Windy City Wisdom, a Chicago Style Media Production

Chicago Style Media
  • 5.0 (2)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

Windy City Wisdom, a Chicago Style Media production, dives into the real stories behind Chicagoland’s most driven entrepreneurs and business leaders. Each episode features candid conversations that explore how local visionaries built their brands, overcame challenges, and continue to impact their communities. From city startups to suburban staples, we highlight the people shaping the business landscape in and around Chicago. Want to be a guest on the show? We’d love to hear your story. Email us at: patrick@chicagostylemedia.com

Episodes

  1. JAN 25

    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 companies, and regularly explains major legal issues for outlets like The New York Times, CNN, NPR, and Fox News. In this conversation, he cuts through the noise to explain what the Constitution truly protects, how free speech applies to private companies and social media, and why so much public debate around the First Amendment misses the mark. In this episode, we cover:• What the First Amendment actually protects• Free speech vs private platforms• Social media and constitutional limits• Why free speech is widely misunderstood Windy City Wisdom is a long-form conversation series exploring ideas, leadership, business, and culture through thoughtful, no-nonsense conversations. www.chicagostylemedia.com 🎧 Subscribe for weekly episodes.📲 Follow the show for clips and updates. This episode is for informational purposes only and does not constitute legal advice.

    39 min

  2. 02/13/2023

    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

    50 min

  3. 02/03/2023

    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

    29 min

  4. 01/28/2023

    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

    23 min

  5. 01/24/2023

    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

    33 min
  6. Windy City Wisdom

    01/17/2023

    Windy City Wisdom

    An introduction to Windy City Wisdom, where we talk with business owners about their entrepreneurial journey

    4 min
  • 6 Episodes

Ratings & Reviews

5
out of 5
2 Ratings

About

Windy City Wisdom, a Chicago Style Media production, dives into the real stories behind Chicagoland’s most driven entrepreneurs and business leaders. Each episode features candid conversations that explore how local visionaries built their brands, overcame challenges, and continue to impact their communities. From city startups to suburban staples, we highlight the people shaping the business landscape in and around Chicago. Want to be a guest on the show? We’d love to hear your story. Email us at: patrick@chicagostylemedia.com

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