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

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. You’re here to evolve. This is Inside the Speakeasy. And once you’re in… You don’t go back.

Episodes

August 12, 2025 44 mins

Sometimes the biggest thing holding us back isn’t our skills or circumstances, it’s the way we see ourselves. And in a world where AI is changing the game every day, the way we think matters more than ever. John Assaraf knows this firsthand. He went from a rocky start in Montreal to building five multimillion-dollar companies, writing two New York Times bestsellers, and showing up in films like The Secret, all because he learned ho...

Mark as Played

Marketing has changed a lot, and if you’ve felt the pressure to keep up, you’re not alone. Between AI tools popping up everywhere and audiences craving more realness, it’s hard to know what actually works. That’s exactly what we get into with Alex Cattoni, a longtime friend of mine and the brilliant mind behind the Copy Posse. We talk about what it really takes to connect with people online and why authenticity is everything right ...

Mark as Played

Traditional education isn’t cutting it for most people anymore. Julian Melanson saw that early on and decided to do something about it. From making videos as a kid to building the world’s bestselling AI course on Udemy, his journey is anything but typical. In this episode, we talk about how a 10-day silent retreat and a curious mind led him to completely rethink how we learn, especially with tools like ChatGPT changing the game.

Jul...

Mark as Played

It’s wild how many successful entrepreneurs were shaped by something hard early in life, and how that pain quietly fuels their drive to build big things. In this episode, we’re unpacking that with Gemma Stone, a former Psychologist turned Entrepreneur Coach, who’s helped visionaries turn their inner battles into real breakthroughs. We talk about what happens when your past becomes your power and your pressure, and how to tell the d...

Mark as Played

There’s something powerful that happens when you stop trying to reach everyone and start building for the right people. That’s what today’s conversation with Mark Stern is all about—how honing in on your niche and leading with value can completely shift your business. We’re talking about the Law of Reciprocity, how thoughtful experiences can spark real connection, and why making it easy for people to support you actually leads to m...

Mark as Played

Most business owners don’t think about selling until they’re ready to walk away—then suddenly it’s a mad dash to clean things up. It’s like realizing your house needs work the day before the open house. Jonathan Brown (aka JB), Founder of White Buffalo Advisors, says that mindset is all backward. In this episode, he shares why building your business as if it’s for sale—whether or not you ever plan to sell—is one of the smartest thi...

Mark as Played

Outsourcing doesn’t have to be expensive, complicated, or stuck in the old way of doing things.

In this episode, Eric explores how the outsourcing game is being reinvented—from outdated task delegation to a smarter, system-first approach that saves money and empowers both entrepreneurs and virtual assistants.

From his early entrepreneurial struggles and the unexpected turn that led to a five-year global adventure, Beejel shares the p...

Mark as Played

What if the secret to standing out online… is just being more human? In this episode, Eric sits down with Joshua B. Lee—entrepreneur, author, and the founder of Standout Authority—to talk about the power of connection in a noisy, automated world.

From his early days running ads on MySpace to navigating the crash of 2008 and rebuilding everything from the ground up, Joshua gets real about the lessons that shaped him—not just as a mar...

Mark as Played

Some people teach. Others truly change lives with what they teach. Jasmine Jonte has done both—and in this episode, she shares how her time in one of the toughest classrooms in the country shaped her approach to building courses that actually work. We talk about the real power of education, and how to turn what you know into something that helps people grow, take action, and get results. Tune in for clear, helpful insight from some...

Mark as Played

There’s something wild about reaching a major milestone—like selling your company—only to realize you’re not sure who you are without it. That’s exactly where Serial Entrepreneur and 19x Bestselling Author, Mike Koenigs, found himself, and it sparked a whole new chapter. In this episode, we talk about how AI became a game-changer in his journey of reinvention, and how it can do the same for other founders feeling stuck, anxious, or...

Mark as Played

Have you ever noticed how the way someone talks to you can either lift you up or shut you down? That’s the kind of real-life stuff we’re getting into with Michael Bernoff—an expert at helping people communicate better, lead with confidence, and actually connect. We talked about how just changing a few words in how you speak (yes, even to yourself) can totally shift how you show up in the world. 

Michael’s the Founder of the Human Co...

Mark as Played

Masterminds aren’t just about big business moves—they’re about finding your people, the ones who get it and push you to grow. That’s exactly what we’re talking about today with my partner and long-time friend, Glen Ledwell. He’s built a powerhouse mastermind (Flight Club) that’s about real connection, confidence, and community. Glen opens up about the early days, the awkwardness of charging his peers, and what finally clicked to tu...

Mark as Played

Most people think internet marketing is just funnels, emails, and chasing algorithms—but for David Gonzalez, it’s always been about real people and real relationships. For over 16 years, he’s been hosting the Internet Marketing Party, where he’s built a space for connection, collaboration, and plenty of win-win deals. In this episode, David shares what it really takes to build a strong network without feeling salesy or transactiona...

Mark as Played

When AI started taking over the headlines, a lot of us were left wondering—where the heck do we even begin? That’s exactly why I brought on my good friend Brad Costanzo, who somehow manages to make AI feel way less intimidating and way more human. Brad’s the Founder of Accelerated Intelligence AI and a brilliant mind when it comes to helping business owners and creators figure out how to actually use AI to get results. In this epis...

Mark as Played

In this mind-blowing episode, we dive deep into the world of AI clones and digital twins, exploring how Joe Fier, AI expert and podcasting pioneer, and Eric Berman, founder of the transformative Speakeasy Mastermind, are revolutionizing business success.

Joe shares his incredible journey from podcasting guru to leading AI-driven innovation, including his role in implementing cutting-edge Delphi technology—a powerful AI tool that all...

Mark as Played

Sales Without the Sleaze: How Rich Boggs Built a $40M Vision-Driven Empire”

What if your sales team didn’t just close deals—but changed lives?

In this episode, Eric Berman sits down with Rich Boggs, the heart-forward sales strategist behind the Brave Thinking Institute’s leap from $400K to over $40 million in annual revenue. Rich pulls back the curtain on his seven-step Vision-Driven Selling Framework, a system that powers his 42-per...

Mark as Played

Popular Podcasts

    Football’s funniest family duo — Jason Kelce of the Philadelphia Eagles and Travis Kelce of the Kansas City Chiefs — team up to provide next-level access to life in the league as it unfolds. The two brothers and Super Bowl champions drop weekly insights about the weekly slate of games and share their INSIDE perspectives on trending NFL news and sports headlines. They also endlessly rag on each other as brothers do, chat the latest in pop culture and welcome some very popular and well-known friends to chat with them. Check out new episodes every Wednesday. Follow New Heights on the Wondery App, YouTube or wherever you get your podcasts. You can listen to new episodes early and ad-free, and get exclusive content on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. And join our new membership for a unique fan experience by going to the New Heights YouTube channel now!

    The Breakfast Club

    The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

    Fudd Around And Find Out

    UConn basketball star Azzi Fudd brings her championship swag to iHeart Women’s Sports with Fudd Around and Find Out, a weekly podcast that takes fans along for the ride as Azzi spends her final year of college trying to reclaim the National Championship and prepare to be a first round WNBA draft pick. Ever wonder what it’s like to be a world-class athlete in the public spotlight while still managing schoolwork, friendships and family time? It’s time to Fudd Around and Find Out!

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

    24/7 News: The Latest

    The latest news in 4 minutes updated every hour, every day.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.