1 of 2: 🎙️ Courageous Conversations: Can We Disagree Without Destroying Each Other? | Simon Greer

🔥 When was the last time you had a conversation with someone who saw the world completely differently from you… and walked away with more respect, not more rage?

SHOW DESCRIPTION:

Polarization has become the oxygen we breathe, but what if there’s another way?

In this raw, edge-of-your-seat conversation, Dov Baron sits down with Simon Greer, founder of Bridging the Gap, to tackle the question we’re all secretly asking: Can we still talk across divides without losing our minds… or our humanity?

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Raised in a left-wing Jewish family on Manhattan’s Upper West Side, Simon grew up in an environment where dinner conversations weren’t just political, they were ideological battlegrounds. His early life, from Jewish Communist summer camps to a career in progressive politics, shaped him into a fighter for “change.”

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But here’s the twist: Simon realized he wasn’t just fighting for change, he was fighting to be right.

Then came his personal identity crisis. The loss of his job and his carefully crafted “progressive warrior” persona shattered everything. Out of that rubble, he made a radical pivot: seeking out the very people he once demonized, white working-class conservatives, business leaders, evangelical Christians, even prison guards and formerly incarcerated people, to ask a new question:

“How can we build bridges without asking anyone to give up their tribe?”

👉 This isn’t about polite bipartisanship. It’s about impossible conversations, sitting down with people who fundamentally disagree with you (even about your eternal soul) and still finding a way to honor each other’s humanity.

Simon shares:

• 🏕️ What Jewish Communist summer camp taught him about identity & tribe (and why those early ideologies still matter).

• 🥊 How losing everything freed him from a rigid identity — and how that same breaking point might be the catalyst for healing America.

• 🌉 Why bridging divides isn’t about erasing differences — but honoring them.

• 📜 The powerful story of a Muslim friend whose family fought Israel — and how they became allies.

• 🛑 The truth about polarization: It’s not that we have tribes; it’s that we’re being played into them.

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This isn’t just another podcast episode. It’s a field guide for leaders who are ready to do the uncomfortable work of listening, learning, and leading differently.

About Simon Greer

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Simon Greer is the founder of Bridging the Gap, a national initiative training the next generation of civic leaders to engage across divides with honesty and courage. He has advised movements, mentored changemakers, and spent decades at the intersection of faith, politics, and social change. Contact Simon Greer: https://www.linkedin.com/in/simon-greer-5b8549b2/

 

What You’ll Learn in This Episode

✅ Why “normal” isn’t healthy, it’s just what you grew up with. ✅ How to push past the billboard version of someone to find the real human underneath. ✅ Why identity-shattering moments (even job loss) can be the greatest gift you never wanted. ✅ The difference between bipartisanship and true bridging — and why the latter is harder, deeper, and absolutely necessary. ✅ How to hold your tribe with pride, without turning someone else’s tribe into the enemy.

🎧 This Episode Will Hook You to the End

This conversation is uncomfortably honest, deeply human, and wildly hopeful. It doesn’t offer kumbaya clichés. Instead, it asks you to step into the messy, sacred middle, where the future of leadership, and perhaps the country lies.

💥 Listener Challenge

After listening, ask yourself: What’s one “impossible” conversation I’ve been avoiding… and what might happen if I had it?

 

📌 Hashtags for Apple & LinkedIn Discovery

#CourageousConversations #BridgingTheGap #Leadership #SimonGreer #DovBaron #FutureOfLeadership #Tribalism #IdentityCrisis #Polarization #HumanConnection