Entrepreneurship Episodes

In this powerful solo episode, Rich dives into the art of showing up for others even when it costs you time, comfort, or convenience. He shares personal reflections as a Marine Corps veteran, husband, father, and business owner about why real relationships are built in the uncomfortable moments. This episode challenges listeners to choose connection over convenience and lead by example in their families and communities.

Melissa Roos shares her journey from growing up seven miles outside a small Iowa town to becoming a six-book mystery romance author. She opens up about overcoming shyness, embracing indie publishing, revealing secrets one page at a time, and why reader feedback fuels her creative fire. If you love strong female leads, emotional depth, and suspense that keeps you guessing, this conversation will inspire you.

Jenny C. Cohen shares an unforgettable journey of resilience—surviving breast cancer, navigating family trauma, and using dance as a powerful path to healing and embodiment. From elite performance stages to the hardest moments of motherhood, Jenny reveals how reconnecting to your body can restore hope, confidence, and purpose. This is a raw, inspiring conversation about visibility, truth, and turning pain into power.

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 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 …

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

Energy healer and spiritual teacher Cheryl Stelte joins Rich to unpack why so many high-achieving women feel stuck even when life looks “successful” on the outside. From her Vancouver Island spiritual awakening to her Azarius Energy Healing method and “receive what’s offered” practice, Cheryl explains how early-rooted wounds, especially around the throat chakra, block fulfillment—and how to release them. You’ll hear practical tools, powerful stories, and a life-changing exercise to make better decisions now by asking what will matter on your deathbed.  Sponsored by Harford County Health Department

Rapper, producer, and entrepreneur Robert “B-Cide” Cardillo joins Rich to share the raw story behind his memoir, Myelin My Shoes—from underground tours and handing out mixtapes to launching a streetwear brand from a wheelchair after an MS diagnosis at 28. He breaks down how creativity became therapy, what the music business really teaches you, and why he refuses to let chronic illness define the art—or the hustle. If you need proof that purpose outlasts pain, this one’s for you.  Sponsored by Daniel McGhee and the Victory Team

Owner/operator Brittany Russin Smith shares how she turned a love of baking and community into The Hive at Rumsey—Harford County’s collaborative commissary kitchen—and The Honey Loft upstairs venue. She walks through vendor partnerships, micro-weddings, BYO alcohol logistics, and what it takes to run a flexible event space on the water in Joppatowne. If you care about local entrepreneurship, food businesses, and community-powered growth, this one’s packed with practical insights.  Sponsored by Four Seasons Landscape & Construction Services

Life coach and 25-year real estate pro Michelle Taylor shares how she healed deep trauma and transformed it into a movement she calls Repurposed Rising—a global vision to help women do their inner work and lead with purpose. She breaks down coaching vs. therapy, daily rituals, meditation insights, and why forgiveness is her superpower. Co-host Wendy Beck jumps in with powerful reflections and resources you can use today. Sponsored by Harford County Living

Live from Edgewood American Legion Post 17, Rich celebrates 10 years and 750+ episodes with special guests Kristy Breslin, Sensei Sydney Brackins, and the Delbridge family who helped launch the show’s in-person era. They swap origin stories, community wins, and wild ideas (hello, “Santa Smackdown”), then the co-hosts take the mics for a candid Q&A on growth, recovery impact, and what’s next. Sponsors and local shout-outs abound—this one’s a love letter to Harford County and beyond.  Sponsored by Freedom Federal Credit Union, Daniel McGhee & the Victory Team, and Eco-Cool HVAC

John Carter’s life reads like a movie: teenage enforcer, shot in the head and left for dead, spiraling into addiction, and then a decade-long prison sentence. In this raw, uplifting conversation, John shares the plan that saved him, the people who didn’t give up on him, and how fitness, service dogs, and service to others rebuilt his life into one of purpose. If you need a wake-up call on grit, accountability, and second chances, this is it.  Sponsored by Elite Power Washing

Business leader and mentor Irina Alexander joins Rich to unpack a neuroscience-rooted framework for staying regulated under pressure—especially in high-stress fields like first response and frontline leadership. She explains her C.A.R.E.S.™ approach (Communication, Awareness, Resilience, Emotional literacy, Self-mastery), why “knowing isn’t enough,” and how resilience is the byproduct of daily practices. Irina also shares candid stories of burnout, recovery, and the practical tools that help people shift from reactivity to regulation.  Sponsored by Maryland Pickers

Rich sits down with Greg Derwart, Chris Coleman, and Robyn Burke to unpack what a true mastermind is—and what it isn’t. Using Napoleon Hill, Ben Franklin’s Junto, and real community examples, they show how purpose, harmony, and structure turn brainstorming into outcomes for businesses, nonprofits, and families. It’s a grounded conversation about building something that matters, online and off. Sponsored by Four Seasons Landscape & Construction Services

Former IT consultant Ron Kinscherf shares how a backyard moment with his grandson sparked a rich universe of ant characters—and an 11‑book run in just four years. We dig into his newest book “Adorable,” the craft choices that keep parents engaged, and the quiet life lessons his stories deliver for kids and adults alike.  Sponsored by Real Life Prosthetics