UGLY TALK: SIDE HUSTLE TO FULL-TIME REVENUE IN CHICAGO

Schedule

Thu Sep 24 2026 at 05:00 pm to 07:00 pm

UTC-05:00
Location

Prism Spaces | Chicago, IL

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Founders and business builders break down how they went from earning extra income to running full-time businesses, sharing the wins, setback
About this Event

Turning a side hustle into a real business is exciting. Navigating permits, licenses, and compliance is not. Many founders discover that Chicago’s regulatory maze becomes one of the biggest obstacles to growth long before finding customers does.



🎯 Why You Should Attend
  • ​Understand the regulatory hurdles that catch most founders by surprise.
  • ​Learn practical ways to navigate permits, licensing, and compliance with confidence.
  • ​Hear how founders successfully transitioned from side hustle to full-time business.
  • ​Gain clarity on when to formalize your business and what steps matter most.
  • ​Connect with founders and experts who have already navigated Chicago's small business ecosystem.



🙋 Who's Getting In This Room
  • ​Founders turning side hustles into full-time businesses
  • ​Small business owners navigating Chicago's regulatory landscape
  • ​Operators, advisors, and legal professionals supporting business growth
  • ​Community leaders and ecosystem partners helping entrepreneurs succeed



🎤 Who’s Taking the Stage
  • ​A founder who successfully turned a side hustle into a full-time business in Chicago
  • ​A business owner who has navigated permits, licensing, and compliance while growing a company
  • ​An expert helping entrepreneurs understand Chicago's regulatory landscape and avoid common pitfalls



💬 What's on the Table
  • ​From side hustle to business When it's time to make the leap and what changes next.
  • ​Navigating the regulatory maze Permits, licensing, compliance, and the requirements founders often overlook.
  • ​Avoiding costly mistakes The common missteps that delay growth and how to prevent them.
  • ​Building with confidence Practical strategies for growing a business while staying compliant.
  • ​Making Chicago work for you How founders can use local resources, communities, and support systems to build successfully.



Who's Backing This

​SBAC supports the small business community through nonpartisan, policy-driven advocacy and by fostering connectivity and collaboration through engagement and events.

​ – Media partner spotlighting modern entrepreneurs (featured on Apple News + Google News).


​⭐ About Ugly Talk:

​Started in 2019, Ugly Talk has been transforming business setbacks into breakthrough “aha!” moments by hosting unfiltered, no-nonsense events where battle-tested entrepreneurs share their raw lessons and insights.

​With a growing presence in cities like New York, Chicago, San Francisco, and Miami, we’ve built a vibrant community of thousands of founders and industry leaders making a profound impact on the entrepreneurial landscape.

​Official Website: UglyTalk.com

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Where is it happening?

Prism Spaces, 1212 North Ashland Avenue, Chicago, United States

Event Location & Nearby Stays:

Tickets

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