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

What happens when you put values at the center of your marketing? For Sarah Hardwick, it turned into a career of building communities that actually care about the brands they support. She opens up about how that approach helped her raise over $150 million through crowdfunding and why understanding what people truly value can change everything for a business. Sarah’s story takes us from starting he...

Ever meet someone who just gets people? That’s Jennifer Hill, an Evolutionary Leader, Entrepreneur, Author, and Speaker. She’s spent her life figuring out what makes us tick, how we connect, why certain people light us up, and how to build relationships that actually last. In this episode, she shares her own journey (including calling herself a “recovering asshole”) and the simple shifts that have...

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 Th...

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 wh...

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...

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 y...

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...

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...

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...

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 lesso...

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 f...

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...

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.  M...

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 pe...

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 wit...

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...

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 Delp...

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 Fr...