Debbie gets real with Kim Miles, the powerhouse behind Miles in Heels Productions, a woman who’s turned charisma into a career and authenticity into an art. Together, they unpack the unfiltered reality of entrepreneurial women who play by their own rules. A TEDx speaker and former media pro, Kim shares her journey from sales hustler to event-production maven, revealing how strategy, humor, and authenticity drive her success. From career pivots to the power of connection, this episode is a masterclass in owning your vibe, breaking molds, and building your empire your way.   Topics 00:26 Introducing Kim Miles: Founder of Miles in Heels 01:49 A Toast to Paper Planes and Bartending Stories 03:23 The Art of Sending Back Drinks 09:34 Kim's Journey: From Syracuse to Financial Advisor 12:47 Embracing the Zigzag Path of Entrepreneurship 14:09 The Birth of Miles and Heels Productions 14:45 Launching MAHJ House: A New Venture 32:26 The Importance of Knowing Your Worth 36:49 The Value of Knowing Your Worth 37:23 Behind the Scenes: The Hidden Efforts 38:06 The Importance of Asking for What You Deserve 39:40 Overthinking and Its Impact 42:00 The Power of Human Connection 47:00 Authenticity in Branding 56:15 Networking and Building Relationships 01:08:29 Embracing Different Life Paths 01:13:23 Conclusion and Final Thoughts

In this playful and heartfelt episode, Debbie gets a little help from her friend Koren who flips the script and interviews her! What starts as a simple intro quickly turns into a laughter-filled deep dive into Debbie’s wild and wonderful journey: from her podcasting past and writing adventures to the emotional rollercoaster of IVF. Expect honest moments, hilarious stories, and a few surprises as the two longtime friends swap tales about parenthood, creative passions, and the curveballs life throws your way. It’s the perfect mix of laughs, love, and real talk setting the tone for what’s to come on the podcast!   Topics 00:45 Opening Up: Personal Stories and Friendship 05:36 Debbie's Background and Podcast Journey 10:54 Wedding Stories and Industry Insights 25:22 Health Challenges and Personal Reflections 27:59 Technical Difficulties and Humor 29:55 Women's Health and Personal Struggles 31:51 IVF Journey and Emotional Challenges 34:21 Support Systems and Coping Mechanisms 36:50 Balancing Career and Motherhood 42:14 Dinner Party Dream Guests 45:56 Reflections on Value and Parenting 51:51 Conclusion and Future Plans

Debbie kicks back with Boston comic Corey Rodrigues for a hilarious and no-holds-barred convo that was so much fun, they had to split it into two episodes.  They swap stories about life on stage, the wild ride of trying to stay healthy, and the weird pressure to lose weight when you really just want fries. Things get real as they dive into awkward workplace vibes, the rise of AI tools like ChatGPT (yes, we’re talking robot coworkers), and why keeping it authentic matters more than ever. With plenty of laughs, sharp takes, and maybe a drink or two, this episode brings the funny while still hitting those “yeah, I feel that” moments.   Topics 00:00 Fish and Snail Adventures 00:43 Chat GPT: The Email Assistant 01:28 The Ethics of Using AI in Arguments 03:12 AI in Writing and Comedy 05:44 Humanoids and the Future of AI 18:50 The World Record Backflip Challenge 33:30 Chat GPT Limitations 34:03 Flipping Feats and Social Media 35:15 Christine Joins the Conversation 36:45 Workplace Relationships and Fraternization 41:50 Gender Dynamics in the Workplace 47:34 Personal Stories and Reflections 59:37 Wrapping Up and Final Thoughts  

Debbie kicks back with Boston comic Corey Rodrigues for a hilarious and no-holds-barred convo that was so much fun, they had to split it into two episodes.  They swap stories about life on stage, the wild ride of trying to stay healthy, and the weird pressure to lose weight when you really just want fries. Things get real as they dive into awkward workplace vibes, the rise of AI tools like ChatGPT (yes, we’re talking robot coworkers), and why keeping it authentic matters more than ever. With plenty of laughs, sharp takes, and maybe a drink or two, this episode brings the funny while still hitting those “yeah, I feel that” moments.   Topics 00:25 Catching Up and Cocktails 02:08 Weight Loss Journey and Health Challenges 03:57 Body Image and Self-Perception 06:28 Men's Health and Societal Expectations 22:40 Comedy Roots and Personal Background 36:51 Reflecting on Longevity and Success 37:08 The Drive for Betterment 38:06 Contentment vs. Productivity 38:28 Balancing Work and Passion 40:19 The Braces Effect: Overcoming Insecurities 43:55 Managing Stage Fright 56:22 Navigating the Entertainment Industry 01:02:42 Human Nature and Workplace Dynamics  

Debbie is joined by her friend and fellow advocate, Chris Therrien, for a heartfelt conversation about SUNS—Standing Up for Natick Students. Chris explains how the group got started and its mission to push back against misinformation from local parental rights groups while promoting inclusion and equity in schools. They dive into the importance of representation in school curricula (and why "opting out" misses the point), the uphill battle of confronting resistance, and the emotional toll advocacy can take. Through personal stories, candid reflections, and a few laughs, this episode highlights the power of community, the importance of staying informed, and the ongoing fight for fairness and representation in education.

Meet Pam and David Griffin, the duo behind Chocolate Therapy, where every truffle comes with laughter and love. What started as a sweet twist of fate turned into a cocoa-fueled journey from corporate life to chocolate-making. From meeting Robin Roberts to landing on Oprah’s Favorite Things, they share the highs and lows of small business life including pandemic pivots like virtual tastings. With humor, heart, and a lot of chocolate, their story shows what happens when passion meets purpose. Topics 00:25 Meet Pam and David: The Chocolate Therapy Story 01:35 Corporate America to Chocolate Entrepreneurs 02:40 Family and Personal Stories 12:08 Chocolate Therapy's Unique Flavors 27:44 Coffee Business Beginnings 29:01 Opening Cafe Coffee 29:41 Balancing Family and Business 31:04 Premature Birth and Family Support 33:37 Starbucks Competition 37:49 Naming Chocolate Therapy 44:23 Challenges of Running a Business 45:34 Family and Community Support 53:15 Current Ventures and Future Plans 54:16 A Night Out in 2023 54:26 Hotel Partnerships and Challenges 55:09 The Rising Costs of Chocolate 55:52 The Team Behind the Chocolate 57:41 Political Commentary and The Handmaid's Tale 01:00:10 Unexpected Opportunities and Connections 01:08:15 Virtual Classes and Business Adaptations 01:13:57 Wrapping Up and Final Thoughts

Debbie sits down with chef and restaurateur, Chef Chris Coombs, for a lively chat about his wild ride from culinary school to running a restaurant empire. Chris dishes on kitchen chaos, life-changing mentors, and why he steered clear of the party scene in an industry known for excess. They dive into his latest venture, Bosse, a pickleball-meets-dining hotspot, and talk about how the food world is evolving. Chris also gets real about his son's health battles and how they reshaped his outlook on life. It’s a heartfelt, behind-the-scenes look at the hustle, heart, and humor of life in (and out of) the kitchen.

Debbie is joined by the unstoppable Greta Bajrami, co-founder, CEO, and the powerhouse behind Golden Group Roofing. From her roots as an Albanian immigrant and teen mom to building a thriving construction empire with her husband Freddy, Greta’s story is nothing short of inspiring. They dive into the wild ride of entrepreneurship… the wins, the wipeouts, and everything in between. Along the way, Greta shares how integrity, grit, and community helped her rise, even through recent personal health battles. Plus, she spills the tea on her latest ventures: the Rootless app, her buzzing marketing agency, and an exciting new podcast she’s launching with her daughter. This episode is all about resilience, reinvention, and keeping it real.   The Golden Group: https://goldengrouproofing.com/   Topics 00:33 Pouring Drinks and Casual Conversation 02:14 Meeting at the Women's Conference 04:13 Greta's Background and Early Challenges 05:11 Teen Pregnancy and Overcoming Stigma 17:58 Starting Golden Group and Early Struggles 23:31 Turning Point and Business Growth 25:49 The Importance of Charity and Giving Back 26:33 Winning the Golden Hammer Award 28:29 Starting Rootless and Its Mission 29:28 Overcoming Challenges as an Immigrant Entrepreneur 34:52 Weight Loss Journey and Health Challenges 44:51 The Loneliness of Success 50:37 Future Plans and Legacy  

In this heartfelt and engaging episode, Debbie sits down with her longtime neighbor and friend, Chanie Fogelman of the Chabad Center in Natick. They take a warm stroll down memory lane, reflecting on their journey as neighbors and diving into the beauty and meaning of Shabbat. Chanie opens up about the rich traditions of Orthodox Judaism from the deep symbolism of the mikvah to the sacred rituals of marriage, and the unique, inspiring role of a Rebbetzin. She also shares personal stories from her own marriage, her path in education, and the deep-rooted community work she’s passionate about. This conversation is a celebration of faith, family, and the power of living with purpose and tradition.   Chabad Center Natick: https://www.chabadnatick.com/ https://www.facebook.com/chabadnatick/   00:00 Introduction and Welcoming Chanie Fogelman 00:45 First Toast 01:48 Discussing Orthodox Judaism and Matchmaking 04:33 Chanie's Family and Marriage 08:58 Orthodox Jewish Wedding Traditions 13:19 Chanie's Personal Stories and Background 15:06 Life as a Rabbi's Wife 24:27 Shabbat and Community Involvement 34:56 Discussing the Role of Orthodox Jewish Women 36:31 Education and Career Paths for Orthodox Jewish Women 39:46 The Sanctity of Gender and Marriage in Judaism 43:08 The Tradition of Wearing Wigs 48:43 Empowering Jewish Women and Community Involvement 54:51 The Importance of Shabbat 01:00:56 Daily Life and Responsibilities 01:10:43 Concluding Thoughts and Farewell

Deb talks with longtime friend Malik Williams. They dive into the joy of their reunion, discussing their past in the hospitality industry and Malik's impressive career as an Emmy-nominated composer. Over drinks, they explore the struggles and triumphs of maintaining creativity, mental health, and personal growth. Malik shares intimate stories from his challenging upbringing and stresses the importance of fatherhood, community involvement, and mentorship. The conversation is filled with humor, heartfelt moments, and reflections on what it means to be resilient and purposeful in life.   Topics 00:30 Whiskey Talk and Toasts 02:42 Hospitality Days and Reconnecting on LinkedIn 06:54 Parenting and Personal Growth 10:54 Creative Pursuits and Music Industry Insights 28:46 Groupie Life and Celebrity Encounters 29:37 Working with MCA Records 29:45 Life at Bobby Brown's House 30:48 Navigating the Music Industry 32:56 Growing Up in a Big Family 33:35 Mentorship and Giving Back 41:01 Experiences with Racism and Violence 48:24 Reflections on Community and Mentorship 55:21 Martial Arts and Coping Mechanisms 56:06 Mental Health and Personal Growth 58:36 Dealing with Family Tragedies 01:01:09 Emmy Nominated Documentary 01:02:54 Music and Emotional Expression 01:15:09 Physical Activity and Mental Health 01:17:30 Parenting and Personal Reflections 01:20:51 Conclusion and Contact Information