the businesses who have applied! Be sure to RSVP here to watch this year’s finalists pitch their business in front of a panel of expert judges.

Questions? Email or call 773-834-3129