UGLY TALK: SIDE HUSTLE TO FULL-TIME IN CHICAGO

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.

• 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.

• 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.

Scott Baskin - CEO, SBAC

Scott Baskin is the current CEO of the Small Business Advocacy Council. Scott retired as President and CEO of Mark Shale. Mark Shale was Chicago’s largest independent clothing retailer with stores in Chicago, Atlanta, Dallas, Kansas City, and St. Louis. Prior to his business career, Scott served as Chief Legislative Assistant to the late Congressman Abner Mikva. In addition to his professional experience, Scott is an engaged community leader. He is a board member of Uptown United, an economic development organization serving Chicago’s Uptown neighborhood. He was an elected member of the Northside College Prep High School Local Council and chair of its finance committee, past treasurer of the Center for Law and Social Work and past board member of WBEZ, Chicago Public Media. He advises and mentors several Chicago based small and medium size businesses. He is a graduate of Vassar College and Northwestern University School of Law.

Joel Galam - Founder, 312 Sky Eye

Joel Galam is the founder and FAA Part 107 certified drone pilot behind 312 Sky Eye, a Chicago aerial media company specializing in cinematic FPV (First Person View) and aerial storytelling for small businesses, venues, events, and community organizations. After nearly 30 years as a cardiac nurse, Joel recently left healthcare to focus on growing 312 Sky Eye full time.

His nursing career taught him how to remain calm under pressure, prepare carefully, put safety first, and serve people well. He now brings those same qualities to every flight and client relationship. Joel is passionate about supporting Chicago’s small business and creative communities and helping organizations share their stories in ways that get people’s attention. Because he is making this transition right now, Joel can speak honestly about what it takes to turn a side hustle into a full time business.

• 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

SBAC

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

Prism Spaces

Prism Spaces is an independent coworking community in Wicker Park where Chicago's creatives and founders do their best work, powered by the quiet momentum of good people working alongside them.

GREY Journal

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

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

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.

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