On May 29, entrepreneurs, nonprofit leaders, creatives, and purpose-driven founders from across Chicago gathered at 36Squared for our inaugural event, Ignite Chicago: Small Business Growth Intensive.
What began as a capstone of the Wells Fargo/Watson Institute Fellowship quickly became something much bigger.
It became a room full of people asking important questions about what it truly takes to build and sustain a business in today’s market—and a community willing to share honest answers.
Real Conversations About Sustainable Growth
The day began with welcoming remarks from our partners at 36Squared Business Incubator followed by an overview of the day from That’s So Creative founder, CJ Harris.
Our featured panel, “What It Actually Takes to Build and Sustain a Business in Today’s Market,” brought together an incredible group of leaders representing business, finance, economic development, and entrepreneurship:
- Adrienne McFarland, Illinois SBDC at the Chicagoland Chamber of Commerce
- Sharnell Curtis-Martin, CIBC USA
- Quentella Enty, Callie Management Group
- Bill Skeens, Former Founder & CEO of Prairie City Bakery
- Cam Brown, Far South Community Development Corporation
Together, they explored topics ranging from access to capital and financial readiness to operational systems, strategic partnerships, resilience, and adapting to rapid market changes.
One of the most powerful moments came from Bill Skeens, who shared lessons learned from growing Prairie City Bakery into a nationally distributed brand carried in more than 30,000 locations. His message was simple but profound: grow intentionally, stay lean, know your customer, and don’t build before you’ve validated demand.
Throughout the discussion, attendees asked thoughtful questions and engaged deeply with the conversation, proving once again that entrepreneurs are hungry not only for information, but for practical wisdom and authentic community.
Building with Authenticity, an Intimate Conversation with Kim Lewis
One of the highlights of Ignite Chicago was our fireside conversation with Kim Lewis, CEO and Co-Founder of CurlMix and Listener Brands.
Kim shared candidly about the realities of entrepreneurship: navigating uncertainty, leading through difficult seasons, staying authentic while scaling, and resisting the temptation to compare your journey to someone else’s.
Her honesty, transparency, and resilience resonated deeply with attendees and created one of the most memorable moments of the day.
From Inspiration to Implementation
At That’s So Creative, we believe that inspiration without implementation rarely creates lasting change.
The day concluded with our signature AI for Small Business Workshop, led by CJ Harris. During this hands-on session, attendees explored practical ways to use AI tools to strengthen marketing, improve efficiency, streamline operations, and support sustainable growth.
The response was overwhelmingly positive, with many participants sharing that the workshop helped make AI feel approachable, practical, and immediately actionable.
Attendees left with a 30-Day Action Plan designed to help them immediately apply what they learned.
More Than an Event
Ignite Chicago wasn’t just an event.
It was the beginning of something bigger.
Over the past several years, we’ve had the privilege of training and supporting thousands of entrepreneurs through workshops, coaching, and strategic consulting. Ignite Chicago represents the next evolution of that work.
Through TSC Igniter, we’re building an ecosystem of workshops, implementation labs, community experiences, systems support, and practical business education designed specifically for entrepreneurs, nonprofits, and purpose-driven organizations.
Our vision is simple:
To help mission-driven leaders build stronger systems, smarter marketing, and sustainable growth—without losing what makes their work meaningful.
We’re incredibly grateful to our speakers, attendees, volunteers, sponsors, and community partners who made Ignite Chicago possible.
Special thanks to:
- Greenwood Archer Capital
- 36Squared Business Incubator
- Watson Institute
Thank you for believing in this vision and investing in Chicago’s entrepreneurs.
Want to Join Us for the Next Ignite Experience?
This is only the beginning.
More Ignite workshops, implementation labs, and community events are already in the works—and we’d love for you to be part of them.
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We can’t wait to build with you.
— The That’s So Creative Team