As IJ’s media relations director, I love working with the Clinic on Entrepreneurship to tell our clients’ stories and make Chicago a better place to do business. Despite its problems, the Windy City has energy and grit, and every year we get to recognize and reward five standout businesses at South Side Pitch.

This year’s contest, the 12th annual, had a diverse array of entrepreneurs: an eyeglass designer making customizable frames to fit any face; a young brother and sister starting a coffee company in a neighborhood with few community meeting places; a vegan ice cream parlor; a program that teaches girls business and braiding skills; and a musician building an app to connect performers with opportunities.

The finalists were selected from a pool of more than 160 applicants, up significantly from last year. Nearly every seat was taken, and the audience was lively. The whole event is a testament to the Clinic’s work and the success of South Side Pitch. Food and drinks were provided by past contestants and clients, like Moor’s Brewing Co., which won in 2022.

This year’s overall winner was Runaway Cow, a vegan ice cream parlor from the Bridgeport neighborhood. Founder Alison Eichhorn is a full-time high school teacher who grew up in a family that ran a traditional ice cream parlor. When she told her mother that she wanted to open up a dairy-free, egg-free ice cream shop on the South Side, she got discouraging words, but the tasty frozen treats won people over.

Alison told a story about four older women who walk the neighborhood every day and who came in skeptical about the new venture. After she got them to try some ice cream, they left happy and other people from the neighborhood started showing up. Turns out she had served just the right customers and created the word of mouth that made her business start to thrive. This year, when she opened her doors for the season, there was a line formed outside.

While I’ve been to South Side Pitch several times, this year I got to sit in and hear the judges deliberate. Alison won them over with a pitch focused on growing her business on the South Side, how partnerships with vegan restaurants grow the customer base, and a clear plan for how the prize money would fuel further growth.

Two additional prizes, the Community Favorite Award and the Rustandy Center Social Impact Award, went to ChiBrations. Creator Sam Thousand started his pitch by asking the audience to imagine the lively Bronzeville social scene of 100 years ago and playing his trumpet. He wants the ChiBrations app to recreate that golden age by connecting people to gigs, open mic nights, and workshops. 

Chicago has been through some rough times, but it’s amazing to see how people on the South Side have hope for a brighter future. For one night, hundreds of people got to share in the dreams of entrepreneurs who love their communities and work hard to create opportunity.

Andrew Wimer is IJ’s director of media relations.