Contestant FAQs and Rules

South Side Pitch is an annual business pitch competition showcasing and celebrating the many creative and promising South Side businesses and entrepreneurs. Finalists pitch to a panel of judges and a live audience on October 15, 2026, at the Polsky Exchange North Center, competing for over $40,000 in prizes.

The IJ Clinic on Entrepreneurship is the Organizer and host for the competition.    

  • Entry Period: June 15 – August 7, 2026 
  • Review Period: August 8 – August 21, 2026 
    • Applicants may be contacted for verification of application details and must be responsive. 
  • Pitch Perfect (Coaching & Networking): August 13, 2026
    • Meet the Organizer, IJ Clinic, and participate in a coaching session open for all South Side Pitch Applicants at the University of Chicago Law School! 
  • Semifinalists Announced: On or before August 21, 2026, approximately 25 semifinalists are selected by the Organizer. 
  • Semifinalists Video Pitch Submission: On or before September 4, 2026
    • Semifinalists are required to submit a pitch video to compete for a spot in the finals. Video must be 90 seconds and include: 
      • At least 30 seconds of Applicant’s owner’s or founder’s face 
      • Applicant’s owner’s or founder’s voice as main audio 
      • Original content showcasing potential for an in-person pitch — Not a PowerPoint or Pitch Deck Presentation 
  • Public Voting: September 8 – 21, 2026
    • One finalist will be determined by the most online votes, the People’s Choice Award. To cast a vote, go to the South Side Pitch YouTube channel, press like and comment on the video with the name of the business’s neighborhood displayed in the entrants’ video. Each account is limited to one like and one comment (vote) per video. No fake or artificial engagement (bots, paid likes, etc.). Organizer and its parent organization deploy sophisticated detection tools to identify inauthentic activity. The People’s Choice Award is subject to cancellation if inauthentic activity is detected by any Applicant. 
  • Finalists Announced: September 22, 2026
    • The IJ Clinic announces five finalists, including any People’s Choice Award winner. Finalists Coaching Sessions: dates to be announced. 
    • Finalists are required to participate in two coaching sessions which will be held on Saturday mornings to be scheduled in late September or early October. 
  • Live Event: October 15, 2026, 6:00–8:30 PM 
    • Finalists are required to attend in person and present a 3-minute pitch to a panel of judges and live audience (without a PowerPoint or Pitch Deck Presentation) and answer questions from the judges. 

Business Requirements 

  • For-profit 
  • Fewer than 50 employees 
  • Under $1M revenue in 2025
  • Headquartered within in the city limits of Chicago south of Roosevelt Road 
  • Not a franchise 
  • Not a prior South Side Pitch finalist 
  • Not a current or former IJ Clinic client 
  • Beyond idea stage (with customers or pre-revenue with a prototype)
    •  This means you meet at least one of the following at the time of submitting your application:
      • Have a working prototype or minimum viable product (MVP)
      • Have served at least one customer (paying or non-paying)
      • Are pre-revenue but actively testing or piloting your product or service

Individual Requirements 

These individual requirements are applicable to at least one owner or founder of the eligible business, who will pitch the business on a semifinalist video and in-person at the finals if selected. 

  • At least 18 years old 
  • Legal Illinois resident, currently living in Illinois 
  • Must show a meaningful connection to the South Side 
  • Never a director, officer, owner, immediate family or household member of a current or former IJ Clinic client, or employee of the Institute for Justice 

Applicants are judged on being: 

  • South Side Connected: Local roots and ongoing impact on community. 
  • Entrepreneurial: Founder’s story, challenges faced and motivation to start the business. Business model built on adaptability, creativity, and innovation. 
  • Visionary: Plans for the future of the business to grow or adapt. 
  • Showmanship: Engaging, energetic, inspirational presence delivering a clear message with flair.

In 2025, all five South Side Pitch finalists received cash awards: 

  • 1st: $15,000 
  • 2nd: $10,000 
  • 3rd: $6,000 
  • 4th: $3,000 
  • 5th: $1,000 

Finalists must complete a W-9 form for their business entity, an Direct Deposit document for the entity’s bank account (not the owner’s individual bank account) and will receive an IRS-1099 to report the prize award. The “Audience” award (based on live audience votes) may or may not include a cash prize.

All submissions (application, video, pitches) must: 

  • Be original (no AI, plagiarism, or third-party content) 
  • Convey positive images and messages 
  • Avoid offensive, violent, political, or commercial material 
  • Not use others’ name, image, likenesses, trademarks, or music without permission 
  • Follow YouTube rules for video submissions and voting 

Applicant is responsible for timely submitting its application, and each Semifinalist is responsible for timely submitting its video pitch. Organizer is not responsible for any delays or failure to receive and process any submissions whether due to errors in computer transmissions, any website, or network connections, whether human or technical in nature. 

Organizer reserves the right to remove any content that does not adhere to the submission requirements and/or disqualify Applicant, as determined in the Organizer’s sole discretion. 

Applicant retains ownership of the content and ideas in its submissions, and by entering the Contest gives Organizer and South Side Pitch an unlimited, worldwide license and right to share, publish, use, publicize, and publicly perform the content in any way, in any and all media, without limitation, and without compensation or other consideration to Applicant, as well as the same right and license to use the identities, name, likeness, and pictures of Applicant and Applicant’s owners or founders. 

Submission of content does not create an attorney-client relationship with the Organizer. 

The IJ Clinic on Entrepreneurship provides free legal assistance, support and advocacy for low-income entrepreneurs in Chicago. The IJ Clinic also trains the next generation of attorneys from the University of Chicago Law School to be vigorous and creative advocates for entrepreneurs. 

The IJ Clinic on Entrepreneurship is a collaboration of the Institute for Justice, a nonprofit, public interest civil liberties law firm and University of Chicago Law School. 

  • No purchase necessary.
  • Contest subject to applicable federal, state, and local laws and void where prohibited. 
  • Submission of an application to the Contest constitutes Applicant’s full and unconditional agreement to the South Side Pitch contest rules and Organizer’s decisions, which are final and binding in all matters related to the Contest. 
  • Each Applicant receives one entry into the Contest. Failure to meet eligibility criteria or comply with any Contest rules will result in Applicant being disqualified and removed from participating in the Contest and any prize awarded will be forfeited. 
  • Organizer reserves the right, in its sole discretion, to disqualify any Applicant it finds to be tampering with the Contest or to be acting in an unsportsmanlike or disruptive manner. Any attempt by any person to deliberately undermine the legitimate operation of the contest may be a violation of law, and Organizer reserves the right to seek damages to the fullest extent permitted by law.  
  • Organizer reserves the right at its sole discretion at any time to cancel, suspend and/or modify the Contest, or any part of it. 
  • Organizer’s delay or failure to enforce any term of these Contest rules shall not constitute a waiver of that provision. 
  • As a condition of entering, Applicant: (a) releases Organizer,  Sponsors, Judges and others associated with South Side Pitch, from any and all liability, loss or damage incurred with respect to the awarding, receipt, possession, and/or use or misuse of any award or prize; (b) waives all rights to claim punitive, incidental, consequential, or any other damages; (c) all causes of action arising out of or connected with this Contest, or any prize awarded, shall be resolved individually, under Illinois law by mediation, arbitration or other process as specified by Organizer at or after the time of any dispute; and (d) Applicant waives any right to recover attorneys’ fees, court costs or other out of pocket costs. 
  • If anyone claims the content of Applicant’s submission is a violation of others’ rights, Applicant agrees to hold harmless and indemnify Organizer, Sponsors, Judges and others associated with South Side Pitch against any such claims. 
  • Caution: Applicants should be aware that entering the Contest might be considered a publication or disclosure of ideas, and might affect the ability to patent any innovations contained in a submission. 
  • Please see the privacy policy located at https://ij.org/privacy-policy for details of Organizer’s policy regarding the use of personal information collected in connection with this Contest. 

South Side Pitch

Event Details

Date and Time
October 15, 2026 6:00 to 8:30pm
Location
Polsky Exchange North 1452 E 53rd St. Chicago, IL 60615

sponsors