Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

Yes, this podcast regularly features guests.

Windy City Wisdom

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by Chicago Style Media

5.0(5 reviews)

7 episodes

Updated Daily

Accepts GuestsHas SponsorsLocation 🇺🇸

Podcast Overview

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

Language

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Publishing Since

1/17/2023

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Recent Episodes

January 25, 2026

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 misunderstoodWindy City Wisdom is a long-form conversation series exploring ideas, leadership, business, and culture through thoughtful, no-nonsense conversations.<a href="https://www.chicagostylemedia.com/" target="_blank" rel="ugc noopener noreferrer">www.chicagostylemedia.com</a>🎧 Subscribe for weekly episodes. 📲 Follow the show for clips and updates.This episode is for informational purposes only and does not constitute legal advice.

January 10, 2026

What does “free speech” really mean in 2025—and where are the limits most people don’t understand?

In this episode, Patrick McDonald sits 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 misunderstoodWindy City Wisdom is a long-form conversation series exploring ideas, leadership, business, and culture through thoughtful, no-nonsense conversations.<a href="https://www.chicagostylemedia.com" target="_blank" rel="noopener noreferer">www.chicagostylemedia.com</a>🎧 Subscribe for weekly episodes. 📲 Follow the show for clips and updates.This episode is for informational purposes only and does not constitute legal advice.

February 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

7 total episodes available

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Frequently asked questions

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What is Windy City Wisdom?: 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
How often does this podcast release new episodes?: This podcast updates daily.
Where can I listen to this podcast?: This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: Yes, this podcast regularly features guests.

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