Andrew Wimer
Andrew Wimer · September 11, 2025

CHICAGO—For the 12th year in a row, South Side entrepreneurs will have the opportunity to win money, earn acclaim, and get training to fuel their business dreams through the South Side Pitch. The competition will again be held live and open to the public at the Polsky Center for Entrepreneurship and Innovation in Hyde Park. Through Sunday, September 21, members of the public are invited to help pick one of the finalists by viewing short video pitches on YouTube, then liking and commenting on their favorite.

The full list of 25 semifinalist video pitches is available here: https://www.youtube.com/playlist?list=PLVL05snDJzHjvliE65483FHtlrbkOBQZj

“With Chicago in the national spotlight, it seems especially important to highlight the wonderful things entrepreneurs are doing on the South Side,” said Beth Kregor, the director of the Institute for Justice Clinic on Entrepreneurship at the University of Chicago. “We’re excited to highlight their stories of how they got started and their visions for the future of the business. We invite the public to join in the celebration and to vote for their favorite. We hope these small businesses’ stories can inspire other South Siders to dream big!”

South Side Pitch allows incredible entrepreneurs to share their success stories and the impacts their businesses have in a “Shark Tank” style contest, with the final contestants presenting their pitches during the live event on October 16. Applicants compete to win several great prizes, including over $36,000 in cash prizes and a free business financial plan from a Chicago-based Prudential advisor for the 1st Place winner. Like previous years, every finalist is guaranteed a prize.

Last year’s first-place winner was InHeirit a Longwood Manor company that works to expand access to estate planning. InHeirit used their prize money to finalize their digital platform, which is available now in beta version: https://app.getinheirit.com/.

South Side Pitch is hosted by the Institute for Justice Clinic on Entrepreneurship. The contest is sponsored by the Polsky Center for Entrepreneurship and Innovation, the University of Chicago Office of Civic Engagement, and United Airlines. 

The Institute for Justice Clinic on Entrepreneurship provides free legal assistance, access to resources, and advocacy for low-income Chicago entrepreneurs. To learn more about the IJ Clinic, visit www.staging.ij.org/clinic.