Business Episodes

Gino Barbaro shares his journey from running a restaurant to building a $450 million real estate portfolio, all while redefining what success truly means. This conversation goes beyond business, diving into family, faith, values, and the mindset needed to create lasting wealth and legacy. If you want success without sacrificing what matters most, this is one to hear.

What if the thing you’ve been trying to hide is actually your greatest strength? In this powerful conversation, Willie Blake shares how he transformed his struggle with dyslexia into a competitive advantage. This episode is a must-listen for anyone who has ever felt behind, broken, or unsure of their potential.

At 69, Ande Lyons is proving that life doesn’t slow down with age, it opens up. In this conversation, she shares how breaking free from limiting beliefs about aging can unlock new purpose, opportunities, and fulfillment. If you’ve ever felt like time is running out, this episode will change your perspective.

Billy Fanshawe shares how a college idea turned into a patented vodka brand that’s shaking up a crowded industry. From navigating intense regulations to building a business from scratch, his journey is a masterclass in persistence and innovation. If you’re an entrepreneur or just curious about what makes a product stand out, this episode is worth your time.

This episode dives into the story behind Harford’s Heart Magazine and the people who keep it thriving. Sandy Kapinos and Debbie Umbarger share how the publication has stayed true to its mission of community, connection, and storytelling for over two decades. It’s a powerful reminder of why local voices and authentic stories still matter.

Podcasting expert Arielle Nissenblatt joins Rich Bennett to discuss the evolving future of podcasting and why audio-only shows may be more powerful than ever. Arielle shares insights on podcast discovery, audience connection, and why strong storytelling and sound matter more than flashy video. If you are a podcaster or podcast listener wondering where the medium is heading, this conversation offers clarity, encouragement, and practical perspective.

Leadership sounds great in theory, but the real test happens when leaders must have difficult conversations, motivate disengaged teams, and build trust under pressure. Leadership expert Ronald Reich joins Rich Bennett to discuss the biggest mistakes managers make and why emotional intelligence, clear expectations, and strong relationships matter more than authority. With nearly three decades of experience, Ron shares practical advice leaders can start applying immediately.

What does it really take to design learning that works? In this episode of Conversations with Rich Bennett, Rich is joined by instructional designer, professor, and podcast host Jackie Pelegrin, who brings nearly two decades of experience in higher education and curriculum design. Jackie breaks down what instructional design actually is, why so many online courses fail to engage learners, and how education must be built with intention, empathy, and real-world outcomes in mind. The conversation also explores AI in education, adult learning challenges, podcasting as a teaching tool, and how Jackie turned one of her most popular podcast series into a book. Whether you’re an educator, trainer, podcaster, or lifelong learner, this episode delivers practical insights and behind-the-scenes wisdom on designing learning experiences that truly stick.

What if just seven words could change your life? In this powerful episode of Conversations with Rich Bennett, Rich sits down with award-winning author and publisher Aurora Winter to explore how the right message can transform heartbreak into healing, stories into income, and ideas into lasting impact. Aurora shares deeply personal experiences of loss, resilience, and reinvention, along with practical insights on why most authors fail to market their books and how entrepreneurs can build real brands through storytelling. From grief recovery to publishing strategy, video marketing, and AI tools, this conversation is packed with wisdom for anyone ready to share their story and make it matter. Listen in and discover how your words can work for you 24/7.

Carefree Kitchens is more than a cabinet company. It’s a living example of what the American Dream can look like when it’s built on faith, family, integrity, and service. In this episode of Conversations with Rich Bennett, Rich is joined by cohost Joe Ayler for a powerful conversation with the family behind Carefree Kitchens. What begins as an immigration story quickly unfolds into a decades-long journey of entrepreneurship, resilience, and doing business the right way even when it’s hard. From arriving in the United States with nothing, to surviving economic downturns, to building a multi-generational family business that prioritizes people over profit, this episode is filled with wisdom for business owners, leaders, and anyone chasing a dream bigger than themselves. This is a conversation about legacy, reputation, leadership, and why success means more than money when faith and family lead the way.

Most podcast guests show up, share great insights, and walk away with nothing to show for it. In this episode of Conversations with Rich Bennett, podcast guesting expert Lyndsay Phillips explains why that happens and how to fix it. Lyndsay breaks down how entrepreneurs should treat every podcast appearance like a strategic launch, from choosing the right topic to guiding the conversation and repurposing the content long after the episode goes live. You’ll learn how to avoid common guesting mistakes, create conversations that convert, and turn podcast interviews into visibility, authority, and real business results. If you’ve ever been on a podcast and wondered why it didn’t lead to opportunities, this episode is a must-listen.

What happens when a veteran, podcaster, and truth-teller shows up every day for over a decade? In this episode of Conversations with Rich Bennett, Rich sits down with Pete A. Turner, host of The Break It Down Show, to talk about what it really takes to build a podcast that matters. Pete shares real, no-nonsense advice on consistency, monetization, evergreen content, guest relationships, and why most people quit before they ever find their voice. From taking his podcast on the road to using PodMatch to build meaningful connections, this conversation is packed with insight for podcasters, creators, and anyone trying to do meaningful work. If you’ve ever thought about starting a podcast or wondered why yours isn’t growing, this is an episode you don’t want to miss.

From living out of his truck at 27 to generating over $90 million in tech sales, Mark J. Silverman’s story is one of resilience, reinvention, and real leadership. In this powerful episode of Conversations with Rich Bennett, Mark opens up about addiction, long-term sobriety, ADHD, fear, faith, and what it truly means to lead with presence and humanity. Mark shares how listening to guidance changed his life, why fear never disappears, and how meditation, structure, and self-awareness have shaped his success as a coach, author, and speaker. He also dives into writing best-selling books with ADHD, navigating leadership as a spiritual practice, and why helping even one person makes it all worth it. This is an honest, inspiring conversation for leaders, entrepreneurs, creatives, and anyone rebuilding their life with purpose.

What do you do when a simple family outing turns into a disaster? For David Sauers, that moment sparked the creation of Royal Restrooms, a luxury restroom company now operating in over 50 locations nationwide. In this episode of Conversations with Rich Bennett, David shares the unforgettable story that inspired his business, how he left a successful banking career, and why execution matters more than perfection. From weddings and festivals to disaster relief and courthouse events, Royal Restrooms has redefined what people expect from mobile sanitation. This is a candid, funny, and inspiring conversation for entrepreneurs, business owners, and anyone sitting on an idea they haven’t acted on yet.

Imagine hearing clearly without the stigma, discomfort, or massive price tag of traditional hearing aids. In this episode of Conversations with Rich Bennett, Rich talks with Michael Leung, founder of the Flow Group in Calgary, about Flow True Balance 2.0, an open-ear bone conduction hearing device built for real life conversations, TV, and everyday connection. Michael opens up about his journey from Hong Kong to Canada, losing his mom at 11, living through vision loss and major setbacks, and how those experiences shaped his mission. You’ll hear how Flow differs from typical hearing aids, why seniors are adopting it fast, how it may help reduce tinnitus for some users, and why it is designed to keep you aware of your surroundings. Rich also shares a big idea for Lions Clubs and other community organizations to help more people access better hearing options. Learn more: theinnerflo.ca

What if your next client didn’t just sign a contract, but became a lifelong fan? In this episode, Rich Bennett sits down with Mark Stern, CEO of Custom Box Agency, to break down how physical “box experiences” can transform the customer lifecycle, from acquisition to onboarding to retention. Mark shares how businesses can gamify progress, define success for their customers, and create memorable experiences people actually keep, revisit, and talk about. You’ll hear real examples for online courses, real estate, book launches, and even how physical kits can help guests stand out when pitching podcasts. Sponsor: Daniel McGhee and The Victory Team, victoryteamsells.com Learn more: customboxagency.com

When a kid pulling golf balls out of ponds grows up to build one of the most influential platforms in podcasting, you know there’s a story worth hearing. In this episode, I’m joined by Alex Sanfilippo, founder of PodMatch and host of Podcasting Made Simple. We talk about his journey from the aerospace world to faith-based blogging and podcasting, to launching PodMatch in 2020 and watching it explode just as the world went into lockdown. Alex shares how a simple idea – “like a dating app, but for podcast interviews” – became a global tool that helps hosts find the right guests and guests find the right stages. We also dig into why Alex gives half of PodMatch’s profit back to podcasters through the PodValue initiative, what most hosts get wrong about sharing links to their shows, and how he’s building features like a built-in Workflow and review swaps to help podcasters grow sustainably. If you host a podcast, dream of starting one, or just love a good entrepreneurship story ro…

In this solo episode, host Rich Bennett pulls back the curtain on podcast advertising and shares what most businesses and nonprofits never hear before they sponsor a show. He explains why podcasting is such a powerful medium, why downloads do not equal listeners, and what really matters when you are deciding where to invest your marketing dollars. Rich walks through the key questions every smart sponsor should ask a podcaster: How long has the show been active? Who is actually listening? What hosting platform do they use? Does that platform insert its own ads, including possible competitors, right into your paid spot? Is the show a true podcast with an RSS feed, or just a video series calling itself one? He also shares how his own journey from Harford County Living to a podcast heard in more than 125 countries shaped the way he treats sponsors as true partners, not just logo placements. From guest opportunities and category exclusivity to giving sponsors full access to episode f…

When a business valuer told Australian marketer Wes Towers that his web and SEO agency “wasn’t worth much” because AI was coming for it, he was already in the middle of a divorce and feeling like everything was falling apart. Instead of walking away, Wes decided to confront the disruption head-on and rebuild his business around what AI cannot replace: human trust, clarity, and connection. In this episode, Wes shares how he went from crying under his desk to having his best financial year ever, why “search everywhere optimization” matters for trades and construction brands, and how to use AI as a powerful amplifier instead of a generic content machine. We also dig into the biggest website mistake that quietly kills sales, why you still absolutely need a website even if you are active on social media, and how Wes is changing his own habits as a founder. If you are a business owner, marketer, or trades leader trying to figure out where you fit in an AI-driven world, this conversati…

Jason Clark’s career started in a high school graphic arts program, running printing presses and drawing metal band logos on chalkboards. Today, he is the Chief Marketing Officer at Via Studio, a creative agency that has spent more than 25 years helping mission-driven organizations, nonprofits, and public institutions bring their brands to life. In this conversation, Jason and I get real about what still works in branding and marketing in a world full of AI, algorithms, and endless digital noise. We talk about his early work creating interactive CD-ROM training for GE Appliances, the award-winning rebrand of Kentucky’s Bernheim Forest, and why we might have moved from the “information age” into the “identity age.” Jason shares how to build logos and campaigns that actually mean something, why community feedback is now non-negotiable, and how AI can be a powerful assistant without replacing human creativity. We also have some fun with bourbon, clear ice, and the Mr. Boston Barten…

Former bartender and opiate addict Eric Turney hit multiple rock bottoms, including jail and failed treatment attempts, before a surprise wake up call changed everything. When he and his partner learned they were expecting their first child, Eric decided he was done burning bridges. He got serious about 12 step recovery and took a chance on a new life as an entry level sales rep at a small promotional products company. Today, Eric is the President and Sales and Marketing Director of The Monterey Company, a custom branded merch company founded in 1989 that creates premium challenge coins, lapel pins, belt buckles, hats, apparel, and more for brands like Google, Amazon, Target, Bentley, Lions Clubs, military units, and local organizations. After the founder offered employees the chance to buy the business, Eric and his partners stepped up and took it over. In this conversation, Eric and I dig into his journey through addiction and recovery, how he rebuilt his life and career, and …

Mental health is still one of the hardest things for people to talk about, even while more of us are willing to use words like anxiety, depression, and trauma. In this episode, Rich is joined once again by licensed clinical social worker and executive leader Jennifer Redding, founder of Harford Counseling and co-founder of Pebbles Throw Consulting, to dig into what real trauma-informed care looks like in everyday life and at work.  Jennifer breaks down why mental health has long been seen as a “character flaw,” how social media encourages self-diagnosis and labels, and why there is a big difference between a tough season and a clinical condition. She shares the origin story of Harford Counseling, explains how trauma and substance use are intertwined, and talks about the importance of treating people as whole human beings rather than separating “mental health,” “addiction,” and “life problems” into different boxes. The conversation then shifts into the workplace. Jennifer introdu…

In this episode of Conversations with Rich Bennett, Rich sits down with Dr. Christiane Schroeter — TEDx speaker, university professor, entrepreneur, bestselling author, and host of the Happy Healthy Hustle podcast. Christiane shares her Petite Practice method and breaks down how small, intentional steps can create massive personal and professional change. Rich and Christiane dive into confidence, clarity, mindset, and the realities of building a business without feeding the overwhelm. From teaching more than 10,000 students to launching a top-ranked podcast, Christiane brings humor, heart, and practical strategy that entrepreneurs, creators, and dreamers can put into action immediately. They also explore cultural stories, cookies, German baking, vulnerability, TEDx insights, and why consistency is the real engine behind long-term success. Whether you're starting a business, launching a podcast, or simply trying to grow with more intention, this episode offers tools, perspective,…

Maryland State Senator and IBEW Local 24 leader Cory V. McCray joins Rich and Dan to share how a paid electrical apprenticeship rewired his life—from Baltimore City and the juvenile system to business owner and public service. Cory breaks down how union apprenticeships work, why mentors and discipline matter, and how practical pathways can lift families and entire communities. A grounded, honest guide for anyone who cares about second chances and real opportunity.  Sponsored by Daniel McGhee and the Victory Team