Building Chicago’s Startup Ecosystem, Venture Capital & the Business of Professional Sports

In this episode of Ted Listens, host Ted Novak sits down with Kevin Willer, Partner at Chicago Ventures. From the early days of Chicago's tech community to the economics of professional soccer, Kevin shares firsthand perspectives on building businesses, recognizing opportunities, and investing in communities.

Kevin helped launch 1871, Chicago's influential startup incubator, and has spent more than a decade investing in ambitious founders through Chicago Ventures, whose portfolio includes companies like Cameo, SpotHero, G2, and Project44.

In this episode, we explore:

• How 1871 helped transform Chicago's startup ecosystem.

• What venture capitalists really look for in founders, and why great ideas alone aren't enough.

• The impact of AI, quantum computing, and emerging technologies on Chicago's next generation of businesses.

• Why Kevin invests in professional soccer clubs across the U.S., Canada, and England.

• The business opportunity behind soccer's growth and the increasing value of professional sports franchises.

• What Chicago needs to do to attract investment, develop talent, and compete with other major innovation hubs.

Learn more about Kevin: https://www.linkedin.com/in/kwiller/
Learn more about Chicago Ventures: https://www.chicagoventures.com/

Explore more episodes: https://www.tedlistenspodcast.com/

Learn more about Ted: https://www.linkedin.com/in/tednovak/
Learn more about Clique Studios: https://www.cliquestudios.com/

#ChicagoBusiness #ChicagoPodcast #VentureCapital #Entrepreneurship #ChicagoStartups #1871 #ChicagoVentures #SportsBusiness #KevinWiller #TedListens

What happens when the technology you built your career around starts changing underneath you?

Ramon Tramontini has faced that question more than once.

In this episode of Ted Listens, Ted Novak sits down with Ramon, President of International Operations at OGI, to talk about his path from writing software as a teenager in Brazil to building technology companies, navigating failure, moving to Chicago, and leading international growth.

Ramon shares why he believes the biggest mistake companies make with AI is trying to automate before understanding the process itself. As he puts it, AI won’t automatically fix a messy organization... it can simply accelerate the mess.

Ted and Ramon also discuss:

• Starting and losing an early software business
• Taking a career step backward to learn a new technology stack
• Building a business in the U.S. after moving from Brazil
• The cultural differences between Brazilian and American business
• Why systems thinking is central to solving business problems
• Hidden bottlenecks inside organizations
• Why the problem a client asks you to solve may not be the real problem
• The shift from large IT projects to shorter, outcome-focused work
• Ramon’s return to school to study AI and machine learning
• What the next decade of technology may look like

It’s a conversation about reinvention, entrepreneurship, technology, and staying focused on the problem instead of the tool.

More on Ramon: https://www.linkedin.com/in/ramontramontini/

More on Ted:https://cliquestudios.com/authors/ted-novak

What does success actually look like when you stop living by someone else’s definition?

In this episode of Ted Listens, I sit down with coach Kyle Mercer for a conversation about entrepreneurship, executive coaching, personal growth, leadership, relationships, career fulfillment, and the beliefs that shape the way we live and work.

Kyle has spent more than 30 years coaching entrepreneurs, business leaders, and people navigating major transitions. His approach, which he calls the Inquiry Method, starts with curiosity rather than advice: understanding what is really happening beneath the problem before trying to solve it.

We talk about why successful entrepreneurs and executives can still feel stuck, burned out, or disconnected from their work; how childhood and family dynamics can influence adult behavior; and why Kyle says “every family is a cult.” We also explore how to rethink career success, business ownership, leadership, and personal fulfillment without assuming you need to blow up your life and start over.

Kyle walks through how the Inquiry Method works, including the role of emotional patterns, identity, co-regulation, self-awareness, and human connection. He explains why asking “What does success mean to you?” can completely change the way someone thinks about their career, business, relationships, and future.

We also discuss how these ideas apply directly to leadership and sales: listening before prescribing, understanding what someone actually wants, asking for consent before offering advice, and shifting from “What can I get from this?” to “What would success look like for both of us?”

Along the way, Kyle turns the questions back on me, and I end up thinking differently about why I became an entrepreneur, what I actually enjoy about my work, and what success means to me today. We also discover an unexpected shared connection to legendary bassist Victor Wooten and his approach to music, collaboration, and helping other people shine.

This episode is for entrepreneurs, founders, executives, consultants, business owners, and anyone questioning what comes next in their career or life.

Topics include executive coaching, entrepreneur coaching, business leadership, burnout, career change, personal development, mindset, self-awareness, business coaching, relationships, emotional patterns, the Inquiry Method, defining success, and building a life you actually enjoy.

More about Kyle: www.kylemercer.com