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Inside the Speakeasy Podcast - Your Key to Hidden Strategies & Success Stories from Top Entrepreneurs

Welcome to Inside the Speakeasy—the entrepreneur podcast that hands you the keys to rooms most never get access to.

Hosted by Eric Berman, this show is for founders, startup builders, marketers, and empire-minded creators who are done with surface-level noise and ready to unlock the hidden strategies, pivotal success stories, and raw truths behind elite business growth.

This is your key to the real game—the unfiltered conversations happening behind closed doors, at mastermind retreats, in late-night deal rooms, and during the “what the hell do I do now?” breakdowns that never make it to LinkedIn.

You’ll hear from the scrappiest, boldest, most unreasonably driven entrepreneurs in the U.S.—the ones who are scaling to 7–8 figures, failing forward, innovating under pressure, and rewriting the rules of success while no one’s watching.

No recycled advice. No fake “10X hacks.” Just what’s actually working right now—from people actually doing it.

Because let’s be honest:

You’re doing well.

You’re sharp.

But deep down… you know you’re still playing small.

So stop chasing comfort.

You’re not here for safe.

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This is Inside the Speakeasy.

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Inside the Speakeasy Podcast - Your Key to Hidden Strategies & Success Stories from Top Entrepreneurs

The Biggest Culture Killer Leaders Don’t Talk About

September 30, 2025 • Speakeasy Mastermind • Season 1 • Episode 23

Fear has a sneaky way of creeping into organizations and keeping good ideas from ever seeing the light of day. Ryan Berman knows this better than most; he’s made a career out of helping companies stop letting fear run the show and start building a culture of courage instead. As the Founder of Courageous and Author of Return on Courage, Ryan has worked with everyone from Google to the Atlanta Falcons, showing leaders what’s possible when they choose courage over comfort. His perspective is simple but powerful: change is tough, but staying stuck is even tougher.

Ryan breaks down what he calls the Courage Formula: knowledge, faith, and action, and explains how those three ingredients can move people and teams past hesitation. We talk about what courage really looks like in leadership, and why it’s something every single person, not just CEOs, can tap into. He shares stories from his own path, including the leap from advertising to becoming a trusted advisor for some of the biggest brands out there.

You’ll also hear some behind-the-scenes stories, the values that guide Ryan’s work, and even a glimpse into his new book Head of Mentals, which digs into overcoming negative self-talk. If you’ve ever felt stuck, second-guessed yourself, or wondered how to get your team moving in the right direction, this episode will give you a new way to think about it. More than that, it’ll leave you feeling like courage might be closer and more achievable than you think.

Key Timestamps:

[00:00:00] Welcome to Inside the Speakeasy Podcast

[00:02:30] Corporate fear-fighting strategies.

[00:03:22] Addressing fear in leadership.

[00:06:40] Creative business journey.

[00:15:21] The essence of courageous leadership.

[00:16:04] The journey of launching Courage.

[00:20:33] Definition of courage redefined.

[00:22:19] Courage through knowledge, faith, action.

[00:27:58] Courageous decision-making in business.

[00:29:01] Importance of core values.

[00:39:46] The value of collisions.