UGLY TALK: SIDE HUSTLE TO FULL-TIME IN CHICAGO

UGLY TALK: SIDE HUSTLE TO FULL-TIME IN CHICAGO

📅 September 24, 2026
🕐 5:00 PM CT

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

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

GREY Journal – 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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​📢 ​Important Notice for Ugly Talk Attendees

Admission & Confirmation
Attendance is by approval only. Approved guests will receive a confirmation email along with a calendar invite. Invitations are non-transferable. Additional event details will be shared as the event approaches.

Code of Conduct
By attending, you agree to:

  • Maintain respect and professionalism, adhering to all venue rules, policies, and applicable laws.

  • Refrain from harassment, discrimination, unwelcome sexual advances (verbal or physical), intimidation, or inappropriate photography/recording.

  • Report any violations to the event hosts immediately.

Violations may result in immediate removal from the event and exclusion from future invitations.

Liability & Risk
Participation is voluntary and at your own risk. The event organizers, hosts, sponsors, and venue are not liable for personal injury, lost or stolen belongings, or any other damages incurred during the event.

Media Consent
By attending, you grant the event organizers and affiliated entities the right to capture, use, and distribute photos, videos, and audio recordings of you for promotional, marketing, and other lawful purposes, including digital and print media, advertising, and social media. You waive any right to inspect or approve the final materials and release all claims related to their use.

Communications
By registering, you agree to receive marketing and promotional communications from Ugly Talk and its co-hosts, partners, and sponsors. You may unsubscribe at any time.

Agreement
If you do not agree to this Code of Conduct, please refrain from attending the event.

​🚀 Join us to stay updated on upcoming Ugly Talk events!

Official Event Page: [Link]

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Location

📍 Prism Spaces, 1212 N Ashland Ave Ste 202, Chicago, IL 60622, USA

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