Entrepreneurship Episodes

Sponsored by Eco-Cool HVAC  In this inspiring episode, Esther Avant—coach, speaker, entrepreneur, and host of the To Your Health podcast—joins Rich to discuss how small, sustainable changes can lead to big transformations. From her early passion for fitness to becoming a military spouse and succ…

Sponsored by Tar Heel Construction Group  In this engaging roundtable, Rich Bennett sits down with nonprofit consultant Katie Ramirez, alongside co-hosts Greg Derwart and Robyn Burke, for a candid discussion on the realities of nonprofit work. They dive into the importance of strong boards, smar…

Sponsored by Your Pet AuPair  When life crumbled around her—art career, finances, marriage—Stephanie Jackson hit rock bottom. Instead of giving up, she rebuilt her life and launched Practical Sanctuary, pioneering Sensory Interior Design, a unique blend of neuroscience, psychology, and art to cr…

In this powerful episode of Conversations with Rich Bennett, Gavin Masumiya shares his emotional journey from a shy, self-conscious child to a confident speaker, coach, and musical artist. Through freestyle rap, public speaking, and deeply personal songwriting—especially after the loss of his mothe…

Send us a text Sponsored by American Auto Repair In this episode of Conversations with Rich Bennett , Michael V. Morgan shares how intentional networking transformed his career trajectory—from Penn State and a fraternity brot...

Sponsored by Chesapeake Podcast Network  In this candid and insightful episode, Rich Bennett chats with Seth Goldstein, a former journalist turned digital marketing expert and podcast coach. Seth shares how his career in journalism led to burnout and PTSD, and how he rebuilt himself through web …

Send us a text Sponsored by WHFC 91.1 FM In this vibrant, unfiltered conversation, Rich Bennett sits down with romance authors Cardyn Brooks, Kristie Wolf, and Samantha Heil to explore the booming world of romance literature—...

In this episode of Conversations with Rich Bennett, marketing powerhouse Julie Matzen joins Rich and co-host Michelle Hayes to share how her innovative platform, Boarderline, is transforming the way small and mid-sized businesses access expert marketing advice. Julie explains how AI, strategic plan…

Sponsored by Harford County Living After being fired from her federal government job, Megan Ewing didn’t crumble; she transformed. In this powerful episode, Megan shares her deeply personal journey of rebuilding her life and redefining success. From overcoming imposter syndrome to launching two …

Sponsored by Tar Heel Construction Group In this inspiring episode, Martin Grams shares the journey of founding The Screaming Bean, a community-driven coffee shop in Aberdeen, Maryland. Martin discusses how the café goes beyond serving exceptional coffee by actively supporting local charities, f…

Sponsored by Eco-Cool HVAC What if one simple act of kindness could spark a global movement? In this powerful episode, Rich Bennett talks with Luke Mickelson, founder of Sleep in Heavenly Peace , who left behind a successful sales career to build beds for children in need. What began in his gara…

Sponsored by Four Seasons Landscape & Construction Services In this episode of Conversations with Rich Bennett, Rich sits down with Maria Chapman, a remarkable entrepreneur and advocate. Despite battling rare neuromuscular conditions, Maria rebuilt her life through writing and founded Connected …

Sponsored by Living Well Healthcare Ready to scale your business the smart way? In this episode, Tracy Beavers shares how she transitioned from corporate burnout to building a thriving coaching empire by mastering list growth and online visibility. If you’re serious about creating consistent inc…

Sponsored by CleverCat Marketing What do toilet paper, jazz, and brand loyalty have in common? In this episode of Conversations with Rich Bennett, Ethan Decker reveals the surprising science behind how brands grow—and why small businesses struggle more than they think. From the Double Jeopardy L…

Sponsored by Harford County Living Discover how AI expert Shahar Boyayan is helping businesses transform customer relationships through smart, hyper-personalized automation. From emotional consumer insights to real-world applications that save time and boost sales, this episode is packed with st…

Sponsored by Tar Heel Construction Group Drewbie Wilson joins Rich Bennett to share how he turned his life around—from tipping the scales at 315 pounds to becoming a 7-figure sales leader and entrepreneur. He breaks down the mindset, discipline, and daily habits that help him (and his clients) c…

Sponsored by Richardson Farms From lacrosse fields to the shelves of Whole Foods, Gregory Vetter’s wild journey took a homemade salad dressing and turned it into a $300M clean food brand—only to lose it all. In this raw and revealing conversation, Greg opens up about bold risks, painful lessons,…

In this episode of Conversations with Rich Bennett, Evgeniy Kharam shares powerful insights on overcoming fear and mastering soft skills to succeed in sales—whether in cybersecurity, tech, or any industry. He breaks down how to turn fear into confidence, connect with clients, and win more deals by …

Sponsored by Freedom Federal Credit Union In this episode of Conversations with Rich Bennett, publishing expert Terry Whalin reveals the insider secrets to landing a book deal and navigating the complex world of traditional publishing. With decades of experience as an author, editor, and acquisi…

Want to build a high-performance organization? In this episode of Conversations with Rich Bennett, host Rich Bennett and cohost Greg Derwart sit down with Ryan McShane, founder of HR Evolution, to reveal the secrets to creating thriving workplaces, boosting employee engagement, and leading with imp…

In this episode of Conversations with Rich Bennett, Rich is joined by co-host Joe Ayler, owner of Tar Heel Construction Group, for an eye-opening discussion with Paul Reed, co-founder of Roofers in Recovery. Paul shares his powerful journey to sobriety and explains how his organization is helping m…

Send us a text Sponsored by Daniel McGhee and The Victory Team In this episode of Conversations with Rich Bennett , David Griffiths shares his journey from struggling with social media growth to amassing over 1.5 million foll...

In this episode of Conversations with Rich Bennett, author Erica D’Arcangelo shares the inspiring story behind her book A Story About Pizza, which chronicles her family’s journey from coal mines in Pennsylvania to running a thriving, family-owned pizzeria. Discover how tradition, resilience, and a …

Sponsored by Harford County Living In this episode of Conversations with Rich Bennett, Rich celebrates the podcast’s 10th anniversary and is joined by co-host Michelle Hayes and special guest Paul Yosua, co-owner of Das Bierhalle. Together, they explore Paul’s inspiring journey from working at Sta…