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

Leadership and people management can feel like the difference between a business that moves smoothly and one that constantly feels on the edge, and that’s exactly where today’s conversation begins. You’ll hear how the right approach to hiring, communication, and team dynamics can shift a business from constant friction to real momentum. Lindsay White, Leadership Coach, Fractional CHRO, and longtim...

Have you ever felt like something’s holding you back, but you can’t quite put your finger on it? Melissa Marina Johnston, Intuitive Life Purpose Coach and Keynote Speaker, digs into the hidden forces in your subconscious that shape your choices and keep you stuck. In this episode, she shares how to spot energy and profit leaks that quietly drain your potential and simple ways to reclaim your power...

Have you ever felt like letting go of control is impossible, even when you know you need to? Atiba de Souza, author of The Delegation Trap and a world-class connector, joins the show to break down exactly how to hand off tasks without losing your sanity. We talk about everything from hiring people who really align with your values to building a team that can actually think for itself.  Atiba share...

Running a business can feel like trying to solve a puzzle without the picture on the box, especially when it comes to marketing. That’s exactly what Russell Lundstrom, a lifelong entrepreneur turned “Marchitect,” helps us figure out in this episode. After decades of building multiple 7-figure businesses, Russell has cracked the code on how to simplify marketing and find real clarity in your messag...

Every 8-figure company starts with a single insight. In this episode, Michael shares how a simple observation from his agency work sparked the creation of Spiffy, a SaaS product that grew into a thriving, high-impact business. He takes us on the journey from recognizing a real market need to building a solution that customers couldn’t wait to adopt. Michael reveals how identifying a “thirsty-hungr...

Sometimes the difference between struggling and thriving in business comes down to strategy, and knowing which moves actually matter. Joe Apfelbaum, LinkedIn Expert, AI Nerd, and CEO of evyAI, and former Rabbi, shares how he built his business from living in a Brooklyn basement to running a thriving SaaS company. He shares what he learned from his mom’s entrepreneurial spirit, how he navigated the...

Eric Berman usually does the interviewing, but this time, he’s in the hot seat as his long-time friend and business partner, Robert Poling, takes over the mic. They talk about how Speakeasy Mastermind came to life, the wild early days of entrepreneurship, and all the lessons they picked up along the way, including a few from surviving the dot-com crash. Robert, who’s built Brandetize into a powerh...

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 Falco...

Changing the way people learn online is not just about piling on more information; it’s about creating an experience that makes people want to keep showing up. That’s something Marisa Murgatroyd knows better than anyone. She went from being an artist who was told she had “no marketable skills” to building a multi-million-dollar business helping thousands of people create courses that actually get...

E-commerce has created more millionaires in the past two decades than almost any other industry, but scaling profitably isn’t as simple as it looks. That’s exactly what Josh Marsden, CEO of ARM5™ Formula Co., has lived through while helping entrepreneurs and investors grow profitable online businesses. Since 2013, he’s generated over $100M in sales and now focuses on acquiring and scaling brands i...

Meta ads can feel like a mystery, especially when you’re running campaigns in tricky, highly regulated niches. That’s why today’s conversation with Jacob Beau, Ex-Facebook Employee, Meta Ads Insider, and Founder & CEO of Concept, is so valuable. He’s now helping brands in some of the toughest industries actually scale without losing their sanity. He’s managed huge budgets, solved compliance ni...

Think about the last brand that really stuck with you, chances are, it wasn’t just a logo or a slogan you remembered. It was how they made you feel. That’s the heartbeat of branding, and it’s exactly what Andrea Reindl has spent nearly three decades helping people figure out. In our conversation, she shares the simple questions that can completely change the way you think about building a brand th...

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...