PODCAST · business
Windy City Wisdom
by Chicago Style Media
We talk with entrepreneurs in the Chicagoland area about their business journey.
Episodes
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What does “free speech” really mean in 2026—and where are the limits most people don’t understand?
In this episode, we sit down with Barry McDonald, a constitutional law professor who has spent decades studying how the First Amendment actually works in real life—not just in theory. Barry has clerked for the Chief Justice of the United States Supreme Court, advised governments and technology...
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Chicago Pizza Tours joins Windy City Wisdom
Jon Porter founded Chicago Pizza Tours back in January 2010. Since then, over 85,000 people have enjoyed a tour of some of the finest pizza in the world. www.chicagostylemedia.com
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Lisa Gasparian of Café Crèmerie joins the show to showcase her business journey.
You’ll be craving the fresh, savory sweets of Café Crèmerie after this episode. Lisa talks about the challenges, successes and everything that went into starting the European-style cafe in the heart of River North. www.chicagostylemedia.com
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Rob Morrison Real Estate Team joins Windy City Wisdom.
Hear from one of the most successful realtors in the country. Rob Morrison dives into his start in the real estate industry and what drives him to be better every single day. www.chicagostylemedia.com
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Classic Alaska Charters joins Windy City Wisdom
Born in the Chicago area, Captain Rob Scherer set his sights on Alaska at a young age and never looked back. Tune in and hear about how he got started and how he’s built Classic Alaska Charters into what it is today! www.chicagostylemedia.com
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Windy City Wisdom
An introduction to Windy City Wisdom, where we talk with business owners about their entrepreneurial journey
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ABOUT THIS SHOW
We talk with entrepreneurs in the Chicagoland area about their business journey.
HOSTED BY
Chicago Style Media
CATEGORIES
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Frequently Asked Questions
How many episodes does Windy City Wisdom have?
Windy City Wisdom currently has 6 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Windy City Wisdom about?
We talk with entrepreneurs in the Chicagoland area about their business journey.
How often does Windy City Wisdom release new episodes?
Windy City Wisdom has 6 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Windy City Wisdom?
You can listen to Windy City Wisdom on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Windy City Wisdom?
Windy City Wisdom is created and hosted by Chicago Style Media.
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