Business Episodes

What if the biggest thing standing between you and your next chapter is simply trusting yourself? In this inspiring conversation, Rich sits down with author, publisher, and storytelling guide Nicolette Halladay to discuss the transformative power of storytelling, self-trust, and finding the courage to share your story with the world. Nicolette shares her entrepreneurial journey, how Inspired Hearts Publishing was born, why so many people struggle with visibility and imposter syndrome, and how writing a book often transforms the author just as much as the reader. This episode is packed with encouragement for aspiring authors, entrepreneurs, and anyone navigating a major life transition.

What does it take for a family business to thrive for more than 218 years? In this heartfelt conversation, Howard McComas IV shares the remarkable history of McComas Funeral Home, one of the oldest family-owned businesses in Harford County and among the oldest family-owned funeral homes in America. Howard opens up about the importance of relationships, community involvement, grief support, honoring veterans, and helping families navigate life's most difficult moments with compassion and dignity.

Michael Reed returns to Conversations with Rich Bennett to share the next chapter of his extraordinary journey through grief, healing, and purpose. Since his last appearance, Michael has become a certified grief coach, continued his education in behavioral health, published two additional books, and reached a major milestone in his own healing process. In this deeply moving conversation, Michael discusses The Million Stages of Healing, his children's grief workbook The Owl and the Ladybug, and how he has learned to carry the love of his wife and daughters forward while helping others navigate loss. This episode is a powerful reminder that grief is not the end of the story and that healing is possible.

After a brain tumor surgery left one side of his face completely paralyzed, John Kippen spent more than a decade hiding from the world. What began as a painful journey of isolation eventually became a mission to help others embrace their differences and discover their own strength. In this powerful conversation, John shares how magic, storytelling, resilience, and human connection transformed his life. From performing for Alex Trebek and meeting legends like Siegfried & Roy to helping coaching clients overcome adversity, John's story is a reminder that our greatest challenges can become our greatest gifts.

Financial stress impacts nearly every part of life, but most people were never taught how to properly manage money, retirement, or investing. In this episode, Paul Applegate shares his journey from law enforcement to becoming a financial advisor with Edward Jones and explains why helping everyday people build financial confidence became his passion. Paul opens up about PTSD, emergency funds, retirement planning, budgeting, and why relationships and trust matter more than numbers alone. This conversation is packed with practical financial advice and honest life lessons that can help listeners feel more secure about their future.

Kyle Asperger shares how failure, entrepreneurship, and self-exploration shaped his unconventional approach to marketing and life. From running a marketing agency to reinventing himself as a coach, he breaks down why standing out matters more than ever in an AI-driven world. This episode is a raw, honest conversation about risk, identity, and building something that actually means something.

Anthony Spark shares how true success goes far beyond money, diving into identity, fulfillment, and personal integrity. Drawing from 20 years of experience in business and coaching, he explains why having the right mindset, values, and balance in life matters more than financial wins. This episode is a powerful reminder that success without joy is a losing game.

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…